9H-Fluoren-9-one (9-Fluorenone) [C13H8O] by Asch

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827 reactions in Reaxys

2018-06-21 23h:29m:07s (UTC)

1. Query

Search as: Product, As drawn, No mixtures ) AND (RX.PRO='9-fluorenone'))

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Rx-ID: 131976 View in Reaxys 1/827 Yield 100 %

Conditions & References With aluminum oxide, potassium permanganate in 1,2-dichloro-ethane, Time= 118h, Ambient temperature, other reagent, reaction time, Product distribution Noureldin, Nazih A.; Zhao, Dongyuan; Lee, Donald G.; Journal of Organic Chemistry; vol. 62; nb. 25; (1997); p. 8767 - 8772 View in Reaxys

100 %

With potassium hydroxide, 18-crown-6 ether, oxygen in 1,2-dimethoxyethane, Time= 1h, T= 20 °C Artamkina, G. A.; Grinfel'd, A. A.; Beletskaya, I. P.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 32; nb. 2; (1983); p. 345 - 352; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 2; (1983); p. 383 - 391 View in Reaxys

100 %

With aluminum oxide, potassium permanganate, water in 1,2-dichloro-ethane, Time= 118h, Ambient temperature Zhao; Lee; Synthesis; nb. 9; (1994); p. 915 - 916 View in Reaxys

100 %

With aluminum oxide, potassium permanganate, Time= 0.166667h, T= 140 °C , Irradiation Oussaid, Abdelouahad; Loupy, Andre; Journal of Chemical Research - Part S; nb. 9; (1997); p. 342 - 343 View in Reaxys

100 %

With tert.-butylhydroperoxide, RuIII-Montmorillonite K10 in acetonitrile, Time= 4h, Heating Nikalje, Milind D.; Sudalai; Tetrahedron; vol. 55; nb. 18; (1999); p. 5903 - 5908 View in Reaxys

100 %

With 18-crown-6 ether, oxygen in 1,2-dimethoxyethane, T= 100 °C Yamada, Kenta; Shibamoto, Hiroshi; Tanigawa, Yusuke; Ishikawa, Hiroyuki; Nishida, Jun-Ichi; Kitamura, Chitoshi; Kurata, Hiroyuki; Kawase, Takeshi; Synlett; vol. 27; nb. 14; (2016); p. 2085 - 2090; Art.No: ST-2016-W0275-C View in Reaxys

99 %

With tetrabutylammomium bromide, oxygen, N -hydroxyphthalimide in water, Time= 6h, T= 80 °C , p= 760Torr Matsunaka, Katsuhisa; Iwahama, Takahiro; Sakaguchi, Satoshi; Ishii, Yasutaka; Tetrahedron Letters; vol. 40; nb. 11; (1999); p. 2165 - 2168 View in Reaxys

99 %

With tert.-butylhydroperoxide, sodium hydrogencarbonate, dirhodium(II) tetrakis(caprolactam) in decane, 1,2-dichloro-ethane, Time= 16h, T= 20 °C Catino, Arthur J.; Nichols, Jason M.; Choi, Hojae; Gottipamula, Sidhartha; Doyle, Michael P.; Organic Letters; vol. 7; nb. 23; (2005); p. 5167 - 5170 View in Reaxys

99 %

Stage 1: With tert.-butylhydroperoxide, 3 A molecular sieve in decane, ethyl acetate, Time= 0.5h, T= 20 °C Stage 2: With manganese triacetate in decane, ethyl acetate, Time= 48h, T= 20 °C Shing, Tony K. M.; Yeung, Ying-Yeung; Su, Pak L.; Organic Letters; vol. 8; nb. 14; (2006); p. 3149 - 3151 View in Reaxys

99 %

With pyridine, tert.-butylhydroperoxide, iron(III) chloride, Time= 24h, T= 82 °C Nakanishi, Masafumi; Bolm, Carsten; Advanced Synthesis and Catalysis; vol. 349; nb. 6; (2007); p. 861 - 864 View in Reaxys

> 99 %

With pyridine, tert.-butylhydroperoxide, air, K(1+)*AuCl4 (1-)*0.5H2O=K[AuCl4]*0.5H2O in decane, Time= 24h, T= 90 °C

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Li, Huanrong; Li, Zhiping; Shi, Zhangjie; Tetrahedron; vol. 65; nb. 9; (2009); p. 1856 - 1858 View in Reaxys 99 %

With tert.-butylhydroperoxide, 4C12H25O4S(1-)*Fe2O(4+)*10H2O in water, Time= 24h, T= 20 °C Nagano, Takashi; Kobayashi, Shu; Chemistry Letters; vol. 37; nb. 10; (2008); p. 1042 - 1043 View in Reaxys

99 %

With pyridine, tert.-butylhydroperoxide, iodine in water, T= 80 °C , chemoselective reaction Zhang, Jintang; Wang, Zhentao; Wang, Ye; Wan, Changfeng; Zheng, Xiaoqi; Wang, Zhiyong; Green Chemistry; vol. 11; nb. 12; (2009); p. 1973 - 1978 View in Reaxys

99 %

With pyridine, tert.-butylhydroperoxide in decane, acetonitrile, Time= 24h, T= 80 °C Li, Ruilian; Zhao, Jian; Yang, Fengxia; Zhang, Yingchao; Ramella, Daniele; Peng, Yu; Luan, Yi; RSC Advances; vol. 7; nb. 81; (2017); p. 51142 - 51150 View in Reaxys

99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C12H8Cl3FeN2O4Zr4, oxygen, sodium nitrite in acetonitrile, Time= 24h, T= 60 °C , p= 760.051Torr Shu, Xin; Yu, Ying; Jiang, Yi; Luan, Yi; Ramella, Daniele; Applied Organometallic Chemistry; vol. 31; nb. 12; (2017); Art.No: E3862 View in Reaxys

> 99 %

With oxygen in octane, Time= 1h, T= 80 °C , p= 760.051Torr , Schlenk technique, Reagent/catalyst Nakai, Satoru; Uematsu, Tsubasa; Ogasawara, Yoshiyuki; Suzuki, Kosuke; Yamaguchi, Kazuya; Mizuno, Noritaka; ChemCatChem; vol. 10; nb. 5; (2018); p. 1096 - 1106 View in Reaxys

98 %

With 1-butyl hydroperoxide, bis-(triphenylsilyl oxide)dioxochromium in dichloromethane, Time= 48h, Ambient temperature Muzart; N'Ait Ajjou; Synthetic Communications; vol. 23; nb. 15; (1993); p. 2113 - 2118 View in Reaxys

98 %

With potassium permanganate, copper(II) sulfate, Time= 0.166667h, T= 20 °C , microwave irradiation Shaabani, Ahmad; Lee, Donald G.; Tetrahedron Letters; vol. 42; nb. 34; (2001); p. 5833 - 5836 View in Reaxys

98 %

1.1 :We initially studied oxidation of methylene substituted benzylic aromatics to ketones (Scheme 1, R.not equal.H). When a mixture of fluorene with 10 equivalents 70percent aqueous TBHP was irradiated with microwave in a sealed vessel for 10 minutes (250 W, 170° C.), an almost quantitative yield of fluorenone was isolated (Table 1). As a control experiment, when we simply refluxed the same reaction mixture by conventional oil bath heating for 8 hours, only a trace amount of fluorenone could be detected by TLC. Oxidation of another substrate with a doubly activated benzylic position, diphenylmethane, also afforded benzophenone in high yield. For the mono-activated methylene units, ethylbenzene to acetophenone and tetrahydronaphthalene to alpha-tetralone, the oxidations under this green protocol also went smoothly. The results are summarized in Table 1 With tert.-butylhydroperoxide in water, Time= 0.166667h, T= 170 °C , Microwave irradiation, Sealed vessel, Product distribution / selectivity Patent; Hong Kong Baptist University; US7488843; (2009); (B1) English View in Reaxys

98 %

With tert.-butylhydroperoxide, Time= 0.166667h, T= 170 °C , Microwave irradiation He, Hao; Pei, Bao-Jian; Lee, Albert W. M.; Green Chemistry; vol. 11; nb. 11; (2009); p. 1857 - 1861 View in Reaxys

98 %

With 2,6-dicarboxypyridinium fluorochromate in acetonitrile, Time= 1h, T= 20 °C Sarrafi, Yaghoub; Tajbakhsh, Mahmood; Hosseinzadeh, Rahman; Sadatshahabi, Marzieh; Alimohammadi, Kamal; Synthetic Communications; vol. 42; nb. 5; (2012); p. 678 - 685

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View in Reaxys 98%

With air, graphene-supported KOH composite in N,N-dimethyl-formamide, Time= 16h, T= 20 °C , Reagent/catalyst, Solvent Zhang, Xin; Ji, Xuan; Su, Ruifei; Weeks, Brandon L.; Zhang, Zhao; Deng, Songlu; ChemPlusChem; vol. 78; nb. 7; (2013); p. 703 - 711 View in Reaxys

98 %

With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate, oxygen, sodium acetate, nickel dibromide, Time= 48h, T= 120 °C , p= 760.051Torr Urgoitia; Sanmartin; Herrero; Domínguez; Chemical Communications; vol. 51; nb. 23; (2015); p. 4799 - 4802 View in Reaxys

98 %

With tert.-butylhydroperoxide, C24H18N6O3*Cu(1+)*I(1-) in water, Time= 8h, T= 20 °C , Reagent/catalyst, Time Wang, Xiaolu; Liu, Mengjia; Wang, Yuqing; Fan, Hongyan; Wu, Jie; Huang, Chao; Hou, Hongwei; Inorganic Chemistry; vol. 56; nb. 21; (2017); p. 13329 - 13336 View in Reaxys

97 %

With tert.-butylhydroperoxide, cobalt(II) ethyl phosphonate in acetonitrile, Time= 18h, T= 40 °C Jurado-Gonzalez, Magdalena; Sullivan, Alice C.; Wilson, John R. H.; Tetrahedron Letters; vol. 44; nb. 22; (2003); p. 4283 4286 View in Reaxys

97 %

With C14H14N6O2, oxygen, sodium acetate, palladium diacetate, Time= 48h, T= 120 °C , p= 760.051Torr Urgoitia, Garazi; Maiztegi, Ainhoa; Sanmartin, Raul; Herrero, María Teresa; Domínguez, Esther; RSC Advances; vol. 5; nb. 125; (2015); p. 103210 - 103217 View in Reaxys

96 %

With manganese(IV) oxide, potassium permanganate in dichloromethane, Time= 22h, T= 20 °C Shaabani, Ahmad; Mirzaei, Peiman; Naderi, Soheila; Lee, Donald G.; Tetrahedron; vol. 60; nb. 50; (2004); p. 11415 - 11420 View in Reaxys

96 %

With pyridine, Py-NHPI, oxygen, 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate, cobalt hexafluorophosphate, Time= 24h, T= 65 °C , p= 760Torr Wang, Jia-Rui; Liu, Lei; Wang, Ye-Feng; Zhang, Ying; Deng, Wei; Guo, Qing-Xiang; Tetrahedron Letters; vol. 46; nb. 27; (2005); p. 4647 - 4651 View in Reaxys

96 %

With air, caesium carbonate in dimethyl sulfoxide, Time= 3.5h, T= 20 °C Park, Kwanghee Koh; Tsou, Lun K.; Hamilton, Andrew D.; Synthesis; nb. 21; (2006); p. 3617 - 3620 View in Reaxys

96 %

With tert.-butylhydroperoxide, potassium iodide in water, acetonitrile, Time= 9h, T= 20 °C Kumar, R. Arun; Maheswari, C. Uma; Ghantasala, Satheesh; Jyothi; Reddy, K. Rajender; Advanced Synthesis and Catalysis; vol. 353; nb. 2-3; (2011); p. 401 - 410 View in Reaxys

95 %

With tert.-butylhydroperoxide, chromium(VI) oxide in dichloromethane, Time= 18h, Ambient temperature Muzart, Jacques; Tetrahedron Letters; vol. 28; nb. 19; (1987); p. 2131 - 2132 View in Reaxys

95 %

4.2 Typical procedure for arylalkanes oxidation General procedure: A stock solution of CuCl2·2H2O in water (0.0171 g/mL) was prepared (by dissolving 0.171 g in 10 mL H2O). To a Teflon screw cap glass tube, catalyst A (100 μL of a stock solution, 0.01 mmol of CuCl2, 2.1mg, 0.01 mmol of neocuproine) was added. Then 0.7 mL of H2O, 0.2 mmol of arylalkanes, and 70 percent aq tert-butyl hydroperoxide (200 μL, 1.4 mmol) were added in each case. The mixture was stirred vigorously at room temperature till to its reaction time specified in the Tables 2 and 3. The reaction mixture was then diluted with ethyl acetate and the products dissolved in ethyl acetate layer were analyzed by GC using internal standard 1,4-di-tert-butylbenzene (19.4 mg, 0.1 mol). For product separation, the aqueous phase

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was extracted with ethyl acetate (3×10 mL). The combined extracts were dried over anhydrous MgSO4 and filtered. The filtrate was concentrated and product isolation was carried out by TLC. The pure products of benzophenone, 9-fluorenone (Table 2, entries 2 and 3) and 4-methoxyacetophenone (Table 3 entry 2) were obtained from drying their ethyl acetate extract without chromatographic workup. Filtration of the reaction mixture afforded pure 9-xanthenone (Table 2, entry 4). With tert.-butylhydroperoxide, 2.9-dimethyl-1,10-phenanthroline, copper(II) choride dihydrate in water, Time= 1h, T= 20 °C , Reagent/catalyst Hossain, Md. Munkir; Shyu, Shin-Guang; Tetrahedron; vol. 72; nb. 29; (2016); p. 4252 - 4257 View in Reaxys 95 %

General procedure for oxygenation of benzylic C-H bonds General procedure: Charged 0.5 mmol of 3-(9H-fluoren-2-yl)prop-2-yn-1-ol 13a (110 mg, 0.5 mmol), 0.5 mL of [bmim]Br and TBHP (0.5 mL, 3.6 mmol) were taken in a round bottom flask and heated to 55 °C until completion of the reaction. The reaction course was monitored by TLC. After completion of the reaction, the reaction mixture was extracted using ethyl acetate (3 * 4 mL). The organic layer was concentrated under vacuum and purified by column chromatography on silica gel to afford the desired product as 2-(3-hydroxyprop-1-yn-1-yl)-9H-fluoren-9-one 13b Yellow Solid; With tert.-butylhydroperoxide, 1-n-butyl-3-methylimidazolim bromide in water, Time= 20h, T= 55 °C , Temperature, Solvent, Reagent/catalyst Naidu, Shivaji; Reddy, Sabbasani Rajasekhara; Journal of Molecular Liquids; vol. 222; (2016); p. 441 - 445 View in Reaxys

94 %

With potassium permanganate, Rexyn 101 H ion exchange resin in dichloromethane, Time= 7.3h, Heating Shaabani, Ahmad; Teimouri, Fatemeh; Lee, Donald G.; Synthetic Communications; vol. 33; nb. 6; (2003); p. 1057 - 1065 View in Reaxys

94 %

With caesium carbonate, dimethyl sulfoxide, T= 125 °C Chebolu, Rajesh; Bahuguna, Ashish; Sharma, Reena; Mishra, Vivek Kumar; Ravikumar; Chemical Communications; vol. 51; nb. 84; (2015); p. 15438 - 15441 View in Reaxys

94 %

With tert.-butylhydroperoxide in water, Time= 1.5h, T= 60 °C , Green chemistry Bhardwaj, Madhvi; Sharma, Harsha; Paul, Satya; Clark, James H.; New Journal of Chemistry; vol. 40; nb. 6; (2016); p. 4952 - 4961 View in Reaxys

94 %

With 18-crown-6 ether, potassium tert-butylate, oxygen in N,N-dimethyl-formamide, Time= 3h, T= 0 - 20 °C , Inert atmosphere Wang, Huiqiao; Wang, Zhong; Huang, Hongchun; Tan, Jiajing; Xu, Kun; Organic Letters; vol. 18; nb. 21; (2016); p. 5680 5683 View in Reaxys

93 %

With oxygen, Ru-Co-Al-CO3 HT in chlorobenzene, Time= 3h, T= 70 °C Matsushita, Tsuyoshi; Ebitani, Kohki; Kaneda, Kiyotomi; Chemical Communications; nb. 3; (1999); p. 265 - 266 View in Reaxys

93 %

With potassium hydroxide, 4,4',5,5'-tetra(1H,1H,2H,2H,3H,3H-heptadecafluoroundecyl)dibenzo-18-crown-6 ether, oxygen in perfluoro-1,3-dimethylcyclohexane, Time= 1h, T= 60 °C Pozzi, Gianluca; Quici, Silvio; Fish, Richard H.; Advanced Synthesis and Catalysis; vol. 350; nb. 14-15; (2008); p. 2425 2436 View in Reaxys

93 %

With 1,4-dichloro-1,4-diazoniabicyclo[2,2,2]octane bis-chloride, water, Time= 0.5h, T= 40 °C , pH= 7 Habibzadeh, Setareh; Tajbakhsh, Mahmood; Journal of Chemical Research; nb. 11; (2009); p. 696 - 698 View in Reaxys

93 %

With sodium ortho-iodobenzenesulfonate, Oxone, tetra(n-butyl)ammonium hydrogensulfate in acetonitrile, Time= 10h, T= 60 °C

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Cui, Li-Qian; Liu, Kai; Zhang, Chi; Organic and Biomolecular Chemistry; vol. 9; nb. 7; (2011); p. 2258 - 2265 View in Reaxys 93 %

With tert.-butylhydroperoxide, C56H53ClN3P2Ru(1+)*F6P(1-) in benzene, Time= 18h, T= 25 °C , Inert atmosphere, Schlenk technique Hsu, Shih-Fan; Plietker, Bernd; ChemCatChem; vol. 5; nb. 1; (2013); p. 126 - 129 View in Reaxys

93 %

With tert.-butylhydroperoxide, copper(l) iodide, dimethyl 3-methyl-9-oxo-7-(4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyloxy)benzyl)-2,4-di(pyridin-2-yl)-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarboxylate in water, Time= 12h, T= 50 °C , Green chemistry Ang, Wei Jie; Chng, Yong Sheng; Lam, Yulin; RSC Advances; vol. 5; nb. 99; (2015); p. 81415 - 81428 View in Reaxys

93 %

With tert.-butylhydroperoxide, manganese(IV) oxide in dichloromethane, water, Time= 22h, T= -20 °C , Reflux, chemoselective reaction Serra, Stefano; European Journal of Organic Chemistry; vol. 2015; nb. 29; (2015); p. 6472 - 6478 View in Reaxys

93 %

With tert.-butylhydroperoxide, manganese(II,III) oxide in acetonitrile, Time= 3h, T= 70 °C Skliri, Euaggelia; Papadogiorgakis, Stelios; Lykakis, Ioannis N.; Armatas, Gerasimos S.; ChemPlusChem; vol. 82; nb. 1; (2017); p. 136 - 143 View in Reaxys

92 %

With potassium permanganate on Y-Zeolite in 1,2-dichloro-ethane, Time= 96h, Ambient temperature Sreekumar; Padmakumar, Raghavakaimal; Tetrahedron Letters; vol. 38; nb. 29; (1997); p. 5143 - 5146 View in Reaxys

92 %

With aluminum oxide, Ru(OH)x, oxygen in 1,2-dichloro-benzene, Time= 4h, T= 169.85 °C , p= 760Torr Kamata, Keigo; Kasai, Jun; Yamaguchi, Kazuya; Mizuno, Noritaka; Organic Letters; vol. 6; nb. 20; (2004); p. 3577 - 3580 View in Reaxys

92 %

With sodium bromate, 1-n-butyl-3-methylimidazolim bromide, Time= 8h, T= 70 °C Shaabani, Ahmad; Farhangi, Elham; Rahmati, Abbas; Monatshefte fur Chemie; vol. 139; nb. 8; (2008); p. 905 - 908 View in Reaxys

92 %

With oxygen, potassium hydroxide in tetrahydrofuran, Time= 24h, T= 20 °C Zhang, Xin; Ji, Xuan; Jiang, Shanshan; Liu, Lili; Weeks, Brandon L.; Zhang, Zhao; Green Chemistry; vol. 13; nb. 7; (2011); p. 1891 - 1896 View in Reaxys

92 %

With tert.-butylhydroperoxide, sodium hypochlorite in water, ethyl acetate, Time= 0.00277778h, T= 25 °C , microreactor Lv, Xiao-Ming; Kong, Ling-Jie; Lin, Qi; Liu, Xiao-Feng; Zhou, Ya-Ming; Jia, Yu; Synthetic Communications; vol. 41; nb. 21; (2011); p. 3215 - 3222 View in Reaxys

92 %

With N -hydroxyphthalimide, oxygen in acetonitrile, Time= 3h, T= 70 °C , p= 760.051Torr , Irradiation, Green chemistry Jafarpour, Maasoumeh; Kargar, Hossein; Rezaeifard, Abdolreza; RSC Advances; vol. 6; nb. 30; (2016); p. 25034 - 25046 View in Reaxys

92 %

With tert.-butylhydroperoxide, [C6H5CH2N(CH3)2H]2[Ru(2,6-pyridinedicarboxylate)Cl3] in dichloromethane, water, Time= 16h, T= 40 °C , Catalytic behavior Zhang, Yuecheng; Zhao, Liyuan; Zhang, Hongyu; Huang, Rong; Zhao, Jiquan; Applied Organometallic Chemistry; vol. 31; nb. 9; (2017); Art.No: E3709 View in Reaxys

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91 %

With 2-Picolinic acid, sodium tetrahydroborate, bismuth(III) oxide, tert.-butylhydroperoxide in pyridine, water, acetic acid, Time= 16h, T= 100 °C Bonvin, Yannick; Callens, Emmanuel; Larrosa, Igor; Henderson, David A.; Oldham, James; Burton, Andrew J.; Barrett, Anthony G. M.; Organic Letters; vol. 7; nb. 21; (2005); p. 4549 - 4552 View in Reaxys

91 %

With potassium permanganate, manganese(II) sulfate, Time= 3.3h, T= 20 °C Shaabani, Ahmad; Rahmati, Abbas; Sharifi, Masoumeh; Rad, Jafar Mogimi; Aghaaliakbari, Behnaz; Farhangi, Elham; Lee, Donald G.; Monatshefte fur Chemie; vol. 138; nb. 7; (2007); p. 649 - 651 View in Reaxys

91 %

8 : EXAMPLE 8; Oxidation of Fluorene to Fluorenone Oxidation Fluorene (1.66 grams, 0.01 mol) and N-hydroxy phthalimide (1.8 g, 0.011 mol) were dissolved in acetone (100 ml). The mixture was stirred vigorously at room temperature and solid sodium dichromate monohydrate (1.38 g, 0.0046 mol) and chromium perchlorate hexahydrate (1.17 g, 0.0025 mol) were added. After 10 and 20 hours of continuous stirring at room temperature, additional amounts of solid sodium dichromate monohydrate (1.38 g, 0.0046 mol) and chromium perchlorate hexahydrate (1.17 g, 0.0025 mol) were added at each time interval. After 30 hours of continuous stirring at room temperature an additional amount of solid sodium dichromate monohydrate (1.38 g, 0.0046 mol) was added and the reaction mixture stirred continuously until the reaction had run to completion (48 hours). Separation Solvent was removed under vacuum and dichloromethane (50 ml) added to the residue. The organic layer was filtered through a bed of celite and the filter cake washed three times with dichloromethane. The combined organic filtrate was washed with water, saturated sodium bicarbonate solution and water. The washed filtrate was dried and the solvent distilled to yield fluorenone. The crude fluorenone was recrystallized from methanol to yield fluorenone (1.64 grams) having a melting point of 82-84° C. Yield Total yield of fluorenone was 1.64 grams (91.0percent). With N -hydroxyphthalimide, sodium dichromate, chromium(III) perchlorate in acetone, Time= 48h, T= 20 °C , Product distribution / selectivity Patent; Humanetics Corporation; US6384251; (2002); (B1) English View in Reaxys

91 %

With pyridine, tert.-butylhydroperoxide, [Fe(triflate)2(N-(pyridin-2-ylmethylene)aniline)2] in water, T= 20 °C , Inert atmosphere Shejwalkar, Pushkar; Rath, Nigam P.; Bauer, Eike B.; Dalton Transactions; vol. 40; nb. 29; (2011); p. 7617 - 7631 View in Reaxys

91 %

With tert.-butylhydroperoxide, [V12B18Zn3O63H12]*5H2O*10H3N*10H(1+)*3C4H13N3, acetic acid in water, acetonitrile, Time= 24h, T= 65 °C Chen, Hong; Deng, Youqian; Yu, Zhengbao; Zhao, Huishuang; Yao, Qingxia; Zou, Xiaodong; Baeckvall, Jan-E.; Sun, Junliang; Chemistry of Materials; vol. 25; nb. 24; (2013); p. 5031 - 5036 View in Reaxys

91 %

With tert.-butylhydroperoxide, copper(II) acetate monohydrate in water, Time= 8h, T= 80 °C , Catalytic behavior, Reagent/catalyst Wu, Jianglong; Liu, Yan; Ma, Xiaowei; Liu, Ping; Gu, Chengzhi; Dai, Bin; Chinese Journal of Chemistry; vol. 35; nb. 9; (2017); p. 1391 - 139 View in Reaxys

90 %

With sodium chlorite, N -hydroxyphthalimide in water, acetonitrile, Time= 1h, T= 50 °C Silvestre, Samuel M.; Salvador, Jorge A.R.; Tetrahedron; vol. 63; nb. 11; (2007); p. 2439 - 2445 View in Reaxys

90 %

With chromium(VI) oxide, periodic acid in acetonitrile, Time= 0.5h, T= 20 °C Yamazaki, Shigekazu; Organic Letters; vol. 1; nb. 13; (1999); p. 2129 - 2132 View in Reaxys

90 %

1 : 7.4.1. Determination of isolated yields in CH3CN, typical procedure for 9H-fluoren-9-one General procedure: The substrate fluorene (0.098 g, 0.589 mmol) and the catalyst [Fe(12)(OTf)2] (0.013 g, 0.017 mmol) were dissolved in CH3CN (2.0 mL) The oxidant H2O2 (0.182 mL, 30 wt.percent in H2O, 1.77 mmol) was added dropwise and the dark

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solution was shaken for 2 h at room temperature. The CH3CN solvent was removed under vacuum. The product fluorenone was isolated by column chromatography as yellow solid (0.096 g, 0.532 mmol, 90percent) using silica gel and CHCl3 as eluent. Analytical data for all oxidation products in Table 1 are given in the Supporting information. With [Fe[(S)-N-benzyl-2-phenyl-2-(pyridin-2-ylmethoxy)-N-(pyridin-2-ylmethyl)ethanamine](OTf)2], dihydrogen peroxide in water, acetonitrile, Time= 2h, T= 20 °C , Inert atmosphere, Reagent/catalyst, Solvent Lenze, Matthew; Sedinkin, Sergey L.; Bauer, Eike B.; Journal of Molecular Catalysis A: Chemical; vol. 373; (2013); p. 161 171 View in Reaxys 90 %

With tert.-butylhydroperoxide, copper(l) iodide, N-(4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyloxy)benzyl)-1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)methanamine, sodium dodecyl-sulfate in water, Time= 2h, T= 50 °C , Green chemistry, Temperature, regioselective reaction Ang, Wei Jie; Lam, Yulin; Organic and Biomolecular Chemistry; vol. 13; nb. 4; (2015); p. 1048 - 1052 View in Reaxys

90 %

With oxygen in 1,2-dichloro-benzene, Time= 6h, T= 150 °C , p= 3800.26Torr , Autoclave Uematsu, Tsubasa; Miyamoto, Yumi; Ogasawara, Yoshiyuki; Suzuki, Kosuke; Yamaguchi, Kazuya; Mizuno, Noritaka; Catalysis Science and Technology; vol. 6; nb. 1; (2016); p. 222 - 233 View in Reaxys

90 %

With Iron(III) nitrate nonahydrate, N -hydroxyphthalimide, oxygen in acetonitrile, Time= 40h, T= 25 °C , p= 760.051Torr Miao, Chengxia; Zhao, Hanqing; Zhao, Quanyi; Xia, Chungu; Sun, Wei; Catalysis Science and Technology; vol. 6; nb. 5; (2016); p. 1378 - 1383 View in Reaxys

90 %

2. Experimental details and characterization datafor products 2 General procedure: A mixture of 1 (0.2 mmol), Co(ClO4)2 (0.02 mmol), Oxone (1.2 mmol), CH3CN (2 mL) and H2O (2 mL) was stirred in a sealed tube at 25 °C for 3 h. After the reaction was completed (as monitored by TLC), the mixture was placed and allowed to separate into layers. Then the upper organic layer was separated, dried with anhydrous Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by preparative TLC (petroleum ether/ethyl acetate = 10:1, v/v) to yield 2. With oxone, cobalt(II) perchlorate in water, acetonitrile, Time= 3h, T= 25 °C , Sealed tube Yang, Yiwen; Ma, Hongxia; Tetrahedron Letters; vol. 57; nb. 47; (2016); p. 5278 - 5280 View in Reaxys

89 %

With Celite, pyridinium chlorochromate in benzene, Time= 10h, Heating Rathore, Rajendra; Saxena, Nishi; Chandrasekaran, S.; Synthetic Communications; vol. 16; nb. 12; (1986); p. 1493 - 1498 View in Reaxys

89 %

With potassium permanganate, Montmorillonite K10, Time= 24h, T= 23 °C Shaabani, Ahmad; Bazgir, Ayoob; Teimouri, Fatemeh; Lee, Donald G; Tetrahedron Letters; vol. 43; nb. 29; (2002); p. 5165 5167 View in Reaxys

89 %

With 30percent peracetic acid, resin-PPh2-Ru(PPh3)2Cl2 in ethyl acetate, 1,2-dichloro-ethane, Time= 2h, Heating Leadbeater; Journal of Organic Chemistry; vol. 66; nb. 6; (2001); p. 2168 - 2170 View in Reaxys

88 %

With 18-crown-6 ether, (COCl2)2 in hexane, Time= 2h, T= -15 - -10 °C Nagano, Tetsuo; Yokoohji, Kiyomi; Hirobe, Masaaki; Tetrahedron Letters; vol. 25; nb. 9; (1984); p. 965 - 968 View in Reaxys

88 %

With tert.-butylhydroperoxide, chromium-pillared montmorillonite in 2,2,4-trimethylpentane, dichloromethane, Time= 38h, Ambient temperature

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Choudary, Boyapati M.; Prasad, Annavajhula Durga; Bhuma, Vendantam; Swapna, Vinukonda; Journal of Organic Chemistry; vol. 57; nb. 22; (1992); p. 5841 - 5844 View in Reaxys 88 %

General procedure for the oxidation of diphenylmethane to benzophenone General procedure: In a 25 mL pressure tube, ZnBr2 (10 mol percent) and a stirring bar were added. After the addition of diphenylmethane (1 mmol), trifluoroacetic acid (0.2 mL) and 1,4-dioxane (2 mL) by syringe, H2O2 (4 mmol; 30percent aqueous) was added in one pot to the solution and the final solution was kept at 100 °C for 16 h. Then hexadecane (100 mg) and ethyl acetate (3 mL) were injected, a part of solution was taken for GC and GC–MS analysis after properly mixed. All the products are commercially available. #10; With dihydrogen peroxide, trifluoroacetic acid, zinc dibromide in 1,4-dioxane, water, Time= 16h, T= 100 °C Wu, Xiao-Feng; Tetrahedron Letters; vol. 53; nb. 45; (2012); p. 6123 - 6126 View in Reaxys

88 %

With manganese(IV) oxide in N,N-dimethyl-formamide, Time= 6 - 24h, T= 80 °C , Inert atmosphere, Reflux Nammalwar, Baskar; Fortenberry, Chelsea; Bunce, Richard A.; Lageshetty, Sathish Kumar; Ausman, Kevin D.; Tetrahedron Letters; vol. 54; nb. 15; (2013); p. 2010 - 2013 View in Reaxys

87 %

With potassium carbonate, 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-one in benzene, Time= 96h, Ambient temperature Ochiai, Masahito; Ito, Takao; Takahashi, Hideo; Nakanishi, Akinobu; Toyonari, Mika; Sueda, Takuya; Goto, Satoru; Shiro, Motoo; Journal of the American Chemical Society; vol. 118; nb. 33; (1996); p. 7716 - 7730 View in Reaxys

87 %

With sodium azide, [bis(acetoxy)iodo]benzene, water in acetonitrile, Time= 0.333333h, T= 20 °C Telvekar, Vikas N.; Sasane, Kulbhushan A.; Synthetic Communications; vol. 42; nb. 9; (2012); p. 1325 - 1329 View in Reaxys

87 %

With oxygen in water, Time= 7h, Reflux Albadi, Jalal; Alihosseinzadeh, Amir; Jalali, Mehdi; Mansournezhad, Azam; Applied Organometallic Chemistry; vol. 32; nb. 3; (2018); Art.No: E4193 View in Reaxys

86 %

With tert.-butylhydroperoxide, tris(triphenylphosphine)ruthenium(II) chloride in benzene, Time= 2h, Ambient temperature Murahashi; Oda; Naota; Kuwabara; Tetrahedron Letters; vol. 34; nb. 8; (1993); p. 1299 - 1302 View in Reaxys

86 %

With <2,2',3,3',5,5'-hexaphenyl-(1,1'-biphenyl)-4,4'-dioxyl>, oxygen, copper(l) chloride in various solvent(s), Time= 13h, T= 95 °C Barbiero; Kim; Hay; Tetrahedron Letters; vol. 35; nb. 32; (1994); p. 5833 - 5836 View in Reaxys

86 %

With oxygen, chloroamine-T, meso-tetrakis(tetraphenyl)porphyrin iron(III) chloride in acetonitrile, Time= 24h, T= 20 °C , p= 760Torr Li, Shi-Jun; Wang, Yan-Guang; Tetrahedron Letters; vol. 46; nb. 46; (2005); p. 8013 - 8015 View in Reaxys

86 %

With tert.-butylhydroperoxide, tris(triphenylphosphine)ruthenium(II) chloride in benzene, Time= 2h, T= 20 °C Murahashi; Komiya; Oda; Kuwabara; Naota; Journal of Organic Chemistry; vol. 65; nb. 26; (2000); p. 9186 - 9193 View in Reaxys

86 %

With tert.-butylhydroperoxide, [(pymox-Me2)2RuCl2]+BF4- in dichloromethane, water, Time= 2h, T= 20 °C Yi, Chae S.; Kwon, Ki-Hyeok; Lee, Do W.; Organic Letters; vol. 11; nb. 7; (2009); p. 1567 - 1569 View in Reaxys

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86 %

With [bis(acetoxy)iodo]benzene, tert-butyl hydroxyperoxide, 3-chloro-benzenecarboperoxoic acid in ethyl acetate, Time= 9h, T= 20 °C Xu, Yuan; Yang, Zhenping; Hu, Jiantao; Yan, Jie; Synthesis (Germany); vol. 45; nb. 3; (2013); p. 370 - 374; Art.No: SS-2012-F0873-OP View in Reaxys

86 %

General procedure for oxidation of alkanes with NaIO4 catalyzed by [Mn(TNH2PP)Cl(at)MWCNT] General procedure: To a mixture of alkane (1 mmol), [Mn(TNH2PP)Cl(at)MWCNT] (350 mg, 0.05 mmol) and imidazole (0.2 mmol) in CH3CN (10 mL) was added a solution of NaIO4 (2 mmol) in H2O (10 mL). The reaction mixture was stirred magnetically at room temperature. The progress of the reaction was monitored by GC. At the end of the reaction, the reaction mixture was diluted with Et2O (20 mL) and filtered. The catalyst was thoroughly washed with Et2O and combined washings and filtrates were purified on silica-gel plates or with a silica-gel column. IR and 1H NMR spectral data confirmed the identities of the products. With 1H-imidazole, sodium periodate, 5,10,15,20-tetrakis-(4-aminophenyl) manganese(III) porphyrin chloride in water, acetonitrile, Time= 2h, T= 25 °C Araghi, Mehdi; Bokaei, Forough; Polyhedron; vol. 53; (2013); p. 15 - 19 View in Reaxys

86 %

12 : Example 12: fluorene 0.2 mmol,Copper powder 0.02 mmolAnd Selectfluor 0.06 mmol are added in turn into a 10 mL pressure-resistant sealed container.Add 2 mL of a mixture of acetonitrile and water (CH3CN/H2O = 400:1).The mixture was stirred at room temperature and TLC was followed. The reaction was completed after 4 hours.The reaction solution was diluted with 10 mL of dichloromethane and filtered to obtain a clear solution.Evaporate the solvent and use column chromatography (eluent ratio: petroleum ether to ethyl acetate volume ratio 20:1)After separation, the eluent was collected and the solvent was distilled off to obtain fluorenone with a yield of 86percent. With copper, Selectfluor in water, acetonitrile, Time= 4h, T= 20 °C , Reagent/catalyst Patent; Zhejiang University of Technology; Liu Yunkui; Zhang Wei; Zhang Wenxia; (9 pag.); CN105085205; (2018); (B) Chinese View in Reaxys

85 %

With dinitrogen monoxide, Ru(5,10,15,20-tetramesitylporphyrin)(O)2 in benzene, T= 200 °C , p= 7600Torr Hashimoto, Kentaro; Tanaka, Hirotaka; Ikeno, Taketo; Yamada, Tohru; Chemistry Letters; nb. 6; (2002); p. 582 - 583 View in Reaxys

85 %

With dinitrogen monoxide, dioxo(tetramesitylporphyrinato)ruthenium(VI) in benzene, Time= 20h, T= 200 °C , p= 7600Torr Tanaka, Hirotaka; Hashimoto, Kentaro; Suzuki, Kyosuke; Kitaichi, Yasunori; Sato, Mitsuo; Ikeno, Taketo; Yamada, Tohru; Bulletin of the Chemical Society of Japan; vol. 77; nb. 10; (2004); p. 1905 - 1914 View in Reaxys

85 %

With sodium hypochlorite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, cobalt(II) diacetate tetrahydrate in dichloromethane, water, Time= 6h, T= 0 - 5 °C , pH= 8.3 Jin, Can; Zhang, Li; Su, Weike; Synlett; nb. 10; (2011); p. 1435 - 1438; Art.No: W06511ST View in Reaxys

85 %

With pyridine, iso-butyl hydroperoxide, C24H26FeN6 (2+)*2CF3O3S(1-) in water, acetonitrile, Time= 5h, T= 20 °C , Inert atmosphere Lenze, Matthew; Martin, Erin T.; Rath, Nigam P.; Bauer, Eike B.; ChemPlusChem; vol. 78; nb. 1; (2013); p. 101 - 116 View in Reaxys

84 %

With o-iodosobenzoic acid, oxygen in acetonitrile, Time= 24h, T= 80 °C , Green chemistry, Reagent/catalyst, Solvent, Time Bindu, Vittam Hima; Parvathaneni, Sai Prathima; Rao, Vaidya Jayathirtha; Catalysis Letters; vol. 147; nb. 6; (2017); p. 1434 - 1440 View in Reaxys

83 %

With Shirasagi KL activated carbon, oxygen in m-xylene, Time= 24h, T= 120 °C

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Kawabata, Hirotoshi; Hayashi, Masahiko; Tetrahedron Letters; vol. 45; nb. 28; (2004); p. 5457 - 5459 View in Reaxys 83 %

With PEG-1000, carbon dioxide, oxygen, cobalt(II) acetate, Time= 12h, T= 100 °C , p= 75007.5Torr , Autoclave, Neat (no solvent) Wang, Jin-Quan; He, Liang-Nian; New Journal of Chemistry; vol. 33; nb. 8; (2009); p. 1637 - 1640 View in Reaxys

83 %

2 : 3.2 A typical procedure for DDQ/TBN-catalyzed aerobic oxidation of diarylmethanes General procedure: A Teflon-lines 316 L stainless steel autoclave (300 mL) equipped with magnetic stirring bar was charged with substituted diarylmethanes 1 (2 mmol), 136.2 mg DDQ (0.6 mmol, 30 mol percent), 41.2 mg TBN (0.4 mmol, 20 mol percent), 480 mg acetic acid (8 mmol) and 20 mL TeCA. The autoclave was closed and charged with oxygen to 0.3 MPa. Then the autoclave was placed in an oil bath, which was preheated to 130 °C. The mixture was then stirred for a certain time until the reaction was completed. The autoclave was taken out from the oil bath, cooled to room temperature and carefully depressurized. The mixture was concentrated under reduced pressure and purified by column chromatography to give the desired diarylketones. With tert.-butylnitrite, oxygen, acetic acid, 2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,1,2,2-tetrachloroethane, Time= 20h, T= 130 °C , Autoclave Ma, Jiaqi; Hu, Zhiming; Li, Meichao; Zhao, Weijuan; Hu, Xinquan; Mo, Weimin; Hu, Baoxiang; Sun, Nan; Shen, Zhenlu; Tetrahedron; vol. 71; nb. 38; (2015); p. 6733 - 6739 View in Reaxys

83 %

Cu-Catalyzed Aerobic C–H Oxygenation of 1a; Typical Procedure: General procedure: To a test tube charged with CuCl (2.0 mg, 0.02 mmol) andisochroman (1a; 251 μL, 2.0 mmol) in t-BuOH (20 mL) wasadded TBHP (5.0–6.0 M in decane, 10.9 μL, 0.6 mmol) and themixture was stirred and heated at 50 °C for 12 h under open air.After cooling to room temperature, the reaction was quenchedwith 25percent aqueous ammonia solution and water then themixture was extracted with EtOAc. The separated organic layerwas dried over Na2SO4 and products were concentrated after filtration.The residue was purified by silica gel column chromatography(EtOAc/hexane, 1:10) to give isochromanone (2a) as acolorless oil in 83percent yield. With tert.-butylhydroperoxide, copper(l) chloride in decane, tert-butyl alcohol, Time= 12h, T= 50 °C Tanaka, Hirotaka; Oisaki, Kounosuke; Kanai, Motomu; Synlett; vol. 28; nb. 13; (2017); p. 1576 - 1580 View in Reaxys

82 %

With oxygen, 9,10-Dicyanoanthracene, Paraquat, iron(II) chloride in methanol, acetonitrile, Time= 4h, Ambient temperature, Irradiation Santamaria, Jean; Jroundi, Rachid; Tetrahedron Letters; vol. 32; nb. 34; (1991); p. 4291 - 4294 View in Reaxys

82 %

With N -hydroxyphthalimide, 1,4-diamino-2,3-dichloroanthraquinone, oxygen in acetonitrile, T= 80 °C , p= 1875.15 2250.18Torr Yang, Guanyu; Zhang, Qiaohong; Miao, Hong; Tong, Xinli; Xu, Jie; Organic Letters; vol. 7; nb. 2; (2005); p. 263 - 266 View in Reaxys

82 %

Typical procedure for the oxidation of tetraline General procedure: N-Hydroxyphthalimide (0.01 g, 0.06 mmol) was added to a two-necked flask equipped with a gas bubbling tube containing colloidal of CoPcCell (0.05 g), tetraline (0.13 g, 1.00 mmol) and KOH (0.25 mmol) in o-xylene (5 mL). The mixture was stirred under reflux conditions in O2 atmosphere provided with a balloon. The reaction temperature was raised to refluxing o-xylene. The progress of the reaction was followed by TLC. Upon completion, CoPcCell was separated by filtration and washed with acetone (5 mL). Tetralone was isolated from the mixture using column chromatography with n-hexane:ethyl acetate (10:1) in 88percent yield. With N -hydroxyphthalimide, 6-((cobalt(II) 4,9,16,23-tetraaminephthalocyanin-4-yl))cellulose, oxygen, potassium hydroxide in o-xylene, Time= 10h, Reflux, Green chemistry Shaabani, Ahmad; Keshipour, Sajjad; Hamidzad, Mona; Shaabani, Shabnam; Journal of Molecular Catalysis A: Chemical; vol. 395; (2014); p. 494 - 499 View in Reaxys

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81 %

With tert.-butylhydroperoxide in hexane, T= 130 °C , Sealed tube Tan, Jiajing; Zheng, Tianyu; Yu, Yuqi; Xu, Kun; RSC Advances; vol. 7; nb. 25; (2017); p. 15176 - 15180 View in Reaxys

80 %

With pyridine, tert.-butylhydroperoxide, C28H23BrFeNO3P in decane, Time= 36h, T= 20 °C Shejwalkar, Pushkar; Rath, Nigam P.; Bauer, Eike B.; Molecules; vol. 15; nb. 4; (2010); p. 2631 - 2650 View in Reaxys

80 %

With tert.-butylhydroperoxide, sodium hydrogencarbonate, bis-[(trifluoroacetoxy)iodo]benzene in dichloromethane, Time= 6h, T= -30 - 20 °C Catir, Mustafa; Kilic, Hamdullah; Synlett; nb. 9; (2010); p. 1319 - 1322 View in Reaxys

80 %

With 1,4-bis(triphenylphosphonium)butane cerium nitrate in water, acetic acid, Time= 0.583333h, Reflux Heidari, Mohammad; Ershadifar, Mohammad; Hamid, Masoumeh; Badri, Rashid; Journal of the Chemical Society of Pakistan; vol. 38; nb. 5; (2016); p. 944 - 947 View in Reaxys

79 %

With oxygen, copper(l) chloride, N-hydroxy-3,4,5,6-tetraphenylphthalimide in acetonitrile, Time= 48h, T= 35 °C , atmospheric pressure Nechab, Malek; Einhorn, Cathy; Einhorn, Jacques; Chemical Communications; nb. 13; (2004); p. 1500 - 1501 View in Reaxys

76 %

With potassium permanganate, sulfuric acid, triethylamine in chloroform, Ambient temperature Li, Wen-Shan; Liu, Lilian Kao; Synthesis; nb. 4; (1989); p. 293 - 295 View in Reaxys

76 %

With 2-Picolinic acid, manganese(II) perchlorate hexahydrate, dihydrogen peroxide, sodium acetate in acetonitrile, T= 0 - 20 °C Dong, Jia Jia; Unjaroen, Duenpen; Mecozzi, Francesco; Harvey, Emma C.; Saisaha, Pattama; Pijper, Dirk; De Boer, Johannes W.; Alsters, Paul; Feringa, Ben L.; Browne, Wesley R.; ChemSusChem; vol. 6; nb. 9; (2013); p. 1774 - 1778 View in Reaxys

74 %

16 : EXAMPLE 16; Oxidation of Fluorene to Fluorenone Oxidation Fluorene (1.66 grams, 0.01 mol) and N-hydroxy phthalimide (1.8 g, 0.011 mol) were dissolved in acetone (45 ml) and water (5 ml). The mixture was stirred vigorously at room temperature and solid chromium trioxide (1.0 g, 0.001 mol) was added. After 6 and 12 hours of continuous stirring at room temperature, an additional amount of solid chromium trioxide (1.0 g, 0.001 mol) was added at each time interval, and the reaction mixture stirred continuously until the reaction had run to approximately 90percent completion (24 hours). Separation Solvent was removed under vacuum and dichloromethane (50 ml) added to the residue. The organic layer was filtered through a bed of celite and the filter cake washed three times with dichloromethane. The combined organic filtrate was washed with water, saturated sodium bicarbonate solution, and water, and then dried. The solvent was distilled to yield crude fluorenone. The crude fluorenone was recrystallized from methanol to yield 1.2 g (74percent yield based on 90percent conversion) of fluorenone having a melting point of 82-84° C. With chromium(VI) oxide, N -hydroxyphthalimide in water, acetone, Time= 24h, T= 20 °C , Product distribution / selectivity Patent; Humanetics Corporation; US6384251; (2002); (B1) English View in Reaxys

74 %

With oxygen, Time= 24h, T= 150 °C , p= 760.051Torr , Autoclave Malekafzali; Malinovska; Patureau; New Journal of Chemistry; vol. 41; nb. 15; (2017); p. 6981 - 6985 View in Reaxys

72 %

With potassium permanganate in acetonitrile, Time= 15h, T= 20 °C Shaabani, Ahmad; Tavasoli-Rad, Farahnaz; Lee, Donald G.; Synthetic Communications; vol. 35; nb. 4; (2005); p. 571 - 580 View in Reaxys

71 %

With dihydrogen peroxide in m-xylene, Time= 18h, T= 95 °C

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Nishida, Shunsuke; Hayashi, Masahiko; Synlett; vol. 23; nb. 11; (2012); p. 1683 - 1685 View in Reaxys 70 %

With 3,6-bis(triphenylphosphonium)cyclohexene peroxodisulfate in water, acetonitrile, Time= 0.416667h, Heating Badri, Rashid; Soleymani, Mousa; Synthetic Communications; vol. 32; nb. 15; (2002); p. 2385 - 2389 View in Reaxys

70 %

With dihydrogen peroxide in water, Time= 8h, T= 80 °C , p= 760.051Torr , Green chemistry Hosseini-Sarvari, Mona; Ataee-Kachouei, Tahereh; Moeini, Fatemeh; RSC Advances; vol. 5; nb. 12; (2015); p. 9050 - 9056 View in Reaxys

68 %

With chromium(VI) oxide, sulfuric acid in acetone, Time= 0.5h, T= 5 - 15 °C Rangarajan, Radhika; Eisenbraun, E.J.; Journal of Organic Chemistry; vol. 50; nb. 14; (1985); p. 2435 - 2438 View in Reaxys

67 %

With iron(III) chloride, 2,3-dicyano-5,6-dichloro-p-benzoquinone in water, acetonitrile, T= 80 °C , Inert atmosphere Evoniuk, Christopher J.; Hill, Sean P.; Hanson, Kenneth; Alabugin, Igor V.; Chemical Communications; vol. 52; nb. 44; (2016); p. 7138 - 7141 View in Reaxys

66 %

With oxygen, 2-ethoxycarbonyl-1-cyclopentanone, cobalt(II) [bis(salicylidene-N-(methyl-3-hydroxypropionate))] in acetonitrile, Time= 15h, T= 60 °C Punniyamurthy, T.; Iqbal, Javed; Tetrahedron Letters; vol. 35; nb. 23; (1994); p. 4003 - 4006 View in Reaxys

66 %

With <bis(salicylidene-N-methyl 3-hydroxypropionate)>cobalt, oxygen, 2-ethoxycarbonyl-1-cyclopentanone in acetonitrile Punniyamurthy; Bhatia, Beena; Reddy, M. Madhava; Maikap, Golak C.; Iqbal, Javed; Tetrahedron; vol. 53; nb. 22; (1997); p. 7649 - 7670 View in Reaxys

66 %

4. Typical procedure for oxidation of alkylbenzenes and toluene General procedure: Ethylbenzene (3a) (0.0531 g, 0.5 mmol), K2S2O8 (0.2703 g, 1.0 mmol), pyridine (0.0158 g, 0.2 mmol) and CH3CN (1.0 mL) were added to an oven-dried pressure vessel with a magnetic stir bar. Then the pressure vessel was filled with dioxygen and the reaction mixture was stirred at 80 °C for 16 hours (oil bath). After the completion of the reaction, the solvent was evaporated and the reaction mixture was purified with column chromatography (eluenet: ethyl acetate/PE = 1/10) to give acetophenone (4a) (0.0535 g yield 89percent). With pyridine, dipotassium peroxodisulfate, oxygen in acetonitrile, Time= 16h, T= 80 °C , p= 760.051Torr , Green chemistry Hu, Yixin; Zhou, Lihong; Lu, Wenjun; Synthesis (Germany); vol. 49; nb. 17; (2017); p. 4007 - 4016 View in Reaxys

65 %

With ZnCrCO3-HTlc in toluene, Time= 48h, T= 130 °C , Oxidation, Product distribution, Further Variations: Reagents Choudary, B. M.; Bhuma, V.; Narender, N.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 36; nb. 3; (1997); p. 278 - 280 View in Reaxys

65 %

With Bromotrichloromethane, Ir(2-(2,4-difluorophenyl)-5-trifluoromethylpyridine)2(4,4'-di-tert-butyl-2,2'-bipyridine)PF6, water, potassium carbonate in acetonitrile, T= 20 °C , Irradiation, Inert atmosphere, regioselective reaction Pandey, Ganesh; Laha, Ramkrishna; Singh, Deepak; Journal of Organic Chemistry; vol. 81; nb. 16; (2016); p. 7161 - 7171 View in Reaxys

62 %

With 3-carboxypyridinium trifluoroacetochromate in dichloromethane, Time= 3h, T= 20 °C Aydin, Fatma; Ozen, Recep; Organic Preparations and Procedures International; vol. 39; nb. 6; (2007); p. 616 - 620 View in Reaxys

62 %

With oxygen in 1,3,5-trimethyl-benzene, Time= 50h, T= 149.84 °C

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Yoshida, Akihiro; Takahashi, Youichi; Ikeda, Tsuyoshi; Azemoto, Kazuki; Naito, Shuichi; Catalysis Today; vol. 164; nb. 1; (2011); p. 332 - 335 View in Reaxys 61 %

With sodium bismuthate, acetic acid in water, acetone, Time= 36h, Heating Banik, Bimal K.; Venkatraman; Mukhopadhyay, Chhanda; Becker, Frederick F.; Tetrahedron Letters; vol. 39; nb. 40; (1998); p. 7247 - 7250 View in Reaxys

61 %

With sodium bismuthate, acetic acid in water, acetone, Time= 36h, Heating, Oxidation Banik, Bimal K.; Ghatak, Anjan; Mukhopadhyay, Chhanda; Becker, Frederick F.; Journal of Chemical Research - Part S; nb. 3; (2000); p. 108 - 109 View in Reaxys

61 %

With sodium bismuthate, acetic acid in water, acetone, Time= 36h, Heating / reflux Patent; Board of Regents, The University of Texas System; US6362200; (2002); (B1) English View in Reaxys

60 %

With [(hydrotris(3,5-diphenylpyrazole-1-yl)borate)FeII(mandelate)(H2O)], oxygen, T= 20 °C Paria, Sayantan; Chatterjee, Sayanti; Paine, Tapan Kanti; Inorganic Chemistry; vol. 53; nb. 6; (2014); p. 2810 - 2821 View in Reaxys

59 %

With dipyridinium dichromate, adogen 464, dihydrogen peroxide, sodium carbonate in various solvent(s), Time= 24h, Heating, Oxidation Delaval, Nicolas; Bouquillon, Sandrine; Henin, Francoise; Muzart, Jacques; Journal of Chemical Research - Part S; nb. 4; (1999); p. 286 - 287 View in Reaxys

59 %

4.4. Oxidation of hydrocarbons possessing methyl or methylene groups General procedure: In a typical preparation, a 7.5 mL vial was charged with GO (100 mg), substrate (50 mg), CHCl3 (0.5 mL) and a magnetic stir bar. The vial was then sealed with a Teflon-lined cap under ambient atmosphere and heated at 70 °C, 120 °C or 120 °C for 24 h. The reaction mixture was then cooled to room temperature and washed with CH2Cl2 (50 mL). The filtrate was collected and the solvent was removed under vacuum to obtain the crude product, which was then purified by silica chromatography (CH2Cl2, hexanes, EtOAc/CH2Cl2 or CH2Cl2/hexanes as the eluent). The oxidation reactions involving toluene, 4-nitrotoluene, cyclohexadiene, cyclohexene, and cyclohexane were performed using CDCl3 instead of CHCl3 and conversions were determined directly by 1H NMR spectroscopy. All products matched spectroscopic data reported previously in the literature (see ESI). With graphite oxide in chloroform, Time= 24h, T= 120 °C Jia, Hong-Peng; Dreyer, Daniel R.; Bielawski, Christopher W.; Tetrahedron; vol. 67; nb. 24; (2011); p. 4431 - 4434 View in Reaxys

58 %

With (5,10,15,20-tetrakis(p-methoxyphenyl)-21H,23H-porphyrinate)cobalt(II), oxygen, isobutyraldehyde in acetonitrile, Time= 3h, Ambient temperature Mandal, Ajay Kumar; Iqbal, Javed; Tetrahedron; vol. 53; nb. 22; (1997); p. 7641 - 7648 View in Reaxys

57 %

With chromium (VI) oxide in toluene, Time= 1h, Heating, microwave-irradiation Lukasiewicz, Marcin; Bogdal, Dariusz; Pielichowski, Jan; Advanced Synthesis and Catalysis; vol. 345; nb. 12; (2003); p. 1269 - 1272 View in Reaxys

57 %

With Montmorillonite-K10, water, potassium bromide, Time= 24h, T= 80 °C Dohi, Toshifumi; Takenaga, Naoko; Goto, Akihiro; Fujioka, Hiromichi; Kita, Yasuyuki; Journal of Organic Chemistry; vol. 73; nb. 18; (2008); p. 7365 - 7368 View in Reaxys

14/345

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55 %

With tert.-butylhydroperoxide, sodium hydroxide, tungsten(VI) oxide in water, Time= 12h, T= 80 °C Shaikh, Tanveer Mahammad Ali; Sudalai, Arumugam; European Journal of Organic Chemistry; nb. 29; (2008); p. 4877 4880 View in Reaxys

55 %

Typical procedure for the aerobic oxidation of isochromans, xanthenes and fluorenes General procedure: After an about 45 mL glass tube was charged with 2 mL acetonitrile, 0.5 mmol substrate and 0.075 mmol HNO3, the system was flushed with oxygen gas three times. Subsequently, the reaction tube was sealed and heated with magnetic stirring at 140 °C for 3 h. When the reaction time was reached, the reaction mixture was cooled to room temperature. Finally, evaporation of solvent followed by column chromatography yielded the targeted product. GC yields were obtained by the GC analysisof the mixture from another parallel experiment. With oxygen, nitric acid in acetonitrile, Time= 3h, T= 140 °C , p= 760.051Torr Tian, Xinzhe; Ren, Fangping; Zhao, Bo; Ren, Yun-Lai; Zhao, Shuang; Wang, Jianji; Catalysis Communications; vol. 106; (2018); p. 44 - 49 View in Reaxys

54 %

With oxygen, tetraethylammonium fluoride in acetonitrile, Time= 24h, Ambient temperature, Reactions of fluoride ion activated fluorene, Product distribution, Mechanism Clark, James H.; Goodall, David M.; White, Michael S.; Tetrahedron Letters; vol. 24; nb. 10; (1983); p. 1097 - 1100 View in Reaxys

54 %

With oxygen, tetraethylammonium fluoride in acetonitrile, Time= 24h, Ambient temperature Clark, James H.; Goodall, David M.; White, Michael S.; Tetrahedron Letters; vol. 24; nb. 10; (1983); p. 1097 - 1100 View in Reaxys

54 %

With N -hydroxyphthalimide in ethyl acetate, Time= 3h, T= 60 - 70 °C , Irradiation Jafarpour, Maasoumeh; Feizpour, Fahimeh; Rezaeifard, Abdolreza; RSC Advances; vol. 6; nb. 60; (2016); p. 54649 - 54660 View in Reaxys

52 %

With iodobenzene, 3-chloro-benzenecarboperoxoic acid, potassium bromide in acetonitrile, Time= 18h, T= 60 °C Xu, Yuan; Hu, Jian Tao; Yan, Jie; Chinese Chemical Letters; vol. 23; nb. 8; (2012); p. 891 - 894 View in Reaxys

50 %

With sodium hypochlorite, tetra(n-butyl)ammonium hydrogensulfate, sodium bromide in hexane, Time= 8h, T= 25 °C , Oxidation Clark; Grigoropoulou; Scott; Synthetic Communications; vol. 30; nb. 20; (2000); p. 3731 - 3735 View in Reaxys

50 %

With [{nBu4N}5{PV2Mo10O40}], dinitrogen monoxide in benzonitrile, Time= 48h, T= 150 °C , p= 760Torr Ben-Daniel, Revital; Neumann, Ronny; Angewandte Chemie - International Edition; vol. 42; nb. 1; (2003); p. 92 - 95 View in Reaxys

47 %

With hydrogenchloride, tetrakis(tetrabutylammonium)decatungstate(VI), oxygen in water, acetonitrile, Time= 0.75h, T= 20 °C , Flow reactor, Irradiation Laudadio, Gabriele; Govaerts, Sebastian; Wang, Ying; Ravelli, Davide; Koolman, Hannes F.; Fagnoni, Maurizio; Djuric, Stevan W.; Noël, Timothy; Angewandte Chemie - International Edition; vol. 57; nb. 15; (2018); p. 4078 - 4082; Angew. Chem.; vol. 130; nb. 15; (2018); p. 4142 - 4146,5 View in Reaxys

40 %

With tert.-butylhydroperoxide in water, acetonitrile, Time= 24h, T= 60 °C , Reagent/catalyst Ding, Yu-Jia; Zhang, Chun-Pei; Wang, Yong-Qing; Lin, Xiao-Ming; Zhu, Ximiao; Zhang, Da-Liang; Duan, Xian-Jian; Cai, Yue-Peng; CrystEngComm; vol. 17; nb. 35; (2015); p. 6693 - 6698 View in Reaxys

40 %

With C38H33BFeN6O3, oxygen in acetonitrile, Time= 1.5h, T= 20 °C

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Sheet, Debobrata; Paine, Tapan Kanti; Chemical Science; vol. 7; nb. 8; (2016); p. 5322 - 5331 View in Reaxys 39 %

With [Mn(IV)(O)(BQCN)(H2O)](2+) in water, acetonitrile, T= 0 °C , Inert atmosphere, Kinetics, Concentration Sawant, Sarvesh C.; Wu, Xiujuan; Cho, Jaeheung; Cho, Kyung-Bin; Kim, Sun Hee; Seo, Mi Sook; Lee, Yong-Min; Kubo, Minoru; Ogura, Takashi; Shaik, Sason; Nam, Wonwoo; Angewandte Chemie - International Edition; vol. 49; nb. 44; (2010); p. 8190 - 8194 View in Reaxys

38 %

With ruthenium trichloride, Oxone, iodobenzene in water, acetonitrile, Time= 20h, T= 20 °C Yusubov, Mekhman S.; Zhdankin, Viktor V.; Mendeleev Communications; vol. 20; nb. 4; (2010); p. 185 - 191 View in Reaxys

36 %

With [(N1,N2-dimethyl-N1,N2-bis(6-methyl-2-pyridylmethyl)ethane-1,2-diamine)FeII(benzilate)](ClO4), oxygen in acetonitrile, T= 20 °C , Reagent/catalyst Chakraborty, Biswarup; Jana, Rahul Dev; Singh, Reena; Paria, Sayantan; Paine, Tapan Kanti; Inorganic Chemistry; vol. 56; nb. 1; (2017); p. 359 - 371 View in Reaxys

31 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, Time= 72h, T= 100 °C , p= 760.051Torr Zhang, Bo; Cui, Yuxin; Jiao, Ning; Chemical Communications; vol. 48; nb. 37; (2012); p. 4498 - 4500 View in Reaxys

27 %

With ozone in dichloromethane, Time= 1h, T= 25 °C , other reaction times;, Mechanism, Kinetics, Rate constant Pryor, William A.; Gleicher, Gerald J.; Church, Daniel F.; Journal of Organic Chemistry; vol. 49; nb. 14; (1984); p. 2574 2578 View in Reaxys

19 %

With copper(II) choride dihydrate, oxygen, hydroquinone, Time= 16h, T= 30 °C , Sealed tube, Irradiation, Green chemistry Finney, Laura C.; Mitchell, Lorna J.; Moody, Christopher J.; Green Chemistry; vol. 20; nb. 10; (2018); p. 2242 - 2249 View in Reaxys

18 %

6.2 General procedure for oxidation of benzyl halides, alcohols, and aromatic hydrocarbons General procedure: To 16 mL of acetonitrile/water (1:1 v/v) mixture was added 0.5–1.2 mmol of the starting compound. The contents were heated at reflux with introduction of oxone (cf. entries for each case) incrementally over the entire duration of the reaction. For secondary benzyl halides, the reactions were run at room temperature. The progress of the reaction in each case was monitored by TLC analysis. After completion of the reaction, the reaction mixture was cooled to room temperature and the organic matter was extracted with ethyl acetate. The combined organic extract was dried over anhyd Na2SO4 and concentrated in vacuo. Short pad silica gel column chromatography of the residue led to isolation of the pure product. With Oxone in water, acetonitrile, Time= 36h, Reflux Parida, Keshaba Nanda; Jhulki, Samik; Mandal, Susovan; Moorthy, Jarugu Narasimha; Tetrahedron; vol. 68; nb. 47; (2012); p. 9763 - 9768,6 View in Reaxys Parida, Keshaba Nanda; Jhulki, Samik; Mandal, Susovan; Moorthy, Jarugu Narasimha; Tetrahedron; vol. 68; nb. 47; (2012); p. 9763 - 9768 View in Reaxys

17 %

With N -hydroxyphthalimide in pyridine, anodic oxidation Masui, Masaichiro; Hara, Seijiro; Ueshima, Takahiro; Kawaguchi, Tetsuo; Ozaki, Shigeko; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 11; (1983); p. 4209 - 4212 View in Reaxys

15 %

With zinc(II) chlorosulphate in dichloromethane, Time= 16h, Ambient temperature Firouzabadi, H.; Sharifi, A.; Synthesis; nb. 10; (1992); p. 999 - 1002 View in Reaxys

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10 %

With KO2 in dimethyl sulfoxide, Time= 0.5h, T= 60 °C Top, Siden; Jaouen, Gerard; McGlinchey, Michael; Journal of the Chemical Society, Chemical Communications; nb. 14; (1980); p. 643 - 644 View in Reaxys

67 % Turnov.

With oxygen, cobalt(II), bromide in chlorobenzene, Time= 6h, T= 120 °C , other catalysts, Product distribution Koroleva, N. V.; Kuznetsova, L. N.; Bagdadi, A.; Perederii, M. A.; J. Appl. Chem. USSR (Engl. Transl.); vol. 62; nb. 7.2; (1989); p. 1567 - 1572,1451 - 1455 View in Reaxys

87 % Chromat.

With potassium tert-butylate, oxygen, Polyethylenglycol 6000 in benzene, Time= 2h, T= 25 °C , p= 3878.6Torr Neumann, Ronny; Sasson, Yoel; Journal of Organic Chemistry; vol. 49; nb. 7; (1984); p. 1282 - 1284 View in Reaxys With sodium perchlorate, tripropylammonium fluorochromate (VI) in water, acetic acid, T= 30 °C , ΔH(standard), ΔG(standard), ΔS(standard); var temp., Kinetics, Thermodynamic data Bhattacharjee, Urbashi (Baruah); Bhattacharjee, Apurba Krishna; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 29; nb. 12; (1990); p. 1187 - 1191 View in Reaxys With perchloric acid, quinolinium dichromate(VI) in N,N-dimethyl-formamide, T= 40 °C , further temperatures (308-328 K); activation parameters (ΔH(excit.), ΔS(excit.). ΔG(excit.)), Mechanism, Thermodynamic data, Rate constant Sarma, G. C.; Mahanti, M. K.; Bulletin de la Societe Chimique de France; nb. 4; (1991); p. 449 - 453 View in Reaxys With potassium superoxide, oxygen in dimethyl sulfoxide, T= 25 °C , Mechanism, Rate constant Lee-Ruff, Edward; Timms, Neil; Canadian Journal of Chemistry; vol. 58; nb. 20; (1980); p. 2138 - 2141 View in Reaxys With n-butyllithium, oxygen, multistep reaction, other substrates, other oxidizing reagents, Product distribution, Mechanism Harvey, Ronald G.; Abu-shqara, Elias; Yang, ChengXi; Journal of Organic Chemistry; vol. 57; nb. 23; (1992); p. 6313 - 6317 View in Reaxys With lithium tert-butoxide in pyridine, Time= 1.33333h, T= 0 °C , -30 - -10 deg C, E(excit.), Rate constant, Mechanism Sokolov, N. A.; Pereshein, V. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 52; nb. 2; (1982); p. 393 - 397,344 - 347 View in Reaxys With oxygen, wall-catalyzed reaction in the CI source, effect of percentage O2 in N2 on oxidation yield, Mechanism Stemmler, Elizabeth A.; Buchanan, Michelle V.; Organic Mass Spectrometry; vol. 24; (1989); p. 94 - 104 View in Reaxys With potassium hydroxide, 18-crown-6 ether, oxygen in benzene, Time= 3h, p= 760Torr , var. temp, hydroxides, solvents, concentration, Rate constant Yamashita, Junzo; Ishikawa, Shinji; Hashimoto, Harukichi; Bulletin of the Chemical Society of Japan; vol. 53; nb. 3; (1980); p. 736 - 739 View in Reaxys T= 350 - 500 °C , Leiten im Gemisch mit Luft oder mit Luft und Wasserdampf ueber vanadinhaltige Katalysatoren Patent; Selden Co.; US1892768; (1928) View in Reaxys With selenium(IV) oxide, T= 200 - 210 °C Postowsky; Lugowkin; Chemische Berichte; vol. 68; (1935); p. 852,855 View in Reaxys

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With selenium(IV) oxide, water, T= 230 - 240 °C Badger; Journal of the Chemical Society; (1941); p. 535,537 View in Reaxys With potassium permanganate, alkaline aqueous solution Randall; Benger; Groocock; Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences; vol. 165; (1938); p. 439; Chem. Zentralbl.; vol. 110; nb. I; (1939); p. 911 View in Reaxys Bone et al.; Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences; vol. 148; (1935); p. 492,497 View in Reaxys With sodium dichromate, acetic acid Ray; Albertson; Journal of the American Chemical Society; vol. 70; (1948); p. 1954 View in Reaxys Huntress; Hershberg; Cliff; Journal of the American Chemical Society; vol. 53; (1931); p. 2720,2724 View in Reaxys Anantakrishnan; Pasupati; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 13; (1941); p. 211,216 View in Reaxys With sodium dichromate, acetic acid Graebe; Rateanu; Justus Liebigs Annalen der Chemie; vol. 279; (1894); p. 258 View in Reaxys With sodium dichromate, sulfuric acid, acetic acid Fanto; Monatshefte fuer Chemie; vol. 19; (1898); p. 584 View in Reaxys With chromium(III) oxide, sulfuric acid, acetic acid Ferrer; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 20; p. 461; Chem. Zentralbl.; vol. 94; nb. III; (1923); p. 1161 View in Reaxys With pyridine, sodium hydroxide, air Kinoshita et al.; Nippon Kagaku Zasshi; vol. 80; (1959); p. 206; ; (1961); p. 4449 View in Reaxys With pyridine, air, N-benzyl-trimethylammonium hydroxide Sprinzak; Journal of the American Chemical Society; vol. 80; (1958); p. 5449,5452 View in Reaxys With tetrachloromethane, chromyl chloride Wheeler; Canadian Journal of Chemistry; vol. 36; (1958); p. 949 View in Reaxys With chloroform, T= 0 °C , Einleiten von Ozon und Sauerstoff Cavill; Robertson; Whalley; Journal of the Chemical Society; (1949); p. 1567,1570 View in Reaxys With air Hock et al.; Chemische Berichte; vol. 83; (1950); p. 227,234 View in Reaxys With sodium dichromate, acetic acid, man giesst in Wasser

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Schmidt,J.; Wagner; Chemische Berichte; vol. 43; (1910); p. 1800; Justus Liebigs Annalen der Chemie; vol. 387; (1912); p. 159 View in Reaxys 67 % Turnov.

With oxygen, cobalt(II), bromide in chlorobenzene, Time= 6h, T= 120 °C Koroleva, N. V.; Kuznetsova, L. N.; Bagdadi, A.; Perederii, M. A.; J. Appl. Chem. USSR (Engl. Transl.); vol. 62; nb. 7.2; (1989); p. 1567 - 1572,1451 - 1455 View in Reaxys With oxygen, Pseudomonas putida UV4 Boyd, Derek R.; Sharma, Narain D.; Stevenson, Paul J.; Chima, Jagdeep; Gray, David J.; Dalton, Howard; Tetrahedron Letters; vol. 32; nb. 31; (1991); p. 3887 - 3890 View in Reaxys

8.2 % Chro- With 3,3-dimethyldioxirane in acetone, Time= 72h, Ambient temperature mat. Kuck, Dietmar; Schuster, Andreas; Zeitschrift fuer Naturforschung, B: Chemical Sciences; vol. 46; nb. 9; (1991); p. 1223 1226 View in Reaxys 0.342 g

With tert.-butylhydroperoxide, dipyridinium dichromate in benzene, Time= 14h, T= 25 °C Chidambaram, Nallaperumal; Chandrasekaran, Srinivasan; Journal of Organic Chemistry; vol. 52; nb. 22; (1987); p. 5048 5051 View in Reaxys With potassium hydroxide, potassium permanganate, tetra(n-butyl)ammonium hydrogensulfate in dichloromethane, water, Ambient temperature, Yield given Gannon, Sharon M.; Krause, Josef G.; Synthesis; nb. 10; (1987); p. 915 - 917 View in Reaxys Hinzmann, B.; Thurner, J.-U.; Stoesser, R.; Knoll, B.; Tomaschewski, G.; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 25; nb. 8; (1985); p. 301 View in Reaxys With oxygen, CI source Stemmler, Elizabeth A.; Buchanan, Michelle V.; Organic Mass Spectrometry; vol. 24; (1989); p. 94 - 104 View in Reaxys With n-butyllithium, oxygen, 1) THF, cyclohexane, -78 deg C, 1 h, 2a) -78 deg C, 1 h, b) r.t., 2 h, Yield given. Multistep reaction Harvey, Ronald G.; Abu-shqara, Elias; Yang, ChengXi; Journal of Organic Chemistry; vol. 57; nb. 23; (1992); p. 6313 - 6317 View in Reaxys

3.37 mmol

With 2-Picolinic acid, tert.-butylhydroperoxide in pyridine, acetic acid, Time= 20h Barton, Derek H. R.; Wang, Tie-Lin; Tetrahedron; vol. 50; nb. 4; (1994); p. 1011 - 1032 View in Reaxys

2.77 mmol

With tert.-butylhydroperoxide, 2-Picolinic acid, ferric nitrate in pyridine, water, acetic acid, tert-butyl alcohol, Time= 16h, Ambient temperature Barton, Derek H. R.; Chavasiri, Warinthorn; Tetrahedron; vol. 50; nb. 1; (1994); p. 19 - 30 View in Reaxys

80 % Chromat.

With oxygen, N -hydroxyphthalimide in benzonitrile, Time= 20h, T= 100 °C , p= 760Torr Ishii, Yasutaka; Nakayama, Kouichi; Takeno, Mitsuhiro; Sakaguchi, Satoshi; Iwahama, Takahiro; Nishiyama, Yutaka; Journal of Organic Chemistry; vol. 60; nb. 13; (1995); p. 3934 - 3935 View in Reaxys in acetonitrile, T= 55 °C Wang; Mayer; Journal of the American Chemical Society; vol. 119; nb. 6; (1997); p. 1470 - 1471

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View in Reaxys 34 % Chromat.

With 1H-imidazole, sodium periodate, MnTPPS-Ad in water, acetonitrile, Time= 8h, Ambient temperature Tangestaninejad; Moghadam; Synthetic Communications; vol. 28; nb. 3; (1998); p. 427 - 432 View in Reaxys With potassium permanganate, water, aluminum oxide, Time= 0.166667h Nuechter, Matthias; Ondruschka, Bernd; Jungnickel, Anja; Mueller, Ute; Journal of Physical Organic Chemistry; vol. 13; nb. 10; (2000); p. 579 - 586 View in Reaxys

70 % Spectr.

With potassium permanganate, copper(II) sulfate in dichloromethane, Time= 3h, T= 20 °C , ultrasonic irradiation, Oxidation Meciarova, Maria; Toma, Stefan; Heribanova, Andrea; Tetrahedron; vol. 56; nb. 43; (2000); p. 8561 - 8566 View in Reaxys

99 % Turnov.

With aluminum oxide, potassium permanganate, water, Time= 0.166667h, microwave irradiation, Product distribution, Further Variations: Catalysts, Reagents, Temperatures, without microwave irradiation; without H2O Nuechter, Matthias; Ondruschka, Bernd; Trotzki, Ronald; Advanced Synthesis and Catalysis; vol. 342; nb. 7; (2000); p. 720 - 724 View in Reaxys With H5<PMo10V2O40> (HPA-2), oxygen in acetonitrile, Time= 18h, T= 60 °C , p= 760Torr Khenkin, Alexander M.; Neumann, Ronny; Angewandte Chemie, International Edition; vol. 39; nb. 22; (2000); p. 4088 4090; Angewandte Chemie; vol. 112; (2000); p. 4254 - 4256 View in Reaxys

90 % Chromat.

With 1H-imidazole, sodium periodate, Mn(III)meso-(p-sulfonato-Ph)4-β-Br8-porphyrin*Amberl.IRA400 in water, acetonitrile, Time= 10h, T= 20 °C Tangestaninejad; Habibi; Mirkhani; Moghadam; Molecules; vol. 7; nb. 2; (2002); p. 264 - 270 View in Reaxys With tert.-butylhydroperoxide, 2-phenyl-1,2-benzoisoselenazol-3(2H)-one in tert-butyl alcohol, Time= 24h, Heating Giurg; Wojtowicz; Mlochowski; Polish Journal of Chemistry; vol. 76; nb. 4; (2002); p. 537 - 542 View in Reaxys

60 % Chromat.

With 1H-imidazole, sodium periodate, Mn(III) tetrakis(4-aminophenyl)porphyrin on polystyrene in water, acetonitrile, Time= 8h, T= 20 °C Tangestaninejad; Habibi; Mirkhani; Moghadam; Synthetic Communications; vol. 32; nb. 21; (2002); p. 3331 - 3337 View in Reaxys

75 % Chromat.

With 1H-imidazole, sodium periodate, Mn(III)TPPS-PSMP in acetonitrile, Time= 8h, T= 20 °C Tangestaninejad; Habib; Mirkhani; Moghadam; Journal of Chemical Research - Part S; nb. 10; (2001); p. 444 - 445 View in Reaxys With sodium bromate, Rexyn 101 H resin, Time= 8h, T= 116 °C Shaabani, Ahmad; Lee, Donald G.; Synthetic Communications; vol. 33; nb. 8; (2003); p. 1255 - 1260 View in Reaxys

93 % Chromat.

With dihydrogen peroxide, dinuclear cobalt(III)-copper(II) macrocyclic in water, acetonitrile, Time= 5h, T= 80 °C Golchoubian; Ghaziani, A. Nemati Kharat; Polish Journal of Chemistry; vol. 79; nb. 5; (2005); p. 825 - 830 View in Reaxys With dihydroxo manganese(IV) in water, acetone, T= 24 °C , pH= 8.4, Kinetics, Further Variations: pH-values Yin, Guochuan; Danby, Andrew M.; Kitko, David; Carter, John D.; Scheper, William M.; Busch, Daryle H.; Journal of the American Chemical Society; vol. 129; nb. 6; (2007); p. 1512 - 1513 View in Reaxys

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With NH-pyrazole, [Ru(VI)(F28-tpp)O2] in 1,2-dichloro-ethane, T= 24.85 °C , Kinetics, Further Variations: Reagents Che, Chi-Ming; Zhang, Jun-Long; Zhang, Rui; Huang, Jie-Sheng; Lai, Tat-Shing; Tsui, Wai-Man; Zhou, Xiang-Ge; Zhou, Zhong-Yuan; Zhu, Nianyong; Chang, Chi Kwong; Chemistry - A European Journal; vol. 11; nb. 23; (2005); p. 7040 7053 View in Reaxys With tetrabutylammonium phosphomolybdate, racemic methyl phenyl sulfoxide in various solvent(s), Time= 15h, T= 170 °C Khenkin, Alexander M.; Neumann, Ronny; Journal of the American Chemical Society; vol. 124; nb. 16; (2002); p. 4198 4199 View in Reaxys Reaction Steps: 2 1: 21 percent / 6M tert.butyl hydroperoxide / 0.2M 2,4-dimethylpentane-2,4-diol cyclic chromate / CH2Cl2; CCl4 / 8 h / 0 °C 2: 6M tert.butyl hydroperoxide / 0.2M 2,4-dimethylpentane-2,4-diol cyclic chromate / CH2Cl2; CCl4 / 8 h / 0 °C With tert.-butylhydroperoxide, 2,4-dimethylpentane-2,4-diol cyclic chromate in tetrachloromethane, dichloromethane Muzart, Jacques; Tetrahedron Letters; vol. 27; nb. 27; (1986); p. 3139 - 3142 View in Reaxys Reaction Steps: 2 1: oxygen / Erwaermen im UV-Licht 2: aqueous FeSO4 With oxygen, iron(II) sulfate Hock et al.; Chemische Berichte; vol. 83; (1950); p. 227,234 View in Reaxys Reaction Steps: 3 1: alcoholic-etheric potassium ethylate solution / Behandeln mit Natriumchlorid; anschliessend mit verd. Schwefelsaeure 2: alcohol 3: beim Erhitzen ueber den Schmelzpunkt With ethanol, potassium ethoxide Wislicenus; Waldmueller; Chemische Berichte; vol. 41; (1908); p. 3338 View in Reaxys 1 :1) Catalytic oxidation of benzylic positions via redox activation of bismuth; General oxidation procedure 1; To a suspension of bismuth oxide (37 mg, 10 molpercent), in distilled water (1.5 rnL), stirred at room temperature in a microwave vessel, was added sodium borohydride (18 mg, 60 molpercent). An exothermic reaction was observed, with formation of a finely divided, black precipitate of bismuth metal. Washing with water (2x2 mL), removal of the supernatant afforded activated Bi(O). After addition of pyridine (0.8 mL), acetic acid (0.08 mL), picolinic acid (20 mg, 20 molpercent), substrate (0.8 mmol) and -butyl hydroperoxide (70percent in water, 0.66 mL, 6 eq), the vessel was sealed, the mixture sonicated for 30 min, and gradually heated to the indicated temperature, then stirred for the indicated period of time. After completion of the heating period, cooling to EPO <DP n="11"/>room temperature, diluting with diethyl ether, filtration over Celite.(R)., afforded a crude sample, which was analyzed by GCMS. With pyridine, tert.-butylhydroperoxide, acetic acid, 2-Picolinic acid, bismuth in water, Time= 19.5h, T= 100 °C , Conversion of starting material Patent; IC INNOVATIONS LIMITED; WO2006/72798; (2006); (A1) English View in Reaxys 95.8 mol %

8 : EXAMPLE 8 EXAMPLE 8 The reaction was carried out by following the procedure of Example 5 while changing the gas concentration to 460 g/Nm3. The conversion of fluorene was found to be 93.1 mol percent, the selectivity of fluorenone to be 95.8 mol percent, and the yield of fluorenone to be 89.2 mol percent. The highest temperature of the catalyst bed was 480° C. Patent; Nippon Shokubai Co., Ltd.; US5902907; (1999); (A) English View in Reaxys

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T.6 : Synthesis of fluorenone [Test Example 6] Synthesis of fluorenone Fluorene (524 mg, 3.15 mmol), 524 mg of an oxidation catalyst and 5 ml of xylene as solvent were charged into a 100 ml threeneck flask, and were stirred at 120°C for 24 hours under an oxygen atmosphere. The reaction mixture was filtered through Celite, and then the Celite and the oxidation catalyst were washed with ethyl acetate. After the filtrate was condensed with a rotary evaporator, the product was separated by silica gel column chromatography. A resulting yellow crystalline solid was weighed and the yield thereof was defined as a reaction yield. in 5,5-dimethyl-1,3-cyclohexadiene Patent; Japan Envirochemicals, Ltd.; EP1806177; (2007); (A1) English View in Reaxys 81 % Chromat.

With 1H-imidazole, sodium periodate, Mn(III)-salen supported on Amberlite IRA-200 in water, acetonitrile, Time= 0.916667h, T= 20 °C Mirkhani, Valiollah; Moghadam, Majid; Tangestaninejad, Shahram; Bahramian, Bahram; Monatshefte fur Chemie; vol. 138; nb. 12; (2007); p. 1303 - 1308 View in Reaxys With 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin-iron(IV)-oxo, T= 15 °C , Kinetics Jeong, Yu Jin; Kang, Yaeun; Han, Ah-Rim; Lee, Yong-Min; Kotani, Hiroaki; Fukuzumi, Shunichi; Nam, Wonwoo; Angewandte Chemie - International Edition; vol. 47; nb. 38; (2008); p. 7321 - 7324 View in Reaxys 1.1 :We initially studied oxidation of methylene substituted benzylic aromatics to ketones (Scheme 1, R.not equal.H). When a mixture of fluorene with 10 equivalents 70percent aqueous TBHP was irradiated with microwave in a sealed vessel for 10 minutes (250 W, 170° C.), an almost quantitative yield of fluorenone was isolated (Table 1). As a control experiment, when we simply refluxed the same reaction mixture by conventional oil bath heating for 8 hours, only a trace amount of fluorenone could be detected by TLC. Oxidation of another substrate with a doubly activated benzylic position, diphenylmethane, also afforded benzophenone in high yield. For the mono-activated methylene units, ethylbenzene to acetophenone and tetrahydronaphthalene to alpha-tetralone, the oxidations under this green protocol also went smoothly. The results are summarized in Table 1 With tert.-butylhydroperoxide in water, Time= 8h, Heating / reflux, Product distribution / selectivity Patent; Hong Kong Baptist University; US7488843; (2009); (B1) English View in Reaxys With CrMCM-41, oxygen in carbon dioxide, Time= 14h, T= 100 °C , p= 67506.8Torr , Supercritical conditions Dapurkar, Sudhir E.; Kawanami, Hajime; Yokoyama, Toshirou; Ikushima, Yutaka; New Journal of Chemistry; vol. 33; nb. 3; (2009); p. 538 - 544 View in Reaxys

73 %Chromat.

With tert.-butylhydroperoxide, iron(III) 1,3,5-benzenetricarboxylate in acetonitrile, Time= 88h, T= 70 °C Dhakshinamoorthy, Amarajothi; Alvaro, Mercedes; Garcia, Hermenegildo; Journal of Catalysis; vol. 267; nb. 1; (2009); p. 1-4 View in Reaxys With ruthenium trichloride, iodobenzene, potassium hydrogen persulfate in water, acetonitrile, Time= 20h, T= 20 °C Yusubov, Mekhman S.; Zagulyaeva, Aleksandra A.; Zhdankin, Viktor V.; Chemistry - A European Journal; vol. 15; nb. 42; (2009); p. 11091 - 11094 View in Reaxys

38 %Chromat.

With [Mn(V)(tf4tmap)(O)2](3+) in acetonitrile, T= 15 °C , pH= 10.5, aq. borate buffer, Kinetics Arunkumar, Chellaiah; Lee, Yong-Min; Lee, Jung Yoon; Fukuzumi, Shunichi; Nam, Wonwoo; Chemistry - A European Journal; vol. 15; nb. 43; (2009); p. 11482 - 11489 View in Reaxys With oxygen, tetra-(n-butyl)ammonium iodide, sodium hydroxide in water, T= 50 °C

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Saikia, Gunin; Iyer, Parameswar K.; Journal of Organic Chemistry; vol. 75; nb. 8; (2010); p. 2714 - 2717 View in Reaxys 38 %Chromat.

With ruthenium trichloride, iodobenzene, potassium peroxymonosulfate in water, acetonitrile, Time= 20h, T= 20 °C , Inert atmosphere Yusubov, Mekhman S.; Nemykin, Victor N.; Zhdankin, Viktor V.; Tetrahedron; vol. 66; nb. 31; (2010); p. 5745 - 5752 View in Reaxys With phosphomolybdic acid, potassium tert-butylate, oxygen in dimethyl sulfoxide, Time= 20h, Heating Liu, Chang-Hui; Li, Fei; Tang, Rui-Ren; Bulletin of the Korean Chemical Society; vol. 31; nb. 6; (2010); p. 1723 - 1725 View in Reaxys

95 %Spectr. With Br(1-)*C20H27BrN5O2Pd(1+), oxygen, sodium acetate, Time= 72h, T= 20 - 120 °C Urgoitia, Garazi; Sanmartin, Raul; Herrero, Maria Teresa; Dominguez, Esther; Green Chemistry; vol. 13; nb. 8; (2011); p. 2161 - 2166 View in Reaxys 16 %Chromat.

With tetra-O-acetyl riboflavin, water in acetonitrile, Time= 1.66667h, Irradiation Lechner, Robert; Kuemmel, Susanne; Koenig, Burkhard; Photochemical and Photobiological Sciences; vol. 9; nb. 10; (2010); p. 1367 - 1377 View in Reaxys With tert.-butylhydroperoxide, copper(II) choride dihydrate, 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt, tetrabutylammomium bromide, sodium carbonate in water, Time= 17h, T= 20 °C Rahman, Ateeq; Zahrani, S. M. Al; Ajjou, Abdel Aziz Nait; Chinese Chemical Letters; vol. 22; nb. 6; (2011); p. 691 - 693 View in Reaxys

50 %Chromat.

With [(hydrotris(3,5-diphenylpyrazolyl)borate)Fe(II)(benzilate)], oxygen in benzene, T= 20 °C Paria, Sayantan; Que Jr., Lawrence; Paine, Tapan Kanti; Angewandte Chemie - International Edition; vol. 50; nb. 47; (2011); p. 11129 - 11132 View in Reaxys

100 %Chro- With tert.-butylhydroperoxide, C76H72N16O12*2Fe(2+)*HO(1-)*H2O*O4S(2-), acetic acid in water, acetonitrile, Time= 24h, T= 23 mat. °C Djernes, Katherine E.; Moshe, Orly; Mettry, Magi; Richards, Donald D.; Hooley, Richard J.; Organic Letters; vol. 14; nb. 3; (2012); p. 788 - 791 View in Reaxys With tert.-butylhydroperoxide, Time= 5h, T= 90 °C , Neat (no solvent) Anand, Narani; Reddy, Kannapu Hari Prasad; Prasad, Ganjala Venkata Siva; Rama Rao, Kamaraju Seetha; Burri, David Raju; Catalysis Communications; vol. 23; (2012); p. 5 - 9 View in Reaxys General experimental procedure: General procedure: To a clean dry 10 mL round-bottom flask containing 1.0 mmol alkyl aromatics, 3.0 mmol equivalent of 70percent TBHP was added. This was followed by the addition 10 mol percent of amorphous manganese dioxide catalyst and 2 mL acetonitrile solvent. The mixture was stirred at 80 °C. The progress of the reaction was monitored by GC. After completion of the reaction, the reaction mixture was cooled to room temperature and the catalyst was separated by filtration method. The products were identified by GC-MS. The ANMnO2 catalyst was prepared by the reported method. In a typical method with; 1.7 mL of triethanolamine was diluted to 100 mL distilled water to which 200 mL 0.03 mol l-1 KMnO4 was added dropwise under vigorous stirring at room temperature. The brown precipitate obtained was filtered, washed with distilled water until the pH of washed water is 7.0; the precipitate was dried at 100 °C for 24 h and then calcined at 300 °C for 2 h. Catalyst MnO2 is prepared by simple calcination of Mn(NO3)2*4H2O for 13 h at 145 °C by reported procedure. With tert.-butylhydroperoxide, manganese(IV) oxide in acetonitrile, Time= 10h, T= 80 °C Burange, Anand S.; Kale, Sandip R.; Jayaram, Radha V.; Tetrahedron Letters; vol. 53; nb. 24; (2012); p. 2989 - 2992

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View in Reaxys With tert.-butylhydroperoxide, acetic acid in water, acetonitrile, Time= 18h, T= 65 °C Yang, Xiu-Li; Xie, Ming-Hua; Zou, Chao; He, Yabing; Chen, Banglin; O'Keeffe, Michael; Wu, Chuan-De; Journal of the American Chemical Society; vol. 134; nb. 25; (2012); p. 10638 - 10645 View in Reaxys With N -hydroxyphthalimide in acetonitrile, Time= 12h, T= 50 °C , p= 760.051Torr Zhao, Qiang; Zhang, Pengfei; Antonietti, Markus; Yuan, Jiayin; Journal of the American Chemical Society; vol. 134; nb. 29; (2012); p. 11852 - 11855 View in Reaxys With tert.-butylhydroperoxide in acetonitrile, T= 60 °C , p= 760.051Torr Chen, Chih-Wei; Ko, An-Nan; Journal of the Chinese Chemical Society (Taipei, Taiwan); vol. 59; nb. 9; (2012); p. 1104 1110,7 View in Reaxys Reaction Steps: 2 1: potassium acetate / diethyl ether / 4 h / 20 °C / Inert atmosphere 2: iodosylbenzene; tetrafluoroboric acid diethyl ether / dichloromethane / 24 h / 20 °C / Inert atmosphere With tetrafluoroboric acid diethyl ether, iodosylbenzene, potassium acetate in diethyl ether, dichloromethane Havare, Nizam; Plattner, Dietmar A.; Organic Letters; vol. 14; nb. 19; (2012); p. 5078 - 5081,4 View in Reaxys 61.6 %Chromat.

With tert.-butylhydroperoxide, 4C48H36N6*4Cu(1+)*4NO3 (1-) in water, acetonitrile, Time= 24h, T= 60 °C He, Qi-Ting; Li, Xiang-Ping; Chen, Lian-Fen; Zhang, Li; Wang, Wei; Su, Cheng-Yong; ACS Catalysis; vol. 3; nb. 1; (2013); p. 1 - 9 View in Reaxys

98 %Chromat.

With tert.-butylhydroperoxide, Rh2(OAc)4(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), potassium carbonate in dichloromethane, Time= 48h, T= 25 °C , Reagent/catalyst, Temperature, Time, Concentration Coelho, Jaime A. S.; Trindade, Alexandre F.; Wanke, Riccardo; Rocha, Bruno G. M.; Veiros, Luis F.; Gois, Pedro M. P.; Pombeiro, Armando J. L.; Afonso, Carlos A. M.; European Journal of Organic Chemistry; nb. 8; (2013); p. 1471 - 1478 View in Reaxys 2.3 Catalytic activity tests#10; General procedure: Typically, 50 mg of catalyst, 1 mmol of substrate, and 3 mmol of 70percent t-BuOOH (Sigma Aldrich) were taken in a RB flask and constantly stirred at 363 K for 5 h under solvent-free conditions. Unless otherwise specified the above reaction conditions are applicable. The catalyst was separated by filtration and analyzed by GC (GC-17A model, M/s. Shimadzu Instruments, Japan) consisting of FID and OV-1 capillary column (0.53 mm × 30 m) using toluene as external standard. The product identification was made by GC–MS (QP5050 model, M/s. Shimadzu Instruments, Japan) consisting of DB-5 column (0.32 mm dia. and 25 m long, M/s. J & W Scientific, USA). The separated catalyst was washed with methanol and dried under vacuum prior to reuse.#10; With tert.-butylhydroperoxide in neat (no solvent), Time= 5h, T= 89.84 °C Neeli, Chinna Krishna Prasad; Narani, Anand; Marella, Ravi Kumar; Rama Rao, Kamaraju Seetha; Burri, David Raju; Catalysis Communications; vol. 39; (2013); p. 5 - 9 View in Reaxys With chromium (VI) oxide in acetic anhydride Kim, Hee Un; Kim, Ji-Hoon; Suh, Hongsuk; Kwak, Jeonghun; Kim, Dongwook; Grimsdale, Andrew C.; Yoon, Sung Cheol; Hwang, Do-Hoon; Chemical Communications; vol. 49; nb. 93; (2013); p. 10950 - 10952 View in Reaxys With N -hydroxyphthalimide, oxygen in acetonitrile, Time= 5h, T= 130 °C , p= 9000.9Torr Liu, Guiyin; Tang, Ruiren; Wang, Zhen; Catalysis Letters; vol. 144; nb. 4; (2014); p. 717 - 722 View in Reaxys

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With tert.-butylhydroperoxide in water, T= 80 °C , Green chemistry Singh, Ajay K.; Basavaraju; Sharma, Siddharth; Jang, Seungwook; Park, Chan Pil; Kim, Dong-Pyo; Green Chemistry; vol. 16; nb. 6; (2014); p. 3024 - 3030 View in Reaxys 96 %Chromat.

With copper(II) tetrasulfophthalocyanine supported on three-dimensional nitrogendopedgraphene-based frameworks, air in water, Time= 12h, T= 20 °C , p= 760.051Torr Mahyari, Mojtaba; Laeini, Mohammad Sadegh; Shaabani, Ahmad; Chemical Communications; vol. 50; nb. 58; (2014); p. 7855 - 7857 View in Reaxys With tert.-butylhydroperoxide in benzonitrile, Time= 14h, T= 80 °C , Schlenk technique Chen, Yifa; Huang, Xianqiang; Feng, Xiao; Li, Jikun; Huang, Yingyu; Zhao, Jingshu; Guo, Yuexin; Dong, Xinmei; Han, Ruodan; Qi, Pengfei; Han, Yuzhen; Li, Haiwei; Hu, Changwen; Wang, Bo; Chemical Communications; vol. 50; nb. 61; (2014); p. 8374 - 8377 View in Reaxys With tert.-butylhydroperoxide, acetic acid in water, acetonitrile, Time= 6h, T= 60 °C Song, Guo-Qiang; Lu, Ying-Xun; Zhang, Qi; Wang, Fan; Ma, Xiao-Kun; Huang, Xian-Feng; Zhang, Zhi-Hui; RSC Advances; vol. 4; nb. 57; (2014); p. 30221 - 30224 View in Reaxys General procedure for oxidation of alkyl aromatics General procedure: Alkyl aromatics (5 mmol) in 10 mL acetonitrile and the polymer supported cobalt catalyst (60 mg) were in turn introduced into a50 mL round bottomed flask equipped with a condenser and a thermometer in an oil bath. The reaction was carried under oxygen atmosphere (1 atm) with 1 mmol H2O2. Then, the catalyst wasremoved by filtration, and the solvent was evaporated in vacuum. The product was filtered, washed thoroughly with water and extracted with ether, then dried with anhydrous Na2SO4 and analyzed by GC and GC-MS. With dihydrogen peroxide, oxygen in water, acetonitrile, Time= 7h, T= 70 °C , p= 760.051Torr , Green chemistry, Catalytic behavior Islam, Sk Manirul; Ghosh, Kajari; Molla, Rostam Ali; Roy, Anupam Singha; Salam, Noor; Iqubal, Md Asif; Journal of Organometallic Chemistry; vol. 774; (2015); p. 61 - 69 View in Reaxys

> 99 %Chromat.

With pyridine, tert.-butylhydroperoxide, nickel cobalt oxide in water, acetonitrile, Time= 24h, T= 90 °C Wang, Jingjing; Fan, Shuang; Luan, Yi; Tang, Jia; Jin, Zhaokui; Yang, Mu; Lu, Yunfeng; RSC Advances; vol. 5; nb. 4; (2015); p. 2405 - 2410 View in Reaxys With tert.-butylhydroperoxide, [Pd(2,2'-dipyridine amine)(acetylacetone)]2[V6O13(OMe)6] in chlorobenzene, Time= 16h, T= 65 °C Li, Ji-Kun; Huang, Xian-Qiang; Yang, Song; Ma, Hong-Wei; Chi, Ying-Nan; Hu, Chang-Wen; Inorganic Chemistry; vol. 54; nb. 4; (2015); p. 1454 - 1461 View in Reaxys With [(hydrotris(3-phenyl-5-methylpyrazolyl)borate)FeII(phenylpyruvate)], oxygen in acetonitrile, Time= 1.5h, T= 20 °C Sheet, Debobrata; Bhattacharya, Shrabanti; Paine, Tapan Kanti; Chemical Communications; vol. 51; nb. 36; (2015); p. 7681 - 7684 View in Reaxys

89 %Chromat.

With MnO2 nanostructure coated on cellulose, air in o-xylene, Time= 13h, T= 120 °C , p= 760.051Torr , Green chemistry Shaabani, Ahmad; Hezarkhani, Zeinab; Shaabani, Shabnam; RSC Advances; vol. 4; nb. 110; (2014); p. 64419 - 64428 View in Reaxys 2 : General procedure for the oxidation of benzylic methylenes

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General procedure: A mixture of 4,4-diuorodiphenylmethane (178.4 L,1.0 mmol) and P4VPDVB2.5–40percent-Fe(III) catalyst (2.0 molpercent), pyridine (8.0 L,0.1 mmol), TBHP (5.0–6.0 M in decane, 545.0 L, 3.0 mmol) and 1.0 mL acetonitrile was dissolved in a 25 mL single-necked flask fitted with a reflux condenser. The mixture was heated at 80°C for 24 h under air atmosphere in an oil bath. Then the mixture was cooled to 25°C and centrifuged to get a catalyst and supernatant solution. Then the solution was analyzed by Agilent 7890/5975C-GC/MSD using nitrobenzene as an internal standard. A calibration curve for each reactant and product has been built, which is included in the ESI†. The in situ 1H NMR monitoring of the reaction conversion and yield was performed in the DMSO-d6 solvent, the crude sample of entry 11 in Table 3 was filtered for direct 1H NMR analysis (see ESI†). Furthermore, the products of entries 1 and 7 in Table 2 were isolated through column chromatography and the isolated yields were provided. With pyridine, tert.-butylhydroperoxide in acetonitrile, Time= 24h, T= 80 °C Fan, Shuang; Luan, Yi; Wang, Jingjing; Gao, Hongyi; Zhang, Xiaowei; Wang, Ge; Journal of Molecular Catalysis A: Chemical; vol. 404-405; (2015); p. 186 - 192 View in Reaxys With tert.-butylhydroperoxide, [Cu3(4β-(4-carboxyphenyl)-4,2β:6β,4-terpyridine)6(H2O)6]·4H2O in chlorobenzene, Time= 24h, T= 80 °C , Schlenk technique, Reagent/catalyst Xi, Yaru; Wei, Wei; Xu, Yanqing; Huang, Xianqiang; Zhang, Fanzhou; Hu, Changwen; Crystal Growth and Design; vol. 15; nb. 6; (2015); p. 2695 - 2702 View in Reaxys 65 %Chromat.

With N -hydroxyphthalimide, oxygen in acetonitrile, Time= 9h, T= 70 °C Jafarpour, Maasoumeh; Rezaeifard, Abdolreza; Yasinzadeh, Vahid; Kargar, Hossein; RSC Advances; vol. 5; nb. 48; (2015); p. 38460 - 38469 View in Reaxys

99 %Chromat.

With oxygen in o-xylene, Time= 9h, Reflux Shaabani, Ahmad; Hezarkhani, Zeinab; Badali, Elham; RSC Advances; vol. 5; nb. 76; (2015); p. 61759 - 61767 View in Reaxys

95 %Chromat.

2.3 General procedure for oxidation of alkyl arenes General procedure: Alkyl arenes (1 mmol) were added in a two round bottomed glass flask containing a mixture of cobalt-chitosan (5 mol percent, 0.023 g) and NHPI (1 mol percent, 0.016 g)in 10 mL 1,2-dichlorobenzene. The flask was fitted with a reflux condenser and mixture was heated at 80°C with continuous bubbling of air with flow rate of 15 mL min−1. After completion of the reaction (progress of the reaction followed by TLC), catalyst was separated by an external magnet and the reaction mixture was analyzed by gas chromatography. With N -hydroxyphthalimide in 1,2-dichloro-benzene, Time= 4h, T= 80 °C , Catalytic behavior Shaabani, Ahmad; Boroujeni, Mahmoud Borjian; Sangachin, Mona Hamidzad; Journal of Chemical Sciences; vol. 127; nb. 11; (2015); p. 1927 - 1935 View in Reaxys With oxygen, benzoic acid, Time= 9h, T= 135 °C Kuwahara, Yasutaka; Yoshimura, Yukihiro; Yamashita, Hiromi; Catalysis Science and Technology; vol. 6; nb. 2; (2016); p. 442 - 448 View in Reaxys With tert.-butylhydroperoxide in ethylbenzene, water, Time= 12h, T= 80 °C Yang, Shuliang; Peng, Li; Huang, Peipei; Wang, Xiaoshi; Sun, Yongbin; Cao, Changyan; Song, Weiguo; Angewandte Chemie - International Edition; vol. 55; nb. 12; (2016); p. 4016 - 4020; Angew. Chem.; vol. 128; nb. 12; (2016); p. 4084 - 4088,5 View in Reaxys

95 %Chromat.

With porous chitosan–manganese dioxide nanohybrid, air in para-xylene, Time= 4h, T= 100 °C , Green chemistry Shaabani, Ahmad; Borjian Boroujeni, Mahmoud; Laeini, Mohmmad Sadegh; Applied Organometallic Chemistry; vol. 30; nb. 3; (2016); p. 154 - 159 View in Reaxys

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> 99 %Chromat.

With tert.-butylhydroperoxide in water, Time= 6h, T= 80 °C , Green chemistry Ma, Zhishuang; Zhang, Hongye; Yang, Zhenzhen; Ji, Guipeng; Yu, Bo; Liu, Xinwei; Liu, Zhimin; Green Chemistry; vol. 18; nb. 7; (2016); p. 1976 - 1982 View in Reaxys

90 %Chromat.

With sodium bromate, 1,1,3,3-tetramethylguanidine sulfonic acid hydrochloride in water, acetonitrile, Time= 24h, T= 20 °C Shaabani, Ahmad; Laeini, Mohammad Sadegh; Shaabani, Shabnam; Seyyedhamzeh, Mozhdeh; New Journal of Chemistry; vol. 40; nb. 3; (2016); p. 2079 - 2082 View in Reaxys With N -hydroxyphthalimide, oxygen in acetonitrile, Time= 15h, T= 60 °C , p= 7500.75Torr , Catalytic behavior Majumdar, Biju; Bhattacharya, Tamalika; Sarma, Tridib K.; ChemCatChem; vol. 8; nb. 10; (2016); p. 1825 - 1835 View in Reaxys

85 %Chromat.

With potassium hydroxide in para-xylene, Time= 8h, T= 100 °C , Green chemistry Shaabani, Ahmad; Shaabani, Shabnam; Afaridoun, Hadi; RSC Advances; vol. 6; nb. 54; (2016); p. 48396 - 48404 View in Reaxys With tert.-butylhydroperoxide, cetyltrimethylammonim bromide, L-proline, copper dichloride in water, Time= 24h, T= 80 °C , Reagent/catalyst Yu, Peng; Zhou, Yin; Yang, Yingwei; Tang, Ruiren; RSC Advances; vol. 6; nb. 70; (2016); p. 65403 - 65411 View in Reaxys 2.8 Typical procedure for the oxidation of organic substrates catalyzed by Fe3O4APTMS[Co3(PDMT)Cl6] nanoparticles General procedure: To a mixture of catalyst (25mg) in CH3CN (5ml) in a round bottom flask equipped with a magnetic stirrer bar and water-cooled condenser was added the desired organic substrates (10mmol) (in the cases of trans-stilbene (0.5mmol), (styrene and ethylbenzene, 1mmol), (fluorene, diphenylmethane and adamantane, 0.1mmol) and TBHP (1.37ml, 70percent in H2O, 10mmol). The suspension was then heated at reflux for 12h. After the separation of the catalyst by an external magnetic field, the solution was subjected to GC and GC–MS. With tert.-butylhydroperoxide in water, acetonitrile, Time= 5h, Reflux, Catalytic behavior, Time Sharbatdaran, Masoomeh; Farzaneh, Faezeh; Larijani, Majid Mojtahedzadeh; Salimi, Alireza; Ghiasi, Mina; Ghandi, Mehdi; Polyhedron; vol. 115; (2016); p. 264 - 275 View in Reaxys

90 %Chromat.

With potassium carbonate in para-xylene, Time= 8h, T= 100 °C , Green chemistry Shaabani, Ahmad; Afaridoun, Hadi; Shaabani, Shabnam; Applied Organometallic Chemistry; vol. 30; nb. 9; (2016); p. 772 - 776 View in Reaxys With tert.-butylhydroperoxide in acetonitrile, Time= 6h, T= 80 °C Huang, Shen; Zhao, Yukai; Tang, Ruiren; RSC Advances; vol. 6; nb. 93; (2016); p. 90887 - 90896 View in Reaxys

85 %Chromat.

With N -hydroxyphthalimide in para-xylene, Time= 8h, T= 100 °C , Green chemistry Shaabani, Ahmad; Afaridoun, Hadi; Shaabani, Shabnam; Keramati Nejad, Mina; RSC Advances; vol. 6; nb. 99; (2016); p. 97367 - 97375 View in Reaxys With tert.-butylhydroperoxide, [Co(2-hydroxy-1-naphthaldehyde)2(DMF)2] in acetonitrile, Time= 6h, T= 80 °C , Catalytic behavior, Reagent/catalyst Asgharpour, Zeinab; Farzaneh, Faezeh; Abbasi, Alireza; RSC Advances; vol. 6; nb. 98; (2016); p. 95729 - 95739 View in Reaxys

93 %Chromat.

With strontium manganate, oxygen in octane, Time= 12h, T= 79.84 °C

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Kawasaki, Shuma; Kamata, Keigo; Hara, Michikazu; ChemCatChem; vol. 8; nb. 20; (2016); p. 3247 - 3253 View in Reaxys 154 mg

With tert.-butylhydroperoxide, triethylamine, 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride in water, acetonitrile, Time= 15h, T= 80 °C Alanthadka, Anitha; Devi, E. Sankari; Nagarajan, Subbiah; Sridharan, Vellaisamy; Suvitha, Ambigapathy; Maheswari, C. Uma; European Journal of Organic Chemistry; vol. 2016; nb. 28; (2016); p. 4872 - 4880 View in Reaxys With cobalt(II) tetrasulfophthalocyanine supported on wool, air in water, Time= 10h, Reflux, Reagent/catalyst, Solvent, Temperature Shaabani, Ahmad; Hezarkhani, Zeinab; Journal of Porphyrins and Phthalocyanines; vol. 20; nb. 6; (2016); p. 677 - 688 View in Reaxys With tert.-butylhydroperoxide in water, Time= 12h, T= 80 °C , Sealed tube Zhu, Ya-Nan; Cao, Chang-Yan; Jiang, Wen-Jie; Yang, Shu-Liang; Hu, Jin-Song; Song, Wei-Guo; Wan, Li-Jun; Journal of Materials Chemistry A; vol. 4; nb. 47; (2016); p. 18470 - 18477 View in Reaxys With acetato-N,N’-bis(2,6-dimethylphenyl)-2,6-pyridinedicarboxamido-nickel(III) in acetone, T= 25 °C , Kinetics Pirovano, Paolo; Farquhar, Erik R.; Swart, Marcel; McDonald, Aidan R.; Journal of the American Chemical Society; vol. 138; nb. 43; (2016); p. 14362 - 14370 View in Reaxys 2 :With a heating and mixing device, thermometer,Reflux condenser tube 250 ml four-necked flask was charged with commercially available fluorene 33. 2 g, xylene 85 g, ethanol 8. 5 g, solid tetramethylammonium hydroxide 4 g, and then heated to 50 ° C or more industrial fluorene dissolved, 400ml / min of air for oxidation, the reaction temperature of 50 ~ 60 ° C for 4 hours to stop the reaction, the father liquid filtration, vacuum distillation, recycling xylene solvent recycling, the concentrate was yellow fluorenone crystals, with a small amount of water The residue was 92.2percent, the gas chromatographic purity was 99.5percent and the melting point was 83-84 ° C. With tetramethyl ammoniumhydroxide in 5,5-dimethyl-1,3-cyclohexadiene, ethanol, Time= 4h, T= 50 - 60 °C , Solvent Patent; Zhongwei Lianjiao Technology National Engineering Research Center Co.,Ltd; Wang, Guang Xing; Wang, Shou Kai; Li, Qiang; CAI, Hong Tao; Jin, Dan; Wang, LiLi; (6 pag.); CN104230690; (2016); (B) Chinese View in Reaxys With tert.-butylhydroperoxide, N -hydroxyphthalimide, Cu3Al(OH)2(7+)*3.5CO3 (2-) in acetonitrile, Time= 24h, T= 90 °C Zhou, Yin; Tang, Rui-Ren; Song, Dan; Chemical Papers; vol. 70; nb. 7; (2016); p. 888 - 897 View in Reaxys With tert.-butylhydroperoxide, {[Co(C6H3COOH(OC6H4COO)2)(4,4’-bipyridine)(H2O)2]·DMF}n in chlorobenzene, Time= 24h, T= 80 °C Ma, Ranran; Chen, Zhiwei; Cao, Fan; Wang, Suna; Huang, Xianqiang; Li, Yunwu; Lu, Jing; Li, Dacheng; Dou, Jianmin; Dalton Transactions; vol. 46; nb. 7; (2017); p. 2137 - 2145 View in Reaxys

32.42 g

1 :The mass fraction of 95.44percent of industrial fluorene 42.00g, 18-crown -63.20g, xylene 45ml in turn added to250ml fournecked flask, adjust the temperature of the water bath to maintain 50 , with β-methyl naphthalene absorption of exhaust gas entrainment of the solvent,Start the mechanical stirring, adjust the stirring rate of 300 rpm, stirring 10min, adding 6.70g KOH and 10.0ml water. To be mixed evenly, began to pass 300mlx2 / min clean wet air, record the reaction time,The reaction was followed by thin layer chromatography. After 10 hours of reaction, the spotted version of fluorene disappeared,Continue to react for 1h, sampling for gas chromatography analysis, chromatography and fluorene raw materials compared to the lack of fluorene peak,Only increase the peak of fluorenone. Cooling the reaction solution, fluorenone crystallization, filtering the mixture, the filtrate recovery to be recycled,Wash the crystal fluorenone with a small amount of water and place the naturally dried crystals in the air. Weighing 32.42g,The purity was 100percent by gas chromatography. β-methyl naphthalene absorber weight gain and the presence of water droplets. Stage 1: With 18-crown-6 ether in 5,5-dimethyl-1,3-cyclohexadiene, 1-Methylnaphthalene, Time= 0.166667h, T= 50 °C Stage 2: With potassium hydroxide in water, Time= 11h, Temperature, Concentration, Reagent/catalyst, Solvent

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Patent; Baoshun Technology Co., Ltd; Dalian University of Technology; Gao, ZhanXian; Yu, LiMei; Xie, He; Li, HuiFeng; He, YongChao; Shi, ZhengMao; (11 pag.); CN105801389; (2016); (A) Chinese View in Reaxys 99 %Chromat.

With N -hydroxyphthalimide, Zn3Co2W19, 4Cu(2+)*C52H22N4O16 (10-)*Cu(2+)*30H2O*4C3H7NO*7C2H8N(1+)*7NO3 (1-), tetrabutylammomium bromide, oxygen in acetonitrile, Time= 24h, T= 50 °C , p= 760.051Torr Zhao, Min; Wu, Chuan-De; ChemCatChem; vol. 9; nb. 7; (2017); p. 1192 - 1196 View in Reaxys With tert.-butylhydroperoxide, [Cu(II)(1,2-diaminoethane)2]4[Cu(II)(1,2-diaminoethane)2(H2O)2]2[PNb12O40V(V)V(IV)O2] (OH)2·11H2O in water, benzonitrile, Time= 24h, T= 60 °C , Schlenk technique, Catalytic behavior Hu, Jufang; Dong, Jing; Huang, Xianqiang; Chi, Yingnan; Lin, Zhengguo; Li, Jikun; Yang, Song; Ma, Hongwei; Hu, Changwen; Dalton Transactions; vol. 46; nb. 25; (2017); p. 8245 - 8251 View in Reaxys With tert.-butylhydroperoxide in water, Time= 7h, T= 20 °C Liu, Wengang; Zhang, Leilei; Liu, Xin; Liu, Xiaoyan; Yang, Xiaofeng; Miao, Shu; Wang, Wentao; Wang, Aiqin; Zhang, Tao; Journal of the American Chemical Society; vol. 139; nb. 31; (2017); p. 10790 - 10798 View in Reaxys With N -hydroxyphthalimide, oxygen in acetonitrile, Time= 9h, T= 60 °C , p= 760.051Torr , Reagent/catalyst Fan, Shuang; Dong, Wenjun; Huang, Xiubing; Gao, Hongyi; Wang, Jingjing; Jin, Zhaokui; Tang, Jia; Wang, Ge; ACS Catalysis; vol. 7; nb. 1; (2017); p. 243 - 249 View in Reaxys

85 %Chromat.

With sodium periodate, [(Npy^CNHC)RuII(2,2'-bipyridine)(CH3CN)2](PF6)(CF3SO3) in water, acetonitrile, Time= 4h, T= 70 °C Gupta, Suraj K.; Choudhury, Joyanta; ChemCatChem; vol. 9; nb. 11; (2017); p. 1979 - 1984 View in Reaxys With tert.-butylhydroperoxide in water, Time= 7h, T= 20 °C Li, Xingwei; Chinese Journal of Catalysis; vol. 39; nb. 1; (2018); p. 1 - 3 View in Reaxys

38 g

5 : Example 4 General procedure: Take 40g 100percent fluorene 250mL three-necked flask was added 45mL xylene, 1.00g tetrabutylammonium bromide,6gNaOH and 9mL of water, heated at 40 water bath to control the mechanical stirring rate 300r / min, into the clean air 200 × 2mL /min, using 1-methylnaphthalene to absorb the xylene in the reaction off-gas. The organic phase is a suspension at the beginning of the reaction. Used in the reaction processThe conversion of fluorene was monitored by TLC. After the reaction for 7h, the fluorene spots disappeared and the reaction was continued for 0.5h to stop the reaction. The reaction solutionTransferred to a 500mL beaker while hot, immediately precipitated crystal, until no more crystals precipitated after filtration, the filtrate was collected 45mL, of whichThe aqueous layer 13mL, 32mL reservoir, take the oil layer chromatography containing fluorene 2.31percent. The crystals were dried to give a light yellow solid 33.0g, chromatographic pointsPurity of fluorenone was 100percent, 1-methylnaphthalene contained 1percent xylene. With tetrabutylammomium bromide, sodium hydroxide in 5,5-dimethyl-1,3-cyclohexadiene, water, Time= 7.5h, T= 40 °C , Reagent/catalyst Patent; Baoshun Technology Co., Ltd.; Dalian University of Technology; Yu Limei; Gao Zhanxian; Yan Jun; Hou Lin; Li Huifeng; He Yongchao; Shi Zhengmao; (8 pag.); CN103804162; (2017); (B) Chinese View in Reaxys 3.2. Oxidation of alkyl arenes; General procedure General procedure: In a typical reaction, an alkyl arene (1.0 mmol), MnO2silk(0.09 g, 10 molpercent of MnO2), and o-xylene (5.0 mL) were added to atwo-necked flask. The mixture was stirred under reflux conditionsand air blowing. The thin layer chromatography (TLC) method was used to investigate the progress of the reaction. Upon completion,analysis of the crude product has been done by GC method. With Manganese dioxide nanostructures coated on natural silk in o-xylene, Time= 10h, Reflux

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Shaabani, Ahmad; Hezarkhani, Zeinab; Badali, Elham; Polyhedron; vol. 107; (2016); p. 176 - 182 View in Reaxys 2.7 Catalytic activity test for selective benzylic oxidation of tetralin in water medium General procedure: In a typical experiment, 50mg of Cu(II)/β-Fe2O3SBA-15 catalyst was dispersed in 2mL of water in 10mL capacity round bottom flask fitted with a water condenser, which is open to air. Subsequently, 1mmol tetralin and 3mmol of TBHP (70percent in aqueous solution) were added and conducted the reaction at 90°C for 6h at constant stirring. After completion of the reaction, catalyst was removed from the product mixture by simple magnetic separation. Then, the product mixture is extracted with ethylacetate followed by drying over anhydrous MgSO4 to remove traces of water and the samples were analyzed by a gas chromatograph (GC-17A, M/s. Shimadzu Instruments, Japan) using an Equity-5 capillary column (0.53mm x 30m). The products were confirmed by GC–MS (QP-5050 model, M/s. Shimadzu Instruments, Japan) equipped with DB-5 capillary column (0.32mm dia. and 25m long, M/s. J & W Scientific, USA). With tert.-butylhydroperoxide in water, Time= 6h, T= 90 °C , Green chemistry, Catalytic behavior Neeli, Chinna Krishna Prasad; Kannapu, Hari Prasad Reddy; Kalevaru, Venkat Narayana; Kamaraju, Seetha Rama Rao; Burri, David Raju; Molecular Catalysis; vol. 453; (2018); p. 74 - 84 View in Reaxys OH

Rx-ID: 271436 View in Reaxys 2/827 Yield 100 %

Conditions & References With potassium carbonate, chlorobenzene in toluene, Time= 12h, T= 105 °C Patent; Symyx Technologies, Inc.; US6350916; (2002); (B1) English View in Reaxys

100 %

With potassium osmate(VI) dihydrate, potassium carbonate, potassium hexacyanoferrate(III) in water, acetonitrile, Time= 0.5h, T= 60 °C , chemoselective reaction Fernandes, Rodney A.; Bethi, Venkati; RSC Advances; vol. 4; nb. 76; (2014); p. 40561 - 40568 View in Reaxys

99 %

With chromium(VI) oxide, methyl-tridecylammonium chloride, sodium perborate in water, benzene, Time= 24h, T= 60 °C Muzart; N'Ait Ajjou; Synthetic Communications; vol. 21; nb. 4; (1991); p. 575 - 580 View in Reaxys

99 %

With sodium bromate, hydrogen bromide in tetrachloromethane, Time= 2h, T= 40 °C Kajigaeshi, Shoji; Nakagawa, Takashi; Nagasaki, Noritaka; Yamasaki, Hiromochi; Fujisaki, Shizuo; Bulletin of the Chemical Society of Japan; vol. 59; nb. 3; (1986); p. 747 - 750 View in Reaxys

99 %

With chromium(VI) oxide, methyl-tridecylammonium chloride, sodium perborate in water, benzene, Time= 24h, T= 60 °C , sodium berborate-acetic acid; other alcohols and unsaturated compounds Muzart; N'Ait Ajjou; Synthetic Communications; vol. 21; nb. 4; (1991); p. 575 - 580 View in Reaxys

99 %

With bismuth(III) nitrate, Montmorillonite, Time= 0.0666667h Samajdar; Becker; Banik; Synthetic Communications; vol. 31; nb. 17; (2001); p. 2691 - 2695

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View in Reaxys 99 %

With dinitrogen monoxide, dioxo(tetramesitylporphyrinato)ruthenium(VI) in 1,2-dichloro-ethane, Time= 7.5h, T= 120 °C , p= 7600Torr Hashimoto, Kentaro; Kitaichi, Yasunori; Tanaka, Hirotaka; Ikeno, Taketo; Yamada, Tohru; Chemistry Letters; nb. 9; (2001); p. 922 - 923 View in Reaxys

99 %

With iodosylbenzene, N,N-ethylenebis(3,5-dichlorosalicylideneiminato)Cr(III)Cl in dichloromethane, Time= 1h, T= 20 °C Kim, Sung Soo; Kim, Dong Won; Synlett; nb. 10; (2003); p. 1391 - 1394 View in Reaxys

99 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, ammonium cerium(IV) nitrate, oxygen in acetonitrile, Time= 2h, T= 82 °C Kim, Sung Soo; Jung, Hyun Chul; Synthesis; nb. 14; (2003); p. 2135 - 2137 View in Reaxys

99 %

With iodosylbenzene, N,N'-bis(3,5-dichlorosalicylidene)-1,2-ethylenediamino-MnCl in acetonitrile, Time= 1.5h, T= 20 °C Kim, Sung Soo; Borisova, Galina; Synthetic Communications; vol. 33; nb. 22; (2003); p. 3961 - 3967 View in Reaxys

99 %

With dinitrogen monoxide, dioxo(tetramesitylporphyrinato)ruthenium(VI) in 1,2-dichloro-ethane, Time= 7.5h, T= 120 °C , p= 7500.6Torr Tanaka, Hirotaka; Hashimoto, Kentaro; Suzuki, Kyosuke; Kitaichi, Yasunori; Sato, Mitsuo; Ikeno, Taketo; Yamada, Tohru; Bulletin of the Chemical Society of Japan; vol. 77; nb. 10; (2004); p. 1905 - 1914 View in Reaxys

99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, N-methyl-N-[3-(4'-diacetoxyiodo)phenoxy-1-propyl]pyrrolidinium 4methylbenzenesulfonate in dichloromethane, Time= 12h, T= 20 °C Suzuki, Yusuke; Iinuma, Masataka; Moriyama, Katsuhiko; Togo, Hideo; Synlett; vol. 23; nb. 8; (2012); p. 1250 - 1256 View in Reaxys

99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, calcium methylate in acetonitrile, T= 0 - 20 °C Reddy, Sabbasani Rajasekhara; Stella, Selvaraj; Chadha, Anju; Synthetic Communications; vol. 42; nb. 23; (2012); p. 3493 - 3503 View in Reaxys

99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, N-methyl-N-[3-(4-diacetoxyiodo)phenoxy-1-propyl]pyrrolidinium 4methylbenzenesulfonate in dichloromethane, Time= 12h, T= 20 °C , Inert atmosphere Iinuma, Masataka; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 69; nb. 14; (2013); p. 2961 - 2970 View in Reaxys

99 %

With sodium hypochlorite in 1,2-dimethoxyethane, water, Time= 4h, T= 20 °C Fukuda, Naohiro; Kajiwara, Takeshi; Katou, Tomoaki; Majima, Keisuke; Ikemoto, Tomomi; Synlett; vol. 24; nb. 11; (2013); p. 1438 - 1442; Art.No: ST-2013-U0273-L View in Reaxys

99 %

A typical procedure for the catalytic oxidation of alcohols General procedure: The catalyst solutionwas prepared by dissolving complex 3(36.1 mg,0.05mmol) in methanol (5.0 mL).Under a nitrogen atmosphere, the mixture of an alcohol substrate (2.0 mmol) and1.0 mL of the catalyst solution (0.01mmol) in 20mL acetone was stirred at 56 Cfor 10 minutes. tBuOK(22.4mg, 0.2 mmol)was then added to initiate the reaction.At the stated time, 0.1 mL of the reaction mixture was sampled and immediately diluted with 0.5 mL acetone pre-cooled-to-0 C for GC or NMR analysis. After the reaction was complete, the reaction mixture was condensed under reduced pressure and subject to purification by flash silica gel column chromatography to afford the corresponding ketone product, which was identified by comparison with the authentic sample through NMR and GC analysis. With [(2-(benzoimidazol-2-yl)-6-(3,5-dimethylpyrazol-1-yl)pyridine)RuCl2(PPh3)], potassium tert-butylate, acetone in methanol, Time= 0.0833333h, T= 56 °C , p= 750.075Torr , Inert atmosphere, Oppenauer Oxidation, Catalytic behavior

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Wang, Qingfu; Du, Wangming; Liu, Tingting; Chai, Huining; Yu, Zhengkun; Tetrahedron Letters; vol. 55; nb. 9; (2014); p. 1585 - 1588 View in Reaxys 99 %

General Procedure for the oxidation of alcohols employing nitroxyl radical / imide / NaOCl without K2CO3. General procedure: To a mixture of the alcohol (7.679 mmol), and cyanuric acid (0.1 equiv, 0.384 mmol) in 40 mL of ethyl acetate was added TEMPO or AZADO (3 molpercent, 0.230 mmol) at 0-10°C. 12percent NaOCl (1.2 equiv, 9.215 mmol, Wako Pure Chemical Industries, Ltd.) was added dropwise with keeping >pH 7 at 0-10°C. The mixture was then stirred for 1 hour. The reaction mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to afford the corresponding product. With sodium hypochlorite solution, 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl, isocyanuric acid in ethyl acetate, Time= 1h, T= 0 - 10 °C , pH= &#62; 7 Fukuda, Naohiro; Izumi, Minoru; Ikemoto, Tomomi; Tetrahedron Letters; vol. 56; nb. 25; (2015); p. 3905 - 3908 View in Reaxys

98 %

With benzyltriphenylphosphonium dichromate in acetonitrile, Time= 0.25h, Heating, Oxidation Hajipour, Abdol Reza; Mohammadpoor-Baltork, Iraj; Niknam, Kurosh; Organic Preparations and Procedures International; vol. 31; nb. 3; (1999); p. 335 - 341 View in Reaxys

98 %

With NaClO adsorbed on montmorillonite K10 in dichloromethane, Time= 0.583333h, T= 20 °C , Oxidation Hashemi, Mohammed M.; Beni, Yousef A.; Journal of Chemical Research - Part S; nb. 5; (2000); p. 224 - 225 View in Reaxys

98 %

With periodic acid, pyridinium chlorochromate in acetonitrile, Time= 2h, T= 0 - 20 °C Hunsen, Mo; Tetrahedron Letters; vol. 46; nb. 10; (2005); p. 1651 - 1653 View in Reaxys

98 %

With [bis(acetoxy)iodo]benzene, iodine in acetonitrile, Time= 0.5h, T= 20 °C Karade; Tiwari; Huple; Synlett; nb. 13; (2005); p. 2039 - 2042; Art.No: D10605ST View in Reaxys

98 %

With 1-[4-(diacetoxyiodo)benzyl]-3-methylimidazolium BF4, 1-ethyl-3-methylimidazolium tetrafluoroborate in acetonitrile, Time= 12h, T= 30 °C Qian, Weixing; Jin, Erlei; Bao, Weiliang; Zhang, Yongmin; Angewandte Chemie - International Edition; vol. 44; nb. 6; (2005); p. 952 - 955 View in Reaxys

98 %

With [RuVI(5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato(2-))O2], tetra(n-butyl)ammonium hydroxide, oxygen in bromotrichloromethane, water, Time= 24h, T= 90 °C , p= 760.051Torr Korotchenko, Vasily N.; Severin, Kay; Gagne, Michel R.; Organic and Biomolecular Chemistry; vol. 6; nb. 11; (2008); p. 1961 - 1965 View in Reaxys

98 %

With tetrabutylammonium acetate, palladium diacetate, 8-hydroxyquinoline-2-sulfonic acid in toluene, Time= 6h, T= 100 °C , p= 22502.3Torr Dornan, Laura M.; Clendenning, Grainne M. A.; Pitak, Mateusz B.; Coles, Simon J.; Muldoon, Mark J.; Catalysis Science and Technology; vol. 4; nb. 8; (2014); p. 2526 - 2534 View in Reaxys

98 %

General procedure for oxidation of secondary alcohol General procedure: Charged 0.5 mmol of 1,3-diphenylprop-2-yn-1-ol 15a (104 mg, 0.5 mmol), 0.5 mL of [bmim]Br and TBHP (0.5 mL, 3.6 mmol) were taken in a round bottom flask and heated to 55 °C until completion of the reaction. The reaction course was monitored by TLC. After completion of the reaction, the crude mixture was extracted with ethyl acetate (3 * 4 mL). The organic layer was concentrated under reduced pressure and purified by column chromatography on silica gel to afford the desired product, 1,3-diphenylprop-2-yn-1-one 15b as yellow oil;

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With tert.-butylhydroperoxide, 1-n-butyl-3-methylimidazolim bromide, Time= 12h, T= 55 °C Naidu, Shivaji; Reddy, Sabbasani Rajasekhara; Journal of Molecular Liquids; vol. 222; (2016); p. 441 - 445 View in Reaxys 98 %

With strontium manganate, oxygen in toluene, Time= 5h, T= 79.84 °C Kawasaki, Shuma; Kamata, Keigo; Hara, Michikazu; ChemCatChem; vol. 8; nb. 20; (2016); p. 3247 - 3253 View in Reaxys

98 %

General Procedure for the Oxidative Reaction General procedure: A solution of diphenylmethanol (1 mmol), NBS (1.3equiv.), KOAc (1.5 equiv.) H2O (1.5 mL), and CH2Cl2 (0.5mL) was magnetically stirred in 25 mL flask at room temperaturefor 10 h. The reaction mixture was added into water(10 mL), and extracted with EtOAc (3 × 10 mL). The combinedEtOAc extracts were dried over anhydrous MgSO4,filtrated, and then the solvent was removed under reducedpressure. The residue was purified by the flash columnchromatography on silica gel with PE or PE/EtOAc as theeluent to obtain the desired products. The oxidation productswere identified by GC-MS and 1H NMR. With N-Bromosuccinimide, potassium acetate in dichloromethane, water, Time= 10h, T= 20 °C , Green chemistry Wu, Jianglong; Liu, Yan; Liu, Ping; Gu, Chengzhi; Letters in Organic Chemistry; vol. 14; nb. 4; (2017); p. 254 - 260 View in Reaxys

97 %

With 4-(N-t-butylchlorosulfinimidoyl)polystyrene, N-ethyl-N,N-diisopropylamine in dichloromethane, Time= 0.5h, T= -78 °C , Product distribution, Further Variations: Reagents, Temperatures Matsuo, Jun-ichi; Kawana, Asahi; Yamanaka, Hiroyuki; Kamiyama, Hiroaki; Bulletin of the Chemical Society of Japan; vol. 76; nb. 7; (2003); p. 1433 - 1440 View in Reaxys

97 %

With oxygen, potassium carbonate, palladium diacetate in N,N-dimethyl acetamide, Time= 5h, T= 100 °C , p= 760.051Torr Zhou, Jin; Li, Xiaoyan; Sun, Hongjian; Canadian Journal of Chemistry; vol. 86; nb. 8; (2008); p. 782 - 790 View in Reaxys

97 %

General Procedure for NaBr-Catalyzed Oxidation General procedure: Under nitrogen atmosphere, to a solution of substrate alcohol (0.5 mmol) in aceticacid (1.0 mL) was added a stock-solution of aqueous NaBr solution (1.94 M, 25 μL)and 30percent aqueous H2O2 (50 μL, 0.5 mmol). After stirring the mixture for one hour at60 °C, additional 30percent aqueous H2O2 (50 μL, 0.5 mmol) was added, and stirring wascontinued for another one hour. After cooling, the mixture was poured into a saturatedaqueous NaHCO3 solution (ca. 30 mL) with the aid of CH2Cl2, and resulting mixturewas extracted with CH2Cl2. The combined organic layers were dried over anhydrousMgSO4, filtered and concentrated in vacuo. The residue was chromatographed onsilica gel (flash column or preparative TLC) to afford the corresponding ketone. With dihydrogen peroxide, acetic acid, sodium bromide in water, Time= 2h, T= 60 °C , Inert atmosphere Komagawa, Hiromi; Maejima, Yukako; Nagano, Takashi; Synlett; vol. 27; nb. 5; (2016); p. 789 - 793 View in Reaxys

97 %

With Iron(III) nitrate nonahydrate, oxygen, 2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,2-dichloro-ethane, Time= 3h, T= 60 °C , Schlenk technique, Green chemistry Hu, Yongke; Chen, Lei; Li, Bindong; Catalysis Communications; vol. 103; (2018); p. 42 - 46 View in Reaxys

96 %

With bis(quinuclidine)bromine(I) bromide, pyridinium trifluroacetate in dichloromethane, water, Time= 5h, Ambient temperature Blair, Larry K.; Hobbs, Steven; Bagnoli, Nicholas; Husband, Leslie; Badika, Ndofunsu; Journal of Organic Chemistry; vol. 57; nb. 5; (1992); p. 1600 - 1603 View in Reaxys

96 %

With silver tetrafluoroborate, bis(quinuclidine)bromine(I) tetrafluoroborate in dichloromethane, Time= 0.5h Blair, Larry K.; Parris, Kevin D.; Lee, On Fai Daniel; Jenkins, Karen F.; Feese, Robin Chaney; et al.; Journal of Organic Chemistry; vol. 51; nb. 26; (1986); p. 5454 - 5456

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View in Reaxys 96 %

With sodium carbonate, acetone, 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt, bis(1,5-cyclooctadiene)diiridium(I) dichloride in water, Time= 4h, T= 90 °C , Oppenauer-type oxidation Ajjou, Abdelaziz Nait; Tetrahedron Letters; vol. 42; nb. 1; (2001); p. 13 - 16 View in Reaxys

96 %

With N -hydroxyphthalimide, ammonium cerium(IV) nitrate, oxygen in acetonitrile, Time= 2.5h, Heating Kim, Sung Soo; Rajagopal, Gurusamy; Synthetic Communications; vol. 34; nb. 12; (2004); p. 2237 - 2243 View in Reaxys

96 %

With sodium carbonate, acetone, 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt, bis(1,5-cyclooctadiene)diiridium(I) dichloride in water, Time= 4h, T= 90 °C Ajjou, Abdelaziz Nait; Pinet, Jean-Louis; Canadian Journal of Chemistry; vol. 83; nb. 6-7; (2005); p. 702 - 710 View in Reaxys

96 %

With periodic acid, tripropylammonium fluorochromate (VI) in acetonitrile, Time= 2h, T= 0 °C Hunsen, Mo; Journal of Fluorine Chemistry; vol. 126; nb. 9-10; (2005); p. 1356 - 1360 View in Reaxys

96 %

With dimethyl sulfoxide, triethylamine in dichloromethane, Time= 8h, T= -40 - 20 °C Pandey, Sanjay K.; Bisai, Alakesh; Singh, Vinod K.; Synthetic Communications; vol. 37; nb. 23; (2007); p. 4099 - 4103 View in Reaxys

96 %

With Oxone, 3,3'-diiodo-2,2',6,6'-tetramethoxy-4,4'-biphenyldicarboxylic acid in nitromethane, water, Time= 5.8h, T= 30 - 35 °C Seth, Saona; Jhulki, Samik; Moorthy, Jarugu Narasimha; European Journal of Organic Chemistry; nb. 12; (2013); p. 2445 2452 View in Reaxys

95 %

With tert.-butylhydroperoxide, bis-(tributyltin oxide) dioxochromium(VI) in dichloromethane, Time= 5.5h, T= 40 °C Muzart, Jacques; Synthetic Communications; vol. 19; nb. 11-12; (1989); p. 2061 - 2068 View in Reaxys

95 %

With 1,2-dimethyl-3-[6-(methylsulfinyl)hexyl]-1H-imidazolium triflate, oxalyl dichloride, triethylamine in dichloromethane, acetonitrile, T= -78 - 20 °C , Swern oxidation He, Xun; Chan, Tak Hang; Tetrahedron; vol. 62; nb. 14; (2006); p. 3389 - 3394 View in Reaxys

95 %

General Procedure General procedure: A mixture of benzylic alcohol (1.0mmol), urea hydrogen peroxide (1.5 mmol) and calciumchloride (0.5 mmol) was stirred in PEGDME250 (2 mL) at 70oC for 4 h. After cooling the mixture to room temperature theproduct is extracted into diethyl ether (3 × 20 mL), washedwith water and dried over MgSO4. The combined etherextracts were concentrated under reduced pressure and thecrude product was purified by flash column chromatography(ethyl acetate/n-hexane = 1:3, v/v) to give the desired carbonylcompound. With urea hydrogen peroxide adduct, calcium chloride, Time= 4h, T= 70 °C Ha, Su Jeong; Jung, Eun-Young; Kim, Won Mi; Lee, Jong Chan; Bulletin of the Korean Chemical Society; vol. 35; nb. 2; (2014); p. 629 - 630 View in Reaxys

95 %

General procedure for the oxidation of aliphatic or aromatic secondary alcohols (4a-l) toketones (5a-l) General procedure: A mixture of secondary alcohol (4) (1.0 mmol), UHP (2.0-3.0 mmol), 10 molpercent (CF3SO3)3La and[bmim]BF4 (5 mmol) was placed in a 50 mL RB flask fitted with a calcium chloride guard tube.The reaction mixture was stirred magnetically in an oil-bath maintained at 70°C for anappropriate time as mentioned in Table 2. The progress of the reaction was monitored by TLCusing petroleum ether:ethyl acetate (70:30). After completion of the reaction, the reactionmixture was cooled to room temperature and washed with diethyl ether (3×10 mL). Thecombined ethereal layer was washed with water

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(2×10 mL) and dried over anhyd. Na2SO4. Theethereal extract was concentrated on a rotary evaporator to give corresponding ketone. With urea hydrogen peroxide adduct, lanthanum(lll) triflate, Time= 0.833333h, T= 70 °C , Ionic liquid, Green chemistry Saluja, Pooja; Magoo, Devanshi; Khurana, Jitender M.; Synthetic Communications; vol. 44; nb. 6; (2014); p. 800 - 806 View in Reaxys 95 %

Procedure General procedure: The starting alcohol (1 mmol), KOH (3.0mmol) and catalyst (10 molpercent Pd) were added to a Schlenkflask. In another Schlenk flask, the oxygen in the solvent(MeOH : H2O = 5:1, v/v, 6.0 mL) was removed by the freezepumpthaw and purging method. The aqueous solvent was transferred to the reaction flask of the starting alcohol by cannulation. Afterwards, chlorobenzene (3.0 mmol) was added using a syringe, and the reaction was kept under argon. Upon completion of the reaction based on TLC monitoring, the Pd/C was filtered off on celite and the solvent was removed by rotary evaporation. A brine solution was added to the residue and the product was extracted using methylene chloride. The organic layer was collected, dried with anhydrous magnesium sulfate, and concentrated byrotary evaporation. The mixture was purified via column chromatography using various hexane/EtOAc eluent systems. All products were known and characterized by comparing their 1H NMR spectra with those that have been published in the literature. With 10% palladium on activated carbon; Degussa type, chlorobenzene, potassium hydroxide in methanol, water, Time= 3h, T= 60 °C , Inert atmosphere, Temperature Lim, Minkyung; Oh, Seungchan; Rhee, Hakjune; Bulletin of the Korean Chemical Society; vol. 32; (2011); p. 3179 - 3182 View in Reaxys

95 %

With tert.-butylhydroperoxide, copper(II) acetate monohydrate in water, Time= 8h, T= 80 °C Wu, Jianglong; Liu, Yan; Ma, Xiaowei; Liu, Ping; Gu, Chengzhi; Dai, Bin; Chinese Journal of Chemistry; vol. 35; nb. 9; (2017); p. 1391 - 139 View in Reaxys

94 %

With oxygen, potassium carbonate in dimethyl sulfoxide, Time= 5h, T= 100 °C Rosevear, Judi; Wilshire, John F. K.; Australian Journal of Chemistry; vol. 44; nb. 8; (1991); p. 1097 - 1114 View in Reaxys

94 %

93 %

With sodium hypochlorite, tetrabutylammomium bromide in water, ethyl acetate, Time= 0.5h, Ambient temperature Mirafzal, Gholam A.; Lozeva, Albena M.; Tetrahedron Letters; vol. 39; nb. 40; (1998); p. 7263 - 7266 View in Reaxys

93 %

With oxygen, pyrographite in xylene, Time= 12h, T= 120 °C Sano, Yuki; Tanaka, Takanori; Hayashi, Masahiko; Chemistry Letters; vol. 36; nb. 12; (2007); p. 1414 - 1415 View in Reaxys

93 %

With sodium methylate, potassium iodide in methanol, T= 20 °C , Electrochemical reaction

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Okimoto, Mitsuhiro; Yoshida, Takashi; Hoshi, Masayuki; Chiba, Tomohito; Maeo, Kei; Synthetic Communications; vol. 41; nb. 21; (2011); p. 3134 - 3139 View in Reaxys 93 %

With N-Bromosuccinimide, 1-butyl-3-methylimidazolium Tetrafluoroborate, Time= 1h, T= 70 °C Khurana, Jitender M.; Chaudhary, Ankita; Kumar, Sanjay; Organic Preparations and Procedures International; vol. 45; nb. 3; (2013); p. 241 - 245 View in Reaxys

93 %

IBS-catalysed alcohol oxidation in CTAB micelle; general procedure General procedure: The alcohol (2 mmol) was added to a solution of IBS (0.02 mmol, 0.01 eq), oxone (2.2 mmol, 1.1 equiv.) and 3 wtpercent CTAB solution (5 mL). The mixture was stirred at room temperature. The reaction was monitored by TLC. After completion, the solution was extracted with CH2Cl2 (3 × 10 mL). The combined organic phase was then filtered through a pad of silica gel and evaporated under vacuum to afford the desired product. With 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide, Oxone, cetyltrimethylammonim bromide in water, Time= 2h, T= 20 °C , Green chemistry, chemoselective reaction Liu, Yangyang; Wang, Boliang; Journal of Chemical Research; vol. 38; nb. 7; (2014); p. 427 - 431 View in Reaxys

93 %

Typical procedure for the oxidation of 1-phenyl-ethanol General procedure: 1-Phenyl-ethanol (0.14 g, 1.00 mmol) was added to a two-necked flask equipped with a gas bubbling tube containing colloidal of CoPcCell (0.05 g) and KOH (0.25 mmol) in o-xylene (5 mL) at room temperature. The mixture was stirred at room temperature under O2 atmosphere provided with a balloon. The progress of the reaction was followed by thin layer chromatography (TLC). Upon completion, CoPcCell was separated by filtration and washed with acetone (5 mL). Acetophenone was isolated from the mixture using column chromatography with n-hexane in 90percent yield. With 6-((cobalt(II) 4,9,16,23-tetraaminephthalocyanin-4-yl))cellulose, oxygen, potassium hydroxide in o-xylene, Time= 4h, T= 20 °C , Green chemistry Shaabani, Ahmad; Keshipour, Sajjad; Hamidzad, Mona; Shaabani, Shabnam; Journal of Molecular Catalysis A: Chemical; vol. 395; (2014); p. 494 - 499 View in Reaxys

93 %

With phosphomolybdic acid, oxygen, tetrabutylammonium acetate, palladium diacetate in ethyl acetate, Time= 1h, T= 100 °C , p= 22502.3Torr Dornan, Laura M.; Muldoon, Mark J.; Catalysis Science and Technology; vol. 5; nb. 3; (2015); p. 1428 - 1432 View in Reaxys

92 %

With potassium carbonate, chlorobenzene, CyJohnPhos, bis(dibenzylideneacetone)-palladium(0) in toluene, Time= 12h, T= 105 °C Guram, Anil S.; Bei, Xiaohong; Turner, Howard W.; Organic Letters; vol. 5; nb. 14; (2003); p. 2485 - 2487 View in Reaxys

92 %

With dihydrogen peroxide in ethanol, water, Time= 10h, T= 75 °C , close atmosphere Kidwai, Mazaahir; Bhardwaj, Saurav; Applied Catalysis A: General; vol. 387; nb. 1-2; (2010); p. 1 - 4 View in Reaxys

92 %

General Procedure. General procedure: To a stirred solution of a benzylic alcohol (1.0 mmol) in 1 mL [bmim]BF4 was added 65percent nitric acid (0.5 mmol) and copper(II) bromide (0.5 mmol). The reaction mixture was stirred in the air at 60 °C for 4 h and the reaction monitored by TLC for the complete consumption of the benzylic alcohol. The solution was cooled to room temperature and the product is extracted into ethyl acetate (2 20 mL), washed with water and dried over MgSO4. After removal of the solvent under reduced pressure, the crude product was purified by flash chromatography (ethyl acetate/n-hexane = 1:5, v/v) to yield the desired carbonyl compound. With nitric acid, copper(ll) bromide, Time= 4h, T= 60 °C , Ionic liquid, Reagent/catalyst, Solvent

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Lim, Chae Mi; Ha, Su Jeong; Lee, Jong Chan; Bulletin of the Korean Chemical Society; vol. 33; nb. 12; (2012); p. 4258 4260 View in Reaxys 91 %

With potassium nitrososulfonate, adogen 464 in benzene, Time= 12h Morey, Jeronimo; Dzielenziak, Adam; Saa, Jose Manuel; Chemistry Letters; (1985); p. 263 - 264 View in Reaxys

91 %

With aluminium trichloride, 1-decyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate in acetonitrile, Time= 2h, Heating Hajipour; Bagheri; Ruoho; Russian Journal of Organic Chemistry; vol. 42; nb. 6; (2006); p. 844 - 848 View in Reaxys

91 %

With oxygen, 2.2percent V/C in various solvent(s), Time= 8h, T= 105 °C , p= 750.075Torr Guram, Anil; Hagemeyer, Alfred; Lugmair, Claus G.; Turner, Howard W.; Volpe Jr., Anthony F.; Weinberg, W. Henry; Yaccato, Karin; Advanced Synthesis and Catalysis; vol. 346; nb. 2-3; (2004); p. 215 - 230 View in Reaxys

91 %

With sodium tetrahydroborate, oxygen, potassium carbonate, 10 wt. % palladium on activated carbon in methanol, water, Time= 1h, T= 20 °C An, Gwangil; Lim, Minkyung; Chun, Kwon-Soo; Rhee, Hakjune; Synlett; nb. 1; (2007); p. 95 - 98 View in Reaxys

90 %

With chlorine-triphenylphosphine, dimethyl sulfoxide, triethylamine in dichloromethane, Time= 3.25h, T= -78 - 20 °C Bisai, Alakesh; Chandrasekhar; Singh, Vinod K.; Tetrahedron Letters; vol. 43; nb. 46; (2002); p. 8355 - 8357 View in Reaxys

90 %

With iodine, oxygen in acetonitrile, Time= 3h, T= 20 °C , Irradiation Farhadi, Saeid; Zabardasti, Abedien; Babazadeh, Zaynab; Tetrahedron Letters; vol. 47; nb. 50; (2006); p. 8953 - 8957 View in Reaxys

90 %

With sodium tetrahydroborate, 1% Pd/C, water, oxygen, potassium carbonate in ethanol, Time= 1h, T= 20 °C An, Gwangil; Ahn, Hyunseok; De Castro, Kathlia A.; Rhee, Hakjune; Synthesis; nb. 3; (2010); p. 477 - 485; Art.No: F19009SS View in Reaxys

90 %

With trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane in acetonitrile, Time= 0.333333h, T= 20 °C Azarifar, Davood; Najminejad, Zohreh; Khosravi, Kaveh; Journal of the Iranian Chemical Society; vol. 10; nb. 5; (2013); p. 979 - 983 View in Reaxys

90 %

With ammonium nitrate, hydrogenchloride, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in water, acetonitrile, Time= 3h, T= 60 °C , Green chemistry Prebil, Rok; Stavber, Gaj; Stavber, Stojan; European Journal of Organic Chemistry; vol. 2014; nb. 2; (2014); p. 395 - 402 View in Reaxys

90 %

General procedure for the Swern-type oxidation reaction General procedure: A solution of DMSO (3.0 mmol) in CH2Cl2 (2.0 mL) was added toa solution of 1 (1.2 mmol) in CH2Cl2 (5.0 mL) at 30 C, and themixture was stirred for 20 min at the same temperature. The alcoholsubstrate (1.0 mmol) was added, and the mixture was stirredfor another 20 min before the dropwise addition of Et3N(3.0 mmol). The mixture was subsequently left to warm to room temperature (20 min) and concentrated under reduced pressure.The product was isolated by flash column chromatography. Stage 1: With 7,7-dichlorocyclohepta-1,3,5-triene in dichloromethane, dimethyl sulfoxide, Time= 0.333333h, T= -30 °C , Inert atmosphere, Swern Oxidation Stage 2: With triethylamine in dichloromethane, dimethyl sulfoxide, Time= 0.333333h, T= -30 - 20 °C , Inert atmosphere, Swern Oxidation Nguyen, Thanh Vinh; Hall, Michael; Tetrahedron Letters; vol. 55; nb. 50; (2014); p. 6895 - 6898

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View in Reaxys 90 %

With manganese(II) triflate, 1-Adamantanecarboxylic acid, C32H38N4O2, dihydrogen peroxide in water, acetonitrile, Time= 2h, T= 0 °C , chemoselective reaction Dai, Wen; Lv, Ying; Wang, Lianyue; Shang, Sensen; Chen, Bo; Li, Guosong; Gao, Shuang; Chemical Communications; vol. 51; nb. 56; (2015); p. 11268 - 11271 View in Reaxys

90 %

With ammonium nitrate, hydrogenchloride, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in acetonitrile, T= 60 °C , Green chemistry, chemoselective reaction Prebil, Rok; Stavber, Gaj; Stavber, Stojan; European Journal of Organic Chemistry; vol. 2014; nb. 2; (2014); p. 395 - 402 View in Reaxys

89 %

With polymer-supported sulfinimidoyl chloride, N-ethyl-N,N-diisopropylamine in dichloromethane, Time= 0.5h, T= -78 °C Matsuo, Jun-ichi; Kawana, Asahi; Pudhom, Khanitha; Mukaiyama, Teruaki; Chemistry Letters; nb. 2; (2002); p. 250 - 251 View in Reaxys

89 %

With 10% rhodium on carbon, sodium carbonate in water, Time= 6h, T= 100 °C , Inert atmosphere Sawama, Yoshinari; Morita, Kosuke; Yamada, Tsuyoshi; Nagata, Saori; Yabe, Yuki; Monguchi, Yasunari; Sajiki, Hironao; Green Chemistry; vol. 16; nb. 7; (2014); p. 3439 - 3443 View in Reaxys

89 %

With potassium carbonate in water, dimethyl sulfoxide, Time= 0.833333h, T= 60 °C Dehghan, Mahsa; Motaharinejad, Atieh; Saadat, Mostafa; Ahdenov, Reza; Babazadeh, Mirzaagha; Hosseinzadeh-Khanmiri, Rahim; RSC Advances; vol. 5; nb. 112; (2015); p. 92335 - 92343 View in Reaxys

88 %

With aluminium trichloride, 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate in acetonitrile, Time= 4h, Heating Hajipour, Abdol R.; Bagheri, Hamid R.; Ruoho, Arnold E.; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 44; nb. 3; (2005); p. 577 - 580 View in Reaxys

88 %

With nitric acid, phosphorus pentoxide, silica gel, Time= 0.0666667h Hajipour, Abdol R.; Guo, Lian-Wang; Ruoho, Arnold E.; Molecular Crystals and Liquid Crystals; vol. 456; nb. 1; (2006); p. 85 - 93 View in Reaxys

88 %

With p-CO2H-IBX in N,N-dimethyl-formamide, Time= 4h, T= 55 - 60 °C Kommreddy, Amitha; Bowsher, Michael S.; Gunna, Meena R.; Botha, Kirankumar; Vinod, Thottumkara K.; Tetrahedron Letters; vol. 49; nb. 28; (2008); p. 4378 - 4382 View in Reaxys

88 %

With ammonium cerium (IV) nitrate, [Hmim]HSO4, Time= 0.583333h, T= 80 °C , neat (no solvent), chemoselective reaction Hajipour; Khazdooz; Ruoho; Journal of the Iranian Chemical Society; vol. 8; nb. 2; (2011); p. 382 - 387 View in Reaxys

88 %

General procedure for the oxidative reaction General procedure: Caution. tert-Butyl hydroperoxide is an exceptionally dangerous chemical that is highly reactive, flammable, and toxic. It is corrosive to skin and mucous membranes and causes respiratory distress when inhaled. A solution of secondary alcohol (1 mmol) and 70percent TBHP (6 or 10 equiv.) was stirred at 100 °C for 24 h. The reaction mixture was quenched with the saturated solution of sodium thiosulfate (5 mL) and extracted with dichloromethane (3 x 10 mL). The combined dichloromethane extracts were dried over anhydrous Na2SO4 and filtered, and then the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel with PE or PE/EtOAc as the eluent to obtain the desired products. With tert.-butylhydroperoxide in water, Time= 24h, T= 100 °C

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Wu, Jianglong; Liu, Yan; Ma, Xiaowei; Liu, Ping; Gu, Chengzhi; Dai, Bin; Synthetic Communications; vol. 46; nb. 21; (2016); p. 1747 - 1758 View in Reaxys 87 %

With tert.-butylhydroperoxide, chromium(VI) oxide in dichloromethane, Time= 7h, Ambient temperature Muzart, Jacques; Tetrahedron Letters; vol. 28; nb. 19; (1987); p. 2133 - 2134 View in Reaxys

87 %

With 3,6-bis(triphenylphosphonium)cyclohexene dichromate in acetonitrile, Time= 2h, Heating Badri, Rashid; Mostoufi, Azar; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 181; nb. 7; (2006); p. 1513 1519 View in Reaxys

86 %

With potassium hydroxide in o-xylene, Time= 0.5h, T= 20 °C Shaabani, Ahmad; Keshipour, Sajjad; Hamidzad, Mona; Seyyedhamzeh, Mozhdeh; Journal of Chemical Sciences; vol. 126; nb. 1; (2014); p. 111 - 115 View in Reaxys

86 %

2.4 Typical procedure for the oxidation of benzylalcohol General procedure: Benzylalcohol (0.1 g, 1.0 mmol) was added to a two-necked flask equipped with a gas bubbling tube containing colloidal of Co(II)-EDANC (0.2 g) and KOH (0.5 mmol) in o-xylene (5mL). Air was bubbled at arate of 5mL/min into the reaction mixture and the progress of the reaction was followed by thin-layer chromatography (TLC). Upon completion, Co(II)-EDANC was separated by filtration and washed with CH3CN (2 × 5mL). The filtrate solvent was evaporated under vacuum and benzylalcohol was purified with column chromatography with n-hexane:ethylacetate (2:1) in 95percent yield. With potassium hydroxide in o-xylene, Time= 0.5h, T= 20 °C Shaabani, Ahmad; Keshipour, Sajjad; Hamidzad, Mona; Seyyedhamzeh, Mozhdeh; Journal of Chemical Sciences; vol. 126; nb. 1; (2014); p. 111 - 115 View in Reaxys

86 %

General procedure for oxidation of alcohols: General procedure: Oven dried round bottom flask was charged with Eosin Y (5 mmol) alcohol (1 mmol) and 3 equiv. of TBHP (5.5 M in decane) in dry ACN. The resulting mixture was degassed for 15 mins, followed by back filling N2, and then irradiated under Blue LED light (12W, 455 nm) at room temperature (25 oC). After reaction completion monitored through TLC, the mixture was diluted with 15 ml of 10percent NaHCO3 solution, and extracted with EtOAc (3 × 20 ml). The combined organic extracts were washed with brine (20 ml), dried over Na2SO4, and concentrated on vacuo. Purification of the crude product on silica gel using EtOAc:Hexane as solvent system afforded the desired product. With tert.-butylhydroperoxide, eosin y in decane, acetonitrile, Time= 36h, T= 25 °C , Inert atmosphere, Irradiation, Molecular sieve, Green chemistry, chemoselective reaction Devari, Shekaraiah; Rizvi, Masood Ahmad; Shah, Bhahwal Ali; Tetrahedron Letters; vol. 57; nb. 30; (2016); p. 3294 - 3297 View in Reaxys

85 %

With ammonium nitrate in dichloromethane, Time= 0.666667h, T= 20 °C Zarei, Amin; Bulletin of the Korean Chemical Society; vol. 33; nb. 7; (2012); p. 2149 - 2155 View in Reaxys

84 %

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione, Time= 3h, T= 70 °C Moorthy, Jarugu Narasimha; Singhal, Nidhi; Venkatakrishnan; Tetrahedron Letters; vol. 45; nb. 28; (2004); p. 5419 - 5424 View in Reaxys

84 %

With 5,6-difluoro-2-(1-phenylethyl)benzo[d][1,2]selenazol-3(2H)-one, bromine in dichloromethane, Time= 30h, T= -35 °C Balkrishna, Shah Jaimin; Prasad, Ch Durga; Panini, Piyush; Chopra, Deepak; Kumar, Sangit; Detty, Michael R.; Journal of Organic Chemistry; vol. 77; nb. 21; (2012); p. 9541 - 9552,12 View in Reaxys

83 %

General Procedure for the Study of the Substrate Scope of ICl as Oxidant

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General procedure: Starting alcohols (1.00 g, 1.0 eq) specified in Table 3 were dissolved in 10 mL of dried CH2Cl2 (for substrates in entries 8–20 in Table 3, 30 mL of dried CH2Cl2 was used), and the resulting mixture was stirred in an ice-water bath, followed by addition of Cs2CO3 (3.0 eq). The suspension was stirred at this temperature, and ICl (1.5 eq) dissolved in 2 mL of CH2Cl2 was added dropwise. After addition, the reaction mixture was stirred at room temperature until the reaction completed as indicated by TLC analysis, which was conducted at 0.5-h intervals.The reaction mixture was subjected to aqueous workup described previously to yield the pure carbonyl compounds specified in Table 3. With Iodine monochloride, caesium carbonate in dichloromethane, Time= 20h, T= 0 - 20 °C , Green chemistry Wei, Peng; Zhang, Datong; Gao, Zhigang; Cai, Wenqing; Xu, Weiren; Tang, Lida; Zhao, Guilong; Synthetic Communications; vol. 45; nb. 12; (2015); p. 1457 - 1470 View in Reaxys 83 %

With C29H35Cl2IrN2O2, sodium acetate in 2,2,2-trifluoroethanol, Time= 20h, Inert atmosphere, Reflux, Schlenk technique Gülcemal, Süleyman; Gülcemal, Derya; Whitehead, George F. S.; Xiao, Jianliang; Chemistry - A European Journal; vol. 22; nb. 30; (2016); p. 10513 - 10522 View in Reaxys

83 %

With potassium phosphate, carbon dioxide in dimethyl sulfoxide, Time= 48h, T= 90 °C Riemer, Daniel; Mandaviya, Bhavdip; Schilling, Waldemar; Götz, Anne Charlotte; Kühl, Torben; Finger, Markus; Das, Shoubhik; ACS Catalysis; vol. 8; nb. 4; (2018); p. 3030 - 3034 View in Reaxys

82 %

With triphenylmethylphosphonium dichromate, Time= 0.116667h, T= 20 °C , Neat (no solvent), chemoselective reaction Hajipour, Abdol R.; Safaei, Somayeh; Ruoho, Arnold E.; Synthetic Communications; vol. 39; nb. 20; (2009); p. 3687 - 3692 View in Reaxys

82 %

With manganese(III) triacetate dihydrate, 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane, Time= 6h, T= 22 °C Cosner, Casey C.; Cabrera, Pablo J.; Byrd, Katherine M.; Adams Thomas, Asia M.; Helquist, Paul; Organic Letters; vol. 13; nb. 8; (2011); p. 2071 - 2073 View in Reaxys

81 %

With iodine in Triethylene glycol dimethyl ether, Time= 0.1h, T= 130 °C , microwave irradiation Mukhopadhyay; Becker; Banik; Journal of Chemical Research - Part S; nb. 1; (2001); p. 28 - 31 View in Reaxys

81 %

With potassium permanganate in acetonitrile, T= 5 - 20 °C Shaabani, Ahmad; Tavasoli-Rad, Farahnaz; Lee, Donald G.; Synthetic Communications; vol. 35; nb. 4; (2005); p. 571 - 580 View in Reaxys

80 %

With <Mn3O(OAc)6(OAc)(HOAc)>*5H2O, lithium chloride in acetic acid, Time= 0.8h, Heating Futami; Hishino; Kurosawa; Bulletin of the Chemical Society of Japan; vol. 62; nb. 11; (1989); p. 3567 - 3571 View in Reaxys

80 %

With cerium(III) sulfate, barium bromate in water, acetonitrile, Time= 7h, Heating Shaabani, Ahmad; Lee, Donald G.; Synthetic Communications; vol. 33; nb. 11; (2003); p. 1845 - 1854 View in Reaxys

80 %

With oxygen, p-benzoquinone in acetone, Time= 16h, Irradiation, Reagent/catalyst Mitchell, Lorna J.; Moody, Christopher J.; Journal of Organic Chemistry; vol. 79; nb. 22; (2014); p. 11091 - 11100 View in Reaxys

78 %

With oxygen, 2,3-dicyano-5,6-dichloro-p-benzoquinone, sodium nitrite in dichloromethane, acetic acid, Time= 8h, T= 20 °C Wang, Lianyue; Li, Jun; Yang, Hua; Lv, Ying; Gao, Shuang; Journal of Organic Chemistry; vol. 77; nb. 1; (2012); p. 790 794 View in Reaxys

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77 %

With dihydrogen peroxide in m-xylene, Time= 18h, T= 95 °C Nishida, Shunsuke; Hayashi, Masahiko; Synlett; vol. 23; nb. 11; (2012); p. 1683 - 1685 View in Reaxys

73 %

With tetrabutylammomium bromide, palladium dichloride, Time= 48h, T= 120 °C Ganchegui, Benjamin; Bouquillon, Sandrine; Henin, Francoise; Muzart, Jacques; Tetrahedron Letters; vol. 43; nb. 37; (2002); p. 6641 - 6644 View in Reaxys

72 %

General procedure General procedure: The substrate and riboflavin tetraacetatewere weighed into a mortar in stoichiometric amounts andgently homogenized with a spatula, followed by grinding with apestle and mortar. The reaction mixture was filled into the rodmill test tube and the mass was determined. Subsequently, therotating glass rod was pressed into the test tube, forming a filmbetween the test tube and the glass rod. The reaction was carriedout by rotation of the glass rod (80 rpm) and parallel irradiationwith the 455 nm LEDs for 24 hours. After the reaction, theproduct was isolated by flash column chromatography (gradientof ethyl acetate in petroleum ether). With tetra-O-acetyl riboflavin in neat (no solvent), Time= 24h, Irradiation, Milling Obst, Martin; König, Burkhard; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2358 - 2363 View in Reaxys

68 %

2.5. Typical procedure for alcohol oxidation General procedure: The reaction mixture of Primary or secondary alcohol (1 mmol),RuIIICl2 (AsPh3)2 (Ph-DPMP) Schiff base complex (0.1 mmol), NMO(1.1 mmol) and dichloromethane (2 mL) was stirred at room temperature.The filtrate obtained was evaporated under reduced pressureand the residual mass was dissolved in a mixture of ethylacetate/hexane (1:4) and then passed through a short column ofsilica gel using hexane/ethyl acetate (4:1) as eluent. Removal ofsolvent and usual workup gave the corresponding aldehydes andketones, which were identified by comparing their physical andspectral data with those of authentic compounds reported in literature[27]. With RuCl2(AsPh3)2(Ph-DPMP), 4-methylmorpholine N-oxide in dichloromethane, Time= 1.41667h, T= 20 °C Raja, K. Kanmani; Indra Gandhi; Lekha; Easwaramoorthy; Rajagopal; Journal of Molecular Structure; vol. 1060; nb. 1; (2014); p. 49 - 57 View in Reaxys

12 %

With 7,9-Me2-c-hepta[b]pyrimido[5,4-d]furan-8(7H),10(9H)dionylium in acetonitrile, Time= 40h, UV-irradiation Naya, Shin-Ichi; Miyama, Hisashi; Yasu, Kenji; Takayasu, Tohru; Nitta, Makoto; Tetrahedron; vol. 59; nb. 10; (2003); p. 1811 - 1821 View in Reaxys With oxygen, aluminum tri-tert-butoxide, benzene, T= 25 - 30 °C , Reagens 4: Anthrachinon; Reagens 5: Kupfer(II)-oleat Baker; Stanonis; Journal of the American Chemical Society; vol. 70; (1948); p. 2594 View in Reaxys Barbier; Annales de Chimie (Cachan, France); vol. <5> 7; (1876); p. 510; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1876); p. 418 View in Reaxys With tetrachloromethane, N-Bromosuccinimide Barakat et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 1670 View in Reaxys With potassium hydroxide, potassium permanganate, tetra(n-butyl)ammonium hydrogensulfate in dichloromethane, water, Ambient temperature, Yield given Gannon, Sharon M.; Krause, Josef G.; Synthesis; nb. 10; (1987); p. 915 - 917 View in Reaxys

91 % Turnov.

With dipyridinium dichromate, dihydrogen peroxide, sodium carbonate, adogen 464 in 1,2-dichloro-ethane, Time= 24h, T= 80 °C

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Muzart, Jacques; Ajjou, Abdelaziz N'Ait; Ait-Mohand, Samia; Tetrahedron Letters; vol. 35; nb. 13; (1994); p. 1989 - 1990 View in Reaxys With disodium hydrogenphosphate, benzyltrimethylammonium tribromide in tetrachloromethane, water, Time= 24h, T= 60 °C , Yield given Kajigaeshi, Shoji; Kawamukai, Hiroshi; Fujisaki, Shizuo; Bulletin of the Chemical Society of Japan; vol. 62; nb. 8; (1989); p. 2585 - 2588 View in Reaxys 91 % Turnov.

With sodium carbonate, adogen 464, palladium dichloride in 1,2-dichloro-ethane, Time= 11h, Heating Ait-Mohand; Henin; Muzart; Tetrahedron Letters; vol. 36; nb. 14; (1995); p. 2473 - 2476 View in Reaxys With N-chlorobenzotriazole in water, acetic acid, T= 30 °C , substituted fluoren-9-ols, other temperatures, ΔH(excit.), ΔS(excit.), E(activ.), Mechanism, Kinetics, Thermodynamic data Kuselan, P.; Venkatasubramanian, N.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 21; nb. 12; (1982); p. 1095 - 1097 View in Reaxys With 4-nitro-1-chlorobenzotriazole in water, acetic acid, T= 29.85 °C , Kinetics, Further Variations: Solvents, ratio Ulagi; Kuselan; Karunakaran; Monatshefte fur Chemie; vol. 132; nb. 7; (2001); p. 799 - 804 View in Reaxys With air, cyclohepta[b]pyrimido[5,4-d]furan-8,10-dionylium BF4 - in acetonitrile, Time= 16h, Irradiation Naya, Shin-Ichi; Miyama, Hisashi; Yasu, Kenji; Takayasu, Tohru; Nitta, Makoto; Tetrahedron; vol. 59; nb. 27; (2003); p. 4929 - 4938 View in Reaxys With tert.-butylhydroperoxide, tetrabutyl-ammonium chloride, 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt, sodium carbonate in water, Time= 24h, T= 20 °C Ferguson, Gabriel; Ajjou, Abdelaziz Nait; Tetrahedron Letters; vol. 44; nb. 51; (2003); p. 9139 - 9142 View in Reaxys With aluminum oxide, Ru(OH)x, oxygen in para-xylene, Time= 0.166667h, T= 129.85 °C , p= 760Torr Kamata, Keigo; Kasai, Jun; Yamaguchi, Kazuya; Mizuno, Noritaka; Organic Letters; vol. 6; nb. 20; (2004); p. 3577 - 3580 View in Reaxys With potassium carbonate, chlorobenzene, CyJohnPhos, bis(dibenzylideneacetone)-palladium(0) in toluene, Time= 12h, T= 105 °C Bei, Xiaohong; Hagemeyer, Alfred; Volpe, Anthony; Saxton, Robert; Turner, Howard; Guram, Anil S.; Journal of Organic Chemistry; vol. 69; nb. 25; (2004); p. 8626 - 8633 View in Reaxys

100 %Spectr.

With oxygen, cinnamic acid, <n-Bu4N>VO3 in acetonitrile, Time= 2h, T= 80 °C , Inert atmosphere Ohde, Christian; Limberg, Christian; Chemistry - A European Journal; vol. 16; nb. 23; (2010); p. 6892 - 6899 View in Reaxys

100 %Spectr.

With oxygen, Time= 4h, T= 80 °C , pH= 9, aq. buffer Saio, Daisuke; Amaya, Toru; Hirao, Toshikazu; Advanced Synthesis and Catalysis; vol. 352; nb. 13; (2010); p. 2177 - 2182 View in Reaxys With (dppf)RuCl2(enethylenediamine), potassium tert-butylate in tert-butyl alcohol, Time= 5h, T= 130 °C , Inert atmosphere Baratta, Walter; Bossi, Gianluca; Putignano, Elisabetta; Rigo, Pierluigi; Chemistry - A European Journal; vol. 17; nb. 12; (2011); p. 3474 - 3481 View in Reaxys

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Reaction Steps: 2 1: potassium hydride / acetonitrile 2: TEMPO+ClO4– / acetonitrile / 3 h / 20 °C With TEMPO+ClO4–, potassium hydride in acetonitrile Zhu, Xiao-Qing; Chen, Xi; Mei, Lian-Rui; Organic Letters; vol. 13; nb. 9; (2011); p. 2456 - 2459 View in Reaxys 80 %Spectr. With C16H15ClN4O2Pd, oxygen, sodium acetate, Time= 48h, T= 20 - 120 °C Urgoitia, Garazi; Sanmartin, Raul; Herrero, Maria Teresa; Dominguez, Esther; Green Chemistry; vol. 13; nb. 8; (2011); p. 2161 - 2166 View in Reaxys With 2C24H20P(1+)*C80H92O12S8V2 (2-), oxygen in acetonitrile, Time= 1h, T= 80 °C , Molecular sieve Werncke, C. Gunnar; Limberg, Christian; Knispel, Christina; Mebs, Stefan; Chemistry - A European Journal; vol. 17; nb. 43; (2011); p. 12129 - 12135 View in Reaxys With Au/CeO2, oxygen, caesium carbonate in chlorobenzene, Time= 2h, T= 90 °C , p= 760.051Torr Wang, Min; Wang, Feng; Ma, Jiping; Li, Mingrun; Zhang, Zhe; Wang, Yehong; Zhang, Xiaochen; Xu, Jie; Chemical Communications; vol. 50; nb. 3; (2014); p. 292 - 294 View in Reaxys 98 %Chromat.

With copper(II) tetrasulfophthalocyanine supported on three-dimensional nitrogendopedgraphene-based frameworks, air in water, Time= 8h, T= 20 °C , p= 760.051Torr Mahyari, Mojtaba; Laeini, Mohammad Sadegh; Shaabani, Ahmad; Chemical Communications; vol. 50; nb. 58; (2014); p. 7855 - 7857 View in Reaxys

97 %Chromat.

With oxygen, potassium carbonate in water, Time= 1h, T= 25 °C , p= 760.051Torr , Reagent/catalyst Mahyari, Mojtaba; Shaabani, Ahmad; Behbahani, Mohammad; Bagheri, Akbar; Applied Organometallic Chemistry; vol. 28; nb. 8; (2014); p. 576 - 583 View in Reaxys

92 %Chromat.

With potassium carbonate in o-xylene, Time= 8h, T= 20 °C , p= 760.051Torr , Green chemistry Shaabani, Ahmad; Hezarkhani, Zeinab; Shaabani, Shabnam; RSC Advances; vol. 4; nb. 110; (2014); p. 64419 - 64428 View in Reaxys

97 %Chromat.

With oxygen, potassium carbonate in o-xylene, Time= 6h, T= 20 °C Shaabani, Ahmad; Hezarkhani, Zeinab; Badali, Elham; RSC Advances; vol. 5; nb. 76; (2015); p. 61759 - 61767 View in Reaxys

85 %Chromat.

2.4 General procedure for the oxidation of aromatic alcohols General procedure: Alcohols (1 mmol) were added in a two round bottomed glass flask containing a mixture of cobalt chitosan (5 mol percent, 0.023 g) and K2CO3 (0.5 mmol,0.069 g) in 10 mL p-xylene. The flask was fitted with a reflux condenser and mixture was heated at 80°C with continuous bubbling of air with flow rate of 15 mLmin−1. After completion of the reaction (progress of the reaction followed by TLC), catalyst was separated by an external magnet and the reaction mixture was analyzed by gas chromatography using a CP-Sil-8 fused silica capillary column. With potassium carbonate in para-xylene, Time= 1.33333h, T= 85 °C Shaabani, Ahmad; Boroujeni, Mahmoud Borjian; Sangachin, Mona Hamidzad; Journal of Chemical Sciences; vol. 127; nb. 11; (2015); p. 1927 - 1935 View in Reaxys

95 %Chromat.

With porous chitosan–manganese dioxide nanohybrid, air in para-xylene, Time= 1h, T= 80 °C , Green chemistry Shaabani, Ahmad; Borjian Boroujeni, Mahmoud; Laeini, Mohmmad Sadegh; Applied Organometallic Chemistry; vol. 30; nb. 3; (2016); p. 154 - 159

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View in Reaxys 58 %Spectr. With C33H33N5O8Ru, dihydrogen peroxide in water, ethyl acetate, Time= 24h, T= 70 °C , Schlenk technique, Inert atmosphere Isozaki, Katsuhiro; Yokoi, Tomoya; Yoshida, Ryota; Ogata, Kazuki; Hashizume, Daisuke; Yasuda, Nobuhiro; Sadakane, Koichiro; Takaya, Hikaru; Nakamura, Masaharu; Chemistry - An Asian Journal; vol. 11; nb. 7; (2016); p. 1076 - 1091 View in Reaxys 85 %Chromat.

With potassium hydroxide in para-xylene, Time= 5h, T= 80 °C , Green chemistry Shaabani, Ahmad; Shaabani, Shabnam; Afaridoun, Hadi; RSC Advances; vol. 6; nb. 54; (2016); p. 48396 - 48404 View in Reaxys

95 %Chromat.

With potassium carbonate in para-xylene, Time= 2h, T= 80 °C , Green chemistry Shaabani, Ahmad; Afaridoun, Hadi; Shaabani, Shabnam; Applied Organometallic Chemistry; vol. 30; nb. 9; (2016); p. 772 - 776 View in Reaxys

90 %Chromat.

With potassium hydroxide in para-xylene, Time= 4h, T= 80 °C , Green chemistry Shaabani, Ahmad; Afaridoun, Hadi; Shaabani, Shabnam; Keramati Nejad, Mina; RSC Advances; vol. 6; nb. 99; (2016); p. 97367 - 97375 View in Reaxys With cobalt(II) tetrasulfophthalocyanine supported on wool, air in water, Time= 6h, T= 20 °C , Reagent/catalyst, Solvent, Temperature Shaabani, Ahmad; Hezarkhani, Zeinab; Journal of Porphyrins and Phthalocyanines; vol. 20; nb. 6; (2016); p. 677 - 688 View in Reaxys

93 %Spectr. General procedure: General procedure: V1 (27.6 mg, 0.028 mmol) and substrate (0.5 mmol) were placed in a 20mL schlenk flask, and then the mixed MeCN/THF (1:1) solvent (3 mL) was added. The mixture was stirred at 60 C for an appropriate time under O2(balloon) or atmospheric air. After the reaction was completed, Et2O was added tothe reaction mixture. The resulting suspension was filtered and rinsed with Et2O. The combined filtrate was concentrated in vacuo. The yield of the oxidation products was confirmed by 1H NMR spectroscopy using 1,2-diphenylethane or 1,3,5-trimethoxybenzene as the internal standard. Purification of 2a–2c was performed by silica gel chromatography using hexane and EtOAc as the eluent to afford the analytically pure ketones. The isolated products were identified by comparing their 1H NMR spectra with those of authentic samples. With [VO(ReO4)(4,4'-di-tert-butyl-2,2'-bipyridine)2][0.25SO4*0.5ReO4], oxygen in tetrahydrofuran, acetonitrile, Time= 10h, T= 60 °C , p= 750.075Torr , Schlenk technique, chemoselective reaction Kobayashi, Daiki; Kodama, Shintaro; Ishii, Youichi; Tetrahedron Letters; vol. 58; nb. 33; (2017); p. 3306 - 3310 View in Reaxys 3.3. Oxidation of alcohols; General procedure General procedure: In a typical reaction, an alcohol (1.0 mmol) was added to a twoneckedflask containing MnO2silk (0.09 g, 10 molpercent of MnO2),K2CO3 (0.50 mmol), and o-xylene (5.0 mL) and stirred under airblowing at room temperature. The progress of the reaction was followedby TLC and GC method. After completion of reaction and filtrationof mixture, the filtrate was analyzed by GC method. With potassium carbonate in o-xylene, Time= 8h, T= 20 °C Shaabani, Ahmad; Hezarkhani, Zeinab; Badali, Elham; Polyhedron; vol. 107; (2016); p. 176 - 182 View in Reaxys Br

Rx-ID: 2070187 View in Reaxys 3/827

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Yield

Conditions & References

91 %

With sodium hypochlorite in acetonitrile, Time= 2h, Ambient temperature, Irradiation Khurana, Jitender M.; Sahoo, Prabhat K.; Titus, Susa S.; Maikap, Golak C.; Synthetic Communications; vol. 20; nb. 9; (1990); p. 1357 - 1361 View in Reaxys

91 %

With sodium hypochlorite in acetonitrile, Time= 2h, Ambient temperature, Irradiation, other benzylic halides, var. reaction time and var. molar ratio halide:NaOCl, Product distribution Khurana, Jitender M.; Sahoo, Prabhat K.; Titus, Susa S.; Maikap, Golak C.; Synthetic Communications; vol. 20; nb. 9; (1990); p. 1357 - 1361 View in Reaxys

86 %

With oxygen, kieselguhr, copper(l) chloride in toluene, Time= 4h, Heating, Oxidation Hashemi, Mohammed M.; Ahmadi Beni, Yousef; Journal of Chemical Research - Part S; nb. 7; (1999); p. 434 - 435 View in Reaxys

80 %

With sodium periodate in dichloromethane, T= 40 - 50 °C , Ionic liquid Hullio, Ahmed Ali; Mastoi; Khan, Khalid; Asian Journal of Chemistry; vol. 23; nb. 12; (2011); p. 5411 - 5418 View in Reaxys

78 %

With sodium periodate in N,N-dimethyl-formamide, Time= 0.75h, T= 150 °C Das, Sasmita; Panigrahi; Maikap, Golak C.; Tetrahedron Letters; vol. 44; nb. 7; (2003); p. 1375 - 1377 View in Reaxys

56 %

Stage 1: With pyridine, Time= 6h, T= 70 °C Stage 2: With [Ru(bipyridine)3]Cl2, caesium carbonate in N,N-dimethyl acetamide, Time= 48h, T= 25 °C , Irradiation Su, Yijin; Zhang, Liangren; Jiao, Ning; Organic Letters; vol. 13; nb. 9; (2011); p. 2168 - 2171 View in Reaxys Reaction Steps: 2 1: 65 percent / potassium t-butoxide 2: H2O With potassium tert-butylate, water Gong, Yong; Bausch, Mark J.; Wang, Linhua; Tetrahedron Letters; vol. 42; nb. 1; (2001); p. 1 - 4 View in Reaxys Reaction Steps: 2 1.1: 3 h / 150 °C 2.1: sodium t-butanolate / N,N-dimethyl-formamide / 0.08 h / 25 °C / Inert atmosphere 2.2: 8 h / 25 °C With sodium t-butanolate in N,N-dimethyl-formamide Huang, Tianzeng; Chen, Tieqiao; Han, Li-Biao; Journal of Organic Chemistry; vol. 83; nb. 5; (2018); p. 2959 - 2965 View in Reaxys O Br

Rx-ID: 30916463 View in Reaxys 4/827 Yield

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Liu, Tao-Ping; Liao, Yuan-Xi; Xing, Chun-Hui; Hu, Qiao-Sheng; Organic Letters; vol. 13; nb. 9; (2011); p. 2452 - 2455 View in Reaxys Reaction Steps: 2 1.1: TurboGrignard / tetrahydrofuran / 2 h / -15 °C 1.2: 0.5 h / -15 °C 2.1: palladium diacetate; caesium carbonate; tetra-(n-butyl)ammonium iodide / toluene / 16 h / 110 °C / Inert atmosphere With TurboGrignard, palladium diacetate, tetra-(n-butyl)ammonium iodide, caesium carbonate in tetrahydrofuran, toluene Gao, Qian; Xu, Senmiao; Organic and Biomolecular Chemistry; vol. 16; nb. 2; (2018); p. 208 - 212 View in Reaxys OH

Rx-ID: 47082790 View in Reaxys 5/827 Yield

Conditions & References

70 %

With palladium diacetate, tetra-(n-butyl)ammonium iodide, caesium carbonate in toluene, Time= 16h, T= 110 °C , Inert atmosphere, Catalytic behavior, Reagent/catalyst, Solvent Gao, Qian; Xu, Senmiao; Organic and Biomolecular Chemistry; vol. 16; nb. 2; (2018); p. 208 - 212 View in Reaxys O

Rx-ID: 47082890 View in Reaxys 6/827 Yield

Conditions & References Reaction Steps: 2 1.1: TurboGrignard / tetrahydrofuran / 2 h / -15 °C 1.2: 0.5 h / -15 °C 2.1: palladium diacetate; caesium carbonate; tetra-(n-butyl)ammonium iodide / toluene / 16 h / 110 °C / Inert atmosphere With TurboGrignard, palladium diacetate, tetra-(n-butyl)ammonium iodide, caesium carbonate in tetrahydrofuran, toluene Gao, Qian; Xu, Senmiao; Organic and Biomolecular Chemistry; vol. 16; nb. 2; (2018); p. 208 - 212 View in Reaxys

O O O

Rx-ID: 47548755 View in Reaxys 7/827 Yield 97 %

Conditions & References Stage 1: With sodium t-butanolate in N,N-dimethyl-formamide, Time= 0.0833333h, T= 25 °C , Inert atmosphere Stage 2: With oxygen in N,N-dimethyl-formamide, Time= 8h, T= 25 °C , stereoselective reaction Huang, Tianzeng; Chen, Tieqiao; Han, Li-Biao; Journal of Organic Chemistry; vol. 83; nb. 5; (2018); p. 2959 - 2965 View in Reaxys

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O O I

Rx-ID: 48070503 View in Reaxys 8/827 Yield

Conditions & References

92 %

With palladium diacetate, caesium carbonate, 2-Methoxybenzoic acid, tricyclohexylphosphine in dimethyl sulfoxide, Time= 0.216667h, T= 110 °C , Inert atmosphere, Reagent/catalyst Konishi, Hideyuki; Futamata, Suguru; Wang, Xi; Manabe, Kei; Advanced Synthesis and Catalysis; vol. 360; nb. 9; (2018); p. 1805 - 1809 View in Reaxys O

O O N

S I

O O

Rx-ID: 48070504 View in Reaxys 9/827 Yield

Conditions & References

With palladium diacetate, caesium carbonate, 2-Methoxybenzoic acid, tricyclohexylphosphine in dimethyl sulfoxide, Time= 1h, T= 110 °C , Inert atmosphere Konishi, Hideyuki; Futamata, Suguru; Wang, Xi; Manabe, Kei; Advanced Synthesis and Catalysis; vol. 360; nb. 9; (2018); p. 1805 - 1809 View in Reaxys O

O O Br

Rx-ID: 48070508 View in Reaxys 10/827 Yield 72 %

Conditions & References With palladium diacetate, caesium carbonate, 2-Methoxybenzoic acid, tricyclohexylphosphine in dimethyl sulfoxide, Time= 14h, T= 110 °C , Inert atmosphere Konishi, Hideyuki; Futamata, Suguru; Wang, Xi; Manabe, Kei; Advanced Synthesis and Catalysis; vol. 360; nb. 9; (2018); p. 1805 - 1809 View in Reaxys O

NH 2

Rx-ID: 786391 View in Reaxys 11/827 Yield

Conditions & References Diazotization Graebe; Ullmann; Justus Liebigs Annalen der Chemie; vol. 291; (1896); p. 16 View in Reaxys Diazotization.Verkochen mit Wasser Graebe; Ullmann; Chemische Berichte; vol. 27; (1894); p. 3484 View in Reaxys

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Staedel; Chemische Berichte; vol. 27; (1894); p. 3363; Chemische Berichte; vol. 28; (1895); p. 111 View in Reaxys With hydrogenchloride, Diazotization Graebe; Ullmann; Justus Liebigs Annalen der Chemie; vol. 291; (1896); p. 16 View in Reaxys 80 %Chromat., 20 %Chromat.

General procedure: Aniline (1mmol, 0.095mL), silica sulfuric acid (0.75g) and sodium nitrite (1.7mmol, 0.12g) were ground in a mortar with a pestle for a few minutes to obtain a homogeneous mixture. Then, four drops of water were gradually added and the mixture was ground for 10min to give phenyl diazonium silica sulfate. Five drops of water were added to phenyl diazonium silica sulfate (1mmol) and the resulting mixture was simply blended and then placed into a covered petri dish. Then, the petri dish was placed in an oven at 60°C for 15min. After that, the reaction mixture was diluted with EtOAc (15mL) and filtered after vigorous stirring. The residue was extracted with EtOAc (2×10mL) and the combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to afford the crude product. Further purification was performed by flash column chromatography and the pure phenol was obtained in 81percent (0.076g). Stage 1: With sodium nitrite in water, T= 20 °C , Milling, Green chemistry Stage 2: With water, Time= 0.5h, T= 80 °C , Neutral conditions, Green chemistry Zarei, Amin; Khazdooz, Leila; Aghaei, Hamidreza; Gheisari, Mohammad Mehdi; Alizadeh, Shahrzad; Golestanifar, Laleh; Tetrahedron; vol. 73; nb. 49; (2017); p. 6954 - 6961 View in Reaxys OH

Rx-ID: 855718 View in Reaxys 12/827 Yield 98 %

Conditions & References With chloro(1,5-cyclooctadiene)rhodium(I) dimer, 2,2-dimethylpropanoic anhydride, 1,2-bis-(diphenylphosphino)ethane, potassium iodide, Time= 0.5h, T= 160 °C , Inert atmosphere, Microwave irradiation, Sealed tube, Wavelength, Reagent/catalyst Fukuyama, Takahide; Maetani, Shinji; Miyagawa, Kazusa; Ryu, Ilhyong; Organic Letters; vol. 16; nb. 12; (2014); p. 3216 3219 View in Reaxys

92 %

With trifluoromethylsulfonic anhydride, Triphenylphosphine oxide in 1,2-dichloro-ethane, Time= 0.5h, T= 25 °C Hendrickson, James B.; Hussoin, Md. Sajjat; Journal of Organic Chemistry; vol. 54; nb. 5; (1989); p. 1144 - 1149 View in Reaxys

90 %

With trifluorormethanesulfonic acid in 1,2-dichloro-ethane, Time= 24h, T= 80 °C , Reagent/catalyst, Solvent Sun, Denan; Li, Bijin; Lan, Jingbo; Huang, Quan; You, Jingsong; Chemical Communications; vol. 52; nb. 18; (2016); p. 3635 - 3638 View in Reaxys

82 %

With Nafion-H in various solvent(s), Time= 3h, T= 180 °C , Acylation, Friedel-Crafts intramolecular acylation Olah, George A.; Mathew, Thomas; Farnia, Morteza; Prakash, G. K. Surya; Katherine; Donald; Synlett; nb. 7; (1999); p. 1067 - 1068 View in Reaxys

80 %

3. Synthesis of 3 General procedure: A mixture of 1 (0.5 mmol),DMSO (50percent aq, 3 mL), Pd(OTf)2 (5 molpercent), Ag2CO3 (2equiv) was stirred at 140βC under air atmosphere for 24 h. The reaction mixture was washed water and the aqueous phase was extracted with ethyl acetate (3 times). The combined organic layer was washed with brine, dried over Na2SO4, and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography to give the corresponding products. (3a–3i1, 3k– 3m1, 3o-3p1, according to the literature) With bis(trifluoromethyl sulfate)palladium, tert-butylisonitrile, water, silver carbonate in dimethyl sulfoxide, Time= 24h, T= 140 °C , Catalytic behavior, Reagent/catalyst, Solvent, Temperature

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Cai, Zhiqiang; Hou, Xu; Hou, Ling; Hu, Zhiquan; Zhang, Bo; Jin, Zhengsheng; Synlett; vol. 27; nb. 3; (2016); p. 395 398; Art.No: ST-2015-W0682-L View in Reaxys 78 %

With 2,6-dimethylpyridine, fac-tris(2-phenylpyridinato-N,C2')iridium(III), dimethyl dicarbonate in N,N-dimethyl-formamide, Time= 20h, T= 25 °C , Schlenk technique, Inert atmosphere, Irradiation, Catalytic behavior, Reagent/catalyst, Solvent Ruzi, Rehanguli; Zhang, Muliang; Ablajan, Keyume; Zhu, Chengjian; Journal of Organic Chemistry; vol. 82; nb. 23; (2017); p. 12834 - 12839 View in Reaxys

76 %

Stage 1: With n-butyllithium, potassium tert-butylate in benzene, Time= 1h, T= 60 °C Stage 2: With n-butyllithium in benzene, Time= 2h, T= 60 °C Stage 3: With water in benzene, T= 20 °C Tilly, David; Samanta, Subhendu S.; De, Asish; Castanet, Anne-Sophie; Mortier, Jacques; Organic Letters; vol. 7; nb. 5; (2005); p. 827 - 830 View in Reaxys With sulfuric acid Weger; Doering; Chemische Berichte; vol. 36; (1903); p. 878 View in Reaxys Graebe; Aubin; Chemische Berichte; vol. 20; (1887); p. 845; Justus Liebigs Annalen der Chemie; vol. 247; (1888); p. 275 View in Reaxys With calcium oxide Fittig; Ostermayer; Justus Liebigs Annalen der Chemie; vol. 166; (1873); p. 363 View in Reaxys With phosphorus pentachloride Bachmann; Clarke; Journal of the American Chemical Society; vol. 49; (1927); p. 2093 View in Reaxys Reaction Steps: 2 1: 98 percent / s-BuLi; cyclohexane 2: MsOH / 50 - 60 °C With methanesulfonic acid, cyclohexane, sec.-butyllithium Tilly, David; Samanta, Subhendu S; Faigl, Ferenc; Mortier, Jacques; Tetrahedron Letters; vol. 43; nb. 46; (2002); p. 8347 8350 View in Reaxys Reaction Steps: 2 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 °C 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; tri-tert-butyl phosphine / o-xylene / 24 h / 160 °C / Inert atmosphere With bis(1,5-cyclooctadiene)diiridium(I) dichloride, oxalyl dichloride, tri-tert-butyl phosphine, N,N-dimethyl-formamide in dichloromethane, o-xylene Nagata, Tomoya; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro; Journal of Organic Chemistry; vol. 79; nb. 19; (2014); p. 8960 - 8967 View in Reaxys Reaction Steps: 2 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.75 h / 20 °C / Inert atmosphere 2: 1,1,1,3',3',3'-hexafluoro-propanol / 4 h / 20 °C / Inert atmosphere With oxalyl dichloride, 1,1,1,3',3',3'-hexafluoro-propanol, N,N-dimethyl-formamide in dichloromethane, 2: |Friedel-Crafts Acylation Motiwala, Hashim F.; Vekariya, Rakesh H.; Aubé, Jeffrey; Organic Letters; vol. 17; nb. 21; (2015); p. 5484 - 5487 View in Reaxys With thionyl chloride, Reflux

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Raffa, Demetrio; Plescia, Fabiana; Maggio, Benedetta; Raimondi, Maria Valeria; D'Anneo, Antonella; Lauricella, Marianna; Daidone, Giuseppe; European Journal of Medicinal Chemistry; vol. 132; (2017); p. 262 - 273 View in Reaxys O

Rx-ID: 1767539 View in Reaxys 13/827 Yield 88.7 %, 11.3 %

Conditions & References With N -hydroxyphthalimide, oxygen, butane-2,3-dione dioxime in acetonitrile, Time= 10h, T= 80 °C , p= 3750.38Torr Zheng, Gengxiu; Liu, Chunhong; Wang, Qiufen; Wang, Mingyu; Yang, Guanyu; Advanced Synthesis and Catalysis; vol. 351; nb. 16; (2009); p. 2638 - 2642 View in Reaxys

63 %, 11 %

With sodium percarbonate, adogen 464, bis-(tributyltin oxide) dioxochromium(VI), toluene-4-sulfonic acid in acetonitrile, Time= 20h, Heating Muzart, Jacques; Aiet-Mohand, Samia; Tetrahedron Letters; vol. 36; nb. 32; (1995); p. 5735 - 5736 View in Reaxys

50 %

With cerium(III) sulfate, barium bromate in water, acetonitrile, Time= 24h, Heating, Title compound not separated from byproducts Shaabani, Ahmad; Lee, Donald G.; Synthetic Communications; vol. 33; nb. 11; (2003); p. 1845 - 1854 View in Reaxys

45 %, 24 %

With N -hydroxyphthalimide, oxygen in ethyl acetate, Time= 10h, T= 70 °C , p= 760.051Torr , Catalytic behavior Rezaeifard, Abdolreza; Khoshyan, Ashkan; Jafarpour, Maasoumeh; Pourtahmasb, Mehrdad; RSC Advances; vol. 7; nb. 26; (2017); p. 15754 - 15761 View in Reaxys

12 % Chromat., 21 %

12 %, 21 % Chromat.

With <(n-C4H9)4N>5PZnMo2W9O39*3H2O, dihydrogen peroxide in chloroform, Time= 24h, Title compound not separated from byproducts Tangestaninejad, Shahram; Yadollahi, Bahram; Chemistry Letters; nb. 6; (1998); p. 511 - 512 View in Reaxys With oxygen, potassium hydride in tetrahydrofuran, Time= 0.0833333h, T= 20 °C , other alkali-metal hydrides; various aprotic solvents; different time, Product distribution Grigoryan, G. S.; Tovmasyan, V. S.; Malkhasyan, A. Ts.; Martirosyan, G. T.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 25; nb. 5.2; (1989); p. 932 - 935; Zhurnal Organicheskoi Khimii; vol. 25; nb. 5; (1989); p. 1036 - 1039 View in Reaxys With sodium hydroxide, sodium tetrahydroborate, oxygen, 18-crown-6 ether in dimethyl sulfoxide, Time= 0.3h, further base, further solvents; influence of solvent polarity, base strength, use of crown ether, Product distribution Grigoryan, G. S.; Tovmasyan, V. S.; Malkhasyan, A. Ts.; Martirosyan, G. T.; Beletskaya, I. P.; Doklady Chemistry; vol. 295; nb. 8; (1987); p. 353 - 356; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 295; nb. 5; (1987); p. 1124 - 1127 View in Reaxys Stage 1: With triethylsilane, [Bu4N]4W10O32, oxygen in acetonitrile, Time= 1h, T= 5 - 10 °C , Irradiation Stage 2: With triphenylphosphine, Further stages.

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Lykakis, Ioannis N.; Orfanopoulos, Michael; Tetrahedron Letters; vol. 45; nb. 41; (2004); p. 7645 - 7649 View in Reaxys Stage 1: With N -hydroxyphthalimide, xanth-9-one, oxygen, tetramethlyammonium chloride in acetonitrile, Time= 4h, T= 60 °C , p= 3750.38Torr , Autoclave Stage 2: With triphenylphosphine in acetonitrile, Time= 0.5h, T= 20 °C Du, Zhongtian; Sun, Zhiqiang; Zhang, Wei; Miao, Hong; Ma, Hong; Xu, Jie; Tetrahedron Letters; vol. 50; nb. 15; (2009); p. 1677 - 1680 View in Reaxys With haem domains of cytochrome P450BM3 from Bacillus megaterium wild-type, NADPH, Enzymatic reaction Whitehouse, Christopher J. C.; Yang, Wen; Yorke, Jake A.; Rowlatt, Benjamin C.; Strong, Anthony J. F.; Blanford, Christopher F.; Bell, Stephen G.; Bartlam, Mark; Wong, Luet-Lok; Rao, Zihe; ChemBioChem; vol. 11; nb. 18; (2010); p. 2549 - 2556 View in Reaxys With Cr2O4 (2-)*Cu(2+), dihydrogen peroxide in acetonitrile, Time= 10h, T= 50 °C Acharyya, Shankha S.; Ghosh, Shilpi; Adak, Shubhadeep; Tripathi, Deependra; Bal, Rajaram; Catalysis Communications; vol. 59; (2015); p. 145 - 150 View in Reaxys With [Mn2(2,5-dihydroxyterephthalate)(H2O)2]·nH2O, oxygen in neat (no solvent), Time= 9h, T= 135 °C , Catalytic behavior, Time Kuwahara, Yasutaka; Yoshimura, Yukihiro; Yamashita, Hiromi; Dalton Transactions; vol. 46; nb. 26; (2017); p. 8415 8421 View in Reaxys -1

F (v4)

B FF

O N

N+

Rx-ID: 2327685 View in Reaxys 14/827 Yield

Conditions & References

84 %

With 1-iodo-2-phenylethyne in acetonitrile, Heating Ramanathan, Mani; Liu, Shiuh-Tzung; Tetrahedron; vol. 73; nb. 30; (2017); p. 4317 - 4322 View in Reaxys

73 %

With potassium acetate, 18-crown-6 ether in 1,1,2-Trichloro-1,2,2-trifluoroethane, Time= 12h, Ambient temperature Beadle, James R.; Korzeniowsky, Stephen H.; Rosenberg, David E.; Garcia-Slanga, Blanche J.; Gokel, George W.; Journal of Organic Chemistry; vol. 49; nb. 9; (1984); p. 1594 - 1603 View in Reaxys

56 %

With anthranilic acid nitrile in acetonitrile, Time= 2h, T= 80 °C , Sealed tube Ramanathan, Mani; Liu, Yi-Hung; Peng, Shie-Ming; Liu, Shiuh-Tzung; Organic Letters; vol. 19; nb. 21; (2017); p. 5840 5843 View in Reaxys O

Rx-ID: 8681242 View in Reaxys 15/827

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Yield

Conditions & References With cesium pivalate, palladium(0)bis(tricyclohexylphosphine) in N,N-dimethyl-formamide, Time= 7h, T= 110 °C , p= 760.051Torr , Carbonylation, cyclization

100 %

Campo; Larock; Organic letters; vol. 2; nb. 23; (2000); p. 3675 - 3677 View in Reaxys With tristricyclohexylphosphine palladium(0), cesium pivalate in N,N-dimethyl-formamide, Time= 7h, T= 110 °C , p= 760.051Torr

100 %

Campo, Marino A.; Larock, Richard C.; Journal of Organic Chemistry; vol. 67; nb. 16; (2002); p. 5616 - 5620 View in Reaxys 58 %

With chloro(1,5-cyclooctadiene)rhodium(I) dimer, sodium carbonate in 5,5-dimethyl-1,3-cyclohexadiene, Time= 48h, T= 130 °C , Inert atmosphere, Reagent/catalyst Furusawa, Takuma; Morimoto, Tsumoru; Nishiyama, Yasuhiro; Tanimoto, Hiroki; Kakiuchi, Kiyomi; Chemistry - An Asian Journal; vol. 11; nb. 16; (2016); p. 2312 - 2315 View in Reaxys

With 1,10-Phenanthroline, palladium diacetate in 1,2-dichloro-ethane, Time= 8h, T= 120 °C , p= 760.051Torr Liu, Li; Qiang, Jian; Bai, Shuhua; Li, Yang; Miao, Chunbao; Li, Jian; Applied Organometallic Chemistry; vol. 31; nb. 12; (2017); Art.No: E3817 View in Reaxys O

Rx-ID: 10401340 View in Reaxys 16/827 Yield 78 %

Conditions & References With carbon tetrabromide, oxygen in neat (no solvent), T= 140 °C Tang, Jing; Zhao, Shijun; Wei, Yuanyuan; Quan, Zhengjun; Huo, Congde; Organic and Biomolecular Chemistry; vol. 15; nb. 7; (2017); p. 1589 - 1592 View in Reaxys

68%

With dipotassium peroxodisulfate, tetraethylammonium bromide in 1,2-dichloro-ethane, Time= 36h, T= 120 °C , Inert atmosphere, Catalytic behavior, Reagent/catalyst, Concentration, Temperature Shi, Zhuangzhi; Glorius, Frank; Chemical Science; vol. 4; nb. 2; (2013); p. 829 - 833 View in Reaxys

62 %

With tert.-butylhydroperoxide in toluene, Time= 18h, T= 100 °C , Inert atmosphere Mishra, Kalpana; Pandey, Ashok Kumar; Singh, Jay Bahadur; Singh, Radhey M.; Organic and Biomolecular Chemistry; vol. 14; nb. 26; (2016); p. 6328 - 6336 View in Reaxys

27 %

With tetrafluoroboric acid, Barluenga reagent in diethyl ether, dichloromethane, Time= 24h, T= -60 °C Barluenga, Jose; Trincado, Monica; Rubio, Eduardo; Gonzalez, Jose M.; Angewandte Chemie - International Edition; vol. 45; nb. 19; (2006); p. 3140 - 3143 View in Reaxys Reaction Steps: 3 1: MgSO4 / toluene / 100 °C 2: cesium pivalate / Pd(OAc)2; 1,1-bis(diphenylphosphino)methane / dimethylformamide / 12 h / 100 °C 3: aq. HCl / acetone With hydrogenchloride, magnesium sulfate, cesium pivalate, palladium diacetate, bis-diphenylphosphinomethane in N,N-dimethyl-formamide, acetone, toluene

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Zhao, Jian; Yue, Dawei; Campo, Marino A.; Larock, Richard C.; Journal of the American Chemical Society; vol. 129; nb. 16; (2007); p. 5288 - 5295 View in Reaxys Reaction Steps: 2 1.1: magnesium sulfate / dichloromethane / 20 °C 2.1: [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 34 h / 80 °C 2.2: 20 °C With [bis(acetoxy)iodo]benzene, boron trifluoride diethyl etherate, magnesium sulfate in dichloromethane, 1,2-dichloro-ethane Sarkar, Satinath; Tadigoppula, Narender; RSC Advances; vol. 4; nb. 77; (2014); p. 40964 - 40968 View in Reaxys Reaction Steps: 2 1: aluminum (III) chloride / nitromethane / 8 h / 100 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran With aluminum (III) chloride, tetrabutyl ammonium fluoride in tetrahydrofuran, nitromethane Chen, Lei; Teng, Wei; Geng, Xin-Le; Zhu, Yi-Fan; Guan, Yong-Hong; Fan, Xiaohui; Applied Organometallic Chemistry; vol. 31; nb. 12; (2017); Art.No: E3863 View in Reaxys O HO B HO

Rx-ID: 11653522 View in Reaxys 17/827 Yield

Conditions & References Reaction Steps: 4 1: Na2CO3 / Pd(OAc)2 / dimethylformamide; H2O / 12 h / 25 °C 2: MgSO4 / toluene / 100 °C 3: cesium pivalate / Pd(OAc)2; 1,1-bis(diphenylphosphino)methane / dimethylformamide / 12 h / 100 °C 4: aq. HCl / acetone With hydrogenchloride, sodium carbonate, magnesium sulfate, cesium pivalate, palladium diacetate, bis-diphenylphosphinomethane in water, N,N-dimethyl-formamide, acetone, toluene Zhao, Jian; Yue, Dawei; Campo, Marino A.; Larock, Richard C.; Journal of the American Chemical Society; vol. 129; nb. 16; (2007); p. 5288 - 5295 View in Reaxys Reaction Steps: 2 1: C42H62ClO3PPd; potassium carbonate / toluene / 5 h / 60 °C 2: Trimethylacetic acid / 2,4-dichlorophenoxyacetic acid dimethylamine; toluene / 10 h / 120 °C With C42H62ClO3PPd, potassium carbonate, Trimethylacetic acid in 2,4-dichlorophenoxyacetic acid dimethylamine, toluene Liu, Tao-Ping; Liao, Yuan-Xi; Xing, Chun-Hui; Hu, Qiao-Sheng; Organic Letters; vol. 13; nb. 9; (2011); p. 2452 - 2455 View in Reaxys Reaction Steps: 2 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / methanol; toluene / 12 h / Inert atmosphere; Reflux 2: alumina / 30 - 250 °C / Inert atmosphere With tetrakis(triphenylphosphine) palladium(0), alumina, potassium carbonate in methanol, toluene Papaianina; Amsharov; Chemical Communications; vol. 52; nb. 7; (2016); p. 1505 - 1508 View in Reaxys Reaction Steps: 2 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 70 °C 2: tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide / 1,2-dichloro-ethane; decane / 16 h / 90 °C / Sealed tube With tert.-butylhydroperoxide, tetrakis(triphenylphosphine) palladium(0), tetra-(n-butyl)ammonium iodide, sodium carbonate in tetrahydrofuran, decane, water, 1,2-dichloro-ethane, 1: |Suzuki Coupling

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Laha, Joydev K.; Jethava, Krupal P.; Patel, Sagarkumar; Patel, Ketul V.; Journal of Organic Chemistry; vol. 82; nb. 1; (2017); p. 76 - 85 View in Reaxys

Rx-ID: 22080081 View in Reaxys 18/827 Yield 86.1 %

Conditions & References With sodium ferrate(VI) in water, Time= 3h, Benzilic Acid Rearrangement Tandon, Praveen K.; Singh, Santosh B.; Singh, Satpal; Kesarwani, Bhawana; Journal of the Indian Chemical Society; vol. 89; nb. 10; (2012); p. 1363 - 1367 View in Reaxys

83.33 %

With Iron(III) nitrate nonahydrate, sodium hypochlorite, gold(III) tetrachloride trihydrate, acetic acid in water, Time= 0.0583333h, T= 100 °C , Microwave irradiation, Green chemistry, Catalytic behavior, Reagent/catalyst Srivastava, Manish; Srivastava, Anamika; Goyal, Ashu; Mishra, Aakanksha; Tomer, Preeti; Dwivedi, Jaya; Kishore; Journal of Physical Organic Chemistry; vol. 30; nb. 2; (2017); Art.No: E3602 View in Reaxys Reaction Steps: 2 1: chromic acid mixture 2: burnt/baked lime/chalk/ With chromic acid, calcium carbonate, calcium oxide Fittig; Ostermayer; Justus Liebigs Annalen der Chemie; vol. 166; (1873); p. 363 View in Reaxys O

Rx-ID: 34265862 View in Reaxys 19/827 Yield

Conditions & References Reaction Steps: 3 1.1: magnesium / tetrahydrofuran / 2 h / 20 - 85 °C 1.2: 0 - 20 °C / Inert atmosphere 2.1: pyridinium chlorochromate; triethylamine / dichloromethane / 20 °C 3.1: palladium diacetate; trifluoroacetic acid; potassium carbonate; silver(l) oxide / 24 h / 140 °C / Schlenk technique; Inert atmosphere With palladium diacetate, potassium carbonate, magnesium, triethylamine, pyridinium chlorochromate, trifluoroacetic acid, silver(l) oxide in tetrahydrofuran, dichloromethane, 2.1: |Nazarov Cyclization / 3.1: |Nazarov Cyclization Li, Hu; Zhu, Ru-Yi; Shi, Wen-Juan; He, Ke-Han; Shi, Zhang-Jie; Organic Letters; vol. 14; nb. 18; (2012); p. 4850 - 4853,4 View in Reaxys Reaction Steps: 3 1: tris-(dibenzylideneacetone)dipalladium(0); XPhos; potassium phosphate monohydrate / 1,4-dioxane; water / 12 h / 100 °C / Sealed tube; Inert atmosphere 2: selenium(IV) oxide; pyridine / 80 °C 3: dipotassium peroxodisulfate / water; acetonitrile / 24 h / 80 °C / Sealed tube With pyridine, selenium(IV) oxide, tris-(dibenzylideneacetone)dipalladium(0), dipotassium peroxodisulfate, potassium phosphate monohydrate, XPhos in 1,4-dioxane, water, acetonitrile

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Laha, Joydev K.; Patel, Ketul V.; Dubey, Gurudutt; Jethava, Krupal P.; Organic and Biomolecular Chemistry; vol. 15; nb. 10; (2017); p. 2199 - 2210 View in Reaxys O

Rx-ID: 34265982 View in Reaxys 20/827 Yield 95 %

Conditions & References With sodium hydride in diethyl ether, Time= 0.5h, T= 25 °C Shipilovskikh, Sergei A.; Rubtsov, Aleksandr E.; Malkov, Andrei V.; Organic Letters; vol. 19; nb. 24; (2017); p. 6760 - 6762 View in Reaxys

87 %

With tetrafluoroboric acid diethyl ether, iodosylbenzene in dichloromethane, Time= 24h, T= 20 °C , Inert atmosphere Havare, Nizam; Plattner, Dietmar A.; Organic Letters; vol. 14; nb. 19; (2012); p. 5078 - 5081,4 View in Reaxys

45 %

With Nitrosobenzene in dichloromethane, Time= 24h, T= 50 °C , Sealed tube Hu, Guang; Ramakumar, Kinthada; Brenner-Moyer, Stacey E.; Journal of Organic Chemistry; vol. 82; nb. 13; (2017); p. 6972 - 6977 View in Reaxys O

HO C

Rx-ID: 39990302 View in Reaxys 21/827 Yield 90 %

Conditions & References With palladium diacetate, caesium carbonate, tricyclohexylphosphine, Trimethylacetic acid in toluene, Time= 12h, T= 100 °C , Inert atmosphere, Glovebox, Schlenk technique, Sealed tube Song, Juan; Wei, Fuliang; Sun, Wei; Li, Ke; Tian, Yanan; Liu, Chao; Li, Yali; Xie, Linghai; Organic Letters; vol. 17; nb. 9; (2015); p. 2106 - 2109 View in Reaxys

90 %

1 : Example 1 Under a nitrogen atmosphere, phenylboronic acid (0.6 mmol, 73.2 mg), cesium carbonate (1.5 mmol, 489 mg), palladium acetate (0.025 mmol, 5.6 mg) were added to a Schlenk reaction tube and placed in a glove box adding three-ring hexyl phosphine (0.05mmol, 14 mg), after taking out the CO gas atmosphere is replaced, in the system adding O bromine monoiodo-benzene (0.5mmol, 64 . 2uL), trimethylacetic acid (0.5mmol, 51 mg), then add 3 ml toluene, stirring 5 minutes, the reaction is 100 °C oil bath pot reaction 12 hours. After the reaction, in the system by adding 3 ml of saturated ammonium chloride solution quenching reaction, all three times by adding 15 ml of ethyl acetate, the combined organic phase, the dried with anhydrous sodium sulfate, column chromatography separation to obtain the product, and the yield is 90percent (breakdown of the 1). With palladium diacetate, caesium carbonate, tricyclohexylphosphine, Trimethylacetic acid in toluene, Time= 12h, T= 100 °C , Schlenk technique, Inert atmosphere, Glovebox Patent; Nanjing University of Posts and Telecommunications; Song Juan; Wei Fuliang; Sun Wei; Li Yali; Xie Linghai; (32 pag.); CN104844400; (2017); (B) Chinese View in Reaxys

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O I

HO C

Rx-ID: 39990310 View in Reaxys 22/827 Yield

Conditions & References

64 %

With palladium diacetate, caesium carbonate, tricyclohexylphosphine, Trimethylacetic acid in toluene, Time= 12h, T= 100 °C , Inert atmosphere, Glovebox, Schlenk technique, Sealed tube Song, Juan; Wei, Fuliang; Sun, Wei; Li, Ke; Tian, Yanan; Liu, Chao; Li, Yali; Xie, Linghai; Organic Letters; vol. 17; nb. 9; (2015); p. 2106 - 2109 View in Reaxys

64 %

17 : Embodiment 17 - 21: in addition to the use of different O-halogenated aromatic outside, other reaction conditions are the same, as follows: Under the protection of nitrogen, in a Schlenk reaction tube adding phenyl boronic acid (0.6mmol, 73.2 mg), cesium carbonate (1.5mmol, 489 mg), palladium acetate (0.025mmol, 5.6 mg), and placed in the glove box, adding three-ring hexyl phosphine (0.05mmol, 14 mg), after taking out the CO gas atmosphere is replaced, in the system adding O-halogenated aromatic hydrocarbon (0.5mmol), trimethylacetic acid (0.5mmol, 51 mg), then add 3 ml toluene, stirring 5 minutes, the reaction is 100 °C oil bath pot reaction 12 hours. After the reaction, in the system by adding 3 ml of saturated ammonium chloride solution quenching reaction, all three times by adding 15 ml of ethyl acetate, the combined organic phase, the dried with anhydrous sodium sulfate, column chromatography, to obtain the product (breakdown of the 2). With palladium diacetate, caesium carbonate, tricyclohexylphosphine, Trimethylacetic acid in toluene, Time= 12h, T= 100 °C , Schlenk technique, Inert atmosphere, Glovebox Patent; Nanjing University of Posts and Telecommunications; Song Juan; Wei Fuliang; Sun Wei; Li Yali; Xie Linghai; (32 pag.); CN104844400; (2017); (B) Chinese View in Reaxys O Br

HO B

Rx-ID: 39990311 View in Reaxys 23/827 Yield 76 %

76 %

18 : Embodiment 17 - 21: in addition to the use of different O-halogenated aromatic outside, other reaction conditions are the same, as follows: Under the protection of nitrogen, in a Schlenk reaction tube adding phenyl boronic acid (0.6mmol, 73.2 mg), cesium carbonate (1.5mmol, 489 mg), palladium acetate (0.025mmol, 5.6 mg), and placed in the glove box, adding three-ring hexyl phosphine (0.05mmol, 14 mg), after taking out the CO gas atmosphere is replaced, in the system adding O-halogenated aromatic hydrocarbon (0.5mmol), trimethylacetic acid (0.5mmol, 51 mg), then add 3 ml toluene, stirring 5 minutes, the reaction is 100 °C oil bath pot reaction 12 hours. After the reaction, in the system by adding 3 ml of saturated ammonium chloride solution quenching reaction, all three times by adding 15 ml of ethyl acetate, the combined organic phase, the dried with anhydrous sodium sulfate, column chromatography, to obtain the product (breakdown of the 2). With palladium diacetate, caesium carbonate, tricyclohexylphosphine, Trimethylacetic acid in toluene, Time= 12h, T= 100 °C , Schlenk technique, Inert atmosphere, Glovebox Patent; Nanjing University of Posts and Telecommunications; Song Juan; Wei Fuliang; Sun Wei; Li Yali; Xie Linghai; (32 pag.); CN104844400; (2017); (B) Chinese View in Reaxys

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NH 2

Rx-ID: 43712915 View in Reaxys 24/827 Yield

Conditions & References Reaction Steps: 3 1.1: dichloromethane / 12 h / Molecular sieve 2.1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 2.2: 24 h / 110 °C 3.1: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water, 2.2: |AzaCope Rearrangement Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1.1: dichloromethane / 12 h / Molecular sieve 2.1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 2.2: 24 h / 110 °C 3.1: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water, 2.2: |AzaCope Rearrangement Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 0.5 h / 0 °C 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 0.55 h / 0 °C / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 28 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 1 h / 0 - 25 °C / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube

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3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 3: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 3: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 3: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 3: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 3: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water

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Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 3: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

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Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 28 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)N,N’-di-(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite / tetrahydrofuran / 24 h / 30 °C / Inert atmosphere; Sealed tube 3: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)-N,N’-di(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite, 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)N,N’-di-(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite / tetrahydrofuran / 24 h / 30 °C / Inert atmosphere; Sealed tube 3: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)-N,N’-di(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite, 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)N,N’-di-(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite / tetrahydrofuran / 24 h / 30 °C / Inert atmosphere; Sealed tube 3: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)-N,N’-di(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite, 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 3: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3

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1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C

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With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 50 °C / Inert atmosphere; Sealed tube 3: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 50 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 50 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 50 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 36 h / 28 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water

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Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,4-diaza-bicyclo[2.2.2]octane; O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)-N,N’-di(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite / acetonitrile / 24 h / 30 °C / Inert atmosphere; Sealed tube 3: hydrogenchloride / water; tetrahydrofuran / 20 °C With 1,4-diaza-bicyclo[2.2.2]octane, hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)-N,N’-di-(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite in tetrahydrofuran, dichloromethane, water, acetonitrile Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; (3,5-dioxa-4-phospha-cyclohepta[2,1a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 3 1: dichloromethane / 6 h / 20 °C / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 50 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys Reaction Steps: 2 1: oxygen / toluene / Reflux 2: water With water, oxygen in toluene Ghosh, Santanu; Jana, Chandan K.; Organic Letters; vol. 18; nb. 22; (2016); p. 5788 - 5791 View in Reaxys Stage 1: With diethylazodicarboxylate in acetonitrile, Time= 1h Stage 2: With hydrogenchloride, water in acetonitrile, Time= 2h Wang; Piva De Silva; Wiebe; Fehr; Davis; RSC Advances; vol. 7; nb. 77; (2017); p. 48848 - 48852 View in Reaxys O

Rx-ID: 45103750 View in Reaxys 25/827 Yield

Conditions & References Reaction Steps: 2

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1: selenium(IV) oxide; pyridine / 80 °C 2: dipotassium peroxodisulfate / water; acetonitrile / 24 h / 80 °C / Sealed tube With pyridine, selenium(IV) oxide, dipotassium peroxodisulfate in water, acetonitrile Laha, Joydev K.; Patel, Ketul V.; Dubey, Gurudutt; Jethava, Krupal P.; Organic and Biomolecular Chemistry; vol. 15; nb. 10; (2017); p. 2199 - 2210 View in Reaxys

O OH

Rx-ID: 45103752 View in Reaxys 26/827 Yield

Conditions & References

72 %

With dipotassium peroxodisulfate in water, acetonitrile, Time= 24h, T= 80 °C , Sealed tube, Reagent/catalyst, Solvent, Temperature, regioselective reaction Laha, Joydev K.; Patel, Ketul V.; Dubey, Gurudutt; Jethava, Krupal P.; Organic and Biomolecular Chemistry; vol. 15; nb. 10; (2017); p. 2199 - 2210 View in Reaxys OH

O B HO

Rx-ID: 45103787 View in Reaxys 27/827 Yield

Conditions & References Reaction Steps: 3 1: tris-(dibenzylideneacetone)dipalladium(0); XPhos; potassium phosphate monohydrate / 1,4-dioxane; water / 12 h / 100 °C / Sealed tube; Inert atmosphere 2: selenium(IV) oxide; pyridine / 80 °C 3: dipotassium peroxodisulfate / water; acetonitrile / 24 h / 80 °C / Sealed tube With pyridine, selenium(IV) oxide, tris-(dibenzylideneacetone)dipalladium(0), dipotassium peroxodisulfate, potassium phosphate monohydrate, XPhos in 1,4-dioxane, water, acetonitrile Laha, Joydev K.; Patel, Ketul V.; Dubey, Gurudutt; Jethava, Krupal P.; Organic and Biomolecular Chemistry; vol. 15; nb. 10; (2017); p. 2199 - 2210 View in Reaxys O

Rx-ID: 45340781 View in Reaxys 28/827 Yield 25 mg

Conditions & References With tert.-butylhydroperoxide, tetra-(n-butyl)ammonium iodide in decane, 1,2-dichloro-ethane, Time= 16h, T= 90 °C , Sealed tube Laha, Joydev K.; Jethava, Krupal P.; Patel, Sagarkumar; Patel, Ketul V.; Journal of Organic Chemistry; vol. 82; nb. 1; (2017); p. 76 - 85 View in Reaxys

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O H

Rx-ID: 45340783 View in Reaxys 29/827 Yield

Conditions & References

15 %

With tert.-butylhydroperoxide, tetra-(n-butyl)ammonium iodide in decane, 1,2-dichloro-ethane, Time= 16h, T= 90 °C , Sealed tube Laha, Joydev K.; Jethava, Krupal P.; Patel, Sagarkumar; Patel, Ketul V.; Journal of Organic Chemistry; vol. 82; nb. 1; (2017); p. 76 - 85 View in Reaxys O

Rx-ID: 45340789 View in Reaxys 30/827 Yield

Conditions & References

53 %

With tert.-butylhydroperoxide, tetra-(n-butyl)ammonium iodide in decane, 1,2-dichloro-ethane, Time= 24h, T= 100 °C , Sealed tube Laha, Joydev K.; Jethava, Krupal P.; Patel, Sagarkumar; Patel, Ketul V.; Journal of Organic Chemistry; vol. 82; nb. 1; (2017); p. 76 - 85 View in Reaxys O Br

Rx-ID: 45340841 View in Reaxys 31/827 Yield

Conditions & References Reaction Steps: 2 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 70 °C 2: tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide / 1,2-dichloro-ethane; decane / 16 h / 90 °C / Sealed tube With tert.-butylhydroperoxide, tetrakis(triphenylphosphine) palladium(0), tetra-(n-butyl)ammonium iodide, sodium carbonate in tetrahydrofuran, decane, water, 1,2-dichloro-ethane, 1: |Suzuki Coupling Laha, Joydev K.; Jethava, Krupal P.; Patel, Sagarkumar; Patel, Ketul V.; Journal of Organic Chemistry; vol. 82; nb. 1; (2017); p. 76 - 85 View in Reaxys O

O Br

Rx-ID: 45340843 View in Reaxys 32/827 Yield

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Laha, Joydev K.; Jethava, Krupal P.; Patel, Sagarkumar; Patel, Ketul V.; Journal of Organic Chemistry; vol. 82; nb. 1; (2017); p. 76 - 85 View in Reaxys O

O H

HO B HO

Rx-ID: 45340869 View in Reaxys 33/827 Yield

Rx-ID: 45340871 View in Reaxys 34/827 Yield

Conditions & References Reaction Steps: 2 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 70 °C 2: tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide / 1,2-dichloro-ethane; decane / 24 h / 100 °C / Sealed tube With tert.-butylhydroperoxide, tetrakis(triphenylphosphine) palladium(0), tetra-(n-butyl)ammonium iodide, sodium carbonate in tetrahydrofuran, decane, water, 1,2-dichloro-ethane, 1: |Suzuki Coupling Laha, Joydev K.; Jethava, Krupal P.; Patel, Sagarkumar; Patel, Ketul V.; Journal of Organic Chemistry; vol. 82; nb. 1; (2017); p. 76 - 85 View in Reaxys O O

–O

S O

I+

F F F

Rx-ID: 46735014 View in Reaxys 35/827 Yield 97 %

Conditions & References With 1,10-Phenanthroline, palladium diacetate in 1,2-dichloro-ethane, Time= 8h, T= 120 °C , p= 760.051Torr , Reagent/catalyst, Solvent, Temperature Liu, Li; Qiang, Jian; Bai, Shuhua; Li, Yang; Miao, Chunbao; Li, Jian; Applied Organometallic Chemistry; vol. 31; nb. 12; (2017); Art.No: E3817 View in Reaxys

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O N O

Rx-ID: 46773307 View in Reaxys 36/827 Yield

Conditions & References

68 %

With fac-tris(2-phenylpyridinato-N,C2')iridium(III) in N,N-dimethyl-formamide, Time= 24h, T= 25 °C , Irradiation Ruzi, Rehanguli; Zhang, Muliang; Ablajan, Keyume; Zhu, Chengjian; Journal of Organic Chemistry; vol. 82; nb. 23; (2017); p. 12834 - 12839 View in Reaxys

O S HN O

Rx-ID: 46792659 View in Reaxys 37/827 Yield

Conditions & References

94 %

Stage 1: With tetrabutyl ammonium fluoride in tetrahydrofuran Stage 2: With hydrogenchloride Chen, Lei; Teng, Wei; Geng, Xin-Le; Zhu, Yi-Fan; Guan, Yong-Hong; Fan, Xiaohui; Applied Organometallic Chemistry; vol. 31; nb. 12; (2017); Art.No: E3863 View in Reaxys

O S

N O

Rx-ID: 46792671 View in Reaxys 38/827 Yield

Conditions & References Reaction Steps: 3 1: water; hydrogenchloride / nitromethane / 10 h / 100 °C 2: aluminum (III) chloride / nitromethane / 8 h / 100 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran With hydrogenchloride, aluminum (III) chloride, tetrabutyl ammonium fluoride, water in tetrahydrofuran, nitromethane

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Chen, Lei; Teng, Wei; Geng, Xin-Le; Zhu, Yi-Fan; Guan, Yong-Hong; Fan, Xiaohui; Applied Organometallic Chemistry; vol. 31; nb. 12; (2017); Art.No: E3863 View in Reaxys -1 (v4)

F B FF

O N+

O–

N+

Rx-ID: 47209091 View in Reaxys 39/827 Yield

Conditions & References General procedure for product analysis of the dediazoniation of diazonium salts in ionic liquid General procedure: The diazonium tetrafluoroborates (10–20 mg) were dissolved in ionic liquids (0.4 mL). The solution was heated using the conditions shown in Table 1. The ionic liquids were extracted with hexane. After removal of the solvent, the residues were analyzed by NMR, and the product distributions are summarized in Table 1. Compounds 2a,22 2b,23 2c,24 2d,23 2e,22 3a,25 3d,26 3e,27 and 3f27 were identified by comparing their NMR spectra with those reported in the literature. The isomers ArOSO(CF3)(NTf) (4a-4f) and ArNTf2 (5a-5f) were attempted to be purified with SiO2 column chromatography using hexaneCH2Cl2 or hexane-ether as an eluent. However, they could not be separated by chromatography. , Time= 6h, T= 50 °C , Overall yield = 79 percentSpectr. Okazaki, Takao; Yamamoto, Hiroyuki; Kitagawa, Toshikazu; Arkivoc; vol. 2018; nb. 2; (2017); p. 50 - 59 View in Reaxys -1 (v4)

B FF

O N

OO S N–

N+

O S

F O

N+

O O

S F

Rx-ID: 47209092 View in Reaxys 40/827 Yield

Conditions & References General procedure for product analysis of the dediazoniation of diazonium salts in ionic liquid General procedure: The diazonium tetrafluoroborates (10–20 mg) were dissolved in ionic liquids (0.4 mL). The solution was heated using the conditions shown in Table 1. The ionic liquids were extracted with hexane. After removal of the solvent, the residues were analyzed by NMR, and the product distributions are summarized in Table 1. Compounds 2a,22 2b,23 2c,24 2d,23 2e,22 3a,25 3d,26 3e,27 and 3f27 were identified by comparing their NMR spectra with those reported in the literature. The isomers ArOSO(CF3)(NTf) (4a-4f) and ArNTf2 (5a-5f) were attempted to be purified with SiO2 column chromatography using hexaneCH2Cl2 or hexane-ether as an eluent. However, they could not be separated by chromatography. , Time= 6h, T= 50 °C , Overall yield = 91 percentSpectr. Okazaki, Takao; Yamamoto, Hiroyuki; Kitagawa, Toshikazu; Arkivoc; vol. 2018; nb. 2; (2017); p. 50 - 59 View in Reaxys F

Rx-ID: 365400 View in Reaxys 41/827 Yield 80 %

Conditions & References With alumina, T= 30 - 250 °C , Inert atmosphere Papaianina; Amsharov; Chemical Communications; vol. 52; nb. 7; (2016); p. 1505 - 1508 View in Reaxys With sulfuric acid

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Pettit; Tatlow; Journal of the Chemical Society; (1954); p. 1071,1073 View in Reaxys

O O

Rx-ID: 736478 View in Reaxys 42/827 Yield 88 %

Conditions & References With dihydrogen peroxide, iodine in water, acetonitrile, Time= 48h, T= 20 °C Ferreira, Sabrina B.; Kaiser, Carlos R.; Ferreira, Vitor F.; Synlett; nb. 17; (2008); p. 2625 - 2628 View in Reaxys

78%

With oxygen, copper(II) oxide, silver(l) oxide, sodium t-butanolate in N,N-dimethyl-formamide, T= 20 - 150 °C , Schlenk technique, chemoselective reaction Wang, Xing; Chen, Rui-Xi; Wei, Zeng-Feng; Zhang, Chen-Yang; Tu, Hai-Yang; Zhang, Ai-Dong; Journal of Organic Chemistry; vol. 81; nb. 1; (2016); p. 238 - 249 View in Reaxys

75%

With potassium phosphate, oxygen, copper diacetate, p-toluidine, sodium sulfate in dimethyl sulfoxide, Time= 6h, T= 140 °C , Sealed tube Maji, Arun; Rana, Sujoy; Akanksha; Maiti, Debabrata; Angewandte Chemie - International Edition; vol. 53; nb. 9; (2014); p. 2428 - 2432; Angew. Chem.; vol. 126; nb. 9; (2014); p. 2460 - 2464,5 View in Reaxys With alkaline potassium permanganate Anschuetz; Japp; Chemische Berichte; vol. 11; (1878); p. 213 View in Reaxys With sodium hydroxide, air Anschuetz; Japp; Chemische Berichte; vol. 11; (1878); p. 213 View in Reaxys With lead(II) oxide Wittenberg; Meyer,V.; Chemische Berichte; vol. 16; (1883); p. 502 View in Reaxys With calcium oxide, bei der Destillation Anschuetz; Schultz; Chemische Berichte; vol. 9; (1876); p. 1402; Justus Liebigs Annalen der Chemie; vol. 196; (1879); p. 44 View in Reaxys Reaction Steps: 3 1: zinc dust 2: chromic acid mixture 3: burnt/baked lime/chalk/ With chromic acid, calcium carbonate, calcium oxide, zinc Fittig; Ostermayer; Justus Liebigs Annalen der Chemie; vol. 166; (1873); p. 363 View in Reaxys

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OH N

Rx-ID: 1991825 View in Reaxys 43/827 Yield 98 %

Conditions & References With 1-benzyl-4-aza-1-azoniabiyclo<2.2.2>octane peroxodisulfate in acetonitrile, Time= 0.25h, Heating Hajipour, Abdol Reza; Baltork, Iraj Mohammadpoor; Kianfar, Godaraz; Bulletin of the Chemical Society of Japan; vol. 71; nb. 11; (1998); p. 2655 - 2659 View in Reaxys

98 %

With 1-benzyl-4-aza-1-azoniabiyclo<2.2.2>octane peroxodisulfate in acetonitrile, Time= 0.25h, Heating, Oxidation Hajipour; Mohammadpoor-Baltork; Kianfar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 38; nb. 2; (1999); p. 221 - 224 View in Reaxys

98 %

General experimental procedure for deoximation to the corresponding carbonyl compounds General procedure: Oximes (1.0 mmol), Amberlyst-15 (0.02 g), FPA53-NO2(0.02 g), and solvent (1.5 mL) were introduced into a 25-cm-high, 90-mL autoclave with a glass tube inside equipped with magnetic stirrer (Scheme 2). Then the autoclave was charged with oxygen to 0.1 MPa. The reaction mixture was stirred at desirable temperature for special time. Progress of the reaction was monitored by thin-layer chromatography (TLC) or gas chromatography (GC). After the reaction, the resin (Amberlyst-15 and FPA53-NO2) was separated from the reaction mixture by filtration and extracted with 3 mL CH3CN (2 1.5 ml). The solvent was removed under reduced pressure. The residue was further purified by column chromatography on silica gel (300 mesh) with hexane/ethyl acetate to give the corresponding carbonyl compounds. With water, oxygen in acetonitrile, Time= 2h, T= 60 °C , p= 760.051Torr , Autoclave, Green chemistry Guo, Shu; Zeng, Renyou; Li, Caiye; Synthetic Communications; vol. 46; nb. 17; (2016); p. 1446 - 1453 View in Reaxys

97 %

With quinolinium dichromate(VI) in acetonitrile, Time= 2.5h, Heating Sadeghi; Mohammadpoor-Baltork; Azarm; Mazidi; Synthetic Communications; vol. 31; nb. 3; (2001); p. 435 - 438 View in Reaxys

96 %

With aluminium trichloride, 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate, Time= 0.0125h, T= 20 °C Hajipour; Mallakpour; Mohammadpoor-Baltork; Khoee; Synthetic Communications; vol. 31; nb. 8; (2001); p. 1187 - 1194 View in Reaxys

96 %

With 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate in dichloromethane, Time= 0.0125h, Irradiation Hajipour; Mallakpour; Khoee; Synthetic Communications; vol. 32; nb. 1; (2002); p. 9 - 15 View in Reaxys

96 %

With benzyltriphenylphosphonium dichromate, silica gel, Time= 0.0666667h Hajipour; Mallakpour; Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals; vol. 356; (2001); p. 371 - 387 View in Reaxys

95 %

With bismuth(III) chloride, benzyltriphenylphosphonium peroxymonosulfate in acetonitrile, Time= 0.75h, Heating Hajipour; Mallakpour; Baltork; Adibi; Synthetic Communications; vol. 31; nb. 22; (2001); p. 3401 - 3409 View in Reaxys

95 %

With bismuth(III) chloride, benzyltriphenylphosphonium peroxymonosulfate in dichloromethane, Time= 0.0416667h, microwave irradiation Hajipour, Abdol R.; Mallakpour, Shadpour E.; Mohammadpoor-Baltork, Iraj; Adibi, Hadi; Monatshefte fur Chemie; vol. 134; nb. 1; (2003); p. 45 - 49

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View in Reaxys 95 %

With aluminium trichloride, benzyltriphenylphosphonium chlorochromate in acetonitrile, Time= 0.75h, Heating Hajipour, Abdol Reza; Mallakpour, Shadpour E.; Mohammadpoor-Baltork, Iraj; Backnejad, Hossein; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 41; nb. 8; (2002); p. 1740 - 1743 View in Reaxys

94 %

With oxygen, [(4'-(p-MeOC6H4)trpy)-Pt-(4-(C6H5-CC)-C6H4-CC)]ClO4 in acetonitrile, Time= 1h, Irradiation Yang, Yue; Zhang, Dong; Wu, Li-Zhu; Chen, Bin; Zhang, Li-Ping; Tung, Chen-Ho; Journal of Organic Chemistry; vol. 69; nb. 14; (2004); p. 4788 - 4791 View in Reaxys

93 %

With potassium permanganate, tungstate sulfuric acid in dichloromethane, water, Time= 0.166667h, T= 20 °C Karami, Bahador; Montazerozohori, Morteza; Molecules; vol. 11; nb. 9; (2006); p. 720 - 725 View in Reaxys

92 %

With bismuth(III) nitrate, silica gel in tetrahydrofuran, water, Time= 10h, Heating Samajdar, Susanta; Basu, Manas K.; Becker, Frederick F.; Banik, Bimal K.; Synthetic Communications; vol. 32; nb. 13; (2002); p. 1917 - 1921 View in Reaxys

88 %

With benzyltriphenylphosphonium peroxodisulfate in acetonitrile, Time= 0.5h, Heating, Oxidation Mohammadpoor-Baltork, Iraj; Hajipour, Abdol Reza; Mohammadi, Hasan; Bulletin of the Chemical Society of Japan; vol. 71; nb. 7; (1998); p. 1649 - 1653 View in Reaxys

87 %

With sodium hypochlorite in acetonitrile, Time= 0.25h, Ambient temperature Khurana, Jitender Mohan; Ray, Abhijit; Sahoo, Prabhat Kumar; Bulletin of the Chemical Society of Japan; vol. 67; nb. 4; (1994); p. 1091 - 1093 View in Reaxys

87 %

With 3-carboxypyridinium chlorochromate in dichloromethane, Time= 1.5h, Heating Baltork; Pouranshirvani; Synthetic Communications; vol. 26; nb. 1; (1996); p. 1 - 7 View in Reaxys

87 %

With phosphotungstic acid, ferric nitrate, Time= 1h, T= 40 - 45 °C Firouzabadi, Habib; Iranpoor, Nasser; Amani, Kamal; Synthetic Communications; vol. 34; nb. 19; (2004); p. 3587 - 3593 View in Reaxys

78 %

With hexamethylenetetramine, water, Time= 0.00694444h, microwave irradiation Karchaudhuri, Nilay; De, Aparna; Mitra, Alok Kumar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 42; nb. 6; (2003); p. 1537 - 1539 View in Reaxys

75 %

With aluminium trichloride, butyltriphenylphosphonium dichromate in chloroform, Time= 0.75h, Heating, Oxidation Baltork, I. Mohammadpoor; Sadeghi, M. M.; Mahmoodi, N.; Kharamesh, B.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 36; nb. 5; (1997); p. 438 - 441 View in Reaxys

71 %

With dihydrogen peroxide, phosphotungstic acid in various solvent(s), Time= 6h, T= 20 °C , Product distribution, Further Variations: Catalysts Jain, Nidhi; Kumar, Anil; Chauhan, Shive M.S.; Tetrahedron Letters; vol. 46; nb. 15; (2005); p. 2599 - 2602 View in Reaxys

66 % Chromat.

With chloranil in acetonitrile, Time= 1h, Irradiation

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De Lijser, H. J. Peter; Fardoun, Fadia H.; Sawyer, Jody R.; Quant, Michelle; Organic Letters; vol. 4; nb. 14; (2002); p. 2325 - 2328 View in Reaxys O

Rx-ID: 8677955 View in Reaxys 44/827 Yield 100 %

Conditions & References With cesium pivalate, palladium(0)bis(tricyclohexylphosphine) in N,N-dimethyl-formamide, Time= 7h, T= 110 °C , p= 760.051Torr , Carbonylation, cyclization Campo; Larock; Organic letters; vol. 2; nb. 23; (2000); p. 3675 - 3677 View in Reaxys

100 %

With tristricyclohexylphosphine palladium(0), cesium pivalate in N,N-dimethyl-formamide, Time= 7h, T= 110 °C , p= 760.051Torr Campo, Marino A.; Larock, Richard C.; Journal of Organic Chemistry; vol. 67; nb. 16; (2002); p. 5616 - 5620 View in Reaxys

86 %

General procedure for the Pd-catalyzed cyclocarbonylation of 2-bromobiphenyl withparaformaldehyde (Table 1 entry 14). General procedure: A 10-mL dry sealed-tube equipped with a stir bar was charged with Pd(OAc)2 (6.74 mg, 0.03mmol), PCy3·HBF4 (33.14 mg, 0.09 mmol), (CH2O)n (180.18 mg, 6.0 mmol), Na2CO3 (0.6 mmol,63.59 mg), and MgSO4 (70 mg) under a N2 flow. 2.0 mL of toluene, 1a (0.3 mmol, 69.93 mg), andPivOH (0.09 mmol, 10 L) were then added. After degassing the reaction mixture by the freezepump-thaw method three times, the tube was filled with N2. The mixture was then placed in an oilbath preheated at 110 °C for 20 h. After cooling to room temperature, the resulting solution wasfiltered through a celite pad, and the filtrate was concentrated in vacuo. The resulting crude productwas purified by flash column chromatography on silicagel to afford 2a (hexane/AcOEt = 40/1) in75percent yield as a yellow solid. With palladium diacetate, sodium carbonate, magnesium sulfate, tricyclohexylphosphine tetrafluoroborate, Trimethylacetic acid in toluene, Time= 25h, T= 110 °C , p= 760.051Torr , Sealed tube, Inert atmosphere Furusawa, Takuma; Morimoto, Tsumoru; Oka, Nagato; Tanimoto, Hiroki; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi; Chemistry Letters; vol. 45; nb. 4; (2016); p. 406 - 408 View in Reaxys NH

Rx-ID: 9189229 View in Reaxys 45/827 Yield

Conditions & References With hydrogenchloride, water, T= 25 °C , pH= 4, Kinetics, Further Variations: Reagents, pH-values Courtney, Michael C.; MacCormack, Aoife C.; More O'Ferrall, Rory A.; Journal of Physical Organic Chemistry; vol. 15; nb. 8; (2002); p. 529 - 539 View in Reaxys With water Ghosh, Santanu; Jana, Chandan K.; Organic Letters; vol. 18; nb. 22; (2016); p. 5788 - 5791 View in Reaxys

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Rx-ID: 9314235 View in Reaxys 46/827 Yield

Conditions & References

86 %

With sodium bromate, 1-n-butyl-3-methylimidazolim bromide, Time= 140h, T= 70 °C Shaabani, Ahmad; Farhangi, Elham; Rahmati, Abbas; Monatshefte fur Chemie; vol. 139; nb. 8; (2008); p. 905 - 908 View in Reaxys

63 %

With molecular sieve, pyridinium chlorochromate in dichloromethane, Time= 12h, T= 20 °C Fernandes, Rodney A.; Kumar, Pradeep; Tetrahedron Letters; vol. 44; nb. 6; (2003); p. 1275 - 1278 View in Reaxys

87 %Chromat.

With oxygen, potassium carbonate in o-xylene, Time= 9h, T= 20 °C Shaabani, Ahmad; Hezarkhani, Zeinab; Badali, Elham; RSC Advances; vol. 5; nb. 76; (2015); p. 61759 - 61767 View in Reaxys 3.3. Oxidation of alcohols; General procedure General procedure: In a typical reaction, an alcohol (1.0 mmol) was added to a twoneckedflask containing MnO2silk (0.09 g, 10 molpercent of MnO2),K2CO3 (0.50 mmol), and o-xylene (5.0 mL) and stirred under airblowing at room temperature. The progress of the reaction was followedby TLC and GC method. After completion of reaction and filtrationof mixture, the filtrate was analyzed by GC method. With potassium carbonate in o-xylene, Time= 14h, T= 20 °C Shaabani, Ahmad; Hezarkhani, Zeinab; Badali, Elham; Polyhedron; vol. 107; (2016); p. 176 - 182 View in Reaxys

-1

N N

(v4)

(v8)

(v4) O

H O

PO O P

(v4) Ru 2+

(v5) C (v5)(v4) (v5) (v5)

–

(v4)

-1

(v4)

(v4) (v4)

HN NH O PO (v9) (v4) O Ru 2+ P – (v4) (v5) (v5)C (v4) (v5) (v5)

Rx-ID: 39799558 View in Reaxys 47/827 Yield

Conditions & References in dichloromethane, Time= 24h, Inert atmosphere Albertin, Gabriele; Antoniutti, Stefano; Botter, Alessandra; Castro, Jesús; Inorganic Chemistry; vol. 54; nb. 5; (2015); p. 2091 - 2093 View in Reaxys in dichloromethane, Time= 48h, Inert atmosphere Albertin, Gabriele; Antoniutti, Stefano; Bortoluzzi, Marco; Botter, Alessandra; Castro, Jesús; Inorganic Chemistry; vol. 55; nb. 11; (2016); p. 5592 - 5602 View in Reaxys

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Rx-ID: 41656547 View in Reaxys 48/827 Yield

Conditions & References 10 : 4.3. General procedure for the target compounds 3 General procedure: To a stirred solution of pyrazolones 2a–c (1.0 mmol) or pyrazol-5-thiones 2d or 2e (1.0 mmol) and t-BuOK (1.0 mmol, 112 mg) in DMSO (4 mL), gem-difluoroalkenes 1a–o (0.5 mmol) were added. The mixture was then stirred at 60°C for 24 h under an argon atmosphere. The progress of the reaction was monitored by TLC. After the completion of reaction, the mixture was extracted with H2O (20 mL) and ethyl acetate (3×20 mL). The combined organic layer was washed with brine, then dried over anhydrous Na2SO4, filtered, and concentrated under vacuum. The crude residue was then purified by column chromatography on silica gel using n-hexane/ethyl acetate mixture (40/1 to 10/1) as the eluent to afford pure target compound 3. With potassium tert-butylate, 3-methyl-1-phenylpyrazolin-5-(4H)-one in dimethyl sulfoxide, Time= 24h, T= 60 °C , Inert atmosphere, Reagent/catalyst Huang, Tao; Zhao, Xianghu; Ji, Xinfei; Wu, Wei; Cao, Song; Journal of Fluorine Chemistry; vol. 182; (2016); p. 61 - 68 View in Reaxys OH

Rx-ID: 41829441 View in Reaxys 49/827 Yield

Conditions & References

20 %, 50 %

Electroanalytical and electrolysis instrumentation, experimentaltechniques and reagents 100 mg of 1 was electrolyzed in MeCN at the potential2.6 Vvs SCE. After consumption of one mole equivalents of charge theelectrolysis was stopped and catholyte was exposed to air tooxidize 32 and the solvent was evaporated. Thin-layer chroma-tography on silica with hexane-ethyl acetate 12:1 as eluentrevealed the presence in catholyte of two products: 2(Rf, 2 = 0.76) and 3 (Rf, 3 = 0.40). No spot corresponding to 1(Rf, 1 = 0.13) was observed. The products separation by columnchromatography on silica (0.04-0.063 mm) with hexane-ethylacetate 12:1 as eluent gave 3 in 50percent yield and 2 in 20percent. Intenselycolored layer of the insoluble in polar solvent material at the top ofthe column indicated the formation of the resins. The molecularion peaks in mass spectra of the isolated compounds are 166 and180 m/z, i.e. identical to those in spectra of 2 and 3. in acetonitrile, Electrolysis Mendkovich, Andrey S.; Syroeshkin, Mikhail A.; Nasybullina, Darya V.; Mikhailov, Mikhail N.; Gultyai, Vadim P.; Elinson, Mikhail N.; Rusakov, Alexander I.; Electrochimica Acta; vol. 191; (2016); p. 962 - 973 View in Reaxys O

Br F F F

Rx-ID: 41878036 View in Reaxys 50/827 Yield

Conditions & References Reaction Steps: 2 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / methanol; toluene / 12 h / Inert atmosphere; Reflux 2: alumina / 30 - 250 °C / Inert atmosphere With tetrakis(triphenylphosphine) palladium(0), alumina, potassium carbonate in methanol, toluene Papaianina; Amsharov; Chemical Communications; vol. 52; nb. 7; (2016); p. 1505 - 1508 View in Reaxys

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O O

Rx-ID: 42200151 View in Reaxys 51/827 Yield

Conditions & References

82 %

With sodium persulfate, (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid, trifluorormethanesulfonic acid, palladium diacetate in dimethyl sulfoxide, Time= 24h, T= 80 °C , Schlenk technique, Reagent/catalyst, Temperature, Concentration Sun, Denan; Li, Bijin; Lan, Jingbo; Huang, Quan; You, Jingsong; Chemical Communications; vol. 52; nb. 18; (2016); p. 3635 - 3638 View in Reaxys O

Rx-ID: 42800905 View in Reaxys 52/827 Yield

Conditions & References

75 %

General procedure for the Pd-catalyzed cyclocarbonylation of 2-bromobiphenyl withparaformaldehyde (Table 1 entry 14). General procedure: A 10-mL dry sealed-tube equipped with a stir bar was charged with Pd(OAc)2 (6.74 mg, 0.03mmol), PCy3·HBF4 (33.14 mg, 0.09 mmol), (CH2O)n (180.18 mg, 6.0 mmol), Na2CO3 (0.6 mmol,63.59 mg), and MgSO4 (70 mg) under a N2 flow. 2.0 mL of toluene, 1a (0.3 mmol, 69.93 mg), andPivOH (0.09 mmol, 10 L) were then added. After degassing the reaction mixture by the freezepump-thaw method three times, the tube was filled with N2. The mixture was then placed in an oilbath preheated at 110 °C for 20 h. After cooling to room temperature, the resulting solution wasfiltered through a celite pad, and the filtrate was concentrated in vacuo. The resulting crude productwas purified by flash column chromatography on silicagel to afford 2a (hexane/AcOEt = 40/1) in75percent yield as a yellow solid. With palladium diacetate, sodium carbonate, magnesium sulfate, tricyclohexylphosphine tetrafluoroborate, Trimethylacetic acid in toluene, Time= 20h, T= 110 °C , Sealed tube, Inert atmosphere, Reagent/catalyst, Solvent Furusawa, Takuma; Morimoto, Tsumoru; Oka, Nagato; Tanimoto, Hiroki; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi; Chemistry Letters; vol. 45; nb. 4; (2016); p. 406 - 408 View in Reaxys O

Rx-ID: 42800906 View in Reaxys 53/827 Yield 65 %, 12 %

Conditions & References General procedure for the Pd-catalyzed cyclocarbonylation of 2-bromobiphenyl withparaformaldehyde (Table 1 entry 14). General procedure: A 10-mL dry sealed-tube equipped with a stir bar was charged with Pd(OAc)2 (6.74 mg, 0.03mmol), PCy3·HBF4 (33.14 mg, 0.09 mmol), (CH2O)n (180.18 mg, 6.0 mmol), Na2CO3 (0.6 mmol,63.59 mg), and MgSO4 (70 mg) under a N2 flow. 2.0 mL of toluene, 1a (0.3 mmol, 69.93 mg), andPivOH (0.09 mmol, 10 L) were then added. After degassing the reaction mixture by the freezepump-thaw method three times, the tube was filled with N2. The mixture was then placed in an oilbath preheated at 110 °C for 20 h. After cooling to room temperature, the resulting solution wasfiltered through a celite pad, and the filtrate was concentrated in vacuo. The resulting crude productwas purified by flash column chromatography on silicagel to afford 2a (hexane/AcOEt = 40/1) in75percent yield as a yellow solid. With palladium diacetate, sodium carbonate, magnesium sulfate, tricyclohexylphosphine tetrafluoroborate, Trimethylacetic acid in water, toluene, Time= 20h, T= 110 °C , Sealed tube, Inert atmosphere

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Furusawa, Takuma; Morimoto, Tsumoru; Oka, Nagato; Tanimoto, Hiroki; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi; Chemistry Letters; vol. 45; nb. 4; (2016); p. 406 - 408 View in Reaxys O O O

Rx-ID: 43491878 View in Reaxys 54/827 Yield

Conditions & References

6 %, 44 %

With chloro(1,5-cyclooctadiene)rhodium(I) dimer, 1,3-bis-(diphenylphosphino)propane, sodium pivalate in 5,5-dimethyl-1,3cyclohexadiene, Time= 48h, T= 130 °C , Inert atmosphere Furusawa, Takuma; Morimoto, Tsumoru; Nishiyama, Yasuhiro; Tanimoto, Hiroki; Kakiuchi, Kiyomi; Chemistry - An Asian Journal; vol. 11; nb. 16; (2016); p. 2312 - 2315 View in Reaxys O

O O

Rx-ID: 43491880 View in Reaxys 55/827 Yield

Conditions & References

89 %

With chloro(1,5-cyclooctadiene)rhodium(I) dimer, 1,3-bis-(diphenylphosphino)propane, sodium carbonate in 5,5-dimethyl-1,3cyclohexadiene, Time= 48h, T= 130 °C , Inert atmosphere, Reagent/catalyst Furusawa, Takuma; Morimoto, Tsumoru; Nishiyama, Yasuhiro; Tanimoto, Hiroki; Kakiuchi, Kiyomi; Chemistry - An Asian Journal; vol. 11; nb. 16; (2016); p. 2312 - 2315 View in Reaxys O

O O

I Br

Rx-ID: 43491884 View in Reaxys 56/827 Yield 18 %, 31 %

Conditions & References With chloro(1,5-cyclooctadiene)rhodium(I) dimer, 1,3-bis-(diphenylphosphino)propane, sodium carbonate in 5,5-dimethyl-1,3cyclohexadiene, Time= 48h, T= 150 °C , Inert atmosphere Furusawa, Takuma; Morimoto, Tsumoru; Nishiyama, Yasuhiro; Tanimoto, Hiroki; Kakiuchi, Kiyomi; Chemistry - An Asian Journal; vol. 11; nb. 16; (2016); p. 2312 - 2315 View in Reaxys

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O Cl

NH 2

Rx-ID: 43712827 View in Reaxys 57/827 Yield

Conditions & References With citric acid in tetrahydrofuran, water, Time= 4h, T= 20 °C Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

O N

NH 2

Rx-ID: 43712829 View in Reaxys 58/827 Yield

NH 2

Rx-ID: 43712831 View in Reaxys 59/827 Yield

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O O S N

O O

S N

NH 2

Rx-ID: 43712833 View in Reaxys 60/827 Yield

O O S

N N

O O

N N

NH 2

Rx-ID: 43712835 View in Reaxys 61/827 Yield

Conditions & References With hydrogenchloride in tetrahydrofuran, water, T= 20 °C Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

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Br N

NH 2

Rx-ID: 43712837 View in Reaxys 62/827 Yield

O N

NH 2

Rx-ID: 43712839 View in Reaxys 63/827 Yield

F F

O F

F F F

NH 2

Rx-ID: 43712841 View in Reaxys 64/827 Yield

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O O

NH 2

Rx-ID: 43712844 View in Reaxys 65/827 Yield

N N

NH 2

Rx-ID: 43712846 View in Reaxys 66/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 28 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

O O

O N

NH 2

Rx-ID: 43712849 View in Reaxys 67/827

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Yield

NH 2

Rx-ID: 43712851 View in Reaxys 68/827 Yield

NH 2

Rx-ID: 43712853 View in Reaxys 69/827 Yield

O N

NH 2

Rx-ID: 43712855 View in Reaxys 70/827 Yield

Conditions & References With citric acid in tetrahydrofuran, water, Time= 4h, T= 20 °C

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Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

NH 2

Rx-ID: 43712857 View in Reaxys 71/827 Yield

O N

N NH 2

Rx-ID: 43712859 View in Reaxys 72/827 Yield

S O O

N N

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O S N

NH 2

Rx-ID: 43712861 View in Reaxys 73/827 Yield

S O

O S N N NH 2

Rx-ID: 43712863 View in Reaxys 74/827 Yield

N N

NH 2

Rx-ID: 43712865 View in Reaxys 75/827 Yield

Conditions & References With citric acid in tetrahydrofuran, water, Time= 4h, T= 20 °C

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Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

NH 2

Rx-ID: 43712867 View in Reaxys 76/827 Yield

NH 2

Rx-ID: 43712869 View in Reaxys 77/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 50 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

NH 2

Rx-ID: 43712872 View in Reaxys 78/827

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Yield

NH 2

Rx-ID: 43712878 View in Reaxys 79/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

NH 2

Rx-ID: 43712881 View in Reaxys 80/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

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NH 2

Rx-ID: 43712884 View in Reaxys 81/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys F F F

F F

NH 2

Rx-ID: 43712887 View in Reaxys 82/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

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O N

NH 2

Rx-ID: 43712969 View in Reaxys 83/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

O O

NH 2

Rx-ID: 43712978 View in Reaxys 84/827 Yield

Conditions & References Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

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NH 2

Rx-ID: 43712994 View in Reaxys 85/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys O O S O

N O

S N

NH 2

Rx-ID: 43713025 View in Reaxys 86/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 50 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

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NH 2

Rx-ID: 43713037 View in Reaxys 87/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

O N

Rx-ID: 43713040 View in Reaxys 88/827 Yield

Conditions & References Reaction Steps: 2 1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)N,N’-di-(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite / tetrahydrofuran / 24 h / 30 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)-N,N’-di(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite, 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

NH 2

Rx-ID: 43713043 View in Reaxys 89/827 Yield

Conditions & References Reaction Steps: 2

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1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)N,N’-di-(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite / tetrahydrofuran / 24 h / 30 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)-N,N’-di(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite, 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

NH 2

Rx-ID: 43713046 View in Reaxys 90/827 Yield

Br N

NH 2

Rx-ID: 43713055 View in Reaxys 91/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106

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View in Reaxys O O S

N O

N N

NH 2

Rx-ID: 43713056 View in Reaxys 92/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 50 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

NH 2

Rx-ID: 43713061 View in Reaxys 93/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

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F F

O F F F

NH 2

Rx-ID: 43713064 View in Reaxys 94/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys OH

Rx-ID: 43713132 View in Reaxys 95/827 Yield

Conditions & References Reaction Steps: 3 1: dichloromethane / 12 h / Molecular sieve 2: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 28 °C / Inert atmosphere; Sealed tube 3: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, dichloromethane, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

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O N

NH 2

Rx-ID: 43713148 View in Reaxys 96/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

O N

O O

NH 2

Rx-ID: 43713151 View in Reaxys 97/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106

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View in Reaxys

NH 2

Rx-ID: 43713154 View in Reaxys 98/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

N O

NH 2

Rx-ID: 43713166 View in Reaxys 99/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

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N NH 2

Rx-ID: 43713169 View in Reaxys 100/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys O

Rx-ID: 43713173 View in Reaxys 101/827 Yield

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N N

NH 2

Rx-ID: 43713182 View in Reaxys 102/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

O O O

NH 2

Rx-ID: 43713188 View in Reaxys 103/827 Yield

Conditions & References Reaction Steps: 2 1.1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 1.2: 24 h / 110 °C 2.1: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water, 1.2: |Aza-Cope Rearrangement

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O N

NH 2

Rx-ID: 43713194 View in Reaxys 104/827 Yield

O N

S O

O N

NH 2

Rx-ID: 43713201 View in Reaxys 105/827 Yield

Conditions & References Reaction Steps: 2 1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; (3,5-dioxa-4-phospha-cyclohepta[2,1a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube

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2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

Rx-ID: 43713213 View in Reaxys 106/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

O O S N

O S N

NH 2

Rx-ID: 43713333 View in Reaxys 107/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water

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NH 2

Rx-ID: 43713334 View in Reaxys 108/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

NH 2

Rx-ID: 43713385 View in Reaxys 109/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 50 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106

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View in Reaxys N

NH 2

Rx-ID: 43713509 View in Reaxys 110/827 Yield

NH 2

Rx-ID: 43713511 View in Reaxys 111/827 Yield

Conditions & References Reaction Steps: 2 1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,4-diaza-bicyclo[2.2.2]octane; O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)-N,N’-di(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite / acetonitrile / 24 h / 30 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride / water; tetrahydrofuran / 20 °C With 1,4-diaza-bicyclo[2.2.2]octane, hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, O,O’-(R)-1,1’-(dinaphthyl-2,2’-diyl)-N,N’-di-(R,R)-1-(2-methoxyphenyl)ethylphosphoramidite in tetrahydrofuran, water, acetonitrile Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

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S N

NH 2

Rx-ID: 43713519 View in Reaxys 112/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride / water; tetrahydrofuran / 20 °C With hydrogenchloride, bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

NH 2

Rx-ID: 43713521 View in Reaxys 113/827 Yield

NH 2

Rx-ID: 43713523 View in Reaxys 114/827 Yield

Conditions & References With citric acid in tetrahydrofuran, water, Time= 4h, T= 20 °C

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NH 2

Rx-ID: 43713525 View in Reaxys 115/827 Yield

F F

F F F

NH 2

Rx-ID: 43713527 View in Reaxys 116/827 Yield

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NH 2

Rx-ID: 43713529 View in Reaxys 117/827 Yield

NH 2

Rx-ID: 43713531 View in Reaxys 118/827 Yield

NH 2

Rx-ID: 43713533 View in Reaxys 119/827 Yield

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NH 2

Rx-ID: 43713536 View in Reaxys 120/827 Yield

NH 2

Rx-ID: 43713538 View in Reaxys 121/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 50 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

NH 2

Rx-ID: 43713540 View in Reaxys 122/827

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Yield

N NH 2

Rx-ID: 43713542 View in Reaxys 123/827 Yield

NH 2

Rx-ID: 43713544 View in Reaxys 124/827 Yield

NH 2

Rx-ID: 43713546 View in Reaxys 125/827 Yield

Conditions & References With hydrogenchloride in tetrahydrofuran, water, T= 20 °C

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Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys

NH 2

Rx-ID: 43713550 View in Reaxys 126/827 Yield

NH 2

Rx-ID: 43713552 View in Reaxys 127/827 Yield

N S

NH 2

Rx-ID: 43713554 View in Reaxys 128/827 Yield

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View in Reaxys

O N N N N N

NH 2

Rx-ID: 43713556 View in Reaxys 129/827 Yield

N S

NH 2

Rx-ID: 43713558 View in Reaxys 130/827 Yield

Conditions & References Reaction Steps: 2 1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 36 h / 28 °C / Inert atmosphere; Sealed tube 2: citric acid / water; tetrahydrofuran / 4 h / 20 °C With bis(1,5-cyclooctadiene)diiridium(I) dichloride, 1,8-diazabicyclo[5.4.0]undec-7-ene, citric acid, (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine in tetrahydrofuran, water Liu, Jie; Cao, Chao-Guo; Sun, Hong-Bao; Zhang, Xia; Niu, Dawen; Journal of the American Chemical Society; vol. 138; nb. 40; (2016); p. 13103 - 13106 View in Reaxys O

Rx-ID: 43745271 View in Reaxys 131/827 Yield 93 %

Conditions & References With C31H25N2O3PPdS, potassium hydroxide in methanol, water, Time= 6h, T= 50 °C , Green chemistry, Catalytic behavior, Reagent/catalyst, Solvent, Temperature, regioselective reaction Vignesh, Arumugam; Kaminsky, Werner; Dharmaraj, Nallasamy; ChemCatChem; vol. 8; nb. 20; (2016); p. 3207 - 3212 View in Reaxys

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Rx-ID: 33864215 View in Reaxys 132/827 Yield

Conditions & References

88 %

With palladium diacetate, silver(l) oxide in trifluoroacetic acid, Time= 24h, T= 130 °C , Inert atmosphere Gandeepan, Parthasarathy; Hung, Chen-Hsun; Cheng, Chien-Hong; Chemical Communications; vol. 48; nb. 75; (2012); p. 9379 - 9381 View in Reaxys

85 %

With palladium diacetate, potassium carbonate, trifluoroacetic acid, silver(l) oxide, Time= 24h, T= 140 °C , Schlenk technique, Inert atmosphere, Nazarov Cyclization, Reagent/catalyst, Solvent Li, Hu; Zhu, Ru-Yi; Shi, Wen-Juan; He, Ke-Han; Shi, Zhang-Jie; Organic Letters; vol. 14; nb. 18; (2012); p. 4850 - 4853,4 View in Reaxys

82 %

With trifluoroacetic acid, silver(l) oxide in water, Time= 24h, T= 130 °C , Catalytic behavior, Reagent/catalyst, Solvent, chemoselective reaction Kishore, Ramineni; Shanthi Priya, Samudrala; Sudhakar, Medak; Venu, Boosa; Venugopal, Akula; Yadav, Jagjit; Kantam, Mannepalli Lakshmi; Catalysis Science and Technology; vol. 5; nb. 6; (2015); p. 3363 - 3367 View in Reaxys

O O

Rx-ID: 39266311 View in Reaxys 133/827 Yield

Conditions & References

72 %

General procedure General procedure: mixture of Er(OTf)3 (0.0614 g, 0.1 mmol), anisole(0.5407 g, 5 mmol) and benzoic acid (0.1221 g, 1 mmol) was heated undermicrowave irradiation at 220 C for 30 min in a CEM Discover apparatus. Afterbeing cooled, the mixture was extracted with CH2Cl2 (3 15 mL). The organiclayer was decanted, washed with H2O (10 mL), aqueous NaHCO3 (2 20 mL),and brine (10 mL), and dried over MgSO4. The solvent was removed on a rotaryevaporator. The crude product was purified by flash chromatography (nhexane,then 10percent EtOAc in n-hexane) to give 4-methoxybenzophenone(0.153 g, 72percent yield). The purity and identity of the product were confirmedby GC-FID, and from GC–MS spectra which were compared with the spectra inthe NIST library, and by 1H and 13C NMR spectroscopy. With erbium(III) triflate in neat (no solvent), Time= 0.5h, T= 220 °C , Microwave irradiation, Friedel-Crafts Acylation Tran, Phuong Hoang; Hansen, Poul Erik; Nguyen, Hai Truong; Le, Thach Ngoc; Tetrahedron Letters; vol. 56; nb. 4; (2015); p. 612 - 618 View in Reaxys

-1

(v4)

(v5)

C (v5) (v4) (v5)

O (v4) N OP(v4) N 2+ (v8) –Ru O

H O

P (v5)

(v4)

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-1

(v4)

(v4) (v4)

NH O

PO (v9) 2+ O Ru (v4) P – (v4) (v5)(v5) C (v4) (v5) (v5)

Rx-ID: 39799559 View in Reaxys 134/827 Yield

F (v4)

B FF

N+

Rx-ID: 39870898 View in Reaxys 135/827 Yield 6 %Chromat., 50 %Chromat.

Conditions & References With eosin in acetonitrile, Time= 10h, T= 20 °C , p= 60804.1Torr , Autoclave, Irradiation Guo, Wei; Lu, Liang-Qiu; Wang, Yue; Wang, Ya-Ni; Chen, Jia-Rong; Xiao, Wen-Jing; Angewandte Chemie - International Edition; vol. 54; nb. 7; (2015); p. 2265 - 2269; Angew. Chem.; vol. 127; nb. 7; (2015); p. 2293 - 2297,5 View in Reaxys

(v5) (v5) (v3) O C– 2+– (v4)(v3) C (v3) (v5)Ca(v4)(v3) – O (v9) (v5) –O O O (v3) (v3) 2+ (v3) O Ca O – (v3) (v6)(v3) (v5)O 2+O OCa Ca 2+ (v9) (v3) – O O––O C (v3) C (v3) (v4) (v3) (v5) (v4) (v5) (v5)(v5)

Rx-ID: 39962035 View in Reaxys 136/827 Yield 92 %

Conditions & References With iodine in tetrahydrofuran, Time= 1h, T= -78 - 20 °C , Schlenk technique, Inert atmosphere Wei, Baosheng; Li, Heng; Zhang, Wen-Xiong; Xi, Zhenfeng; Organometallics; vol. 34; nb. 7; (2015); p. 1339 - 1344 View in Reaxys O

HO C

Rx-ID: 39990300 View in Reaxys 137/827 Yield 10 %Chromat., 44 %Chromat.

Conditions & References With palladium diacetate, caesium carbonate, triphenylphosphine, Trimethylacetic acid in toluene, Time= 12h, T= 100 °C , Inert atmosphere, Glovebox, Schlenk technique, Sealed tube Song, Juan; Wei, Fuliang; Sun, Wei; Li, Ke; Tian, Yanan; Liu, Chao; Li, Yali; Xie, Linghai; Organic Letters; vol. 17; nb. 9; (2015); p. 2106 - 2109 View in Reaxys

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35 %Chromat., 18 %Chromat.

With palladium diacetate, caesium carbonate, tricyclohexylphosphine in toluene, Time= 12h, T= 100 °C , Inert atmosphere, Glovebox, Schlenk technique, Sealed tube Song, Juan; Wei, Fuliang; Sun, Wei; Li, Ke; Tian, Yanan; Liu, Chao; Li, Yali; Xie, Linghai; Organic Letters; vol. 17; nb. 9; (2015); p. 2106 - 2109 View in Reaxys

HO C

Rx-ID: 39990301 View in Reaxys 138/827 Yield

Conditions & References

41 %Chromat., 44 %Chromat., 9 %Chromat.

With palladium diacetate, caesium carbonate, tricyclohexylphosphine, Trimethylacetic acid in toluene, Time= 24h, T= 110 °C , Inert atmosphere, Glovebox, Schlenk technique, Sealed tube Song, Juan; Wei, Fuliang; Sun, Wei; Li, Ke; Tian, Yanan; Liu, Chao; Li, Yali; Xie, Linghai; Organic Letters; vol. 17; nb. 9; (2015); p. 2106 - 2109 View in Reaxys

O Br

HO C

Rx-ID: 39990303 View in Reaxys 139/827 Yield

Conditions & References

87 %Chromat., 7 %Chromat.

Rx-ID: 40840998 View in Reaxys 140/827 Yield 78 %

Conditions & References With bis(1,5-cyclooctadiene)diiridium(I) dichloride, tri-tert-butyl phosphine in o-xylene, Time= 24h, T= 160 °C , Inert atmosphere Nagata, Tomoya; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro; Journal of Organic Chemistry; vol. 79; nb. 19; (2014); p. 8960 - 8967

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View in Reaxys 12 %

With 1,1,1,3',3',3'-hexafluoro-propanol, Time= 4h, T= 20 °C , Inert atmosphere, Friedel-Crafts Acylation Motiwala, Hashim F.; Vekariya, Rakesh H.; Aubé, Jeffrey; Organic Letters; vol. 17; nb. 21; (2015); p. 5484 - 5487 View in Reaxys

O O

Rx-ID: 41048870 View in Reaxys 141/827 Yield 91 %, 89 %

Conditions & References 2i. Reaction of N-(9H-fluoren-9-ylidene)naphthalen-1-amine oxide (18) with methyl propiolate (2d) N-(9H-Fluoren-9-ylidene)naphthalene-1-amine oxide (18) (0.324 g, 1 mmol) and methyl propiolate (2d) (0.083 g, 1 mmol) in acetonitrile (10 mL) was stirred at 82 oCfor 4 h. Progress of the reaction was monitored by TLC. After the complete consumption of nitrone, solvent was evaporated off and the residue was redissolved in dichloromethane in the same flask. Oxalic acid (0.1 g, 1mmol) adsorbed on of silicagel (1 g) was added to the same pot and the mixture was stirred at room temperature for 1 h. After the completion of the reaction, solvent was removed under reduced pressure. The residue obtained was chromatographed over silica gel using a mixture of hexane and ethyl acetate to give fluorenone (0.164 g, 91 percent)followed by the benzo[g]indole 19 (0.201 g, 89percent). The products were further purified by recrystallization from hexane-dichloromethane mixture. Stage 1: in acetonitrile, Time= 4h, T= 82 °C Stage 2: With oxalic acid adsorbed on silica gel in dichloromethane, Time= 1h, T= 20 °C Natarajan, Rakesh; Rappai, John P.; Unnikrishnan, Peruparampil A.; Radhamani, Sandhya; Prathapan, Sreedharan; Synlett; vol. 26; nb. 17; (2015); p. 2467 - 2471; Art.No: ST-2015-D0473-L View in Reaxys

O O N

Rx-ID: 41048873 View in Reaxys 142/827 Yield

Conditions & References Reaction Steps: 2 1: acetonitrile / 4 h / 82 °C 2: oxalic acid adsorbed on silica gel / dichloromethane / 1 h / 20 °C With oxalic acid adsorbed on silica gel in dichloromethane, acetonitrile, 1: |Aza-Cope Rearrangement Natarajan, Rakesh; Rappai, John P.; Unnikrishnan, Peruparampil A.; Radhamani, Sandhya; Prathapan, Sreedharan; Synlett; vol. 26; nb. 17; (2015); p. 2467 - 2471; Art.No: ST-2015-D0473-L View in Reaxys

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O O N

NH O

O N

Rx-ID: 41048882 View in Reaxys 143/827 Yield 0.19 g, 0.12 g, 0.091 g

Conditions & References 2a. Reaction of N-(9H-fluoren-9-ylidene)aniline oxide (1a) with benzoylphenylacetylene (2a) N-(9H-Fluoren-9-ylidene)aniline oxide (1a) (0.271 g, 1mmol) and benzoylphenylacetylene (2a) (0.211 g, 1mmol) in acetonitrile (10 mL) was stirred at 82 oC for 4h.Progress of the reaction was monitored by TLC. After complete consumption of nitrone, solvent was removed under reduced pressure and the residue was redissolved in dichloromethane (10 mL) in the same flask. Oxalic acid (0.1 g,1mmol) adsorbed on of silica gel (1g) was added to the same pot and the mixture was stirred at room temperature for 1h. After the completion of the reaction, reaction mixture was filtered and solvent was removed under reduced pressure. The residue obtained was chromatographed over silica gel using a mixture of hexane and ethylacetate to give fluorenone (0.120 g, 66percent) followed by indole 6a (0.190g, 64percent) andisoxazoline 5a (0.091 g, 19percent).1e The products were further purified by recrystallization from hexane-dichloromethane mixture. With oxalic acid adsorbed on silica gel in dichloromethane, Time= 1h, T= 20 °C Natarajan, Rakesh; Rappai, John P.; Unnikrishnan, Peruparampil A.; Radhamani, Sandhya; Prathapan, Sreedharan; Synlett; vol. 26; nb. 17; (2015); p. 2467 - 2471; Art.No: ST-2015-D0473-L View in Reaxys

O O N

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O O O

O N

Rx-ID: 41048888 View in Reaxys 144/827 Yield

Conditions & References

0.119 g, 0.081 g, 0.22 g

Reaction of N-(9H-fluoren-9-ylidene)aniline oxide (1a) with cinnamoylphenylacetylene (2b) N-(9H-Fluoren-9-ylidene)aniline oxide (1a) (0.274 g, 1 mmol) and cinnamoylphenylacetylene (2b) (0.230 g, 1 mmol) in acetonitrile (10 mL) was stirred at 82 oC for 4 h. Progress of the reaction was monitored by TLC. After the complete consumption of nitrone, solvent was removed under reduced pressure and the residue was redissolved in dichloromethane in the same flask. Oxalic acid (0.1 g, 1mmol) adsorbed on of silica gel (1g) was added to the same pot and the mixture was stirred at room temperature for 1 h. After the completion of the reaction, solvent was removed under reduced pressure. The residue obtained was chromatographed over silica gel using a mixture of hexane and ethyl acetate to give fluorenone (0.119 g,67percent) followed by the indole 6b (0.220 g, 68percent) and isoxazoline 5b (0.081 g,16percent). The products were further purified by recrystallization from hexane-dichloromethane mixture. With oxalic acid adsorbed on silica gel in dichloromethane, Time= 1h, T= 20 °C Natarajan, Rakesh; Rappai, John P.; Unnikrishnan, Peruparampil A.; Radhamani, Sandhya; Prathapan, Sreedharan; Synlett; vol. 26; nb. 17; (2015); p. 2467 - 2471; Art.No: ST-2015-D0473-L View in Reaxys

O O N

O N

Rx-ID: 41048894 View in Reaxys 145/827 Yield 0.121 g, 0.159 g, 0.075 g

Conditions & References 2c. Reaction of N-(9H-fluoren-9-ylidene)aniline oxide (1a) with acetylphenylacetylene (2c) N-(9H-Fluoren-9-ylidene)aniline oxide (1a) (0.272 g, 1 mmol) and acetylphenylacetylene (2c) (0.140 g, 1 mmol) in acetonitrile (10 mL) was stirred at 82 oC for 4 h. Progress of the reaction was monitored by TLC. After the complete consumption of nitrone, solvent was evaporated off and the residue was redissolved in dichloromethane in the same flask. Oxalic acid (0.09 g, 1mmol) adsorbed on of silicagel (0.5 g) was added to the same pot and the mixture was stirred at room temperaturefor 1 h. After

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the completion of the reaction, reaction mixture was filtered and solvent was removed under reduced pressure. The residue obtained was chromatographed over silica gel using a mixture of hexane and ethyl acetate to give fluorenone (0.121 g, 67percent) followed by the indole 6c (0.159 g, 66percent) and isoxazoline 5c (0.075 g, 18percent). The products were further purified by recrystallization from hexane-dichloromethane mixture. With oxalic acid adsorbed on silica gel in dichloromethane, Time= 1h, T= 20 °C Natarajan, Rakesh; Rappai, John P.; Unnikrishnan, Peruparampil A.; Radhamani, Sandhya; Prathapan, Sreedharan; Synlett; vol. 26; nb. 17; (2015); p. 2467 - 2471; Art.No: ST-2015-D0473-L View in Reaxys

O O N O O O

Rx-ID: 41048900 View in Reaxys 146/827 Yield

Conditions & References

0.151 g, 0.16 g

2d. Reaction of N-(9H-fluoren-9-ylidene)aniline oxide (1a) with methyl propiolate (2d) N-(9H-Fluoren-9-ylidene)aniline oxide (1a) (0.273 g, 1 mmol) and methyl propiolate(2d) (0.084 g, 1 mmol) in acetonitrile (10 mL) was stirred at 82 oC for 4 h. Progress of the reaction was monitored by TLC. After the complete consumption of nitrone, solvent was evaporated off and the residue was redissolved in dichloromethane in the same flask. Oxalic acid (0.1 g, 1 mmol) adsorbed on of silica gel (1 g) was added to the same pot and the mixture was stirred at room temperature for 1 h. After the completion of the reaction, solvent was removed under reduced pressure. The residue obtained was chromatographed over silica gel using a mixture of hexane andethyl acetate to give fluorenone (0.160 g, 87percent) followed by the indole 6d (0.151g, 84percent). The products were further purified by recrystallization from hexane-dichloromethane mixture. With oxalic acid adsorbed on silica gel in dichloromethane, Time= 1h, T= 20 °C Natarajan, Rakesh; Rappai, John P.; Unnikrishnan, Peruparampil A.; Radhamani, Sandhya; Prathapan, Sreedharan; Synlett; vol. 26; nb. 17; (2015); p. 2467 - 2471; Art.No: ST-2015-D0473-L View in Reaxys

N O

O O

Rx-ID: 41048908 View in Reaxys 147/827 Yield

Conditions & References

86 %, 63 %, 2h. Reaction of N-(9H-fluoren-9-ylidene)-3-methylaniline oxide (12) with methyl propiolate (2d) 21 % N-(9H-Fluoren-9-ylidene)-3-methylaniline oxide (12) (0.286 g, 1 mmol) and methylpropiolate (2d) (0.086 g, 1 mmol) in acetonitrile (10 mL) was stirred at 82 oC for 4 h.Progress of the reaction was monitored by TLC. After the complete consumption of nitrone, solvent was evaporated off and the residue was redissolved in dichloromethane in the same flask. Oxalic acid (0.1 g, 1mmol) adsorbed on of silicagel (1 g) was added to the same pot and the mixture was stirred at room temperaturefor 1 h. After the completion of the reaction, solvent was removed under reduced pressure. The residue obtained was chromatographed over silica gel using amixture of hexane and ethyl acetate to give fluorenone (0.155 g, 86percent) followedby the indoles 15 (0.120 g,

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63percent) and 16 (0.041 g, 21percent). The products werefurther purified by recrystallization from hexane-dichloromethane mixture. Stage 1: in acetonitrile, Time= 4h, T= 82 °C , Aza-Cope Rearrangement Stage 2: With oxalic acid adsorbed on silica gel in dichloromethane, Time= 1h, T= 20 °C Natarajan, Rakesh; Rappai, John P.; Unnikrishnan, Peruparampil A.; Radhamani, Sandhya; Prathapan, Sreedharan; Synlett; vol. 26; nb. 17; (2015); p. 2467 - 2471; Art.No: ST-2015-D0473-L View in Reaxys

O O N O O

Rx-ID: 41048910 View in Reaxys 148/827 Yield 0.152 g, 0.194 g

Conditions & References 2e. Reaction of N-(9H-fluoren-9-ylidene)aniline oxide (1a) with methyl phenylpropiolate (2e) N-(9H-Fluoren-9-ylidene)aniline oxide (1a) (0.274 g, 1 mmol) and methylphenylpropiolate(2e) (0.162 g, 1 mmol) in acetonitrile (10 mL) was stirred at 82 oC for 4 h. Progress of the reaction was monitored by TLC. After the complete consumption of nitrone, solvent was evaporated off and the residue was redissolved in dichloromethane in the same flask. Oxalic acid (0.1 g, 1mmol) adsorbed on of silica gel (1 g) was added to the same pot and the mixture was stirred at room temperaturefor 1 h. After the completion of the reaction, solvent was removed under reduced pressure. The residue obtained was chromatographed over silica gel using amixture of hexane and ethyl acetate to give fluorenone (0.152 g, 84 percent)followed by the indole 6f (0.194 g, 82percent). The products were further purified by recrystallization from hexane-dichloromethane mixture. With oxalic acid adsorbed on silica gel in dichloromethane, Time= 1h, T= 20 °C Natarajan, Rakesh; Rappai, John P.; Unnikrishnan, Peruparampil A.; Radhamani, Sandhya; Prathapan, Sreedharan; Synlett; vol. 26; nb. 17; (2015); p. 2467 - 2471; Art.No: ST-2015-D0473-L View in Reaxys

Rx-ID: 41048920 View in Reaxys 149/827 Yield

Conditions & References Reaction Steps: 3 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 5 °C 2: acetonitrile / 4 h / 82 °C 3: oxalic acid adsorbed on silica gel / dichloromethane / 1 h / 20 °C With 3-chloro-benzenecarboperoxoic acid in dichloromethane, acetonitrile, 2: |Aza-Cope Rearrangement Natarajan, Rakesh; Rappai, John P.; Unnikrishnan, Peruparampil A.; Radhamani, Sandhya; Prathapan, Sreedharan; Synlett; vol. 26; nb. 17; (2015); p. 2467 - 2471; Art.No: ST-2015-D0473-L View in Reaxys

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Rx-ID: 41048925 View in Reaxys 150/827 Yield

Conditions & References Reaction Steps: 2 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 5 °C 2.1: acetonitrile / 4 h / 82 °C 2.2: oxalic acid adsorbed on silica gel / 1 h / 20 °C With 3-chloro-benzenecarboperoxoic acid in dichloromethane, acetonitrile, 2.1: |Aza-Cope Rearrangement Natarajan, Rakesh; Rappai, John P.; Unnikrishnan, Peruparampil A.; Radhamani, Sandhya; Prathapan, Sreedharan; Synlett; vol. 26; nb. 17; (2015); p. 2467 - 2471; Art.No: ST-2015-D0473-L View in Reaxys

O N O O O

Rx-ID: 41048929 View in Reaxys 151/827 Yield 0.161 g, 0.158 g

Conditions & References 2f. Reaction of N-(9H-fluoren-9-ylidene)-4-methylaniline oxide (10) with methyl propiolate (2d) N-(9H-Fluoren-9-ylidene)-4-methylaniline oxide (10) (0.285g, 1 mmol) and methylpropiolate (2d) (0.085g, 1 mmol) in acetonitrile (10 mL) was stirred at 82 oC for 4 h. Progress of the reaction was monitored by TLC. After the complete consumption of nitrone, solvent was evaporated off and the residue was redissolved in dichloromethane in the same flask. Oxalic acid (0.09g, 1mmol) adsorbed on of silica gel (1 g) was added to the same pot and the mixture was stirred at room temperaturefor 1 h. After the completion of the reaction, solvent was removed under reduced pressure. The residue obtained was chromatographed over silica gel using amixture of hexane and ethyl acetate to give fluorenone (0.161 g, 88percent) followed by the indole 13 (0.158 g, 84percent). The products were further purified by recrystallization from hexane-dichloromethane mixture. With oxalic acid adsorbed on silica gel in dichloromethane, Time= 1h, T= 20 °C Natarajan, Rakesh; Rappai, John P.; Unnikrishnan, Peruparampil A.; Radhamani, Sandhya; Prathapan, Sreedharan; Synlett; vol. 26; nb. 17; (2015); p. 2467 - 2471; Art.No: ST-2015-D0473-L View in Reaxys

O O

N O O O

Rx-ID: 41048935 View in Reaxys 152/827 Yield 0.15 g, 0.159 g

Conditions & References 2g. Reaction of N-(9H-fluoren-9-ylidene)-2-methylaniline oxide (11) with methyl propiolate (2d) N-(9H-Fluoren-9-ylidene)-2-methylaniline oxide (11) (0.283g, 1 mmol) and methylpropiolate (2d) (0.082 g, 1 mmol) in acetonitrile (10 mL) was stirred at 82 oC for 4 h.Progress of the reaction was monitored by TLC. After the complete consumption ofnitrone, solvent was evaporated off and the residue was redissolved in dichloromethane in the same flask. Oxalic acid (0.1 g,

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1mmol) adsorbed on of silicagel (1 g) was added to the same pot and the mixture was stirred at room temperaturefor 1 h. After the completion of the reaction, solvent was removed under reduced pressure. The residue obtained was chromatographed over silica gel using amixture of hexane and ethyl acetate to give fluorenone (0.150 g, 85 percent) followed by the indole 14 (0.159 g, 82percent). The products were further purified by recrystallization from hexane-dichloromethane mixture. With oxalic acid adsorbed on silica gel in dichloromethane, Time= 1h, T= 20 °C Natarajan, Rakesh; Rappai, John P.; Unnikrishnan, Peruparampil A.; Radhamani, Sandhya; Prathapan, Sreedharan; Synlett; vol. 26; nb. 17; (2015); p. 2467 - 2471; Art.No: ST-2015-D0473-L View in Reaxys

O N

Rx-ID: 41048944 View in Reaxys 153/827 Yield

O O

O N

Rx-ID: 41048947 View in Reaxys 154/827 Yield

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O N

Rx-ID: 41048950 View in Reaxys 155/827 Yield

Rx-ID: 41048954 View in Reaxys 156/827 Yield

Rx-ID: 41048960 View in Reaxys 157/827 Yield

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O O

Rx-ID: 41048967 View in Reaxys 158/827 Yield

O O N

Rx-ID: 41048974 View in Reaxys 159/827 Yield

O O N

HN O O O

Rx-ID: 41344504 View in Reaxys 160/827

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Yield

Conditions & References

33 mg, 15 mg, 305 mg, 50 mg

in acetonitrile, Time= 2h, T= 20 °C Radhamani, Sandhya; Natarajan, Rakesh; Unnikrishnan, Peruparampil A.; Prathapan, Sreedharan; Rappai, John P.; New Journal of Chemistry; vol. 39; nb. 7; (2015); p. 5580 - 5588 View in Reaxys

O O N

N O

O O

O N

Rx-ID: 41344507 View in Reaxys 161/827 Yield 35 mg, 364 mg, 65 mg, 15 mg

Conditions & References in acetonitrile, Time= 2h, T= 20 °C , Solvent Radhamani, Sandhya; Natarajan, Rakesh; Unnikrishnan, Peruparampil A.; Prathapan, Sreedharan; Rappai, John P.; New Journal of Chemistry; vol. 39; nb. 7; (2015); p. 5580 - 5588 View in Reaxys

O O

O N

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N O

O O

HO NH

Rx-ID: 41344508 View in Reaxys 162/827 Yield

Conditions & References

101 mg, 162 in acetonitrile, Time= 2h, T= 20 °C , Cope Rearrangement mg, 199 mg Radhamani, Sandhya; Natarajan, Rakesh; Unnikrishnan, Peruparampil A.; Prathapan, Sreedharan; Rappai, John P.; New Journal of Chemistry; vol. 39; nb. 7; (2015); p. 5580 - 5588 View in Reaxys

O O O N

Rx-ID: 41344509 View in Reaxys 163/827 Yield

Conditions & References

160 mg, 314 With oxalic acid, silica gel in dichloromethane, Time= 1h mg Radhamani, Sandhya; Natarajan, Rakesh; Unnikrishnan, Peruparampil A.; Prathapan, Sreedharan; Rappai, John P.; New Journal of Chemistry; vol. 39; nb. 7; (2015); p. 5580 - 5588 View in Reaxys

O HN

Rx-ID: 41344510 View in Reaxys 164/827 Yield

Conditions & References With oxalic acid, silica gel in dichloromethane, Time= 1h Radhamani, Sandhya; Natarajan, Rakesh; Unnikrishnan, Peruparampil A.; Prathapan, Sreedharan; Rappai, John P.; New Journal of Chemistry; vol. 39; nb. 7; (2015); p. 5580 - 5588 View in Reaxys

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O N

O HN O O

Rx-ID: 41344511 View in Reaxys 165/827 Yield

Conditions & References

10 mg, 12 mg, 22 mg

F O

OH O F

Rx-ID: 41344513 View in Reaxys 166/827 Yield 12 %, 14 %

Conditions & References in acetonitrile, Time= 2h, T= 20 °C , Reflux Radhamani, Sandhya; Natarajan, Rakesh; Unnikrishnan, Peruparampil A.; Prathapan, Sreedharan; Rappai, John P.; New Journal of Chemistry; vol. 39; nb. 7; (2015); p. 5580 - 5588 View in Reaxys

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O N

HO O O

Rx-ID: 41344517 View in Reaxys 167/827 Yield

Conditions & References

164 mg, 328 in acetonitrile, Time= 2h, T= 20 °C mg Radhamani, Sandhya; Natarajan, Rakesh; Unnikrishnan, Peruparampil A.; Prathapan, Sreedharan; Rappai, John P.; New Journal of Chemistry; vol. 39; nb. 7; (2015); p. 5580 - 5588 View in Reaxys O

H 2N

Rx-ID: 41523672 View in Reaxys 168/827 Yield

Conditions & References

76 %

With palladium diacetate, acetic acid, silver(l) oxide, Time= 20h, T= 140 °C , Inert atmosphere, regioselective reaction Ravi Kumar, Devarapalli; Satyanarayana, Gedu; Organic Letters; vol. 17; nb. 23; (2015); p. 5894 - 5897 View in Reaxys O

Rx-ID: 41523673 View in Reaxys 169/827 Yield 76 %

Conditions & References With palladium diacetate, acetic acid, silver(l) oxide, Time= 15h, T= 140 °C , Inert atmosphere, regioselective reaction Ravi Kumar, Devarapalli; Satyanarayana, Gedu; Organic Letters; vol. 17; nb. 23; (2015); p. 5894 - 5897 View in Reaxys O

Rx-ID: 29441783 View in Reaxys 170/827

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Yield

Conditions & References

84 %

With oxygen, palladium diacetate, toluene-4-sulfonic acid in water, 1,2-dichloro-ethane, Time= 24h, T= 100 °C , p= 6080.41Torr , Autoclave Wang, Azhong; Jiang, Huanfeng; Journal of Organic Chemistry; vol. 75; nb. 7; (2010); p. 2321 - 2326 View in Reaxys

61 %

With 2,2'-azobis(isobutyronitrile), oxygen in nitromethane, Time= 12h, T= 60 °C , Schlenk technique Wang, Guang-Zu; Li, Xing-Long; Dai, Jian-Jun; Xu, Hua-Jian; Journal of Organic Chemistry; vol. 79; nb. 15; (2014); p. 7220 - 7225 View in Reaxys

O O

Rx-ID: 33430079 View in Reaxys 171/827 Yield

Conditions & References

76 %

With dipotassium peroxodisulfate, silver(I) acetate in [D3]acetonitrile, Time= 1h, T= 130 °C , Microwave irradiation, Pschorr reaction Seo, Sangwon; Slater, Mark; Greaney, Michael F.; Organic Letters; vol. 14; nb. 10; (2012); p. 2650 - 2653 View in Reaxys

62 %

With dipotassium peroxodisulfate Cheng, Kai; Zhao, Baoli; Qi, Chenze; RSC Advances; vol. 4; nb. 89; (2014); p. 48698 - 48702 View in Reaxys

N N

Rx-ID: 37529995 View in Reaxys 172/827 Yield

Conditions & References

37 %, 5 %, 20 %

With benzene, Time= 1h, Photolysis Dyblenko, Tatiana; Chtchemelinine, Andrei; Reiter, Ryan; Chowdhury, Ruhul Q.; Enaya, Alexander; Afifi, Hanan; Fournier, Rene; Mladenova, Gabriela; Lever, Alfred Barry P.; Lee-Ruff, Edward; Photochemistry and Photobiology; vol. 90; nb. 2; (2014); p. 470 - 475 View in Reaxys O

I O Br

Rx-ID: 38071101 View in Reaxys 173/827

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Yield

Conditions & References Reaction Steps: 3 1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran; water / 12 h / 60 °C / Inert atmosphere 2: sodium hydroxide / water; methanol / 12 h / 20 °C 3: 1,2-bis-(diphenylphosphino)ethane; 2,2-dimethylpropanoic anhydride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium iodide / 40 h / 180 °C / Inert atmosphere; Sealed tube With bis-triphenylphosphine-palladium(II) chloride, chloro(1,5-cyclooctadiene)rhodium(I) dimer, 2,2-dimethylpropanoic anhydride, sodium carbonate, 1,2-bis-(diphenylphosphino)ethane, potassium iodide, sodium hydroxide in tetrahydrofuran, methanol, water Fukuyama, Takahide; Maetani, Shinji; Miyagawa, Kazusa; Ryu, Ilhyong; Organic Letters; vol. 16; nb. 12; (2014); p. 3216 3219 View in Reaxys

O O Br

Rx-ID: 38071116 View in Reaxys 174/827 Yield

Conditions & References Reaction Steps: 2 1: sodium hydroxide / water; methanol / 12 h / 20 °C 2: 1,2-bis-(diphenylphosphino)ethane; 2,2-dimethylpropanoic anhydride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium iodide / 40 h / 180 °C / Inert atmosphere; Sealed tube With chloro(1,5-cyclooctadiene)rhodium(I) dimer, 2,2-dimethylpropanoic anhydride, 1,2-bis-(diphenylphosphino)ethane, potassium iodide, sodium hydroxide in methanol, water Fukuyama, Takahide; Maetani, Shinji; Miyagawa, Kazusa; Ryu, Ilhyong; Organic Letters; vol. 16; nb. 12; (2014); p. 3216 3219 View in Reaxys OH

O Br

Rx-ID: 38071127 View in Reaxys 175/827 Yield

Conditions & References

22 %Spectr. With chloro(1,5-cyclooctadiene)rhodium(I) dimer, 2,2-dimethylpropanoic anhydride, 1,2-bis-(diphenylphosphino)ethane, potassium iodide, Time= 40h, T= 180 °C , Inert atmosphere, Sealed tube Fukuyama, Takahide; Maetani, Shinji; Miyagawa, Kazusa; Ryu, Ilhyong; Organic Letters; vol. 16; nb. 12; (2014); p. 3216 3219 View in Reaxys O

HO B

Rx-ID: 38071139 View in Reaxys 176/827 Yield

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3: 1,2-bis-(diphenylphosphino)ethane; 2,2-dimethylpropanoic anhydride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium iodide / 40 h / 180 °C / Inert atmosphere; Sealed tube With bis-triphenylphosphine-palladium(II) chloride, chloro(1,5-cyclooctadiene)rhodium(I) dimer, 2,2-dimethylpropanoic anhydride, sodium carbonate, 1,2-bis-(diphenylphosphino)ethane, potassium iodide, sodium hydroxide in tetrahydrofuran, methanol, water Fukuyama, Takahide; Maetani, Shinji; Miyagawa, Kazusa; Ryu, Ilhyong; Organic Letters; vol. 16; nb. 12; (2014); p. 3216 3219 View in Reaxys O I O

Rx-ID: 38410633 View in Reaxys 177/827 Yield

Conditions & References Stage 1: With n-butyllithium in tetrahydrofuran, T= -100 °C , Inert atmosphere Stage 2: in tetrahydrofuran, Inert atmosphere Stage 3: With sulfuric acid, water in tetrahydrofuran, Inert atmosphere Durka, Krzysztof; Lulinski, Sergiusz; Dabrowski, Marek; Serwatowski, Janusz; European Journal of Organic Chemistry; vol. 2014; nb. 21; (2014); p. 4562 - 4570 View in Reaxys O Li

N I

Rx-ID: 38689361 View in Reaxys 178/827 Yield

Conditions & References

71 %

Stage 1: With n-butyllithium in tetrahydrofuran, hexane, T= -70 °C , Flow reactor Stage 2: in tetrahydrofuran, T= -20 °C , Flow reactor Stage 3: With water, sodium chloride in tetrahydrofuran, hexane, Flow reactor Nagaki, Aiichiro; Ichinari, Daisuke; Yoshida, Jun-Ichi; Journal of the American Chemical Society; vol. 136; nb. 35; (2014); p. 12245 - 12248 View in Reaxys O

O HO

HO B

Rx-ID: 38867718 View in Reaxys 179/827 Yield

Conditions & References Reaction Steps: 2 1: silver carbonate 2: dipotassium peroxodisulfate With dipotassium peroxodisulfate, silver carbonate Cheng, Kai; Zhao, Baoli; Qi, Chenze; RSC Advances; vol. 4; nb. 89; (2014); p. 48698 - 48702 View in Reaxys

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OH O

O O O O

Rx-ID: 39015990 View in Reaxys 180/827 Yield

Conditions & References

23 %, 19 %

With water, UV-irradiation, Green chemistry Bellardita; Loddo; Mele; Panzeri; Parrino; Pibiri; Palmisano; RSC Advances; vol. 4; nb. 77; (2014); p. 40859 - 40864 View in Reaxys

O N

Rx-ID: 39199290 View in Reaxys 181/827 Yield

Conditions & References

47 %

Stage 1: With [bis(acetoxy)iodo]benzene, boron trifluoride diethyl etherate in 1,2-dichloro-ethane, Time= 34h, T= 80 °C Stage 2: With hydrogenchloride in 1,2-dichloro-ethane, T= 20 °C Sarkar, Satinath; Tadigoppula, Narender; RSC Advances; vol. 4; nb. 77; (2014); p. 40964 - 40968 View in Reaxys HO

Rx-ID: 39987726 View in Reaxys 182/827 Yield 30 %

Conditions & References General Procedure for Cyclization of Diphenylacetic Acid. To a 20 mL two-necked flask with a reflux condenser, a drying tube filled with CaCl2, and a rubber cup were added diphenylacetic acid 3c (0.5 mmol), [CpERhCl2]2 (0.01 mmol, 8.4mg), AgSbF6 (0.04 mmol, 13.7 mg), Cu(OAc)2•H2O (0.02 mmol, 4.5 mg), K2CO3 (0.25 mmol. 35 mg), pivalic acid (0.5 mmol,51 mg), 1-methylnaphthalene (ca. 50 mg) as internal standard, and diglyme (3 mL). Then, the resulting mixture was stirred under air at 120 °C (bath temperature) for 48 h. After cooling, to the reaction mixture were added water (20 mL), ethyl acetate (20 mL) and ethylenediamine (2 mL) and filtered through celite plug. The

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filtrate was extracted with ethyl acetate (20x3 mL)and dried over Na2SO4. After evaporation of the solvents under vacuum, the product 5 was isolated by column chromatography on silica gel using n-hexane/ethyl acetate (10:1) as eluent. With silver hexafluoroantimonate, [(1,3-bis(ethoxycarbonyl)-2,4,5-trimethylcyclopentadienyl)RhCl2]2, copper(II) acetate monohydrate, potassium carbonate, Trimethylacetic acid in diethylene glycol dimethyl ether, Time= 48h, T= 120 °C , Green chemistry Baars, Hannah; Unoh, Yuto; Okada, Takeshi; Hirano, Koji; Satoh, Tetsuya; Tanaka, Ken; Bolm, Carsten; Miura, Masahiro; Chemistry Letters; vol. 43; nb. 11; (2014); p. 1782 - 1784 View in Reaxys

N O

Rx-ID: 41815704 View in Reaxys 183/827 Yield

Conditions & References

17 %, 11 %, With lithium aluminium tetrahydride in tetrahydrofuran, Time= 3h, T= 4 °C , Reflux 15 % Matviiuk, Tetiana; Menendez, Christophe; Carayon, Chantal; Saffon, Nathalie; Voitenko, Zoia; Lherbet, Christian; Baltas, Michel; European Journal of Organic Chemistry; vol. 2014; nb. 29; (2014); p. 6538 - 6546 View in Reaxys O

NH 2

Rx-ID: 786390 View in Reaxys 184/827 Yield 43 %

Conditions & References With tert-Butyl thionitrate in dimethyl sulfoxide, Time= 0.5h, T= 160 °C , other amines; var. solvents, temp., times, Product distribution, Mechanism Oae, Shigeru; Iida, Kazuyuki; Shinhama, Koichi; Takata, Toshikazu; Bulletin of the Chemical Society of Japan; vol. 54; nb. 8; (1981); p. 2374 - 2378 View in Reaxys Diazotization

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Graebe; Ullmann; Justus Liebigs Annalen der Chemie; vol. 291; (1896); p. 16 View in Reaxys Staedel; Chemische Berichte; vol. 27; (1894); p. 3363; Chemische Berichte; vol. 28; (1895); p. 111 View in Reaxys 49 % Chromat.

With p-toluenesulfonyl nitrite in acetonitrile, Time= 1h, Ambient temperature Oae, Shigeru; Iida, Kazuyuki; Shinhama, Koichi; Takata, Toshikazu; Bulletin of the Chemical Society of Japan; vol. 54; nb. 8; (1981); p. 2374 - 2378 View in Reaxys Reaction Steps: 2 1: 93 percent / HBF4 (48percent),isoamyl nitrite / ethanol; H2O / 0.5 h / -5 °C 2: 73 percent / KOAc / 18-crown-6 / 1,1,2-trichloro-1,2,2-trifluoro-ethane / 12 h / Ambient temperature With tetrafluoroboric acid, potassium acetate, isopentyl nitrite, 18-crown-6 ether in ethanol, 1,1,2-Trichloro-1,2,2-trifluoroethane, water Beadle, James R.; Korzeniowsky, Stephen H.; Rosenberg, David E.; Garcia-Slanga, Blanche J.; Gokel, George W.; Journal of Organic Chemistry; vol. 49; nb. 9; (1984); p. 1594 - 1603 View in Reaxys Reaction Steps: 3 1: n-Amyl nitrite / acetic acid / 1 h / 0 °C / Inert atmosphere 2: potassium iodide / acetic acid; water / 3 h / 20 °C / Inert atmosphere 3: copper(l) iodide; potassium phosphate / N,N-dimethyl-formamide / 48 h / 155 °C / Inert atmosphere With potassium phosphate, copper(l) iodide, n-Amyl nitrite, potassium iodide in water, acetic acid, N,N-dimethyl-formamide Haggam, Reda A.; Tetrahedron; vol. 69; nb. 31; (2013); p. 6488 - 6494 View in Reaxys O

Rx-ID: 2142655 View in Reaxys 185/827 Yield 89 %

Conditions & References 4.3. General procedure for the Cu(I)-catalyzed synthesis ofthe methoxy-substituted fluoren-9-ones under thermal conditions 5a-f General procedure: A dry microwave glass vial (10 mL) with magnetic stirrer bar was charged with (2-iodophenyl)(phenyl)methanones 2a-f (1.00 mmol), CuI (0.03 g, 0.15 mmol) and potassium phosphate (0.64 g, 3.00 mmol) under air. The vial was sealed, evacuated and backfilled with argon three times, then freshly distilled dry DMF (6 mL) were added. The reaction mixture was stirred for 48 h at 155 °C until complete consumption of the substrate (TLC control). After cooling to room temperature the reaction mixture was partitioned between 80 mL dichloromethane and 20 mL saturated brine. The aqueous phase was extracted with dichloromethane (3x50 mL). The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo. The crude product obtained was purified by flash column chromatography over silica gel. With potassium phosphate, copper(l) iodide in N,N-dimethyl-formamide, Time= 48h, T= 155 °C , Inert atmosphere, Concentration, Time, Temperature Haggam, Reda A.; Tetrahedron; vol. 69; nb. 31; (2013); p. 6488 - 6494 View in Reaxys With palladium diacetate in various solvent(s), Time= 15h, T= 190 °C , Yield given Ames, D.E.; Opalko, A.; Tetrahedron; vol. 40; nb. 10; (1984); p. 1919 - 1926 View in Reaxys

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Rx-ID: 33001858 View in Reaxys 186/827 Yield

Conditions & References Reaction Steps: 2 1: palladium diacetate; silver(l) oxide / acetic acid / 5 h / 120 °C 2: sulfuric acid / 36 h / 140 °C With sulfuric acid, palladium diacetate, silver(l) oxide in acetic acid Li, Dan-Dan; Yuan, Ting-Ting; Wang, Guan-Wu; Journal of Organic Chemistry; vol. 77; nb. 7; (2012); p. 3341 - 3347 View in Reaxys Reaction Steps: 2 1: Pd(PPh3)2Cl2; potassium phosphate, tribasic, n-hydrate / toluene / 12 h / 100 °C / Schlenk technique; Inert atmosphere 2: water; silver trifluoroacetate; dichloro bis(acetonitrile) palladium(II) / trifluoroacetic acid; N,N-dimethyl acetamide / 24 h / 140 °C / Glovebox; Inert atmosphere With dichloro bis(acetonitrile) palladium(II), potassium phosphate, tribasic, n-hydrate, Pd(PPh3)2Cl2, water, silver trifluoroacetate in N,N-dimethyl acetamide, toluene, trifluoroacetic acid, 2: |Heck Reaction Wan, Jung-Chih; Huang, Jun-Min; Jhan, Yu-Huei; Hsieh, Jen-Chieh; Organic Letters; vol. 15; nb. 11; (2013); p. 2742 2745 View in Reaxys O O O

Rx-ID: 34787223 View in Reaxys 187/827 Yield

Conditions & References 4. General procedure for copper-catalyzed benzylic oxidation (substrate scope) General procedure: A solution of copper(II) trifluoromethanesulfonate (11.1 mg, 0.03 mmol) and ligand 10a (8.4 mg, 0.036 mmol) in dry acetone (5 mL) was stirred at room temperature for 1 h. Phenylhydrazine (3.9 mg, 0.036 mmol) was added to this dark brown solution, and the solution became purple immediately. After stirring for additional 5 min, the benzylic substrate (3 mmol) and the oxidant tert-butyl benzoate (117 mg, 0.6 mmol) were then introduced successively. The mixture was stirred at 30 &deg;C for a certain time until the reaction was completed (determined by the disappearance of perester by TLC). After the solvent was evaporated in vacuum with a rotary evaporator, the residue was purified by silica gel chromatography using petrol ether/EtOAc as eluent to give the desired products. With N-(quinolin-2-ylmethylidene)aniline, copper(II) bis(trifluoromethanesulfonate), phenylhydrazine in acetone, Time= 6h, T= 30 °C , Inert atmosphere, Schlenk technique Zhang, Bo; Zhu, Shou-Fei; Zhou, Qi-Lin; Tetrahedron; vol. 69; nb. 8; (2013); p. 2033 - 2037 View in Reaxys

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O H 2N

HO B OH

Rx-ID: 35680361 View in Reaxys 188/827 Yield

Conditions & References Reaction Steps: 3 1: toluene / 2 h / 110 °C 2: Pd(PPh3)2Cl2; potassium phosphate, tribasic, n-hydrate / toluene / 12 h / 100 °C / Schlenk technique; Inert atmosphere 3: palladium diacetate; water; silver trifluoroacetate / trifluoroacetic acid; N,N-dimethyl acetamide / 24 h / 160 °C With potassium phosphate, tribasic, n-hydrate, Pd(PPh3)2Cl2, water, palladium diacetate, silver trifluoroacetate in N,N-dimethyl acetamide, toluene, trifluoroacetic acid, 3: |Heck Reaction Wan, Jung-Chih; Huang, Jun-Min; Jhan, Yu-Huei; Hsieh, Jen-Chieh; Organic Letters; vol. 15; nb. 11; (2013); p. 2742 2745 View in Reaxys

HO B OH

Rx-ID: 35680362 View in Reaxys 189/827 Yield

Conditions & References Reaction Steps: 3 1: toluene / 2 h / 110 °C 2: Pd(PPh3)2Cl2; potassium phosphate, tribasic, n-hydrate / toluene / 12 h / 100 °C / Schlenk technique; Inert atmosphere 3: water; silver trifluoroacetate; dichloro bis(acetonitrile) palladium(II) / trifluoroacetic acid; N,N-dimethyl acetamide / 24 h / 140 °C / Glovebox; Inert atmosphere With dichloro bis(acetonitrile) palladium(II), potassium phosphate, tribasic, n-hydrate, Pd(PPh3)2Cl2, water, silver trifluoroacetate in N,N-dimethyl acetamide, toluene, trifluoroacetic acid, 3: |Heck Reaction Wan, Jung-Chih; Huang, Jun-Min; Jhan, Yu-Huei; Hsieh, Jen-Chieh; Organic Letters; vol. 15; nb. 11; (2013); p. 2742 2745 View in Reaxys O

O H 2N

Rx-ID: 35680438 View in Reaxys 190/827 Yield 74 %Spectr., 6 %Spectr.

Conditions & References With water, palladium diacetate, silver trifluoroacetate in N,N-dimethyl acetamide, trifluoroacetic acid, Time= 24h, T= 160 °C , Heck Reaction Wan, Jung-Chih; Huang, Jun-Min; Jhan, Yu-Huei; Hsieh, Jen-Chieh; Organic Letters; vol. 15; nb. 11; (2013); p. 2742 2745 View in Reaxys

17 With water, palladium diacetate, titanium chloride in trifluoroacetic acid, Time= 24h, T= 120 °C , Heck Reaction %Spectr., 74 %Spectr. Wan, Jung-Chih; Huang, Jun-Min; Jhan, Yu-Huei; Hsieh, Jen-Chieh; Organic Letters; vol. 15; nb. 11; (2013); p. 2742 2745 View in Reaxys

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Rx-ID: 35680439 View in Reaxys 191/827 Yield

Conditions & References

82 %

With dichloro bis(acetonitrile) palladium(II), water, silver trifluoroacetate in N,N-dimethyl acetamide, trifluoroacetic acid, Time= 24h, T= 140 °C , Glovebox, Inert atmosphere, Heck Reaction Wan, Jung-Chih; Huang, Jun-Min; Jhan, Yu-Huei; Hsieh, Jen-Chieh; Organic Letters; vol. 15; nb. 11; (2013); p. 2742 2745 View in Reaxys N O

O H 2N

O B O

Rx-ID: 35680452 View in Reaxys 192/827 Yield

Conditions & References Reaction Steps: 2 1: Pd(PPh3)2Cl2; potassium phosphate, tribasic, n-hydrate / toluene / 12 h / 100 °C / Schlenk technique; Inert atmosphere 2: palladium diacetate; water; silver trifluoroacetate / trifluoroacetic acid; N,N-dimethyl acetamide / 24 h / 160 °C With potassium phosphate, tribasic, n-hydrate, Pd(PPh3)2Cl2, water, palladium diacetate, silver trifluoroacetate in N,N-dimethyl acetamide, toluene, trifluoroacetic acid, 2: |Heck Reaction Wan, Jung-Chih; Huang, Jun-Min; Jhan, Yu-Huei; Hsieh, Jen-Chieh; Organic Letters; vol. 15; nb. 11; (2013); p. 2742 2745 View in Reaxys N

O B O

Rx-ID: 35680453 View in Reaxys 193/827 Yield

Conditions & References Reaction Steps: 2 1: Pd(PPh3)2Cl2; potassium phosphate, tribasic, n-hydrate / toluene / 12 h / 100 °C / Schlenk technique; Inert atmosphere 2: water; silver trifluoroacetate; dichloro bis(acetonitrile) palladium(II) / trifluoroacetic acid; N,N-dimethyl acetamide / 24 h / 140 °C / Glovebox; Inert atmosphere With dichloro bis(acetonitrile) palladium(II), potassium phosphate, tribasic, n-hydrate, Pd(PPh3)2Cl2, water, silver trifluoroacetate in N,N-dimethyl acetamide, toluene, trifluoroacetic acid, 2: |Heck Reaction Wan, Jung-Chih; Huang, Jun-Min; Jhan, Yu-Huei; Hsieh, Jen-Chieh; Organic Letters; vol. 15; nb. 11; (2013); p. 2742 2745 View in Reaxys

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O H 2N N

Rx-ID: 35680491 View in Reaxys 194/827 Yield

Conditions & References Reaction Steps: 2 1: water; dichloro bis(acetonitrile) palladium(II); silver(l) oxide / trifluoroacetic acid; N,N-dimethyl acetamide / 7 h / 140 °C 2: palladium diacetate; water; silver trifluoroacetate / trifluoroacetic acid; N,N-dimethyl acetamide / 24 h / 160 °C With dichloro bis(acetonitrile) palladium(II), water, palladium diacetate, silver trifluoroacetate, silver(l) oxide in N,N-dimethyl acetamide, trifluoroacetic acid, 2: |Heck Reaction Wan, Jung-Chih; Huang, Jun-Min; Jhan, Yu-Huei; Hsieh, Jen-Chieh; Organic Letters; vol. 15; nb. 11; (2013); p. 2742 2745 View in Reaxys O

Rx-ID: 35680492 View in Reaxys 195/827 Yield

Conditions & References Reaction Steps: 2 1: water; dichloro bis(acetonitrile) palladium(II); silver(l) oxide / trifluoroacetic acid; N,N-dimethyl acetamide / 7 h / 140 °C 2: water; silver trifluoroacetate; dichloro bis(acetonitrile) palladium(II) / trifluoroacetic acid; N,N-dimethyl acetamide / 24 h / 140 °C / Glovebox; Inert atmosphere With dichloro bis(acetonitrile) palladium(II), water, silver trifluoroacetate, silver(l) oxide in N,N-dimethyl acetamide, trifluoroacetic acid, 2: |Heck Reaction Wan, Jung-Chih; Huang, Jun-Min; Jhan, Yu-Huei; Hsieh, Jen-Chieh; Organic Letters; vol. 15; nb. 11; (2013); p. 2742 2745 View in Reaxys O

Rx-ID: 35680493 View in Reaxys 196/827 Yield 67 %

Conditions & References With dichloro bis(acetonitrile) palladium(II), water, silver(l) oxide in N,N-dimethyl acetamide, trifluoroacetic acid, Time= 96h, T= 140 °C , Glovebox, Inert atmosphere, Heck Reaction Wan, Jung-Chih; Huang, Jun-Min; Jhan, Yu-Huei; Hsieh, Jen-Chieh; Organic Letters; vol. 15; nb. 11; (2013); p. 2742 2745 View in Reaxys O

O H 2N

Rx-ID: 35680510 View in Reaxys 197/827 Yield

Conditions & References Reaction Steps: 2

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1: water; dichloro bis(acetonitrile) palladium(II); silver(l) oxide / trifluoroacetic acid; N,N-dimethyl acetamide / 7 h / 140 °C 2: palladium diacetate; water; silver trifluoroacetate / trifluoroacetic acid; N,N-dimethyl acetamide / 24 h / 160 °C With dichloro bis(acetonitrile) palladium(II), water, palladium diacetate, silver trifluoroacetate, silver(l) oxide in N,N-dimethyl acetamide, trifluoroacetic acid, 2: |Heck Reaction Wan, Jung-Chih; Huang, Jun-Min; Jhan, Yu-Huei; Hsieh, Jen-Chieh; Organic Letters; vol. 15; nb. 11; (2013); p. 2742 2745 View in Reaxys Reaction Steps: 2 1: Pd(PPh3)2Cl2; potassium phosphate, tribasic, n-hydrate / toluene / 12 h / 100 °C / Schlenk technique; Inert atmosphere 2: palladium diacetate; water; silver trifluoroacetate / trifluoroacetic acid; N,N-dimethyl acetamide / 24 h / 160 °C With potassium phosphate, tribasic, n-hydrate, Pd(PPh3)2Cl2, water, palladium diacetate, silver trifluoroacetate in N,N-dimethyl acetamide, toluene, trifluoroacetic acid, 2: |Heck Reaction Wan, Jung-Chih; Huang, Jun-Min; Jhan, Yu-Huei; Hsieh, Jen-Chieh; Organic Letters; vol. 15; nb. 11; (2013); p. 2742 2745 View in Reaxys O

HN N O

Rx-ID: 35806017 View in Reaxys 198/827 Yield

Conditions & References Reaction Steps: 2 1: potassium iodide / acetic acid; water / 3 h / 20 °C / Inert atmosphere 2: copper(l) iodide; potassium phosphate / N,N-dimethyl-formamide / 48 h / 155 °C / Inert atmosphere With potassium phosphate, copper(l) iodide, potassium iodide in water, acetic acid, N,N-dimethyl-formamide Haggam, Reda A.; Tetrahedron; vol. 69; nb. 31; (2013); p. 6488 - 6494 View in Reaxys

O O O

Rx-ID: 36474021 View in Reaxys 199/827 Yield 96 %

Conditions & References With sulfuric acid, Time= 1h, T= 20 °C , Inert atmosphere, Friedel-Crafts Acylation Puenner, Florian; Schieven, Justin; Hilt, Gerhard; Organic Letters; vol. 15; nb. 18; (2013); p. 4888 - 4891 View in Reaxys O

Rx-ID: 36828530 View in Reaxys 200/827 Yield

Conditions & References With [PPh4][VOCl2(2,2'-thiobis(2,4-di-tert-butylphenolate))]*0.5CH3CN, Reagent/catalyst

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Werncke, C. Gunnar; Limberg, Christian; Metzinger, Ramona; Zeitschrift fur Anorganische und Allgemeine Chemie; vol. 639; nb. 14; (2013); p. 2426 - 2432 View in Reaxys S

Rx-ID: 3932225 View in Reaxys 201/827 Yield

Conditions & References

98 %

With nitrosonium tetrafluoroborate in dichloromethane, Time= 0.5h, Ambient temperature Olah; Arvanaghi; Ohannesian; Surya Prakash; Synthesis; vol. NO. 9; (1984); p. 785 - 787 View in Reaxys

94 %

With 3-carboxypyridinium chlorochromate in acetonitrile, Time= 0.0333333h, microwave irradiation, Product distribution, Further Variations: Reagents, Temperatures, without microwave irradiation; solvent-free Mohammadpoor-Baltork, Iraj; Memarian, Hamid Reza; Bahrami, Kiumars; Monatshefte fur Chemie; vol. 135; nb. 4; (2004); p. 411 - 418 View in Reaxys

93 %

With thionyl chloride, dihydrogen peroxide in ethanol, Time= 0.0333333h, T= 25 °C Bahrami, Kiumars; Khodaei, Mohammad M.; Farrokhi, Azita; Tetrahedron; vol. 65; nb. 36; (2009); p. 7658 - 7661 View in Reaxys

93 %

With dihydrogen peroxide, titanium tetrachloride in acetonitrile, Time= 0.0333333h, T= 25 °C Bahrami, Kiumars; Khodaei, Mohammad M.; Shakibaian, Vida; Khaledian, Donya; Yousefi, Behrooz H.; Journal of Sulfur Chemistry; vol. 33; nb. 2; (2012); p. 155 - 163 View in Reaxys

91 %

With benzyltriphenylphosphonium peroxodisulfate in acetonitrile, Time= 0.25h, Heating Mohammadpoor-Baltork, Iraj; Sadeghi, Majid M. M.; Esmayilpour, Karim; Journal of Chemical Research - Part S; nb. 6; (2003); p. 348 - 350 View in Reaxys

91 %

With chloro-trimethyl-silane, dihydrogen peroxide in ethanol, water, Time= 0.0333333h, T= 25 °C , regioselective reaction Bahrami, Kiumars; Khodaei, Mohammad Mehdi; Tajik, Maryam; Synthesis; nb. 24; (2010); p. 4282 - 4286; Art.No: Z21310SS View in Reaxys

15 %

With bismuth(III) nitrate in acetonitrile, Time= 1h, Heating Mohammadpoor-Baltork, Iraj; Khodaei, Mohammad Mehdi; Nikoofar, Kobra; Tetrahedron Letters; vol. 44; nb. 3; (2003); p. 591 - 594 View in Reaxys

Rx-ID: 4464901 View in Reaxys 202/827 Yield 94 %

Conditions & References With nitric acid, arsenic(III) trioxide in dichloromethane, T= 0 - 5 °C

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Mehta, Goverdhan; Uma; Tetrahedron Letters; vol. 37; nb. 11; (1996); p. 1897 - 1898 View in Reaxys 91 %

Stage 1: With trichloroisocyanuric acid, silica gel, Time= 0.05h, T= 20 °C Stage 2: With water, T= 20 °C Firouzabadi, Habib; Iranpoor, Nasser; Hazarkhani, Hassan; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 177; nb. 11; (2002); p. 2571 - 2577 View in Reaxys

91 %

Stage 1: With 1-benzenesulfinyl piperidine, trifluoromethylsulfonic anhydride in dichloromethane, Time= 0.333333h, T= -60 °C Stage 2: With water in tetrahydrofuran, dichloromethane, T= -60 - 20 °C Crich, David; Picione, John; Synlett; nb. 9 SPEC. ISS.; (2003); p. 1257 - 1258 View in Reaxys

90 %

With tetrachlorosilane, dimethyl sulfoxide in dichloromethane, Time= 1h, T= 20 °C Firouzabadi, Habib; Iranpoor, Nasser; Hazarkhani, Hassan; Karimi, Babak; Journal of Organic Chemistry; vol. 67; nb. 8; (2002); p. 2572 - 2576 View in Reaxys

90 %

With thionyl chloride, dihydrogen peroxide in acetonitrile, Time= 0.05h, T= 25 °C Bahrami, Kiumars; Khodaei, Mohammad Mehdi; Tajik, Maryam; Shakibaian, Vida; Chinese Chemical Letters; vol. 23; nb. 1; (2012); p. 81 - 85 View in Reaxys

Rx-ID: 28676165 View in Reaxys 203/827 Yield

Conditions & References

30 %, 29 %

With dipotassium peroxodisulfate, silver(I) acetate in acetonitrile, Time= 20h, T= 100 °C , Microwave irradiation, Pschorr reaction Seo, Sangwon; Slater, Mark; Greaney, Michael F.; Organic Letters; vol. 14; nb. 10; (2012); p. 2650 - 2653 View in Reaxys With Pd(OAc)2, 2Ag(1+)*CH2O3 (2-) in 1-methyl-pyrrolidin-2-one, Time= 14h, T= 150 °C , Inert atmosphere, regioselective re-

12 %

action Wang, Congyang; Piel, Isabel; Glorius, Frank; Journal of the American Chemical Society; vol. 131; (2009); p. 4194 - 4195 View in Reaxys O

H 2N

Rx-ID: 33001887 View in Reaxys 204/827 Yield 87 %

Conditions & References With sulfuric acid, Time= 36h, T= 140 °C Li, Dan-Dan; Yuan, Ting-Ting; Wang, Guan-Wu; Journal of Organic Chemistry; vol. 77; nb. 7; (2012); p. 3341 - 3347

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View in Reaxys O H 2N

Rx-ID: 33001889 View in Reaxys 205/827 Yield

Rx-ID: 33339505 View in Reaxys 206/827 Yield 5 %, 14 %, 10 %, 17 %

Conditions & References Time= 0.5h, Inert atmosphere, Photolysis Afifi, Hanan; Mikhailine, Alexandre; Mladenova, Gabriela; Chtchemelinine, Andrei; Sultana, Israt; Dyblenko, Tatiana; Danilov, Evgeny; Fournier, Rene; Lee-Ruff, Edward; Arkivoc; vol. 2012; nb. 6; (2012); p. 343 - 354 View in Reaxys

Rx-ID: 33430080 View in Reaxys 207/827 Yield 69 %

Conditions & References With dipotassium peroxodisulfate, silver(I) acetate in [D3]acetonitrile, Time= 20h, T= 100 °C , Microwave irradiation, Pschorr reaction Seo, Sangwon; Slater, Mark; Greaney, Michael F.; Organic Letters; vol. 14; nb. 10; (2012); p. 2650 - 2653 View in Reaxys

With dipotassium peroxodisulfate, silver(I) acetate in propiononitrile, Time= 20h, T= 100 °C , Microwave irradiation, Pschorr reaction

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Seo, Sangwon; Slater, Mark; Greaney, Michael F.; Organic Letters; vol. 14; nb. 10; (2012); p. 2650 - 2653 View in Reaxys O

O Br

O N

O N O

Rx-ID: 33430102 View in Reaxys 208/827 Yield

Conditions & References Reaction Steps: 2 1: n-butyllithium / tetrahydrofuran / Cooling 2: dipotassium peroxodisulfate; silver(I) acetate / [D3]acetonitrile / 1 h / 130 °C / Microwave irradiation With dipotassium peroxodisulfate, n-butyllithium, silver(I) acetate in tetrahydrofuran, [D3]acetonitrile, 2: Pschorr reaction Seo, Sangwon; Slater, Mark; Greaney, Michael F.; Organic Letters; vol. 14; nb. 10; (2012); p. 2650 - 2653 View in Reaxys HO O

O O O

O N

Rx-ID: 33430135 View in Reaxys 209/827 Yield

Conditions & References

25 %, 12 %

N S

N H HO

N N HO N

Rx-ID: 33483871 View in Reaxys 210/827 Yield

Conditions & References

61 %, 26 %, With pyridine, iodine in tetrahydrofuran, Time= 0.0833333h, T= 20 °C 50 %

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Murai, Toshiaki; Nagaya, Eri; Shibahara, Fumitoshi; Maruyama, Toshifumi; Organic and Biomolecular Chemistry; vol. 10; nb. 25; (2012); p. 4943 - 4953 View in Reaxys O I

Rx-ID: 34135314 View in Reaxys 211/827 Yield 60 %

Conditions & References Stage 1: With indium(III) chloride, chloro-trimethyl-silane, aluminium, lithium chloride in tetrahydrofuran, Time= 4h, T= 50 °C , Inert atmosphere Stage 2: With zinc diacetate in tetrahydrofuran, Time= 0.333333h, T= 20 °C , Inert atmosphere Stage 3: With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, 1-methyl-pyrrolidin-2-one, Time= 1h, T= 20 °C , Inert atmosphere Bluemke, Tobias D.; Klatt, Thomas; Koszinowski, Konrad; Knochel, Paul; Angewandte Chemie - International Edition; vol. 51; nb. 39; (2012); p. 9926 - 9930 View in Reaxys O

Rx-ID: 34265832 View in Reaxys 212/827 Yield

Rx-ID: 34265874 View in Reaxys 213/827 Yield

Conditions & References Reaction Steps: 2 1: pyridinium chlorochromate; triethylamine / dichloromethane / 20 °C 2: palladium diacetate; trifluoroacetic acid; potassium carbonate; silver(l) oxide / 24 h / 140 °C / Schlenk technique; Inert atmosphere With palladium diacetate, potassium carbonate, triethylamine, pyridinium chlorochromate, trifluoroacetic acid, silver(l) oxide in dichloromethane, 1: |Nazarov Cyclization / 2: |Nazarov Cyclization Li, Hu; Zhu, Ru-Yi; Shi, Wen-Juan; He, Ke-Han; Shi, Zhang-Jie; Organic Letters; vol. 14; nb. 18; (2012); p. 4850 - 4853,4 View in Reaxys

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Rx-ID: 34583610 View in Reaxys 214/827 Yield

Conditions & References Reaction Steps: 2 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane; diethyl ether / -78 - 20 °C / Inert atmosphere 2: potassium hydroxide / tert-butyl alcohol / 1.5 h / 70 °C With 3-chloro-benzenecarboperoxoic acid, potassium hydroxide in diethyl ether, dichloromethane, tert-butyl alcohol Ulshoefer, Roland; Wedel, Tobias; Sueveges, Bastian; Podlech, Joachim; European Journal of Organic Chemistry; nb. 35; (2012); p. 6867 - 6877 View in Reaxys

S O

Rx-ID: 34583611 View in Reaxys 215/827 Yield 47 %

Conditions & References With potassium hydroxide in tert-butyl alcohol, Time= 1.5h, T= 70 °C Ulshoefer, Roland; Wedel, Tobias; Sueveges, Bastian; Podlech, Joachim; European Journal of Organic Chemistry; nb. 35; (2012); p. 6867 - 6877 View in Reaxys O

Rx-ID: 6871115 View in Reaxys 216/827 Yield 95%

Conditions & References 3 : EXAMPLE 3 EXAMPLE 3 The operation was conducted under the same conditions and with the same quantitative ratios as stated in Example 1; however, the β-methyl naphthalene was replaced by a de-based commercial methyl naphthalene fraction. The yield of fluorenone (95percent) amounted to 972 g.=90percent of theory. Patent; Rutgerswerke Aktiengesellschaft; US4218400; (1980); (A) English View in Reaxys

95%

4 : EXAMPLE 4 EXAMPLE 4

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The operation was conducted under the same conditions and with the same quantitative ratios as stated in Example 1 with the exceptions that instead of pure fluorene, a commercial fluorene fraction with a fluorene content of at least 50percent was used and that the β-methyl naphthalene was replaced by pure quinoline. The yield of fluorenone (95percent) amounted to 1.035 g.=96percent of theory. Patent; Rutgerswerke Aktiengesellschaft; US4218400; (1980); (A) English View in Reaxys 95%

5 : EXAMPLE 5 EXAMPLE 5 Again, the operation was conducted under the same conditions and with the same quantitative ratios as stated in Example 1 with the exceptions that instead of pure fluorene, a commercial fluorene fraction with a fluorene content of at least 50percent was used and that the β-methyl naphthalene was replaced by a raw quinoline fraction. The yield of fluorenone (95percent) amounted to 1.016 kg.=94percent of theory. Patent; Rutgerswerke Aktiengesellschaft; US4218400; (1980); (A) English View in Reaxys

59 %

6 Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; BIELAWSKI, Christopher W.; DREYER, Daniel R.; JIA, Hong-Peng; WO2011/150329; (2011); (A2) English View in Reaxys

48%

F.3 : Example F3 Example F3 A mixture of 10 millimoles of fluorene, 1 millimole of N-hydroxyphthalimide, 0.05 millimole of acetylacetonatovanadium V(AA)3 and 25 milliliters of acetic acid was stirred, in an oxygen atmosphere, at a temperature of 90° C. for 6 hours. In analyzing a product in the reaction mixture by gas chromatography, fluorene was transformed into fluorenone (yield 48percent) with a transformation rate of 54 percent. Patent; Daicel Chemical Industries, Ltd.; US5958821; (1999); (A) English View in Reaxys

28%

F.1 : Example F1 Example F1 In an oxygen atmosphere, a mixture of 10 millimoles of fluorene, 1 millimole of N-hydroxyphthalimide, 0.05 millimole of acetylacetonatomanganese Mn(AA)3 and 25 milliliters of benzonitrile was stirred at a temperature of 100° C. for six hours. Products in the reaction mixture were analyzed with gas chromatography, and fluorene was transformed into fluorenone (yield 28percent) with a transformation rate of 32 percent. Patent; Daicel Chemical Industries, Ltd.; US5958821; (1999); (A) English View in Reaxys Herstellung von <9-14C>-Fluorenon-(9) Ray; Geiser; Science (Washington, DC, United States); vol. 109; (1949); p. 200 View in Reaxys Herstellung von <9-14 C>Fluoren-9-on Ott; Smith; ; (1958); p. 681 View in Reaxys Heidelberger; Rieke; ; (1958); p. 387 View in Reaxys Cirigottis,K.A. et al.; Australian Journal of Chemistry; vol. 27; (1974); p. 2209 - 2228 View in Reaxys Prinzbach,H.; Fischer,U.; Helvetica Chimica Acta; vol. 50; (1967); p. 1692 - 1722 View in Reaxys Horner,L.; Fernekess,H.; Chemische Berichte; vol. 94; (1961); p. 712 - 724 View in Reaxys Schoenberg,A.; Singer,E.; Chemische Berichte; vol. 105; (1972); p. 2246 - 2257 View in Reaxys McDowell,B.L. et al.; Journal of the American Chemical Society; vol. 84; (1962); p. 3531 - 3538

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View in Reaxys Whitesides,G.M.; Ehmann,W.J.; Journal of the American Chemical Society; vol. 92; nb. 19; (1970); p. 5625 - 5640 View in Reaxys Trost,B.M.; Kinson,P.L.; Journal of the American Chemical Society; vol. 97; nb. 9; (1975); p. 2438 - 2449 View in Reaxys Bartlett,P.D.; Landis,M.E.; Journal of the American Chemical Society; vol. 99; (1977); p. 3033 - 3037 View in Reaxys Kuhn,R. et al.; Justus Liebigs Annalen der Chemie; vol. 689; (1965); p. 1 - 20 View in Reaxys Kuhn,R.; Rewicki,D.; Justus Liebigs Annalen der Chemie; vol. 690; (1965); p. 50 - 78 View in Reaxys Fetizon,M. et al.; Tetrahedron; vol. 31; (1975); p. 165 - 170 View in Reaxys Suzuki,K. et al.; Bulletin of the Chemical Society of Japan; vol. 43; (1970); p. 2217 - 2222 View in Reaxys Minabe,M. et al.; Bulletin of the Chemical Society of Japan; vol. 44; (1971); p. 1614 - 1619 View in Reaxys Minabe,M. et al.; Bulletin of the Chemical Society of Japan; vol. 51; (1978); p. 3373 - 3376 View in Reaxys Godfroid,J.-J.; Bulletin de la Societe Chimique de France; (1964); p. 2929 - 2943 View in Reaxys Trippett,S.; Walker,D.M.; Journal of the Chemical Society; (1961); p. 2130 - 2133 View in Reaxys Bailey,A.S. et al.; Journal of the Chemical Society; (1964); p. 5110 - 5118 View in Reaxys Blum,J. et al.; Journal of Organic Chemistry; vol. 35; (1970); p. 3233 - 3237 View in Reaxys Brown,P.M. et al.; Journal of the Chemical Society [Section] C: Organic; (1968); p. 842 - 848 View in Reaxys Zwanenburg,B.; Janssen,W.A.J.; Synthesis; (1973); p. 617 - 620 View in Reaxys Bonini,B.F. et al.; Gazzetta Chimica Italiana; vol. 107; (1977); p. 283 - 288 View in Reaxys Fridman,A.L. et al.; Zhurnal Organicheskoi Khimii; vol. 8; nb. 12; (1972); p. 2457 - 2462,2505 - 2509 View in Reaxys Patent; Schering AG; DE2418503; (1975); ; vol. 84; nb. 30929 View in Reaxys Akermark et al.; Journal of Organic Chemistry; vol. 40; (1975); p. 1365 View in Reaxys Wallenfels; Hanstein; Justus Liebigs Annalen der Chemie; vol. 709; (1967); p. 151 - 169 View in Reaxys Kappe et al.; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 34; (1979); p. 716 View in Reaxys Gait et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1974); p. 1248,1257 View in Reaxys Huisgen et al.; Chemische Berichte; vol. 110; (1977); p. 514,518 View in Reaxys Schoenberg; Praefcke; Chemische Berichte; vol. 99; (1966); p. 205,212 View in Reaxys Tanaka et al.; Nippon Kagaku Kaishi; (1973); p. 126,127-130 View in Reaxys Shevchuk et al.; Zhurnal Organicheskoi Khimii; vol. 7; (1971); p. 1692,1757,1758-1760 View in Reaxys Treibs; Schoellner; Chemische Berichte; vol. 94; (1961); p. 42,47 View in Reaxys Saxena; Kulshreshtha; Journal of the Indian Chemical Society; vol. 48; (1971); p. 137 View in Reaxys Colonge; Daunis; Bulletin de la Societe Chimique de France; (1961); p. 2238,2241 View in Reaxys Bunyan; Hey; Journal of the Chemical Society; (1962); p. 2771,2774

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View in Reaxys Chiba; Kogyo Kagaku Zasshi; vol. 69; (1966); p. 1289,1292 View in Reaxys Battaglia et al.; Synthesis; (1971); p. 378 View in Reaxys Gokel; Durst; Synthesis; (1976); p. 168,180 View in Reaxys Copeland et al.; Journal of the Chemical Society; (1960); p. 3230,3233 View in Reaxys Hawthorne; Wilt; Journal of Organic Chemistry; vol. 25; (1960); p. 2215,2216 View in Reaxys Pratt; van de Castle; Journal of Organic Chemistry; vol. 26; (1961); p. 2973 View in Reaxys Daschewskii; Petrenko; J. Appl. Chem. USSR (Engl. Transl.); vol. 35; (1962); p. 693,673; ; vol. 57; nb. 3374; (1962) View in Reaxys Shimizu et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 5972,5973,5976 View in Reaxys Rawson; Wynberg; Recueil des Travaux Chimiques des Pays-Bas; vol. 90; (1971); p. 39,43, 44 View in Reaxys Pratt; Suskind; Journal of Organic Chemistry; vol. 28; (1963); p. 638,639 View in Reaxys Olah; Welch; Journal of the American Chemical Society; vol. 100; (1978); p. 5396,5397 View in Reaxys Kuo; Nye; Canadian Journal of Chemistry; vol. 51; (1973); p. 1995,1999 View in Reaxys de Champlain; de Mayo; Canadian Journal of Chemistry; vol. 50; (1972); p. 270 View in Reaxys Russell; Thomson; Journal of the Chemical Society; (1962); p. 3379,3383 View in Reaxys Metz; Synthesis; (1972); p. 612 View in Reaxys Balachandran et al.; Journal of Organic Chemistry; vol. 33; nb. 10; (1968); p. 3891 View in Reaxys Wade et al.; Journal of Organic Chemistry; vol. 44; (1979); p. 3724 View in Reaxys Petrenko; Terent'eva; J. Appl. Chem. USSR (Engl. Transl.); vol. 38; (1965); p. 1109,1087 View in Reaxys Krylowa et al.; Neftekhimiya; vol. 16; (1976); p. 581,582; ; vol. 85; nb. 159734; (1976) View in Reaxys Patent; Russell; US3260570; (1966); ; vol. 66; nb. 2378m; (1967) View in Reaxys Pagano; Shechter; Journal of Organic Chemistry; vol. 35; (1970); p. 295,301 View in Reaxys Lewin; Michl; Journal of Organic Chemistry; vol. 38; (1973); p. 1126 View in Reaxys Lewin et al.; Journal of Organic Chemistry; vol. 39; (1974); p. 2747,2748-2752 View in Reaxys Richardson; Hodge; Journal of Organic Chemistry; vol. 35; (1970); p. 1216 View in Reaxys Cardillo et al.; Synthesis; (1976); p. 394 View in Reaxys Soboleva et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 43; (1970); p. 1787,1799,1800,1801 View in Reaxys Allen; Owen; Journal of the Chemical Society [Section] D: Chemical Communications; (1971); p. 848 View in Reaxys Mukaiyama; Echigo; Chemistry Letters; (1978); p. 49 View in Reaxys Scretlas; Cazianis; Tetrahedron; vol. 34; (1978); p. 933,935,939 View in Reaxys Lee; Freedman; Tetrahedron Letters; (1976); p. 1641,1643 View in Reaxys

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Czarny; Journal of the Chemical Society, Chemical Communications; (1976); p. 81 View in Reaxys Otsuka et al.; Justus Liebigs Annalen der Chemie; (1975); p. 626,635 View in Reaxys Patent; Monsanto; GB976611; (1962); ; vol. 62; nb. 7697; (1965) View in Reaxys Patent; Standard Oil Co.; US3038940; (1962); ; vol. 57; nb. 13687e; (1962) View in Reaxys Suzuki et al.; Nippon Kagaku Kaishi; (1979); p. 91,92; ; nb. 56711; (1979) View in Reaxys Andreikov; Rus'yanova; Kinetics and Catalysis; vol. 10; (1969); p. 590 View in Reaxys Pruefcke et al.; Chemische Berichte; vol. 107; (1974); p. 2931,2936 View in Reaxys Lewin; Cohen; Journal of Organic Chemistry; vol. 32; (1967); p. 3844,3849 View in Reaxys Cardillo et al.; Tetrahedron Letters; (1976); p. 3985 View in Reaxys Minabe; Suzuki; Journal of Organic Chemistry; vol. 40; (1975); p. 1298,1302 View in Reaxys Saveant; Binh; Journal of Electroanalytical Chemistry and Interfacial Electrochemistry; vol. 88; (1978); p. 27,30 View in Reaxys Patent; Proskuryakov et al.; SU245758; (1969); Ref. Zh., Khim.; vol. 11; nb. 406P; (1970) View in Reaxys Davies; Hodge; Journal of the Chemical Society [Section] C: Organic; (1971); p. 3158,3163,3164 View in Reaxys Rosini et al.; Journal of Organic Chemistry; vol. 39; (1974); p. 3504 View in Reaxys Ogata et al.; Journal of Organic Chemistry; vol. 40; (1975); p. 615,618 View in Reaxys Gukasyan; Shakhnazaryan; Armyanskii Khimicheskii Zhurnal; vol. 31; (1978); p. 711,712; ; vol. 90; nb. 87116x View in Reaxys Patent; Ruetgerswerke und Teerverwertung; DE1201339; (1965); ; vol. 63; nb. 16277d; (1965) View in Reaxys Huurdeman et al.; Tetrahedron Letters; (1971); p. 3449 View in Reaxys Patel; Politzer; Griffin; Laseter; Biomedical Mass Spectrometry; vol. 5; nb. 12; (1978); p. 664 - 670 View in Reaxys Patent; General Electric; US3875237; (1975); ; vol. 82; nb. 28009 View in Reaxys Sakai; Hattori; Chemistry Letters; (1975); p. 1103 View in Reaxys Olah et al.; Synthesis; (1979); p. 274 View in Reaxys Kajigaeshi; Nippon Kagaku Zasshi; vol. 83; (1962); p. 228; ; vol. 59; nb. 522; (1963) View in Reaxys Attanasi; Gasperoni; Gazzetta Chimica Italiana; vol. 108; (1978); p. 137 View in Reaxys Shirafuji et al.; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 2249 View in Reaxys Fridman et al.; Zhurnal Organicheskoi Khimii; vol. 7; (1971); p. 1126,1154 View in Reaxys Nesmeyanov et al.; Zhurnal Organicheskoi Khimii; vol. 7; (1971); p. 550,556,557-559 View in Reaxys Trost; Kinson; Journal of Organic Chemistry; vol. 37; (1972); p. 1273 View in Reaxys Moritani; Nagai; Nippon Kagaku Zasshi; vol. 86; (1965); p. 157; ; vol. 63; nb. 7789b View in Reaxys Yang; Libman; Journal of Organic Chemistry; vol. 39; (1974); p. 1782 View in Reaxys Patent; Simikow et al.; SU449029; (1975); Ref. Zh., Khim.; vol. 7; nb. N354P; (1976)

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View in Reaxys Chardonnens et al.; Helvetica Chimica Acta; vol. 56; (1973); p. 3044,3048 View in Reaxys Yang; Johnson; Journal of Organic Chemistry; vol. 42; (1977); p. 3754 View in Reaxys Friedman et al.; Journal of Organic Chemistry; vol. 30; (1965); p. 1453,1455 View in Reaxys Sellers; Suschitzky; Journal of the Chemical Society [Section] C: Organic; (1969); p. 2139,2140, 2142 View in Reaxys Funakubo et al.; Tetrahedron Letters; (1963); p. 1069,1071 View in Reaxys Davies; Ennis; Journal of the Chemical Society; (1960); p. 1488,1490 View in Reaxys Wiemann; Godefroid; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 255; (1962); p. 2608 View in Reaxys Ghera et al.; Journal of the American Chemical Society; vol. 98; (1976); p. 3627,3628, 3630 View in Reaxys Soboleva et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 44; (1971); p. 399,392 View in Reaxys Troszkiewicz et al.; Roczniki Chemii; vol. 46; (1972); p. 399,403, 404 View in Reaxys Reader et al.; Journal of Organic Chemistry; vol. 30; (1965); p. 784,787 View in Reaxys Huisgen; Zahler; Chemische Berichte; vol. 96; (1963); p. 736,746 View in Reaxys Narasimhan; Venkatasubramanian; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 17; (1979); p. 143 View in Reaxys Suzuki; Weisburger; Journal of the Chemical Society [Section] C: Organic; (1968); p. 199 View in Reaxys Blum et al.; Tetrahedron Letters; (1967); p. 3665 View in Reaxys Davies; Waring; Journal of the Chemical Society [Section] C: Organic; (1968); p. 2332 View in Reaxys Strating et al.; Recueil des Travaux Chimiques des Pays-Bas; vol. 86; (1967); p. 641 View in Reaxys Markov; Ivanov; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 264; (1967); p. 1659 View in Reaxys De Gunst; Recueil des Travaux Chimiques des Pays-Bas; vol. 88; (1969); p. 801 View in Reaxys Witaker et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 1411,1418 View in Reaxys Cheshire et al.; Tetrahedron; vol. 23; (1967); p. 1669 View in Reaxys Abramovitch; Robson; Journal of the Chemical Society [Section] C: Organic; (1967); p. 1101 View in Reaxys Mukai et al.; Tetrahedron Letters; (1968); p. 1695 View in Reaxys Davis et al.; Journal of the American Chemical Society; vol. 91; (1969); p. 2264 View in Reaxys Bethell; Brown; Chemical Communications (London); (1967); p. 1266 View in Reaxys YIELD YIELD Total yield of fluorenone was 1.71 grams (95.0percent). CHARACTERIZATION The fluorenone had a melting point of 82°-84° C. (melting point for compound listed at 82°-85° C. in the Aldrich Catalogue) and had the following NMR spectrum. 1 H NMR (CDCl , 200 MHz): β 7.67 (t), 7.64 (t), 7.5 (m) and 7.29 (m) 8H, ArH 3

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Patent; Humanetics Corporation; US5869709; (1999); (A) English View in Reaxys SEPARATION SEPARATION The solvent was removed under vacuum and diethyl ether (20 ml) added to the residue. The organic layer was separated, washed with copius amounts of water and then stirred with an aqueous sodium sulfite solution (15percent aqueous solution, 100 ml) for 2 hours at room temperature. The ether layer was separated, washed with water, dried and distilled to yield fluorenone. Patent; Humanetics Corporation; US6111118; (2000); (A) English View in Reaxys Patent; Humanetics Corporation; US5869709; (1999); (A) English View in Reaxys SEPARATION SEPARATION The reaction mixture was concentrated under vacuum and an aqueous sodium sulfite solution (15percent aqueous solution, 100 ml) added over a 2-hour period at room temperature. The resultant product was extracted with isopropyl ether, washed with water, dried and distilled to yield fluorenone. Patent; Humanetics Corporation; US6111118; (2000); (A) English View in Reaxys YIELD YIELD Total yield of fluorenone was 1.71 grams (95.0percent). CHARACTERIZATION The fluorenone had a melting point of 82-84° C. (melting point for compound listed at 82-850° C. in the Aldrich Catalogue) and had the following NMR spectrum. 1 H NMR (CDCl , 200 MHz): β 7.67 (t), 7.64 (t), 7.5 (m) and 7.29 (m) 8H, ArH 3 Patent; Humanetics Corporation; US6111118; (2000); (A) English View in Reaxys (ii) Low molecular weight compounds: fluorene, fluorenone, 2,7-dinitro-9-fluorenone, 2,4,7-trinitro-9-fluorenone, 4H-indeno (1,2,6)thiophen-4-one, ... Patent; Hitachi Chemical Company, Ltd.; US5352834; (1994); (A) English View in Reaxys A series of tests was carried out according to the procedure of Example 2, but employing other keto compounds of formula (II), namely: ... 4,4'-dihydroxybenzophenone (Example 4) 4,4'-diphenylbenzophenone (Example 5) 9-fluorenone (Example 6) 4-benzoylbiphenyl (Example 7). Patent; Rhone-Poulenc Chimie; US5434317; (1995); (A) English View in Reaxys Particularly preferred ketones suitable for the process of the invention include: Benzophenone, ... 2,4-Dimethyl benzophenone, 4,4'-Dimethyl benzophenone, 2,2'-Dimethyl benzophenone, 4,4'-Dimethoxy benzophenone,

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Fluorenone, 4-Hydroxybenzophenone, 4,4'-Dihydroxylbenzophenone, 4-benzoyl biphenyl. Patent; Rhone-Poulenc Chimie; US5414153; (1995); (A) English View in Reaxys 6 : EXAMPLE 6 EXAMPLE 6 The operation was conducted under the same conditions and with the same quantitative ratios as stated in Example 1, with the exceptions that instead of pure fluorene, a commercial fluorene fraction with a fluorene content of 72percent was used and as a suspension agent, β-methyl naphthalene was used. The distillation was conducted with the aid of a 28-tray column under vacuum at a pressure of 150 or 50 mm of mercury. The yield of fluorenone (95percent) amounted to 652 g.=85percent of theory. Patent; Rutgerswerke Aktiengesellschaft; US4218400; (1980); (A) English View in Reaxys 2H

Rx-ID: 8876765 View in Reaxys 217/827 Yield

Conditions & References With 4-nitro-1-chlorobenzotriazole in water, acetic acid, Kinetics Ulagi; Kuselan; Karunakaran; Monatshefte fur Chemie; vol. 132; nb. 7; (2001); p. 799 - 804 View in Reaxys With 2C24H20P(1+)*C56H80O8S2V2 (2-), oxygen in acetonitrile, Time= 1h, T= 80 °C , Molecular sieve Werncke, C. Gunnar; Limberg, Christian; Knispel, Christina; Mebs, Stefan; Chemistry - A European Journal; vol. 17; nb. 43; (2011); p. 12129 - 12135 View in Reaxys

Rx-ID: 28389478 View in Reaxys 218/827 Yield

Conditions & References With hydrogenchloride, water, Time= 8h, T= 100 °C Thirunavukkarasu, Vedhagiri S.; Parthasarathy, Kanniyappan; Cheng, Chien-Hong; Angewandte Chemie - International Edition; vol. 47; nb. 49; (2008); p. 9462 - 9465 View in Reaxys With hydrogenchloride, water, T= 100 °C , Inert atmosphere, Mechanism Thirunavukkarasu, Vedhagiri S.; Cheng, Chien-Hong; Chemistry - A European Journal; vol. 17; nb. 52; (2011); p. 14723 14726 View in Reaxys

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Rx-ID: 30916423 View in Reaxys 219/827 Yield

Conditions & References in 2,4-dichlorophenoxyacetic acid dimethylamine, toluene, Time= 5h, T= 120 °C Liu, Tao-Ping; Liao, Yuan-Xi; Xing, Chun-Hui; Hu, Qiao-Sheng; Organic Letters; vol. 13; nb. 9; (2011); p. 2452 - 2455 View in Reaxys With Trimethylacetic acid in 2,4-dichlorophenoxyacetic acid dimethylamine, toluene, Time= 10h, T= 120 °C , Under air Liu, Tao-Ping; Liao, Yuan-Xi; Xing, Chun-Hui; Hu, Qiao-Sheng; Organic Letters; vol. 13; nb. 9; (2011); p. 2452 - 2455 View in Reaxys

Rx-ID: 30916424 View in Reaxys 220/827 Yield

Conditions & References With Trimethylacetic acid in 2,4-dichlorophenoxyacetic acid dimethylamine, toluene, Time= 5h, T= 120 °C , Under air Liu, Tao-Ping; Liao, Yuan-Xi; Xing, Chun-Hui; Hu, Qiao-Sheng; Organic Letters; vol. 13; nb. 9; (2011); p. 2452 - 2455 View in Reaxys OH

Rx-ID: 30916425 View in Reaxys 221/827 Yield

Conditions & References With Trimethylacetic acid in 2,4-dichlorophenoxyacetic acid dimethylamine, toluene, Time= 10h, T= 120 °C Liu, Tao-Ping; Liao, Yuan-Xi; Xing, Chun-Hui; Hu, Qiao-Sheng; Organic Letters; vol. 13; nb. 9; (2011); p. 2452 - 2455 View in Reaxys O

Rx-ID: 30916461 View in Reaxys 222/827 Yield

Conditions & References Reaction Steps: 2 1: C42H62ClO3PPd; potassium carbonate / toluene / 5 h / 60 °C 2: Trimethylacetic acid / 2,4-dichlorophenoxyacetic acid dimethylamine; toluene / 10 h / 120 °C / Under air With C42H62ClO3PPd, potassium carbonate, Trimethylacetic acid in 2,4-dichlorophenoxyacetic acid dimethylamine, toluene Liu, Tao-Ping; Liao, Yuan-Xi; Xing, Chun-Hui; Hu, Qiao-Sheng; Organic Letters; vol. 13; nb. 9; (2011); p. 2452 - 2455 View in Reaxys

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Rx-ID: 30916462 View in Reaxys 223/827 Yield

Conditions & References Reaction Steps: 2 1: C42H62ClO3PPd; potassium carbonate / toluene / 5 h / 60 °C 2: Trimethylacetic acid / 2,4-dichlorophenoxyacetic acid dimethylamine; toluene / 5 h / 120 °C / Under air With C42H62ClO3PPd, potassium carbonate, Trimethylacetic acid in 2,4-dichlorophenoxyacetic acid dimethylamine, toluene Liu, Tao-Ping; Liao, Yuan-Xi; Xing, Chun-Hui; Hu, Qiao-Sheng; Organic Letters; vol. 13; nb. 9; (2011); p. 2452 - 2455 View in Reaxys O

HO B HO

Rx-ID: 30916467 View in Reaxys 224/827 Yield

HO B HO

Rx-ID: 30916468 View in Reaxys 225/827 Yield

Conditions & References Reaction Steps: 2 1: C42H62ClO3PPd; potassium carbonate / toluene / 5 h / 60 °C 2: Trimethylacetic acid / 2,4-dichlorophenoxyacetic acid dimethylamine; toluene / 5 h / 120 °C / Under air With C42H62ClO3PPd, potassium carbonate, Trimethylacetic acid in 2,4-dichlorophenoxyacetic acid dimethylamine, toluene Liu, Tao-Ping; Liao, Yuan-Xi; Xing, Chun-Hui; Hu, Qiao-Sheng; Organic Letters; vol. 13; nb. 9; (2011); p. 2452 - 2455 View in Reaxys O–

K+

Rx-ID: 31050602 View in Reaxys 226/827 Yield

Conditions & References With TEMPO+ClO4– in acetonitrile, Time= 3h, T= 20 °C

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Zhu, Xiao-Qing; Chen, Xi; Mei, Lian-Rui; Organic Letters; vol. 13; nb. 9; (2011); p. 2456 - 2459 View in Reaxys

NH 2

Rx-ID: 31548619 View in Reaxys 227/827 Yield

Conditions & References

29 %Chromat., 43 %

General procedure (Method A): To a solution of aniline (32.25 mmol) in 30 ml of benzene was added p-TSA (12.25 g, 64.5 mmol), TEOF (4.7 g, 32.25 mmol), CuCl (10 mol percent) at rt, mixture was heated to 50 °C. Maintaining 50 °C, powdered NaNO2 (2.09 g, 32.25 mmol) was added portion wise over 15 min, frothing was observed during the addition which subsided. The reaction mixture was maintained at the same temperature for 30 min to complete the reaction, monitored by TLC. The reaction mixture was cooled to rt, filtered to remove the solid precipitated, washed with EtOAc and organic layer was evaporated to dryness to get sticky residue, which was extracted with petroleum ether (60-80) followed by evaporation of solvent to yield the crude biaryl. It was purified by recrystallization from methanol/column chromatography ethyl acetate/petroleum ether (0.5:10) as eluent. With toluene-4-sulfonic acid, orthoformic acid triethyl ester, copper(l) chloride, sodium nitrite, Time= 0.75h, T= 50 °C , Gomberg-Bachmann-Hey reaction, regioselective reaction Chaturbhuj, Ganesh U.; Akamanchi, Krishnacharya G.; Tetrahedron Letters; vol. 52; nb. 38; (2011); p. 4950 - 4953 View in Reaxys OH

O B O

Rx-ID: 31928291 View in Reaxys 228/827 Yield

Conditions & References Reaction Steps: 2 1: potassium hydrogen bifluoride / methanol; water / 0.25 h / 20 °C 2: dipotassium peroxodisulfate; silver nitrate / water; β,β,β-trifluorotoluene / 1 h / 60 °C With dipotassium peroxodisulfate, potassium hydrogen bifluoride, silver nitrate in methanol, water, β,β,β-trifluorotoluene, 2: borono-Pschorr cyclization Lockner, Jonathan W.; Dixon, Darryl D.; Risgaard, Rune; Baran, Phil S.; Organic Letters; vol. 13; nb. 20; (2011); p. 5628 5631 View in Reaxys K+ -1 O

F B (v4)

F F

Rx-ID: 31928313 View in Reaxys 229/827 Yield 41 %

Conditions & References With dipotassium peroxodisulfate, silver nitrate in water, β,β,β-trifluorotoluene, Time= 1h, T= 60 °C , borono-Pschorr cyclization

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Lockner, Jonathan W.; Dixon, Darryl D.; Risgaard, Rune; Baran, Phil S.; Organic Letters; vol. 13; nb. 20; (2011); p. 5628 5631 View in Reaxys K+ O

-1

(v4)

F F

Rx-ID: 31928315 View in Reaxys 230/827 Yield

Conditions & References

30 %

With dipotassium peroxodisulfate, silver nitrate in water, β,β,β-trifluorotoluene, Time= 1h, T= 60 °C , borono-Pschorr cyclization Lockner, Jonathan W.; Dixon, Darryl D.; Risgaard, Rune; Baran, Phil S.; Organic Letters; vol. 13; nb. 20; (2011); p. 5628 5631 View in Reaxys O

Rx-ID: 31928366 View in Reaxys 231/827 Yield

Conditions & References Reaction Steps: 3 1: tetrahydrofuran / -40 - 20 °C 2: potassium hydrogen bifluoride / methanol; water / 0.25 h / 20 °C 3: dipotassium peroxodisulfate; silver nitrate / water; β,β,β-trifluorotoluene / 1 h / 60 °C With dipotassium peroxodisulfate, potassium hydrogen bifluoride, silver nitrate in tetrahydrofuran, methanol, water, β,β,β-trifluorotoluene, 3: borono-Pschorr cyclization Lockner, Jonathan W.; Dixon, Darryl D.; Risgaard, Rune; Baran, Phil S.; Organic Letters; vol. 13; nb. 20; (2011); p. 5628 5631 View in Reaxys O

O B O

Rx-ID: 31928381 View in Reaxys 232/827 Yield

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(v4) (v3)

Pd (v5)

O F

(v5) (v3) (v4)

N O

Rx-ID: 32293432 View in Reaxys 233/827 Yield

Rx-ID: 32293445 View in Reaxys 234/827 Yield

Rx-ID: 32293446 View in Reaxys 235/827 Yield 78 %

Conditions & References Stage 1: With dipotassium peroxodisulfate, palladium diacetate, trifluoroacetic acid, T= 120 °C , Inert atmosphere Stage 2: With water Thirunavukkarasu, Vedhagiri S.; Cheng, Chien-Hong; Chemistry - A European Journal; vol. 17; nb. 52; (2011); p. 14723 14726 View in Reaxys Reaction Steps: 2 1: dipotassium peroxodisulfate; palladium diacetate; trifluoroacetic acid / 15 h / 120 °C / Inert atmosphere 2: hydrogenchloride; water / 100 °C / Inert atmosphere With hydrogenchloride, dipotassium peroxodisulfate, water, palladium diacetate, trifluoroacetic acid Thirunavukkarasu, Vedhagiri S.; Cheng, Chien-Hong; Chemistry - A European Journal; vol. 17; nb. 52; (2011); p. 14723 14726 View in Reaxys Reaction Steps: 2 1: potassium peroxymonosulfate; palladium diacetate; trifluoroacetic acid / 15 h / 120 °C / Inert atmosphere 2: hydrogenchloride; water / 100 °C / Inert atmosphere With hydrogenchloride, potassium peroxymonosulfate, water, palladium diacetate, trifluoroacetic acid

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Thirunavukkarasu, Vedhagiri S.; Cheng, Chien-Hong; Chemistry - A European Journal; vol. 17; nb. 52; (2011); p. 14723 14726 View in Reaxys

N N

Rx-ID: 32293447 View in Reaxys 236/827 Yield 22 %, 15 %

Conditions & References Stage 1: With potassium peroxymonosulfate, palladium diacetate, trifluoroacetic acid, Time= 15h, T= 120 °C , Inert atmosphere Stage 2: With water Thirunavukkarasu, Vedhagiri S.; Cheng, Chien-Hong; Chemistry - A European Journal; vol. 17; nb. 52; (2011); p. 14723 14726 View in Reaxys O

Rx-ID: 32293468 View in Reaxys 237/827 Yield

Conditions & References Reaction Steps: 2 1: dipotassium peroxodisulfate; trifluoroacetic acid / 15 h / 120 °C / Inert atmosphere 2: hydrogenchloride; water / 100 °C / Inert atmosphere With hydrogenchloride, dipotassium peroxodisulfate, water, trifluoroacetic acid Thirunavukkarasu, Vedhagiri S.; Cheng, Chien-Hong; Chemistry - A European Journal; vol. 17; nb. 52; (2011); p. 14723 14726 View in Reaxys Reaction Steps: 2 1: dipotassium peroxodisulfate; trifluoroacetic acid / 120 °C 2: hydrogenchloride; water / 100 °C / Inert atmosphere With hydrogenchloride, dipotassium peroxodisulfate, water, trifluoroacetic acid Thirunavukkarasu, Vedhagiri S.; Cheng, Chien-Hong; Chemistry - A European Journal; vol. 17; nb. 52; (2011); p. 14723 14726 View in Reaxys

N O

Rx-ID: 2752818 View in Reaxys 238/827 Yield 93 %

Conditions & References With lithium diisopropyl amide in tetrahydrofuran, T= 0 - 20 °C , Inert atmosphere Tilly, David; Fu, Jian-Min; Zhao, Bao-Ping; Alessi, Manlio; Castanet, Anne-Sophie; Snieckus, Victor; Mortier, Jacques; Organic Letters; vol. 12; nb. 1; (2010); p. 68 - 71 View in Reaxys

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84 %

With lithium diisopropyl amide Fu, Jian-min; Zhao, Bao-ping; Sharp, M. J.; Snieckus, V.; Journal of Organic Chemistry; vol. 56; nb. 5; (1991); p. 1683 1685 View in Reaxys

O N

Rx-ID: 29080214 View in Reaxys 239/827 Yield

Conditions & References

89 %

With n-butyllithium in tetrahydrofuran, T= -78 °C , Inert atmosphere Tilly, David; Fu, Jian-Min; Zhao, Bao-Ping; Alessi, Manlio; Castanet, Anne-Sophie; Snieckus, Victor; Mortier, Jacques; Organic Letters; vol. 12; nb. 1; (2010); p. 68 - 71 View in Reaxys O

Rx-ID: 29443413 View in Reaxys 240/827 Yield

Conditions & References With pyridine, tert.-butylhydroperoxide, C28H23BrFeNO3P in decane, T= 20 °C Shejwalkar, Pushkar; Rath, Nigam P.; Bauer, Eike B.; Molecules; vol. 15; nb. 4; (2010); p. 2631 - 2650 View in Reaxys Rx-ID: 29718150 View in Reaxys 241/827

Yield

Conditions & References Stage 1: With water in acetone, Time= 2h, Darkness Stage 2: in acetone, Time= 1h, Irradiation Kou, Jiahui; Li, Zhaosheng; Guo, Yong; Gao, Jun; Yang, Ming; Zou, Zhigang; Journal of Molecular Catalysis A: Chemical; vol. 325; nb. 1-2; (2010); p. 48 - 54 View in Reaxys O Br

Br HO B

Rx-ID: 29756919 View in Reaxys 242/827 Yield

Conditions & References With sodium acetate, palladium diacetate, triphenylphosphine in N,N-dimethyl-formamide, Time= 16h, T= 120 °C , Inert atmosphere, Suzuki coupling Paul, Sunanda; Samanta, Shubhankar; Ray, Jayanta K.; Tetrahedron Letters; vol. 51; nb. 42; (2010); p. 5604 - 5608 View in Reaxys

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O Br

HO B O

Rx-ID: 29756924 View in Reaxys 243/827 Yield

Conditions & References

80 %

With sodium acetate, palladium diacetate, triphenylphosphine in N,N-dimethyl-formamide, Time= 15h, T= 120 °C , Inert atmosphere, Suzuki coupling Paul, Sunanda; Samanta, Shubhankar; Ray, Jayanta K.; Tetrahedron Letters; vol. 51; nb. 42; (2010); p. 5604 - 5608 View in Reaxys

O O

Rx-ID: 30089603 View in Reaxys 244/827 Yield

Conditions & References

33 %Spectr. With potassium peroxymonosulfate, 4-iodobenzoic acid in water, acetonitrile, Time= 14h, T= 60 °C Thottumkara, Prem P.; Vinod, Thottumkara K.; Organic Letters; vol. 12; nb. 24; (2010); p. 5640 - 5643 View in Reaxys

O O

Rx-ID: 30821625 View in Reaxys 245/827 Yield

Conditions & References With toluene-4-sulfonic acid in toluene, Time= 2.5h, T= 80 °C , Inert atmosphere Reddy, Sabbasani Rajasekhara; Titu, Devamani; Chadha, Anju; JAOCS, Journal of the American Oil Chemists' Society; vol. 87; nb. 7; (2010); p. 747 - 754 View in Reaxys N

Rx-ID: 9391740 View in Reaxys 246/827 Yield 76 %, 6 %

Conditions & References With 1-Benzyl-1,4-dihydronicotinamide, oxygen in acetonitrile, Time= 12h, T= 30 °C , Darkness Fang, Xin-Qiang; Xu, Hua-Jian; Jiang, Hong; Liu, You-Cheng; Fu, Yao; Wu, Yun-Dong; Tetrahedron Letters; vol. 50; nb. 3; (2009); p. 312 - 315 View in Reaxys

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5 % Chromat., 65 % Chromat.

With polysiloxane-supported 1-benzyl-1,4-dihydronicotinamide in acetonitrile, Time= 12h, T= 20 °C Zhang, Baolian; Zhu, Xiao-Qing; Lu, Jin-Yong; He, Jiaqi; Wang, Peng G.; Cheng, Jin-Pei; Journal of Organic Chemistry; vol. 68; nb. 8; (2003); p. 3295 - 3298 View in Reaxys

O HO

Rx-ID: 28853524 View in Reaxys 247/827 Yield

Conditions & References

11 %, 70 %

With N,N,N,N,-tetramethylethylenediamine, oxygen, 1,8-diazabicyclo[5.4.0]undec-7-ene, copper(l) chloride in acetonitrile, Time= 36h, T= 0 °C Adimurthy, Subbarayappa; Malakar, Chandi C.; Beifuss, Uwe; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5648 - 5651 View in Reaxys

O I

F O

S O

Rx-ID: 9950013 View in Reaxys 248/827 Yield

Conditions & References With cesium fluoride, tris-(o-tolyl)phosphine, bis(dibenzylideneacetone)-palladium(0) in toluene, acetonitrile, Time= 12h, T= 110 °C

75 %

Zhang, Xiaoxia; Larock, Richard C.; Organic Letters; vol. 7; nb. 18; (2005); p. 3973 - 3976 View in Reaxys Waldo, Jesse P.; Zhang, Xiaoxia; Shi, Feng; Larock, Richard C.; Journal of Organic Chemistry; vol. 73; nb. 17; (2008); p. 6679 - 6685 View in Reaxys

O F

F O

S O

Rx-ID: 9978011 View in Reaxys 249/827 Yield 73 %

Conditions & References With cesium fluoride, tris-(o-tolyl)phosphine, bis(dibenzylideneacetone)-palladium(0) in toluene, acetonitrile, Time= 24h, T= 110 °C Waldo, Jesse P.; Zhang, Xiaoxia; Shi, Feng; Larock, Richard C.; Journal of Organic Chemistry; vol. 73; nb. 17; (2008); p. 6679 - 6685

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View in Reaxys With cesium fluoride, tris-(o-tolyl)phosphine, bis(dibenzylideneacetone)-palladium(0) in toluene, acetonitrile, Time= 24h, T= 110 °C

73 % Chromat.

Zhang, Xiaoxia; Larock, Richard C.; Organic Letters; vol. 7; nb. 18; (2005); p. 3973 - 3976 View in Reaxys O S

Rx-ID: 27929601 View in Reaxys 250/827 Yield

Conditions & References T= 1100 °C , p= 0.25Torr Amick, Aaron W.; Wakamiya, Atsushi; Scott, Lawrence T.; Journal of Organic Chemistry; vol. 73; nb. 13; (2008); p. 5119 5122 View in Reaxys OH

Rx-ID: 27959580 View in Reaxys 251/827 Yield

Conditions & References

0.8 g, 52 %

With chromium(VI) oxide, sulfuric acid in acetone, T= 25 °C Casarini, Daniele; Lunazzi, Lodovico; Mazzanti, Andrea; Journal of Organic Chemistry; vol. 73; nb. 16; (2008); p. 6382 6385 View in Reaxys

O S

Rx-ID: 28194810 View in Reaxys 252/827 Yield

Conditions & References

95 %

With hydrogenchloride in water, acetonitrile, Time= 12h, T= 20 °C Krohn, Karsten; Cludius-Brandt, Stephan; Synthesis; nb. 15; (2008); p. 2369 - 2372; Art.No: T01408SS View in Reaxys

HO OH

Rx-ID: 314677 View in Reaxys 253/827

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Yield

Conditions & References

62 %

With potassium superoxide, tetraethylammonium bromide in N,N-dimethyl-formamide, T= 20 °C Singh, Krishna Nand; Kumar, Rajesh; Shukla, Ajay Kumar; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 46; nb. 8; (2007); p. 1347 - 1351 View in Reaxys With acetone, Sonnenlicht Schoenberg; Mustafa; Journal of the Chemical Society; (1944); p. 67,70; Journal of the Chemical Society; (1945); p. 657,660 View in Reaxys

Rx-ID: 2134405 View in Reaxys 254/827 Yield 48 %

Conditions & References With hypofluorous acid trifluoromethyl ester in chloroform, T= 0 °C Patrick, Timothy B.; Cantrell, Gary L.; Inga, Sandra M.; Journal of Organic Chemistry; vol. 45; nb. 8; (1980); p. 1409 1413 View in Reaxys With hydrogenchloride in acetone Zhao, Jian; Yue, Dawei; Campo, Marino A.; Larock, Richard C.; Journal of the American Chemical Society; vol. 129; nb. 16; (2007); p. 5288 - 5295 View in Reaxys

Rx-ID: 11018214 View in Reaxys 255/827 Yield 93 %

Conditions & References With KF on β-alumina, oxygen, Time= 0.2h, T= 150 °C , p= 3040.2 - 3800.26Torr , microwave irradiation Gershonov, Eytan; Katz, Esther; Karton, Yishai; Zafrani, Yossi; Tetrahedron; vol. 63; nb. 18; (2007); p. 3762 - 3767 View in Reaxys

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Rx-ID: 11018215 View in Reaxys 256/827 Yield

Conditions & References With KF on β-alumina, oxygen, Time= 0.2h, T= 150 °C , p= 760.051Torr , microwave irradiation Gershonov, Eytan; Katz, Esther; Karton, Yishai; Zafrani, Yossi; Tetrahedron; vol. 63; nb. 18; (2007); p. 3762 - 3767 View in Reaxys

Rx-ID: 11101475 View in Reaxys 257/827 Yield

Conditions & References

10 %

With copper(l) iodide, N,N,N,N,-tetramethylethylenediamine, caesium carbonate in toluene, Time= 2h, T= 110 °C De Prithwiraj; Nonappa; Pandurangan, Komala; Maitra, Uday; Wailes, Steve; Organic Letters; vol. 9; nb. 15; (2007); p. 2767 - 2770 View in Reaxys O

Rx-ID: 11253678 View in Reaxys 258/827 Yield

Conditions & References

62 % Spectr., 34 % Spectr.

in acetonitrile, Time= 14h, Irradiation, Title compound not separated from byproducts. Moorthy, Jarugu Narasimha; Samanta, Subhas; Journal of Organic Chemistry; vol. 72; nb. 25; (2007); p. 9786 - 9789 View in Reaxys

O N

Rx-ID: 11626649 View in Reaxys 259/827

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Yield

Conditions & References Reaction Steps: 2 1: cesium pivalate / Pd(OAc)2; 1,1-bis(diphenylphosphino)methane / dimethylformamide / 12 h / 100 °C 2: aq. HCl / acetone With hydrogenchloride, cesium pivalate, palladium diacetate, bis-diphenylphosphinomethane in N,N-dimethyl-formamide, acetone Zhao, Jian; Yue, Dawei; Campo, Marino A.; Larock, Richard C.; Journal of the American Chemical Society; vol. 129; nb. 16; (2007); p. 5288 - 5295 View in Reaxys O Br

triphenylboroxin O

Rx-ID: 11648669 View in Reaxys 260/827 Yield

Rx-ID: 25846972 View in Reaxys 261/827 Yield

Conditions & References Example 641 15 g of pyridinium chlorochromate (PCC) are added under nitrogen to a suspension of 40 g of Celite in 150 ml of dichloromethane. A solution of 10.0 g (35.6 mmol) of the fluorenol 28 in 25 ml of dichloromethane is subsequently added to the suspension. The batch is stirred overnight at room temperature. The Celite is separated off and washed with dichloro-methane. The organic phase is evaporated and passed through silica gel (MTB ether/n-heptane 1:3), giving 9.0 g (91percent) of the fluorenone 29. With pyridinium chlorochromate in dichloromethane Patent; Lietzau, Lars; Bremer, Matthias; Klasen-Memmer, Melanie; US2007/219380; (2007); (A1) English View in Reaxys Br O

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Rx-ID: 10539436 View in Reaxys 262/827 Yield

Conditions & References With potassium hydroxide, cyclohexene in methanol, Time= 1h Oota, Atsushi; Imai, Toshinobu; Yamazaki, Ayumi; Oba, Toru; Karikomi, Michinori; Minabe, Masahiro; Bulletin of the Chemical Society of Japan; vol. 79; nb. 2; (2006); p. 333 - 335 View in Reaxys O

Rx-ID: 12141906 View in Reaxys 263/827 Yield

Conditions & References Reaction Steps: 2 1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -80 °C 1.2: 96 percent / tetrahydrofuran; hexane / -80 - 20 °C 2.1: 27 percent / IPy2BF4; HBF4 / CH2Cl2; diethyl ether / 24 h / -60 °C With tetrafluoroboric acid, n-butyllithium, Barluenga reagent in tetrahydrofuran, diethyl ether, hexane, dichloromethane Barluenga, Jose; Trincado, Monica; Rubio, Eduardo; Gonzalez, Jose M.; Angewandte Chemie - International Edition; vol. 45; nb. 19; (2006); p. 3140 - 3143 View in Reaxys Br

O HO

Rx-ID: 9878592 View in Reaxys 264/827 Yield 86 %

Conditions & References Stage 1: With n-butyllithium in diethyl ether, hexane, T= -78 - 0 °C Stage 2: With water in tetrahydrofuran, diethyl ether, hexane, Time= 0.25h Tilly, David; Samanta, Subhendu S.; De, Asish; Castanet, Anne-Sophie; Mortier, Jacques; Organic Letters; vol. 7; nb. 5; (2005); p. 827 - 830 View in Reaxys O

O HN

Rx-ID: 9896573 View in Reaxys 265/827

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Yield

Conditions & References

40 %, 36 %

With sodium azide, ammonium cerium(IV) nitrate, T= 70 °C , Ritter amidation Nair, Vijay; Suja; Mohanan, Kishor; Tetrahedron Letters; vol. 46; nb. 18; (2005); p. 3217 - 3219 View in Reaxys

O N

Rx-ID: 9952188 View in Reaxys 266/827 Yield

Conditions & References

38 %, 15 %, in water-d2, acetonitrile, Time= 0.833333h, Photolysis, Further byproducts given 3 %, 37 % Kolano, Christoph; Bucher, Goetz; Schade, Olaf; Grote, Dirk; Sander, Wolfram; Journal of Organic Chemistry; vol. 70; nb. 17; (2005); p. 6609 - 6615 View in Reaxys OH

Rx-ID: 9993453 View in Reaxys 267/827 Yield

Conditions & References Stage 1: With phosphorus pentoxide, Time= 0.00833333h, T= 20 °C Stage 2: With nitric acid, Time= 0.0666667h, T= 20 °C Hajipour, Abdol R.; Kooshki, Behzad; Ruoho, Arnold E.; Organic Preparations and Procedures International; vol. 37; nb. 6; (2005); p. 585 - 589 View in Reaxys 2H

O 2H

Rx-ID: 9993673 View in Reaxys 268/827 Yield

Conditions & References With triethylsilane, oxygen, [Bu4N]4W10O32 in acetonitrile, Time= 0.5h, T= 5 - 10 °C , Irradiation

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Lykakis, Ioannis N.; Orfanopoulos, Michael; Tetrahedron Letters; vol. 46; nb. 45; (2005); p. 7835 - 7839 View in Reaxys 2H

O 2H

Rx-ID: 9994804 View in Reaxys 269/827 Yield

Conditions & References With triethylsilane, oxygen, [Bu4N]4W10O32 in acetonitrile, Time= 0.5h, T= 5 - 10 °C , Irradiation Lykakis, Ioannis N.; Orfanopoulos, Michael; Tetrahedron Letters; vol. 46; nb. 45; (2005); p. 7835 - 7839 View in Reaxys O

Rx-ID: 10034742 View in Reaxys 270/827 Yield

Conditions & References With oxygen, W10O32 (4-) in acetonitrile, Time= 1h, Irradiation Lykakis, Ioannis N.; Orfanopoulos, Michael; Tetrahedron Letters; vol. 46; nb. 45; (2005); p. 7835 - 7839 View in Reaxys

O O F O 2

–O

F O

N N

O O

Ca 2+ O

Rx-ID: 10101116 View in Reaxys 271/827 Yield 9 %, 1 %

Conditions & References in N,N-dimethyl-formamide, Time= 0.0833333h, UV-irradiation Player, Tomoko N.; Shinoda, Satoshi; Tsukube, Hiroshi; Organic and Biomolecular Chemistry; vol. 3; nb. 9; (2005); p. 1615 - 1616 View in Reaxys

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2-methyl-2'-formylbiphenyl2-hydroxymethyl-2'-formylbiphenyl

Rx-ID: 10119266 View in Reaxys 272/827 Yield

Conditions & References T= 550 - 825 °C , p= 1Torr , flow-vacuum pyrolysis, Further byproducts given Istrati, Daniela; Marton, George; Draghici, Constantin; Grigore, Adriana; Banciu, Mircea D.; Revue Roumaine de Chimie; vol. 50; nb. 7-8; (2005); p. 719 - 724 View in Reaxys

Rx-ID: 10152946 View in Reaxys 273/827 Yield 35 %

Conditions & References in N,N-dimethyl-formamide, UV-irradiation Player, Tomoko N.; Shinoda, Satoshi; Tsukube, Hiroshi; Organic and Biomolecular Chemistry; vol. 3; nb. 9; (2005); p. 1615 - 1616 View in Reaxys

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O Cl

Rx-ID: 10152956 View in Reaxys 274/827 Yield

Conditions & References

39 %, 2 %

in N,N-dimethyl-formamide, Time= 0.0833333h, UV-irradiation Player, Tomoko N.; Shinoda, Satoshi; Tsukube, Hiroshi; Organic and Biomolecular Chemistry; vol. 3; nb. 9; (2005); p. 1615 - 1616 View in Reaxys Br

2-methyl-2'-formylbiphenyl2-hydroxymethyl-2'-formylbiphenyl Br

Rx-ID: 13132357 View in Reaxys 275/827 Yield

Conditions & References Reaction Steps: 2 1.1: n-BuLi / diethyl ether / 1 h / -15 °C 1.2: 35 percent / diethyl ether / 5 h 2.1: n-BuLi / diethyl ether; hexane / -78 - 0 °C 2.2: 86 percent / H2O / diethyl ether; hexane; tetrahydrofuran / 0.25 h With n-butyllithium in diethyl ether, hexane Tilly, David; Samanta, Subhendu S.; De, Asish; Castanet, Anne-Sophie; Mortier, Jacques; Organic Letters; vol. 7; nb. 5; (2005); p. 827 - 830 View in Reaxys O

O HO

Rx-ID: 122192 View in Reaxys 276/827 Yield 100 %

Conditions & References With sodium perborate in acetic acid, Time= 1.5h, steam bath

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Banerjee, Amalendu; Hazra, Banasri; Bhattacharya, Atashi; Banerjee, Santanu; Banerjee, Gopal C.; Sengupta, Saumitra; Synthesis; nb. 10; (1989); p. 765 - 766 View in Reaxys 98 %

With (NMe4)<CoL>*2H2O*CH3CN (L = ortho-phenylenebis(N'-methyloxamidate)), oxygen, pivalaldehyde in acetonitrile, Time= 2h, Ambient temperature Blay, Gonzalo; Fernandez, Isabel; Formentin, Pilar; Pedro, Jose R.; Rosello, Antonio L.; Ruiz, Rafael; Journaux, Yves; Tetrahedron Letters; vol. 39; nb. 20; (1998); p. 3327 - 3330 View in Reaxys

91 %

With thionyl chloride, Time= 2h, Heating Olah; Wu; Synthesis; nb. 12; (1991); p. 1177 - 1179 View in Reaxys

91 %

With sodium hydroxide, copper(III) periodate, Time= 3h, Heating Banerjee, Amalendu; Mandal, Dinabandhu; Ray, Arindam; Banerjee, Pulak; Banerjee, Gopal Chandra; Journal of the Indian Chemical Society; vol. 72; nb. 3; (1995); p. 205 - 208 View in Reaxys

75 %

in acetic acid, Time= 0.25h, Heating Banerjee, Amalendu; Dutt, Sachchidananda; Sengupta, Dipanjan; Adak, Mohini Mohan; Samaddar, Haraprasad; Journal of the Indian Chemical Society; vol. 60; (1983); p. 275 - 277 View in Reaxys

60 %

With sodium vanadate, perchloric acid, Time= 0.166667h, Heating Dutta, Hasi; Hazra, Banasri; Banerjee, Amalendu; Banerjee, Santanu; Journal of the Indian Chemical Society; vol. 64; (1987); p. 706 - 707 View in Reaxys With potassium bromate, hydrogenchloride, water in acetonitrile, kobs vs. substrate concentration and vs. HCl concentration at 40 deg C; ΔH(excit), ΔS(excit) (temp.-range 30-45 deg C), Kinetics, Thermodynamic data Gupta, Kalyan Kali Sen; Banerjee, Amalendu; Chatterjee, Hrishikesh; Tetrahedron; vol. 48; nb. 25; (1992); p. 5323 - 5330 View in Reaxys With chromic acid Baeyer; Chemische Berichte; vol. 10; (1877); p. 127 View in Reaxys Friedlaender; Chemische Berichte; vol. 10; (1877); p. 534 View in Reaxys With hydrogenchloride, ammonium molybdate in dimethyl sulfoxide, Time= 4h, Heating, Yield given Dutt, Sachchidananda; Banerjee, Santanu; Hazra, Banasri; Banerjee, Amalendu; Banerjee, Gopal Chandra; Journal of the Indian Chemical Society; vol. 64; (1987); p. 704 - 705 View in Reaxys Reaction Steps: 2 1: 90 percent / LiAlH4 / tetrahydrofuran / 0.5 h 2: 22 percent / acetonitrile / 1 h / 20 °C / Flash photolysis With lithium aluminium tetrahydride in tetrahydrofuran, acetonitrile Mladenova, Gabriela; Singh, Gurmit; Acton, Austin; Chen, Lie; Rinco, Olga; Johnston, Linda J.; Lee-Ruff, Edward; Journal of Organic Chemistry; vol. 69; nb. 6; (2004); p. 2017 - 2023 View in Reaxys Reaction Steps: 2 1: 95 percent / Cu2O / acetonitrile / 50 °C 2: 8 percent / NaH / acetonitrile / 0.25 h / 50 °C With sodium hydride, copper(I) oxide in acetonitrile

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Toussaint, Olivier; Capdevielle, Patrice; Maumy, Michel; Tetrahedron; vol. 40; nb. 17; (1984); p. 3229 - 3234 View in Reaxys NH 2

Rx-ID: 9530013 View in Reaxys 277/827 Yield 99 %

Conditions & References With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide, Time= 5h, T= 25 °C Nicolaou; Mathison, Casey J. N.; Montagnon, Tamsyn; Journal of the American Chemical Society; vol. 126; nb. 16; (2004); p. 5192 - 5201 View in Reaxys HO

OH O O

Rx-ID: 9578268 View in Reaxys 278/827 Yield 22 %

Conditions & References in acetonitrile, Time= 1h, T= 20 °C , Flash photolysis Mladenova, Gabriela; Singh, Gurmit; Acton, Austin; Chen, Lie; Rinco, Olga; Johnston, Linda J.; Lee-Ruff, Edward; Journal of Organic Chemistry; vol. 69; nb. 6; (2004); p. 2017 - 2023 View in Reaxys O

O O

Rx-ID: 9599152 View in Reaxys 279/827 Yield

Conditions & References With sodium nitrate, H5PV2Mo10O40, Time= 14h, T= 80 °C Khenkin, Alexander M.; Neumann, Ronny; Journal of the American Chemical Society; vol. 126; nb. 20; (2004); p. 6356 6362 View in Reaxys O

Rx-ID: 9643098 View in Reaxys 280/827

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Yield

Conditions & References

57 %

Stage 1: With n-butyllithium, N,N,N,N,-tetramethylethylenediamine in diethyl ether, hexane, T= -40 - 20 °C Stage 2: in diethyl ether, hexane, T= -70 - 20 °C Kashulin, Igor A.; Nifant'ev, Ilya E.; Journal of Organic Chemistry; vol. 69; nb. 16; (2004); p. 5476 - 5479 View in Reaxys

O O

O OH

Rx-ID: 9643099 View in Reaxys 281/827 Yield

Conditions & References With dipotassium peroxodisulfate, trifluoroacetic acid, palladium(II) trifluoroacetate in dichloromethane, Time= 48h, T= 50 °C , p= 760Torr Shibahara, Fumitoshi; Kinoshita, Shinsuke; Nozaki, Kyoko; Organic Letters; vol. 6; nb. 14; (2004); p. 2437 - 2439 View in Reaxys

Rx-ID: 9652652 View in Reaxys 282/827 Yield

Conditions & References With diphenyl hydrazine in various solvent(s), T= 90 °C , Kinetics, Further Variations: Reagents, Temperatures Blake, Jessie A.; Pratt, Derek A.; Lin, Shuqiong; Walton, John C.; Mulder, Peter; Ingold; Journal of Organic Chemistry; vol. 69; nb. 9; (2004); p. 3112 - 3120 View in Reaxys O

Rx-ID: 9738899 View in Reaxys 283/827 Yield

Conditions & References With copper(II) glycinate in various solvents, T= 20 °C , Kinetics, Further Variations: Reagents, pH-values Hanson, Peter; Rowell, Simon C.; Walton, Paul H.; Timms, Allan W.; Organic and Biomolecular Chemistry; vol. 2; nb. 13; (2004); p. 1838 - 1855 View in Reaxys

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Rx-ID: 9738900 View in Reaxys 284/827 Yield

Conditions & References With copper(II) glycinate in various solvents, T= 20 °C , Sandmeyer hydroxylation, Kinetics, Further Variations: Reagents, pHvalues Hanson, Peter; Rowell, Simon C.; Walton, Paul H.; Timms, Allan W.; Organic and Biomolecular Chemistry; vol. 2; nb. 13; (2004); p. 1838 - 1855 View in Reaxys O

Rx-ID: 9779216 View in Reaxys 285/827 Yield

Conditions & References Stage 1: With triethylsilane, [Bu4N]4W10O32, oxygen in acetonitrile, Time= 1h, T= 5 - 10 °C , Irradiation Stage 2: With triphenylphosphine, Further stages. Lykakis, Ioannis N.; Orfanopoulos, Michael; Tetrahedron Letters; vol. 45; nb. 41; (2004); p. 7645 - 7649 View in Reaxys

O O

Rx-ID: 9829360 View in Reaxys 286/827 Yield

Conditions & References With lithium hydroxide in tetrahydrofuran, methanol, Time= 96h, T= 20 °C Xiao, Xiangshu; Antony, Smitha; Kohlhagen, Glenda; Pommier, Yves; Cushman, Mark; Journal of Organic Chemistry; vol. 69; nb. 22; (2004); p. 7495 - 7501 View in Reaxys

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Rx-ID: 24242878 View in Reaxys 287/827 Yield 4%

Conditions & References G.10 : Example G10 Example G10 A mixture of 10 millimoles of fluorene, 1 millimole of N-hydroxyphthalimide, 0.05 millimole of acetylacetonatozirconium Zr(AA)4, and 25 milliliters of acetic acid was stirred in an oxygen atmosphere at 90° C. for 6 hours. Products in the reaction mixture were analyzed with liquid chromatography, and as a result, fluorene was transformed into fluorenone (yield 42percent) and fluorenol (yield 4percent) with a transformation rate of 68 percent. Patent; Daicel Chemical Industries, Ltd.; US5958821; (1999); (A) English View in Reaxys

G.12 : Example G12 Example G12 A mixture of 10 millimoles of fluorene, 1 millimole of N-hydroxyphthalimide, 0.05 millimole of acetylacetonatocobalt Co(AA)2 and 25 milliliters of acetic acid was stirred in an oxygen atmosphere at 90° C. for 6 hours. Products in the reaction mixture were analyzed with liquid chromatography, and as a result, fluorene was transformed into fluorenone (yield 40percent) and fluorenol (yield 4percent) with a transformation rate of 59 percent. Forty-eight (48) percent of N-hydroxyphthalimide remained after completion of the reaction. Patent; Daicel Chemical Industries, Ltd.; US5958821; (1999); (A) English View in Reaxys

F.4 : Example F4 Example F4 To 25 milliliters of acetic acid were added 10 millimoles of fluorene, 1 millimole of N-hydroxyphthalimide and 0.05 millimole of acetylacetonatocobalt Co(AA)2. The resultant mixture was stirred in an oxygen atmosphere at a temperature of 90° C. for 6 hours, and as a result of analysis of a product in the reaction mixture with gas chromatography, fluorene was transformed into fluorenone (yield 44percent) and fluorenol (yield 3percent) with a transformation rate of 68 percent. Patent; Daicel Chemical Industries, Ltd.; US5958821; (1999); (A) English View in Reaxys

86% and 1percent

5 : EXAMPLE 5 The resulting product in the reaction mixture was analyzed by gas chromatography and was found to yield fluorenon and fluorenol in 86percent and 1percent yields, respectively, at 99percent conversion of fluorene. Patent; Daicel Chemical Industries, Ltd.; EP1459804; (2004); (A1) English View in Reaxys O

N-acetoxy-1,8-naphthalenedicarboximide

Rx-ID: 25838184 View in Reaxys 288/827 Yield 82%

Conditions & References 11 : EXAMPLE 11 EXAMPLE 11 A mixture of 1.00 g of fluorene, 0.154 g of N-acetoxy-1,8-naphthalenedicarboximide obtained by preparation example 2 (10percent by mole relative to fluorene), 9.0 g of acetic acid, 0.008 g of cobalt (II) acetate*4 H2O and 0.008 g of manganese(II) acetate*4 H2O was stirred at 120 °C in an atmosphere of oxygene gas (1 atm = 0.1 MPa) for 6 hours. The resulting product in the reaction mixture was analyzed by gas chromatography and was found to yield fluorenon in 82percent yield at 96percent conversion of fluorene.

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Patent; Daicel Chemical Industries, Ltd.; EP1433527; (2004); (A1) English View in Reaxys O O

O N

cobalt (II) acetate·4 H2O

manganese (II) acetate·4 H2O

Rx-ID: 25838185 View in Reaxys 289/827 Yield

Conditions & References

93%

7 : EXAMPLE 7 EXAMPLE 7 A mixture of 1.00 g of fluorene, 0.055 g of 1,3,5-triacetoxy-hexahydro-1,3,5-triazine-2,4,6-trione (3percent by mole relative to fluorene), 9.0 g of acetic acid, 0.008 g of cobalt (II) acetate*4 H2O and 0.007 g of manganese (II) acetate *4 H2O was stirred at 120 °C in an atmosphere of oxygene gas (1 atm = 0.1 MPa) for 6 hours. The resulting product in the reaction mixture was analyzed by gas chromatography and was found to yield fluorenon in 93percent yield at 99percent conversion of fluorene. With acetic acid Patent; Daicel Chemical Industries, Ltd.; EP1459804; (2004); (A1) English View in Reaxys Cl

Rx-ID: 290950 View in Reaxys 290/827 Yield

Conditions & References

87 %

With water, 3,6-bis(triphenylphosphonium)cyclohexene peroxodisulfate in acetonitrile, Time= 0.366667h, Heating Badri, Rashid; Soleymani, Mousa; Synthetic Communications; vol. 33; nb. 8; (2003); p. 1325 - 1332 View in Reaxys With chromium(III) oxide, sulfuric acid, T= 95 - 97 °C Courtot; Pierron; Bulletin de la Societe Chimique de France; vol. <4>45; (1929); p. 290 View in Reaxys

Rx-ID: 2030912 View in Reaxys 291/827 Yield 100 %

Conditions & References With trichloroisocyanuric acid, silver nitrate in water, acetonitrile, Ambient temperature

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Olah, George A.; Narang, Subhash C.; Salem, George F.; Synthesis; (1980); p. 657 View in Reaxys 98 %

With hydrogenchloride, dihydrogen peroxide in methanol, Ambient temperature Olah, George A.; Narang, Subhash C.; Salem, George F.; Synthesis; (1980); p. 657 View in Reaxys

95 %

With t-butyl bromide, dimethyl sulfoxide, Time= 24h, T= 70 - 75 °C Olah, George A.; Mehrotra, Ashok K.; Narang, Subhash C.; Synthesis; nb. 2; (1982); p. 151 - 152 View in Reaxys

95 %

With chlorine in tetrachloromethane, Time= 0.25h, Ambient temperature Caputo, Romualdo; Ferreri, Carla; Palumbo, Giovanni; Capozzi, Giuseppe; Tetrahedron; vol. 42; nb. 8; (1986); p. 2369 2376 View in Reaxys

90 %

With trimethylsilyl iodide, dimethyl sulfoxide in tetrachloromethane, Time= 6h, T= 75 - 80 °C Olah, George A.; Narang, Subbash C.; Mehrotra, Ashok K.; Synthesis; nb. 11; (1982); p. 965 - 966 View in Reaxys

90 %

88 %

With tert-butylhypochlorite in tetrachloromethane, Time= 1h, Ambient temperature, other reagent El-Wassimy, M.T.M.; Joergensen, K.A.; Lawesson S.-O.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1983); p. 2201 - 2204 View in Reaxys

76 %

With fluorosulfonylchloride in diethyl ether, water, Ambient temperature Olah, George A.; Narang, Subhash C.; Garcia-Luna, Armando; Salem, George F.; Synthesis; nb. 2; (1981); p. 146 View in Reaxys

N O N

Rx-ID: 4506590 View in Reaxys 292/827 Yield 60 %, 10 %

Conditions & References With tetrachloromethane, ammonia, copper(l) chloride in water, dimethyl sulfoxide, T= 20 °C Korotchenko; Shastin; Nenaidenko; Balenkova; Russian Chemical Bulletin; vol. 52; nb. 2; (2003); p. 492 - 497 View in Reaxys Multistep reaction Doetz, Karl Heinz; Pfeiffer, Juergen; Journal of the Chemical Society, Chemical Communications; nb. 8; (1996); p. 895 - 896 View in Reaxys

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N N

NH 2

N N

Rx-ID: 9292086 View in Reaxys 293/827 Yield

Conditions & References With tetraethylammonium hydroxide in dimethyl sulfoxide, T= 30 °C , Kinetics, Product distribution, Further Variations: Reagents, Solvents McDowell, Linda J.; Khodaei, M. Mehdi; Bethell, Donald; Organic and Biomolecular Chemistry; vol. 1; nb. 6; (2003); p. 995 - 1003 View in Reaxys Br O

N P

Rx-ID: 9298314 View in Reaxys 294/827 Yield

Conditions & References T= 155 - 160 °C Khurana, Jitender M.; Chauhan, Sushma; Maikap, Golak C.; Organic and Biomolecular Chemistry; vol. 1; nb. 10; (2003); p. 1737 - 1740 View in Reaxys

Rx-ID: 9312470 View in Reaxys 295/827 Yield

Conditions & References With N,N,N,N,N,N-hexamethylphosphoric triamide, iron(II) oxalate dihydrate, Time= 0.166667h, T= 155 - 160 °C

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Khurana, Jitender M.; Chauhan, Sushma; Maikap, Golak C.; Organic and Biomolecular Chemistry; vol. 1; nb. 10; (2003); p. 1737 - 1740 View in Reaxys Br

Rx-ID: 9333206 View in Reaxys 296/827 Yield

Conditions & References T= 155 - 160 °C Khurana, Jitender M.; Chauhan, Sushma; Maikap, Golak C.; Organic and Biomolecular Chemistry; vol. 1; nb. 10; (2003); p. 1737 - 1740 View in Reaxys

Rx-ID: 9384830 View in Reaxys 297/827 Yield

Conditions & References

0.37 mmol, With [(bipy)2(py)RuO](PF6)2 in acetonitrile, T= 20 °C , Product distribution, Kinetics, Further Variations: Reagents 0.011 mmol Bryant, Jasmine R.; Mayer, James M.; Journal of the American Chemical Society; vol. 125; nb. 34; (2003); p. 10351 - 10361 View in Reaxys N

Rx-ID: 9392786 View in Reaxys 298/827 Yield 17 %

Conditions & References With polysiloxane-supported 1-benzyl-1,4-dihydronicotinamide in acetonitrile, Time= 50h, T= 20 °C Zhang, Baolian; Zhu, Xiao-Qing; Lu, Jin-Yong; He, Jiaqi; Wang, Peng G.; Cheng, Jin-Pei; Journal of Organic Chemistry; vol. 68; nb. 8; (2003); p. 3295 - 3298 View in Reaxys

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N O

Rx-ID: 9393720 View in Reaxys 299/827 Yield

Conditions & References

19 % Chromat., 40 % Chromat.

N OH

Rx-ID: 9394151 View in Reaxys 300/827 Yield

Conditions & References

20 %, 80 %

T= 700 °C , p= 0.02Torr Ibrahim, Yehia A.; Al-Awadi, Nouria A.; Kual, Kamini; Tetrahedron; vol. 59; nb. 29; (2003); p. 5425 - 5430 View in Reaxys

N O

Rx-ID: 9397932 View in Reaxys 301/827 Yield

Conditions & References

40 %, 40 %

T= 700 °C , p= 0.02Torr Ibrahim, Yehia A.; Al-Awadi, Nouria A.; Kual, Kamini; Tetrahedron; vol. 59; nb. 29; (2003); p. 5425 - 5430 View in Reaxys NH 2 N

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9-fluorenol

Rx-ID: 9476654 View in Reaxys 302/827 Yield

Conditions & References

7 %, 21 %, 37 %

With ammonia, copper(l) chloride in water, dimethyl sulfoxide, T= 20 °C Korotchenko; Shastin; Nenaidenko; Balenkova; Russian Chemical Bulletin; vol. 52; nb. 2; (2003); p. 492 - 497 View in Reaxys N O

Rx-ID: 9503775 View in Reaxys 303/827 Yield

Conditions & References

45 %, 30 %

With tetrachloromethane, ammonia in water, dimethyl sulfoxide, T= 20 °C Korotchenko; Shastin; Nenaidenko; Balenkova; Russian Chemical Bulletin; vol. 52; nb. 2; (2003); p. 492 - 497 View in Reaxys NH 2

Rx-ID: 13959274 View in Reaxys 304/827 Yield

Conditions & References Reaction Steps: 2 1: 60 percent / NH3; CuCl; CCl4 / H2O; dimethylsulfoxide / 20 °C With tetrachloromethane, ammonia, copper(l) chloride in water, dimethyl sulfoxide Korotchenko; Shastin; Nenaidenko; Balenkova; Russian Chemical Bulletin; vol. 52; nb. 2; (2003); p. 492 - 497 View in Reaxys Reaction Steps: 2 1: 45 percent / NH3; CCl4 / H2O; dimethylsulfoxide / 20 °C With tetrachloromethane, ammonia in water, dimethyl sulfoxide Korotchenko; Shastin; Nenaidenko; Balenkova; Russian Chemical Bulletin; vol. 52; nb. 2; (2003); p. 492 - 497 View in Reaxys N

Rx-ID: 9004315 View in Reaxys 305/827

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Yield

Conditions & References

72.5 %

With 9,10-dihydro-10-methylacridine, oxygen in acetonitrile, Time= 24h, T= 60 °C Jiang, Hong; Liu, You-Cheng; Li, Jing; Wang, Guan-Wu; Wu, Yun-Dong; Wang, Quan-Ming; Mak, Thomas C. W.; Chemical Communications; nb. 8; (2002); p. 882 - 883 View in Reaxys I

N N

Rx-ID: 9006841 View in Reaxys 306/827 Yield

Conditions & References

56 % Spectr., 24 % Spectr.

With palladium diacetate, triethylamine, triphenylphosphine in water, N,N-dimethyl-formamide, Time= 12h, T= 130 °C

56 % Spectr., 24 % Spectr.

With triethylamine, triphenylphosphine, palladium diacetate in water, N,N-dimethyl-formamide, Time= 12h, T= 130 °C

Pletnev, Alexandre A.; Larock, Richard C.; Tetrahedron Letters; vol. 43; nb. 12; (2002); p. 2133 - 2136 View in Reaxys

Pletnev, Alexandre A.; Larock, Richard C.; Journal of Organic Chemistry; vol. 67; nb. 26; (2002); p. 9428 - 9438 View in Reaxys -1

(v4)

F N

B FF

O N

N+

Rx-ID: 9075612 View in Reaxys 307/827 Yield

Conditions & References With dipotassium hydrogenphosphate, potassium dihydrogenphosphate, tetrakis(acetonitrile)copper(I) tetrafluoroborate in water, acetonitrile, Time= 2h, pH= 8, Product distribution Hanson, Peter; Rowell, Simon C.; Taylor, Alec B.; Walton, Paul H.; Timms, Allan W.; Journal of the Chemical Society. Perkin Transactions 2; nb. 6; (2002); p. 1126 - 1134 View in Reaxys O H C

Rx-ID: 9132836 View in Reaxys 308/827 Yield

Conditions & References With [Mn2O2](3+) in acetonitrile, T= 50 °C , Kinetics, Further Variations: Temperatures Larsen, Anna S.; Wang, Kun; Lockwood, Mark A.; Rice, Gordon L.; Won, Tae-Jin; Lovell, Scott; Sadilek, Martin; Turecek, Frantisek; Mayer, James M.; Journal of the American Chemical Society; vol. 124; nb. 34; (2002); p. 10112 - 10123 View in Reaxys

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Rx-ID: 9190009 View in Reaxys 309/827 Yield

Conditions & References

91 %

With tetrabutylammomium bromide, sodium acetate, palladium diacetate in 1-methyl-pyrrolidin-2-one, Time= 12h, T= 140 °C Prashad, Mahavir; Liu, Yugang; Mak, Xiao Yin; Har, Denis; Repic, Oljan; Blacklock, Thomas J.; Tetrahedron Letters; vol. 43; nb. 47; (2002); p. 8559 - 8562 View in Reaxys

Rx-ID: 9276697 View in Reaxys 310/827 Yield

Conditions & References With methanesulfonic acid, T= 50 - 60 °C Tilly, David; Samanta, Subhendu S; Faigl, Ferenc; Mortier, Jacques; Tetrahedron Letters; vol. 43; nb. 46; (2002); p. 8347 8350 View in Reaxys I

Rx-ID: 14423892 View in Reaxys 311/827 Yield

Conditions & References Reaction Steps: 2 1: 30 percent / pyridine / 6 h / 150 °C 2: 56 percent Spectr. / PPh3; Et3N / Pd(OAc)2 / dimethylformamide; H2O / 12 h / 130 °C With pyridine, triethylamine, triphenylphosphine, palladium diacetate in water, N,N-dimethyl-formamide Pletnev, Alexandre A.; Larock, Richard C.; Journal of Organic Chemistry; vol. 67; nb. 26; (2002); p. 9428 - 9438 View in Reaxys O

Rx-ID: 24059129 View in Reaxys 312/827 Yield 80%

Conditions & References B.3 : Example B3 Example B3 A mixture containing 166 g (1 mol) of fluorene, 16 g (0.1 mol) of N-hydroxyphthalimide, and 1000 mL of acetic acid was allowed to react at 100° C. for 10 hours in an atmosphere of oxygen to obtain a reaction mixture containing 144 g of fluorenone (yield 80percent). From the reaction mixture, acetic acid was distilled off, and to the reaction mixture was added 1000 mL of dibutyl ether and 1000 mL of 0.4N (0.4 mol/L) sodium hydroxide aqueous solution.

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With acetic acid Patent; Miura, Hiroyuki; Watanabe, Hitoshi; Kuwana, Akihiro; Shimamura, Mami; Hirai, Naruhisa; US2002/169331; (2002); (A1) English View in Reaxys

acetylacetonatocobalt

acetylacetonatomanganese O N N N OH O

Rx-ID: 24131217 View in Reaxys 313/827 Yield

Conditions & References

30%

2 : EXAMPLE 2 EXAMPLE 2 A mixture of 3 mmol of fluorene, 0.3 mmol of 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine, 0.015 mmol of acetylacetonatocobalt(II), and 5 ml of acetic acid was stirred at 100° C. in an oxygen atmosphere (1 atm) for 2 hours. A gas chromatographic analysis of products in a reaction mixture found that fluorenone was formed in a yield of 30percent. With acetic acid Patent; Daicel Chemical Industries, Ltd.; US6403521; (2002); (B1) English View in Reaxys

(v4)

(v3) (v3)

CH – O (v6) + O Mn O O

(v3) (v3)

O (v3)

O (v5)(v5) (v5) (v5)

(v8)

O O

(v3)

Rx-ID: 26446794 View in Reaxys 314/827 Yield

Conditions & References

10 %, 8 %, 51 %, 19 %

With oxygen in not given, soln. of Mn complex under O2 (1 atm); solvent removed at ambient temp. under vac.; sepd. by flash column chromy. (silica gel, hexane); detd. by (1)H NMR spectra Decken, Andreas; MacKay, Andrew J.; Brown, Martin J.; Bottomley, Frank; Organometallics; vol. 21; nb. 9; (2002); p. 2006 - 2009 ; (from Gmelin) View in Reaxys

O O N

H N

H 2N

Rx-ID: 8721349 View in Reaxys 315/827

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Yield

Conditions & References With water Gong, Yong; Bausch, Mark J.; Wang, Linhua; Tetrahedron Letters; vol. 42; nb. 1; (2001); p. 1 - 4 View in Reaxys

O Cl

Cl O

O O O N

NH Cl

Cl O

Rx-ID: 8741404 View in Reaxys 316/827 Yield

Conditions & References T= 20 °C , Photolysis, Product distribution Bucher, Goetz; Halupka, Martin; Kolano, Christoph; Schade, Olaf; Sander, Wolfram; European Journal of Organic Chemistry; nb. 3; (2001); p. 545 - 552 View in Reaxys

S N

O HN

S S

Rx-ID: 8860024 View in Reaxys 317/827 Yield 82 %, 3 %

Conditions & References With 1,6-diazabicyclo[5.4.0]undecane, lithium bromide in toluene, acetonitrile, Time= 0.0333333h, T= 20 °C

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Linden; Gebert; Heimgartner; Acta Crystallographica Section C: Crystal Structure Communications; vol. 57; nb. 6; (2001); p. 764 - 766 View in Reaxys O O C

Rx-ID: 8998705 View in Reaxys 318/827 Yield

Conditions & References

58 %

With manganese(IV) oxide, trifluoroacetic acid, trifluoroacetic anhydride, palladium diacetate, Time= 20h, T= 20 °C , p= 750.06Torr Kalinovskii; Pogorelov; Gelbshtein; Akhmetov; Russian Journal of General Chemistry; vol. 71; nb. 9; (2001); p. 1457 - 1462 View in Reaxys

F O

S O

Rx-ID: 9009350 View in Reaxys 319/827 Yield

Conditions & References

73 %, 13 %, With Pt(dba)2*4PPh3 3% Chatani; Kamitani; Oshita; Fukumoto; Murai; Journal of the American Chemical Society; vol. 123; nb. 50; (2001); p. 12686 - 12687 View in Reaxys

O F

F O

S O

Rx-ID: 9009351 View in Reaxys 320/827 Yield 30 %, 13 %

Conditions & References With cesium fluoride, chloro(1,5-cyclooctadiene)rhodium(I) dimer in acetonitrile, Time= 12h, T= 60 °C , p= 1520.1Torr Chatani; Kamitani; Oshita; Fukumoto; Murai; Journal of the American Chemical Society; vol. 123; nb. 50; (2001); p. 12686 - 12687 View in Reaxys

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HO OH

Rx-ID: 9248489 View in Reaxys 321/827 Yield

Conditions & References With [(C5Me5)Ir(μ-H)]2 in toluene, Time= 18h, T= 65 °C Hou; Koizumi; Fujita; Yamazaki; Wakatsuki; Journal of the American Chemical Society; vol. 123; nb. 24; (2001); p. 5812 5813 View in Reaxys

NH N

Rx-ID: 8519535 View in Reaxys 322/827 Yield 76 %

Conditions & References Stage 1: With 3 A molecular sieve, zirconium(IV) tert-butoxide in dichloromethane, Time= 0.5h, complexation Stage 2: With tert.-butylhydroperoxide in dichloromethane, Time= 7h, Oxidation Krohn, Karsten; Steingroever, Klaus; Advanced Synthesis and Catalysis; vol. 342; nb. 2; (2000); p. 192 - 194 View in Reaxys

Rx-ID: 8556018 View in Reaxys 323/827 Yield

Conditions & References With oxygen, ozone in methanol, dichloromethane, T= 0 °C , ozonolysis, Product distribution Schank, Kurt; Beck, Horst; Buschlinger, Michael; Eder, Joerg; Heisel, Thomas; Pistorius, Susanne; Wagner, Christiane; Helvetica Chimica Acta; vol. 83; nb. 4; (2000); p. 801 - 826 View in Reaxys

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Rx-ID: 8556019 View in Reaxys 324/827 Yield

Conditions & References

88 %, 7 %

With oxygen, ozone in dichloromethane, T= -78 °C , ozonolysis, Product distribution, Further Variations: Solvents, Temperatures, Reagents Schank, Kurt; Beck, Horst; Buschlinger, Michael; Eder, Joerg; Heisel, Thomas; Pistorius, Susanne; Wagner, Christiane; Helvetica Chimica Acta; vol. 83; nb. 4; (2000); p. 801 - 826 View in Reaxys

O O

Rx-ID: 8556484 View in Reaxys 325/827 Yield

Conditions & References

98 %, 57 %, With oxygen, ozone in dichloromethane, T= -60 °C , ozonolysis, Product distribution 20 % Schank, Kurt; Beck, Horst; Buschlinger, Michael; Eder, Joerg; Heisel, Thomas; Pistorius, Susanne; Wagner, Christiane; Helvetica Chimica Acta; vol. 83; nb. 4; (2000); p. 801 - 826 View in Reaxys

Rx-ID: 8557968 View in Reaxys 326/827 Yield 29 %, 42 %

Conditions & References With oxygen, N-benzyl-trimethylammonium hydroxide, acetic acid in pyridine, T= -10 - 20 °C , Oxidation Schank, Kurt; Beck, Horst; Buschlinger, Michael; Eder, Joerg; Heisel, Thomas; Pistorius, Susanne; Wagner, Christiane; Helvetica Chimica Acta; vol. 83; nb. 4; (2000); p. 801 - 826 View in Reaxys

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Rx-ID: 8560552 View in Reaxys 327/827 Yield

Conditions & References

7 %, 51 %, 88 %, 40 %

With oxygen, ozone in tetrachloromethane, T= 0 °C , ozonolysis, Product distribution, Further Variations: Solvents, Temperatures Schank, Kurt; Beck, Horst; Buschlinger, Michael; Eder, Joerg; Heisel, Thomas; Pistorius, Susanne; Wagner, Christiane; Helvetica Chimica Acta; vol. 83; nb. 4; (2000); p. 801 - 826 View in Reaxys

scrap tire O S

Rx-ID: 8603917 View in Reaxys 328/827 Yield

Conditions & References With air, T= 650 - 850 °C , Formation of xenobiotics, Oxidation, Further byproducts given. Title compound not separated from byproducts Fullana; Font; Conesa; Blasco; Environmental Science and Technology; vol. 34; nb. 11; (2000); p. 2092 - 2099 View in Reaxys O

O HO

P O

Rx-ID: 8815349 View in Reaxys 329/827 Yield

Conditions & References With N-butylamine in chloroform, retro Abramov reaction, Kinetics Gancarz, Roman; Gancarz, Irena; Deron, Agnieszka; Phosphorus, Sulfur and Silicon and Related Elements; vol. 161; (2000); p. 61 - 69 View in Reaxys

O HO

P O

Rx-ID: 8815351 View in Reaxys 330/827 Yield

Conditions & References With N-butylamine in chloroform, retro Abramov reaction, Kinetics

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Gancarz, Roman; Gancarz, Irena; Deron, Agnieszka; Phosphorus, Sulfur and Silicon and Related Elements; vol. 161; (2000); p. 61 - 69 View in Reaxys

O O

O HO

P O

Rx-ID: 8827943 View in Reaxys 331/827 Yield

N 4

C N O– 2

Na +

Rx-ID: 11001275 View in Reaxys 332/827 Yield 50 %, 50 %

Conditions & References Stage 1: With isopropyl alcohol in tetrahydrofuran, Time= 0.5h Stage 2: With hydrogenchloride in tetrahydrofuran, Further stages. Hou, Zhaomin; Jia, Xueshun; Fujita, Akira; Tezuka, Hiroaki; Yamazaki, Hiroshi; Wakatsuki, Yasuo; Chemistry - A European Journal; vol. 6; nb. 16; (2000); p. 2994 - 3005 View in Reaxys S

H S

Rx-ID: 5272393 View in Reaxys 333/827 Yield 76.8 %, 9.5 %, 2.7 %, 10.8 %

Conditions & References With boron trifluoride diethyl etherate in dichloromethane, Time= 0.5h, T= -78 °C , Cycloaddition Blagoev, Milen; Linden, Anthony; Heimgartner, Heinz; Helvetica Chimica Acta; vol. 82; nb. 12; (1999); p. 2316 - 2335 View in Reaxys

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Rx-ID: 5312850 View in Reaxys 334/827 Yield

Conditions & References

36.4 %, 3.8 %, 31.9 %

With boron trifluoride diethyl etherate in dichloromethane, Time= 0.0166667h, T= -78 °C , Dimerization Blagoev, Milen; Linden, Anthony; Heimgartner, Heinz; Helvetica Chimica Acta; vol. 82; nb. 12; (1999); p. 2316 - 2335 View in Reaxys

O O O

HO O

Rx-ID: 1609021 View in Reaxys 335/827 Yield

Conditions & References

96 %, 1 %

With bis-(tributyltin oxide) dioxochromium(VI), water in dichloromethane, Time= 24h, T= 40 °C Muzart, Jacques; Synthetic Communications; vol. 19; nb. 11-12; (1989); p. 2061 - 2068 View in Reaxys

0.76 mmol, 0.20 mmol

With 2-Picolinic acid, ferric nitrate in pyridine, acetic acid, Time= 0.5h, variation of reaction time; also under air, Product distribution, Mechanism Barton, Derek H. R.; Wang, Tie-Lin; Tetrahedron; vol. 50; nb. 4; (1994); p. 1011 - 1032 View in Reaxys

0.76 mmol, 0.55 mmol

With 2-Picolinic acid in pyridine, acetic acid, Time= 0.5h, Title compound not separated from byproducts Barton, Derek H. R.; Wang, Tie-Lin; Tetrahedron; vol. 50; nb. 4; (1994); p. 1011 - 1032 View in Reaxys With iron(III) chloride in acetonitrile, Time= 1h, Ambient temperature Barton, Derek H. R.; Le Gloahec, Valerie N.; Tetrahedron; vol. 54; nb. 51; (1998); p. 15457 - 15468 View in Reaxys With copper dichloride in dichloromethane, water, Time= 4h, T= 25 °C , Yield given. Yields of byproduct given Rothenberg, Gadi; Feldberg, Liron; Wiener, Harold; Sasson, Yoel; Journal of the Chemical Society. Perkin Transactions 2; nb. 11; (1998); p. 2429 - 2434 View in Reaxys O–

O O

C–

Na +

Rx-ID: 4913266 View in Reaxys 336/827

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Yield

Conditions & References

97 %

With air Hou, Zhaomin; Fujita, Akira; Yamazaki, Hiroshi; Wakatsuki, Yasuo; Chemical Communications; nb. 6; (1998); p. 669 670 View in Reaxys -1 F

OH N

(v4)

B FF

N+

NH O N

Rx-ID: 4932423 View in Reaxys 337/827 Yield

Conditions & References in N,N-dimethyl-formamide, electrochemical reaction, carbon electrode, -1,8V Soucaze-Guillous, Benoit; Lund, Henning; Acta Chemica Scandinavica; vol. 52; nb. 4; (1998); p. 417 - 424 View in Reaxys

OH O O

Rx-ID: 4984583 View in Reaxys 338/827 Yield

Conditions & References With tert.-butylhydroperoxide, tetrabutylammomium bromide, copper dichloride in dichloromethane, water, Time= 4h, T= 25 °C , Yield given. Yields of byproduct given Rothenberg, Gadi; Feldberg, Liron; Wiener, Harold; Sasson, Yoel; Journal of the Chemical Society. Perkin Transactions 2; nb. 11; (1998); p. 2429 - 2434 View in Reaxys O S

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O S

Rx-ID: 5087444 View in Reaxys 339/827 Yield

Conditions & References in methanol, dichloromethane, Time= 48h, T= 50 °C , other solvent, temperatures, reaction times, effects of irradiation, reagent ratio, presence of air, Product distribution Adam, Waldemar; Froehling, Bettina; Weinkoetz, Stephan; Journal of Organic Chemistry; vol. 63; nb. 25; (1998); p. 9154 9155 View in Reaxys

HO OH

Rx-ID: 5094699 View in Reaxys 340/827 Yield

Conditions & References

17 %, 40 %

in acetonitrile, Time= 0.75h, T= 0 °C , Irradiation, other solvent, Product distribution Hoang, Mary; Gadosy, Timothy; Ghazi, Hedieh; Hou, Dong-Feng; Hopkinson, Alan C.; Johnston, Linda J.; Lee-Ruff, Edward; Journal of Organic Chemistry; vol. 63; nb. 21; (1998); p. 7168 - 7171 View in Reaxys N

O N

Rx-ID: 5139438 View in Reaxys 341/827 Yield 28 %, 72 %

Conditions & References With oxygen, sodium hydride in N,N,N,N,N,N-hexamethylphosphoric triamide, benzene, Time= 1.5h Kolyadina; Soldatenkov; Gridunova; Prostakov; Chemistry of Heterocyclic Compounds; vol. 34; nb. 7; (1998); p. 833 - 836 View in Reaxys

pentacarbonyl<9-(9H)-fluorenylidene>chromium(0)

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Rx-ID: 7164517 View in Reaxys 342/827 Yield

Conditions & References

78 %

in various solvent(s), T= 20 °C Pfeiffer, Juergen; Nieger, Martin; Doetz, Karl Heinz; Chemistry - A European Journal; vol. 4; nb. 9; (1998); p. 1843 - 1857 View in Reaxys

pentacarbonyl<9-(9H)-xanthenylidene>chromium(0)

Si O

Rx-ID: 8504887 View in Reaxys 343/827 Yield

Conditions & References With triethylamine, 1.) tert-butyl methyl ether, 40 deg C, 2.) tert-butyl methyl ether, 20 deg C, 2 h, Yield given. Multistep reaction Pfeiffer, Juergen; Nieger, Martin; Doetz, Karl Heinz; Chemistry - A European Journal; vol. 4; nb. 9; (1998); p. 1843 - 1857 View in Reaxys O

Rx-ID: 1869105 View in Reaxys 344/827 Yield

Conditions & References T= 900 °C , p= 0.02Torr , pyrolysis, Product distribution Brown, Roger F. C.; Choi, Neil; Coulston, Karen J.; Eastwood, Frank W.; Wiersum, Ulfert E.; Jenneskens, Leonardus W.; Tetrahedron Letters; vol. 35; nb. 25; (1994); p. 4405 - 4408 View in Reaxys

84 % flash vacuum pyrolysis, Product distribution, Mechanism Spectr., 2 % Spectr., 8 % Bapat, Jayant B.; Brown, Roger F.C.; Bulmer, Glenn H.; Childs, Trevor; Coulston, Karen J.; Eastwood, Frank W.; Taylor, Dennis K.; Australian Journal of Chemistry; vol. 50; nb. 12; (1997); p. 1159 - 1182

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Spectr., 2 % View in Reaxys Spectr. O

Rx-ID: 1992308 View in Reaxys 345/827 Yield

Conditions & References in chloroform-d1, Irradiation, Yield given Adam, Waldemar; Deeg, Oliver; Weinkoetz, Stephan; Journal of Organic Chemistry; vol. 62; nb. 21; (1997); p. 7084 - 7085 View in Reaxys With methanolate in methanol, dichloromethane, T= 25 °C , Rate constant Kice, John L.; Kupczyk-Subotkowska, Lidia; Journal of Organic Chemistry; vol. 56; nb. 4; (1991); p. 1431 - 1433 View in Reaxys

Cl Cl

O Cl

Rx-ID: 4711496 View in Reaxys 346/827 Yield 5.6 %

Conditions & References With palladium diacetate, tetra(n-butyl)ammonium hydrogensulfate, potassium carbonate in N,N-dimethyl-formamide, Time= 51h, T= 119 - 122 °C , Yields of byproduct given Pogodin, Sergey; Biedermann, P. Ulrich; Agranat, Israel; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2285 2287 View in Reaxys With palladium diacetate, tetra(n-butyl)ammonium hydrogensulfate, potassium carbonate in N,N-dimethyl-formamide, Time= 51h, T= 119 - 122 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Pogodin, Sergey; Biedermann, P. Ulrich; Agranat, Israel; Journal of Organic Chemistry; vol. 62; nb. 7; (1997); p. 2285 2287 View in Reaxys

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N O O

O O

Rx-ID: 4756639 View in Reaxys 347/827 Yield

Conditions & References

67 %, 16 %

in chloroform-d1, Time= 2h, T= -20 °C Adam, Waldemar; Biancafort, Lluis; Journal of Organic Chemistry; vol. 62; nb. 6; (1997); p. 1623 - 1629 View in Reaxys

N O N O

O O

Rx-ID: 4756640 View in Reaxys 348/827 Yield

Conditions & References

67 %, 16 %

With 3,3-dimethyldioxirane in chloroform-d1, Time= 2h, T= -20 °C Adam, Waldemar; Biancafort, Lluis; Journal of Organic Chemistry; vol. 62; nb. 6; (1997); p. 1623 - 1629 View in Reaxys Cl Cl

S Cl

Rx-ID: 4796359 View in Reaxys 349/827 Yield

Conditions & References With 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane, Time= 1h, T= 25 °C , Yield given. Yields of byproduct given Braverman, Samuel; Grinstein, Dan; Gottlieb, Hugo E.; Tetrahedron; vol. 53; nb. 40; (1997); p. 13933 - 13944 View in Reaxys

O O

Rx-ID: 4818169 View in Reaxys 350/827 Yield 82 %, 27 %

Conditions & References With 10-(methoxyimino)phenanthren-9-one, Time= 0.166667h, T= 150 °C Nicolaides, Demetrios N.; Awad, R. Wajih; Papageorgiou, Georgios K.; Kojanni, Efthalia; Tsoleridis, Constantinos A.; Journal of Heterocyclic Chemistry; vol. 34; nb. 6; (1997); p. 1651 - 1656 View in Reaxys

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O HO

Rx-ID: 4865102 View in Reaxys 351/827 Yield

Conditions & References

77 %

With phosphorus pentoxide, Time= 0.5h, p= 50 - 100Torr , heating in vacuum Nefedov; Russian Journal of Organic Chemistry; vol. 33; nb. 3; (1997); p. 375 - 377 View in Reaxys Br O O

O Br

Rx-ID: 4891514 View in Reaxys 352/827 Yield

Conditions & References

56 %, 32 %

With triethylamine in water, acetonitrile, Time= 24h, T= 130 °C , sealed tube Rappoport, Zvi; Shainyan, Bagrat A.; Journal of Physical Organic Chemistry; vol. 10; nb. 12; (1997); p. 871 - 878 View in Reaxys O

O O

Rx-ID: 4893650 View in Reaxys 353/827 Yield

Conditions & References flash vacuum pyrolysis, Product distribution, Mechanism Bapat, Jayant B.; Brown, Roger F.C.; Bulmer, Glenn H.; Childs, Trevor; Coulston, Karen J.; Eastwood, Frank W.; Taylor, Dennis K.; Australian Journal of Chemistry; vol. 50; nb. 12; (1997); p. 1159 - 1182 View in Reaxys S O

N N N

O O O

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O NH

S O

Rx-ID: 4895051 View in Reaxys 354/827 Yield

Conditions & References 1.) 80 deg C, 1.5 h; 2.) PhMe, RT, 2 h, Yield given. Multistep reaction. Yields of byproduct given Mloston, Grzegorz; Romanski, Jaroslaw; Linden, Anthony; Heimgartner, Heinz; Helvetica Chimica Acta; vol. 80; nb. 6; (1997); p. 1992 - 2001 View in Reaxys

S S

O S

Rx-ID: 4933294 View in Reaxys 355/827 Yield

Conditions & References

20 % in benzene, Time= 0.666667h, Irradiation, effect of the oxygen atmosphere, Product distribution Spectr., 2 % Kawamura, Yasuhiko; Akitomo, Kohji; Oe, Masaaki; Horie, Tokunaru; Tsukayama, Masao; Tetrahedron Letters; vol. 38; Spectr. nb. 52; (1997); p. 8989 - 8992 View in Reaxys N N S S

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O S

Rx-ID: 4977040 View in Reaxys 356/827 Yield

Conditions & References

61 % Spectr., 15 % Spectr.

in benzene, Time= 0.666667h, Irradiation, effect of the oxygen atmosphere, Mechanism, Product distribution Kawamura, Yasuhiko; Akitomo, Kohji; Oe, Masaaki; Horie, Tokunaru; Tsukayama, Masao; Tetrahedron Letters; vol. 38; nb. 52; (1997); p. 8989 - 8992 View in Reaxys

O C

Rx-ID: 4555887 View in Reaxys 357/827 Yield

Conditions & References Rate constant Kovacs, Dalila; Lee, Ming-Shi; Olson, David; Jackson, James E.; Journal of the American Chemical Society; vol. 118; nb. 34; (1996); p. 8144 - 8145 View in Reaxys O

O N

Rx-ID: 4556104 View in Reaxys 358/827 Yield

P O

Rx-ID: 4556370 View in Reaxys 359/827

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Yield

Rx-ID: 4556822 View in Reaxys 360/827 Yield

O O

C+

Rx-ID: 4557136 View in Reaxys 361/827 Yield

Conditions & References in various solvent(s), T= 20 °C , Rate constant Lew; Wagner; Angelini, Mark P.; Lee-Ruff; Lusztyk; Johnston; Journal of the American Chemical Society; vol. 118; nb. 48; (1996); p. 12066 - 12073 View in Reaxys

O O

I O

Rx-ID: 4560307 View in Reaxys 362/827 Yield

Conditions & References

9 %, 15 %

in dichloromethane, Time= 24h, Ambient temperature Ochiai, Masahito; Ito, Takao; Takahashi, Hideo; Nakanishi, Akinobu; Toyonari, Mika; Sueda, Takuya; Goto, Satoru; Shiro, Motoo; Journal of the American Chemical Society; vol. 118; nb. 33; (1996); p. 7716 - 7730 View in Reaxys O C

Rx-ID: 4581169 View in Reaxys 363/827

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Yield

Rx-ID: 4600918 View in Reaxys 364/827 Yield

Conditions & References Rate constant Kovacs, Dalila; Lee, Ming-Shi; Olson, David; Jackson, James E.; Journal of the American Chemical Society; vol. 118; nb. 34; (1996); p. 8144 - 8145 View in Reaxys

O HO

Rx-ID: 5053962 View in Reaxys 365/827 Yield

Conditions & References

24.7 %, 38.4 %

With No. 380 in benzene, Time= 0.5h, T= 600 °C , thermolysis Soldatenkov; Kolyadina; Kuleshova; Khrustalev; Chemistry of Heterocyclic Compounds; vol. 32; nb. 7; (1996); p. 817 - 821 View in Reaxys

O HO

Rx-ID: 5053963 View in Reaxys 366/827 Yield

Conditions & References

90 %

With K-16 in benzene, Time= 0.5h, T= 600 °C , thermolysis Soldatenkov; Kolyadina; Kuleshova; Khrustalev; Chemistry of Heterocyclic Compounds; vol. 32; nb. 7; (1996); p. 817 - 821 View in Reaxys O

Rx-ID: 2199244 View in Reaxys 367/827 Yield 80 %

Conditions & References With selenium, Time= 3h, T= 250 °C

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Ramana; Potnis; Synthesis; nb. 6; (1993); p. 575 - 576 View in Reaxys 80 %

With selenium, Time= 3h, T= 250 °C Ramana; Potnis; Synthetic Communications; vol. 25; nb. 11; (1995); p. 1751 - 1760 View in Reaxys N N

Rx-ID: 4188751 View in Reaxys 368/827 Yield

Conditions & References

32 %, 18 %

With dirhodium(II) tetrakis<methyl 2-pyrrolidone-5(S)-carboxylate> <Rh2(5S-MEPY)4> in dichloromethane, Heating, further Rh(II) catalyst Doyle, Michael P.; Dyatkin, Alexey B.; Autry, Christopher L.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 6; (1995); p. 619 - 622 View in Reaxys

O O

N N O N

NH H 2N

O O

Rx-ID: 4193608 View in Reaxys 369/827 Yield 7 %, 5 %, 43 %, 3 %, 31 %

Conditions & References in methanol, Time= 1h, T= 30 - 35 °C , Irradiation, other carbamates derived from 9-fluorenone oxime; var. solvents and time, Product distribution, Mechanism Bucher, Goetz; Scaiano; Sinta; Barclay; Cameron; Journal of the American Chemical Society; vol. 117; nb. 13; (1995); p. 3848 - 3855 View in Reaxys

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Rx-ID: 4246388 View in Reaxys 370/827 Yield

Conditions & References With n-butyllithium, thionyl chloride, 1.) hexane, THF, -78 deg C, 5 min, 2.) hexane, THF, -78 deg C, Yield given. Multistep reaction. Yields of byproduct given Oae, Shigeru; Inubushi, Yoichi; Yoshihara, Masakuni; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 103; nb. 1-4; (1995); p. 101 - 110 View in Reaxys

O N

Rx-ID: 4251315 View in Reaxys 371/827 Yield 36 %, 29 %

Conditions & References With oxygen, lithium diisopropyl amide in tetrahydrofuran, hexane, Ambient temperature Braven, J.; Hanson, R. W.; Smith, N. G.; Journal of Heterocyclic Chemistry; vol. 32; nb. 3; (1995); p. 1051 - 1056 View in Reaxys

S S

Rx-ID: 4345621 View in Reaxys 372/827 Yield

Conditions & References With potassium hydroxide, oxygen in tetrahydrofuran, Time= 0.25h, Yield given Lai, Yee-Hing; Lee, Siok-Mun; Tetrahedron Letters; vol. 36; nb. 47; (1995); p. 8679 - 8680 View in Reaxys

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Rx-ID: 4440224 View in Reaxys 373/827 Yield

Conditions & References With monochlorocopper(II), Rate constant Hanson, Peter; Hammond, Roger C.; Gilbert, Bruce C.; Timms, Allan W.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1995); p. 2195 - 2202 View in Reaxys

O O

Rx-ID: 1581392 View in Reaxys 374/827 Yield

Conditions & References Ambient temperature, Irradiation, with/without O2 addition; with/without AcCN solvent, Product distribution, Quantum yield Verbeek, Jan-Maarten; Stapper, Marion; Krijnen, Erik S.; Loon, Jan-Dirk van; Lodder, Gerrit; Steenken, Steen; Journal of Physical Chemistry; vol. 98; nb. 38; (1994); p. 9526 - 9536 View in Reaxys

HO O

O O

Rx-ID: 1581399 View in Reaxys 375/827 Yield

Conditions & References Ambient temperature, Irradiation, with/without O2 addition; with/without AcCN solvent, Product distribution, Quantum yield

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Verbeek, Jan-Maarten; Stapper, Marion; Krijnen, Erik S.; Loon, Jan-Dirk van; Lodder, Gerrit; Steenken, Steen; Journal of Physical Chemistry; vol. 98; nb. 38; (1994); p. 9526 - 9536 View in Reaxys

O O

Rx-ID: 1582130 View in Reaxys 376/827 Yield

O O

Rx-ID: 1582289 View in Reaxys 377/827 Yield

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O O

Rx-ID: 1582361 View in Reaxys 378/827 Yield

O O

Rx-ID: 1595743 View in Reaxys 379/827 Yield

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O O

Rx-ID: 1602781 View in Reaxys 380/827 Yield

O O

Rx-ID: 1602791 View in Reaxys 381/827 Yield

Rx-ID: 2523132 View in Reaxys 382/827 Yield

Conditions & References With acetonitrile, Irradiation, Rate constant Shields, Charles J.; Schuster, Gary B.; Tetrahedron Letters; vol. 28; nb. 8; (1987); p. 853 - 856 View in Reaxys

95 % Chromat.

With β,β,β,β-Tetraphenylporphin-Zink, oxygen in benzene, Time= 0.5h, T= 20 °C , Irradiation, further solvents, Product distribution, Mechanism Sawaki, Yasuhiko; Kato, Hiroshi; Ogata, Yoshiro; Journal of the American Chemical Society; vol. 103; nb. 13; (1981); p. 3832 - 3837

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View in Reaxys With oxygen, Irradiation, thermical induced Stoesser, Reinhard; Thurner, Joern-Uwe; Warncke, Wolfgang; Tomaschewski, Georg; Taplick, Thomas; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 29; nb. 2; (1989); p. 67 - 68 View in Reaxys With (PhO)3PO3 in dichloromethane, T= -15 °C , various diazocompounds, oxidation, Product distribution, Mechanism, Rate constant Shereshovets, V. V.; Korotaeva, N. M.; Vorob'ev, A. S.; Komissarov, V. D.; Furlei, I. I.; Russian Chemical Bulletin; vol. 43; nb. 9; (1994); p. 1479 - 1483; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 9; (1994); p. 1567 - 1571 View in Reaxys

Rx-ID: 2657364 View in Reaxys 383/827 Yield

Conditions & References

10 %, 17 %, With oxygen in toluene, Time= 12h, Heating, Irradiation 18 %, 22 % Abdou, Wafaa M.; Elkhoshnieh, Yehia O.; Sidky, Mahmoud M.; Tetrahedron; vol. 50; nb. 11; (1994); p. 3595 - 3602 View in Reaxys

O O

Rx-ID: 3658745 View in Reaxys 384/827 Yield 4 % Chromat., 13 % Chromat., 4 % Chromat., 10 % Chromat., 9 % Chromat.

Conditions & References T= 520 °C , p= 0.02Torr , further temperatures, time; further 3-phenylimino-3H-indazole, Product distribution Brown, Roger F. C.; Coulston, Karen J.; Eastwood, Frank W.; Australian Journal of Chemistry; vol. 47; nb. 1; (1994); p. 47 60 View in Reaxys

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Rx-ID: 3675455 View in Reaxys 385/827 Yield

Conditions & References With copper(II) sulfate, tert-butyl alcohol, T= 20 °C , other hydrogen donors, other copper salts; var. conc. of regents, Product distribution, Rate constant Hanson, Peter; Hammond, Roger C.; Goodacre, Paul R.; Purcell, Juliet; Timms, Allan W.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 4; (1994); p. 691 - 696 View in Reaxys

Rx-ID: 2027765 View in Reaxys 386/827 Yield 8 % Turnov., 29 % Turnov., 32 % Turnov. 8 % Turnov., 29 % Turnov., 32 % Turnov.

Conditions & References With oxygen in dichloromethane, Time= 12h, Irradiation Breslin, David T.; Fox, Marye Anne; Journal of Physical Chemistry; vol. 97; (1993); p. 13341 - 13347 View in Reaxys With oxygen in dichloromethane, Time= 12h, Irradiation, photoxygenation in other solvents: C6H6, ethyl acetate, CHCl3, C6H12, CH3OH, CH3CN; also in air-saturated solvents; no reaction in degassed solvents, Quantum yield, Mechanism, Product distribution Breslin, David T.; Fox, Marye Anne; Journal of Physical Chemistry; vol. 97; (1993); p. 13341 - 13347 View in Reaxys

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HO O

Rx-ID: 2027766 View in Reaxys 387/827 Yield

Conditions & References

32 % Turnov., 2 % Turnov., 10 % Turnov., 8 % Turnov., 41 % Turnov.

With oxygen in toluene, Time= 12h, Irradiation, when solvent purged with N2 gas, products are different, Product distribution, Mechanism Breslin, David T.; Fox, Marye Anne; Journal of Physical Chemistry; vol. 97; (1993); p. 13341 - 13347 View in Reaxys

O HO

O PH (v5)

Rx-ID: 2148820 View in Reaxys 388/827 Yield

Conditions & References With triethylamine, other reagents (n-butyl- and t-butylamine), Rate constant Gancarz; Tetrahedron Letters; vol. 34; nb. 1; (1993); p. 145 - 148 View in Reaxys

P O

O P

Rx-ID: 2148982 View in Reaxys 389/827 Yield

Conditions & References With triethylamine, other reagents (n-butyl- and t-butylamine), Rate constant Gancarz; Tetrahedron Letters; vol. 34; nb. 1; (1993); p. 145 - 148 View in Reaxys

O O

O HO

H P

O P

Rx-ID: 3235619 View in Reaxys 390/827 Yield

Conditions & References With triethylamine, other reagents (n-butyl- and t-butylamine), Rate constant

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Gancarz; Tetrahedron Letters; vol. 34; nb. 1; (1993); p. 145 - 148 View in Reaxys

N O

O O

O N

N N

Rx-ID: 3378188 View in Reaxys 391/827 Yield

Conditions & References in tetrahydrofuran, T= 25 °C , electrolyse: -1.50 V vs SPRE, 0.15 M n-Bu4NPF6 as the supporting electrolyte; various reaction conditions, Mechanism, Product distribution Mugnier, Yves; Gard, Jean-Christophe; Huang, Youqin; Couture, Yvon; Lasia, Andrzej; Lessard, Jean; Journal of Organic Chemistry; vol. 58; nb. 20; (1993); p. 5329 - 5334 View in Reaxys

O N

Rx-ID: 3505165 View in Reaxys 392/827 Yield

Conditions & References

80 % Spectr.

With oxo(N,N'-ethylenebis-salicylideneiminato)chromium(V) trifluoromethanesulphonate in acetonitrile, T= 21 °C , var. oxo(salen)chromium(V) triflates, Rate constant Rihter, Boris; Srihari, Somu; Hunter, Sandra; Masnovi, John; Journal of the American Chemical Society; vol. 115; nb. 10; (1993); p. 3918 - 3924 View in Reaxys

Rx-ID: 3507177 View in Reaxys 393/827 Yield 81 % Spectr.

Conditions & References With oxo(N,N'-ethylenebis-salicylideneiminato)chromium(V) trifluoromethanesulphonate in acetonitrile, T= 21 °C , other fluorenylidene nitrile ylide and phosphorus ylides, var. oxo(salen)chromium(V) triflates, Rate constant, Mechanism, Product distribution

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Rihter, Boris; Srihari, Somu; Hunter, Sandra; Masnovi, John; Journal of the American Chemical Society; vol. 115; nb. 10; (1993); p. 3918 - 3924 View in Reaxys O

Rx-ID: 283491 View in Reaxys 394/827 Yield

Conditions & References With sodium hydroxide, air Jeanes; Adams; Journal of the American Chemical Society; vol. 59; (1937); p. 2608,2619 View in Reaxys With water, oxygen in acetonitrile, Time= 0.333333h, Irradiation, other solvents, var. pH, solvent isotope effects, Rate constant, Quantum yield Krogh, Erik; Wan, Peter; Journal of the American Chemical Society; vol. 114; nb. 2; (1992); p. 705 - 712 View in Reaxys

P O

Rx-ID: 2175612 View in Reaxys 395/827 Yield

Conditions & References

86 %, 82 %

With oxygen in benzene, Time= 4h, Ambient temperature, Irradiation, with additives, other time, other temperature, other solvent, without O2, Product distribution, Rate constant Kawamura, Yasuhiko; Oda, Toshihiro; Iwano, Yasunori; Tsukayama, Masao; Horie, Tokunaru; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 73; nb. 1-4; (1992); p. 121 - 126 View in Reaxys

O O

Rx-ID: 2207262 View in Reaxys 396/827 Yield

Conditions & References Time= 2h, T= 900 °C , p= 0.005Torr , Product distribution Cadogan; Hutchison; McNab; Tetrahedron; vol. 48; nb. 36; (1992); p. 7747 - 7762 View in Reaxys

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O S

Rx-ID: 2565058 View in Reaxys 397/827 Yield

Conditions & References With diphosphorus tetraiodide in dichloromethane, Time= 1h, Ambient temperature, Yield given. Yields of byproduct given Saimoto, Hiroyuki; Kanzaki, Atsuhiro; Miyazaki, Kazumi; Sashiwa, Hitoshi; Shigemasa, Yoshihiro; Bulletin of the Chemical Society of Japan; vol. 65; nb. 10; (1992); p. 2842 - 2844 View in Reaxys

O S

P S

Rx-ID: 2565059 View in Reaxys 398/827 Yield

Conditions & References

26 %

With phosphorous triiodide in dichloromethane, Time= 1h, Ambient temperature, Yields of byproduct given Saimoto, Hiroyuki; Kanzaki, Atsuhiro; Miyazaki, Kazumi; Sashiwa, Hitoshi; Shigemasa, Yoshihiro; Bulletin of the Chemical Society of Japan; vol. 65; nb. 10; (1992); p. 2842 - 2844 View in Reaxys

O HO

Rx-ID: 1989342 View in Reaxys 399/827 Yield

Conditions & References

6.8 % Chro- With 3,3-dimethyldioxirane in acetone, Time= 72h, Ambient temperature, Yield given mat. Kuck, Dietmar; Schuster, Andreas; Zeitschrift fuer Naturforschung, B: Chemical Sciences; vol. 46; nb. 9; (1991); p. 1223 1226 View in Reaxys 6.8 % Chro- With 3,3-dimethyldioxirane in acetone, Time= 72h, Ambient temperature, Yields of byproduct given mat. Kuck, Dietmar; Schuster, Andreas; Zeitschrift fuer Naturforschung, B: Chemical Sciences; vol. 46; nb. 9; (1991); p. 1223 1226 View in Reaxys 2H

Rx-ID: 2068512 View in Reaxys 400/827 Yield

Conditions & References With perchloric acid, quinolinium dichromate(VI) in N,N-dimethyl-formamide, T= 40 °C , Rate constant

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Sarma, G. C.; Mahanti, M. K.; Bulletin de la Societe Chimique de France; nb. 4; (1991); p. 449 - 453 View in Reaxys Br

Rx-ID: 3312042 View in Reaxys 401/827 Yield

Conditions & References

20 %, 6 %, 75 %

With selenium, 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile, T= 25 °C Abelman, Matthew M.; Tetrahedron Letters; vol. 32; nb. 50; (1991); p. 7389 - 7392 View in Reaxys

–O

O–

(v6)

O Cr

(v6)

H O

F 2

Na +

Rx-ID: 24960737 View in Reaxys 402/827 Yield 2.0 g (57%)

Conditions & References XXXI : 2,4,7-Trifluoro-5-methoxy-9H-fluoren-9-one 2,4,7-Trifluoro-5-methoxy-9H-fluoren-9-one Sodium dichromate dihydrate (2 eq, 0.26 mol, 7.9 g) was added to a solution 2,4,7-trifluoro-5-methoxy-9H-fluorene (3.3 g, 0.013 mol) in 100 mL of acetic acid and the mixture was refluxed for 5 h. The cooled reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extract was washed with saturated aqueous sodium bicarbonate and water, dried over MgSO4, and concentrated to leave 3 g of a yellow solid which was chromatographed on silica gel using 15percent ethyl acetate in hexane to provide 2.0 g (57percent) of the fluorenone: mp 164°-166° C. in acetic acid Patent; Alcon Laboratories, Inc.; US5070100; (1991); (A) English View in Reaxys Patent; Alcon Laboratories, Inc.; US4864028; (1989); (A) English View in Reaxys

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-1

O O F

F C

Rx-ID: 1911233 View in Reaxys 403/827 Yield

Conditions & References in N,N-dimethyl-formamide, T= 25 °C , Rate constant Andrieux, Claude P.; Gelis, Laurence; Medebielle, Maurice; Pinson, Jean; Saveant, Jean-Michel; Journal of the American Chemical Society; vol. 112; nb. 9; (1990); p. 3509 - 3520 View in Reaxys With tetrabutylammonium tetrafluoroborate in N,N-dimethyl-formamide, T= 25 °C , Rate constant Andrieux; Gelis; Saveant; Journal of the American Chemical Society; vol. 112; nb. 2; (1990); p. 786 - 791 View in Reaxys 1

-1

O O F

F C

Rx-ID: 1912247 View in Reaxys 404/827 Yield

-1

O O

F C F

Rx-ID: 1964249 View in Reaxys 405/827 Yield

Conditions & References With tetrabutylammonium tetrafluoroborate in N,N-dimethyl-formamide, T= 22 °C , Rate constant Andrieux, Claude P.; Gelis, Laurence; Medebielle, Maurice; Pinson, Jean; Saveant, Jean-Michel; Journal of the American Chemical Society; vol. 112; nb. 9; (1990); p. 3509 - 3520 View in Reaxys

(v5)

Rx-ID: 2036923 View in Reaxys 406/827

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Yield

Conditions & References

2 %, 90 %

With DMd in dichloromethane, acetone, Time= 2h, T= 5 °C Boyd, Derek R.; Coulter, Peter B.; McGuckin, M. Rosaleen; Sharma, Narain D.; Jennings, W. Brian; Wilson, Valerie E.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 2; (1990); p. 301 306 View in Reaxys O

Rx-ID: 2117393 View in Reaxys 407/827 Yield

Conditions & References

5 %, 91 %

Rx-ID: 2117779 View in Reaxys 408/827 Yield

Conditions & References

9 %, 92 %

Rx-ID: 2119354 View in Reaxys 409/827 Yield 12 %, 31 %

Conditions & References With DMd in dichloromethane, acetone, Time= 2h, T= 5 °C Boyd, Derek R.; Coulter, Peter B.; McGuckin, M. Rosaleen; Sharma, Narain D.; Jennings, W. Brian; Wilson, Valerie E.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 2; (1990); p. 301 306 View in Reaxys

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Rx-ID: 2119750 View in Reaxys 410/827 Yield

Conditions & References

14 %, 4 %

NH (v5)

Rx-ID: 2217733 View in Reaxys 411/827 Yield

Conditions & References

2 %, 39 %

O O V

(v4)

(v6)

(v4)

Rx-ID: 26504065 View in Reaxys 412/827 Yield

Conditions & References

in acetonitrile, Kinetics, Irradiation (UV/VIS) SriHari, Somu; Masnovi, John; Inorganic Chemistry; vol. 29; (1990); p. 3154 - 3157 ; (from Gmelin) View in Reaxys N O N

O F F O

F S – OO

O– S O

(v6)

+ O Cr (v4) O N N

(v4)

(v4) O (v4) O(v4) Cr + N N

H O

Rx-ID: 26661819 View in Reaxys 413/827 Yield 78-88, 70-90

Conditions & References in acetonitrile, Kinetics, byproducts: NCCH3; Irradiation (UV/VIS); irradiation of Co-complex and diazafluorene in degassed solvent; extn. of fluorenone (C6H6); NMR; GC/MS; UV/VIS SriHari, Somu; Masnovi, John; Inorganic Chemistry; vol. 29; (1990); p. 3154 - 3157 ; (from Gmelin)

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View in Reaxys

O O O

Rx-ID: 1767540 View in Reaxys 414/827 Yield

Conditions & References

96 %, 1 %

With tert.-butylhydroperoxide, bis-(tributyltin oxide) dioxochromium(VI) in dichloromethane, Time= 24h, T= 40 °C Muzart, Jacques; Synthetic Communications; vol. 19; nb. 11-12; (1989); p. 2061 - 2068 View in Reaxys

21 %

With tert.-butylhydroperoxide, 2,4-dimethylpentane-2,4-diol cyclic chromate in tetrachloromethane, dichloromethane, Time= 8h, T= 0 °C , Yield given Muzart, Jacques; Tetrahedron Letters; vol. 27; nb. 27; (1986); p. 3139 - 3142 View in Reaxys

21 %

With tert.-butylhydroperoxide, 2,4-dimethylpentane-2,4-diol cyclic chromate in tetrachloromethane, dichloromethane, Time= 8h, T= 0 °C , Yields of byproduct given Muzart, Jacques; Tetrahedron Letters; vol. 27; nb. 27; (1986); p. 3139 - 3142 View in Reaxys

Rx-ID: 1995580 View in Reaxys 415/827 Yield

Conditions & References

97 %

With 1,2-dichlorotetramethylsilane, bis(benzonitrile)palladium(II) dichloride, triphenylphosphine, Time= 15h, T= 145 °C Rich, Jonathan D.; Journal of the American Chemical Society; vol. 111; nb. 15; (1989); p. 5886 - 5893 View in Reaxys O

O OH

Rx-ID: 2050273 View in Reaxys 416/827

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Yield

Conditions & References

31 %, 17 %, With sulfuric acid, dihydrogen peroxide, acetic acid, Ambient temperature 3% Taljaard, Benjamin; Goosen, Andre; McCleland, Cedric W.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1989); p. 931 - 934 View in Reaxys O

Rx-ID: 2050274 View in Reaxys 417/827 Yield

Conditions & References

56 %

With sulfuric acid, dihydrogen peroxide, acetic acid, Ambient temperature Taljaard, Benjamin; Goosen, Andre; McCleland, Cedric W.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1989); p. 931 - 934 View in Reaxys

O OH

Rx-ID: 2076861 View in Reaxys 418/827 Yield

Conditions & References

3.5 %, 4.5 %, 65 %

O O NH

Rx-ID: 2207118 View in Reaxys 419/827 Yield 55 %

Conditions & References With <(Py)2Ag>2Cr2O7, acetic acid in benzene, Time= 6h, Heating

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Firouzabadi, H.; Seddighi, M.; Ahmadi, Z. Arab; Sardarian, A. R.; Synthetic Communications; vol. 19; nb. 19; (1989); p. 3385 - 3396 View in Reaxys O

O N

O O N O

NH N

Rx-ID: 3880518 View in Reaxys 420/827 Yield

Conditions & References

83 %

With <(Py)2Ag>2Cr2O7 in benzene, Time= 6h, Heating Firouzabadi, H.; Seddighi, M.; Ahmadi, Z. Arab; Sardarian, A. R.; Synthetic Communications; vol. 19; nb. 19; (1989); p. 3385 - 3396 View in Reaxys

N O

Cl HO OH

Cl O

N Cl

Cl N OH

Rx-ID: 3981181 View in Reaxys 421/827 Yield

Conditions & References

56 %, 26 %

in acetonitrile, Time= 4h, Ambient temperature Shingaki, Tadao; Kuma, Hiro; Kushi, Yoshihiko; Nagai, Toshikazu; Bulletin of the Chemical Society of Japan; vol. 62; nb. 2; (1989); p. 444 - 450 View in Reaxys

-1

F (v4)

B FF

N+ O

Rx-ID: 4023763 View in Reaxys 422/827 Yield 91 %

Conditions & References With chloro-trimethyl-silane in tetrahydrofuran, N,N-dimethyl-formamide, Time= 1h, T= 60 °C Keumi, Takashi; Umeda, Toshiaki; Inoue, Yoshinori; Kitajima, Hidehiko; Bulletin of the Chemical Society of Japan; vol. 62; nb. 1; (1989); p. 89 - 95 View in Reaxys

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N O

Cl O

N Cl

Cl N OH

Rx-ID: 4032664 View in Reaxys 423/827 Yield

Conditions & References

51 %, 37 %

in acetonitrile, Ambient temperature Shingaki, Tadao; Kuma, Hiro; Kushi, Yoshihiko; Nagai, Toshikazu; Bulletin of the Chemical Society of Japan; vol. 62; nb. 2; (1989); p. 444 - 450 View in Reaxys

N O

Cl O

N Cl

Cl N OH

Rx-ID: 4032665 View in Reaxys 424/827 Yield 37 %, 51 %

Conditions & References in acetonitrile, Ambient temperature Shingaki, Tadao; Kuma, Hiro; Kushi, Yoshihiko; Nagai, Toshikazu; Bulletin of the Chemical Society of Japan; vol. 62; nb. 2; (1989); p. 444 - 450 View in Reaxys

Rx-ID: 1767538 View in Reaxys 425/827 Yield

Conditions & References With oxygen, tert-butylammonium hexafluorophosphate(V) in acetonitrile, Ambient temperature, electrolysis, Pt grid electrodes

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Degrand, Chantal; Prest, Rita; Nour, Mohamed; Phosphorus and Sulfur and the Related Elements; vol. 38; (1988); p. 201 210 View in Reaxys O S

O–

N O

F F

N+

O S

Rx-ID: 1992307 View in Reaxys 426/827 Yield

Conditions & References With n-butyllithium, 1.)hexane, CH2Cl2, -78 deg C, 10-20 min; 2.) THF, -78 deg C, 1 h, room temp., 96 h, Yield given. Multistep reaction. Yields of byproduct given Zoller, Uri; Tetrahedron; vol. 44; nb. 24; (1988); p. 7413 - 7426 View in Reaxys

Rx-ID: 2040846 View in Reaxys 427/827 Yield

Conditions & References With selenium, tert-butylammonium hexafluorophosphate(V), acetonitrile, Ambient temperature, electrolysis, Pt grid electrodes Degrand, Chantal; Prest, Rita; Nour, Mohamed; Phosphorus and Sulfur and the Related Elements; vol. 38; (1988); p. 201 210 View in Reaxys With oxygen, tert-butylammonium hexafluorophosphate(V) in acetonitrile, Ambient temperature, electrolysis, Pt grid electrodes Degrand, Chantal; Prest, Rita; Nour, Mohamed; Phosphorus and Sulfur and the Related Elements; vol. 38; (1988); p. 201 210 View in Reaxys O

Rx-ID: 2073018 View in Reaxys 428/827 Yield 44 %

Conditions & References With silver, sodium hydrogencarbonate, sodium iodide, zinc in 1,2-dimethoxyethane, dimethyl sulfoxide, Time= 0.666667h, T= 60 °C

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Chung, Chi Kong; Ho, Mei Sing; Lun, Kue Sun; Wong, Man On; Wong, Henry N. C.; Tam, Shang Wai; Synthetic Communications; vol. 18; nb. 5; (1988); p. 507 - 510 View in Reaxys N O N

Rx-ID: 3935861 View in Reaxys 429/827 Yield

Conditions & References T= 230 °C , thermolyse, Mechanism, Thermodynamic data Thurner, Joern-Uwe; Donau, Ralf; Stoesser, Reinhard; Tomaschewski, Georg; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 28; nb. 5; (1988); p. 186 - 187 View in Reaxys N N

N N

Rx-ID: 3935862 View in Reaxys 430/827 Yield

Conditions & References With 4-methyl-phenol-formaldehyde resin in cyclohexanone, Irradiation, also thermolysis Thurner, Joern-Uwe; Donau, Ralf; Wolff, Monika; Tomaschewski, Georg; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 28; nb. 10; (1988); p. 373 - 374 View in Reaxys

O Li

Br (v3)

(v6)

(v3)

O O

(v3)

O O

Rx-ID: 26087025 View in Reaxys 431/827 Yield 72 %, 0 %

Conditions & References in tetrahydrofuran, methanol, diethyl ether, To a stirred, cold (-78°C) soln. of Re(CO)5Br in THF is added an ether soln. of 2,2'dilithiobiphenyl (N2). The suspension is slowly warmed to 25°C, cooled again and Br2 in MeOH is added.; Chromy. on silica gel, collecting of the yellow band, and removal of the solvent gives 9-fluorenone, recrystn. (EtOH). The product is analyzed by (1)H-NMR, (13)C-NMR, IR and melting point. Mike, Carl A.; Ferede, Roman; Allison, Neil T.; Organometallics; vol. 7; (1988); p. 1457 - 1459 ; (from Gmelin)

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View in Reaxys 68 %, 6 %

in tetrahydrofuran, methanol, diethyl ether, To a stirred, cold (-78°C) soln. of Re(CO)5Br in THF is added an ether soln. of 2,2'dilithiobiphenyl (N2). The suspension is slowly warmed to -20°C, cooled again and Br2 in MeOH is added.; Chromy. on silica gel, collecting of the yellow bands, and removal of the solvent gives 9-fluorenone and 9,10-phenanthrenequinone, recrystn. (EtOH). The products were analyzed by (1)H-NMR, (13)C-NMR, IR and melting point. Mike, Carl A.; Ferede, Roman; Allison, Neil T.; Organometallics; vol. 7; (1988); p. 1457 - 1459 ; (from Gmelin) View in Reaxys

68 %, 13 %

in tetrahydrofuran, methanol, diethyl ether, To a stirred, cold (-78°C) soln. of Re(CO)5Br in THF is added an ether soln. of 2,2'dilithiobiphenyl (N2). The suspension is slowly warmed to -25°C, cooled again and Br2 in MeOH is added.; Chromy. on silica gel, collecting of the yellow bands, and removal of the solvent gives 9-fluorenone and 9,10-phenanthrenequinone, recrystn (EtOH). The products were analyzed by (1)H-NMR, (13)C-NMR, IR and melting point. Mike, Carl A.; Ferede, Roman; Allison, Neil T.; Organometallics; vol. 7; (1988); p. 1457 - 1459 ; (from Gmelin) View in Reaxys O Li

Br (v3)

(v6)

(v3)

Rx-ID: 26174294 View in Reaxys 432/827 Yield

Conditions & References

71 %

in tetrahydrofuran, diethyl ether, To a stirred, cold (-78°C) soln. of Re(CO)5Br in THF is added dropwise an ether soln. of 2,2'dilithiobiphenyl. The suspension is slowly warmed to room temp.; Chromy. on silica gel, collecting of the yellow band, and removal of the solvent gives 9-fluorenone, recrystn. (EtOH). The product was analyzed by (1)H-NMR, (13)C-NMR, IR and melting point. Mike, Carl A.; Ferede, Roman; Allison, Neil T.; Organometallics; vol. 7; (1988); p. 1457 - 1459 ; (from Gmelin) View in Reaxys

O P (v3)

(v6)

(v3)

(v4)

O (v3)

Rx-ID: 26379970 View in Reaxys 433/827 Yield

Conditions & References

89 %

in diethyl ether, To a stirred, cold soln. of Re(CO)4PPh3Br in ethyl ether was added dropwise an ether soln. of 2,2'-dilithiobiphenyl (under N2). The temp. was increased gradually to room temp.; Chromatography on silica gel, collection of the yellow band, and removal of solvent on the rotary evaporator gave 9-fluorenone. The product was analyzed by (1)H-NMR, (13)C-NMR, IR and melting point. Mike, Carl A.; Ferede, Roman; Allison, Neil T.; Organometallics; vol. 7; (1988); p. 1457 - 1459 ; (from Gmelin) View in Reaxys

(v5)(v5) (v5) (v5)

(v8)

O O (v3)

(v3)

O (v3)

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O (v5) (v5)(v5) (v5)

Mn O O O

(v3)

(v5) (v5)(v5) (v5)

Mn O O

(v8)

(v3)

(v8)

O (v3)

Rx-ID: 26507100 View in Reaxys 434/827 Yield

Conditions & References

27 %, 40 %, With acetyl chloride, AlCl3 in dichloromethane, stirring (20°C, 1 h); pouring into water, washing of org. layer (water), drying, 6 %, 7 % evapn., chromy. (florisil, CH2Cl2) Lobanova, I. A.; Batsanov, A. S.; Zdanovich, V. I.; Struchkov, Yu. T.; Kolobova, N. E.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 37; (1988); p. 580 - 583; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 37; (1988); p. 682 - 684 ; (from Gmelin) View in Reaxys O

Rx-ID: 2068452 View in Reaxys 435/827 Yield

Conditions & References

50 %, 16 %, With dihydrogen peroxide, Bis-<2.4-dinitro-phenyl>-diselenid in dichloromethane, Time= 9h, Ambient temperature, further 26 % cat.; var. time Syper, Ludwik; Tetrahedron; vol. 43; nb. 12; (1987); p. 2853 - 2872 View in Reaxys 50 %, 16 %, With dihydrogen peroxide, Bis-<2.4-dinitro-phenyl>-diselenid in dichloromethane, Time= 9h, Ambient temperature 26 % Syper, Ludwik; Tetrahedron; vol. 43; nb. 12; (1987); p. 2853 - 2872 View in Reaxys O

O O

Rx-ID: 2068453 View in Reaxys 436/827 Yield

Conditions & References

21 %, 60 %

With dihydrogen peroxide, bis(o-nitrophenyl) diselenide in dichloromethane, Time= 14h, Ambient temperature, further cat.; var. time Syper, Ludwik; Tetrahedron; vol. 43; nb. 12; (1987); p. 2853 - 2872 View in Reaxys N

Ag+

C– O

N O

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O O N

O N

Rx-ID: 2070172 View in Reaxys 437/827 Yield

Conditions & References

43 %, 38 %, in benzene, Time= 56h, Ambient temperature 48 % Lianis, Pygmalion S.; Rodios, Nestor A.; Alexandrou, Nicholas E.; Liebigs Annalen der Chemie; (1987); p. 537 - 540 View in Reaxys N

Ag+

C– O

N O O O

N N

Rx-ID: 2070180 View in Reaxys 438/827 Yield

Conditions & References

65 %, 52 %, in benzene, Time= 56h, Ambient temperature 7% Lianis, Pygmalion S.; Rodios, Nestor A.; Alexandrou, Nicholas E.; Liebigs Annalen der Chemie; (1987); p. 537 - 540 View in Reaxys N

Ag+

C– O

N O

N O O N

O O

N O HO

Rx-ID: 2070181 View in Reaxys 439/827 Yield

Conditions & References

45 %, 4.5 in benzene, Time= 55h, Ambient temperature %, 26 %, 37 Lianis, Pygmalion S.; Rodios, Nestor A.; Alexandrou, Nicholas E.; Liebigs Annalen der Chemie; (1987); p. 537 - 540 % View in Reaxys

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Ag+

C– O

N O O O N

Cl Cl

HO HO

Rx-ID: 2070182 View in Reaxys 440/827 Yield

Conditions & References

28 %, 12 %, in benzene, Time= 56h, Ambient temperature 45 %, 10 % Lianis, Pygmalion S.; Rodios, Nestor A.; Alexandrou, Nicholas E.; Liebigs Annalen der Chemie; (1987); p. 537 - 540 View in Reaxys

O O N

Rx-ID: 2076827 View in Reaxys 441/827 Yield

Conditions & References

72 %

With potassium superoxide, 18-crown-6 ether in benzene, Time= 42h, Ambient temperature, Product distribution, Mechanism Ashok, Konda; Scaria, Pallikkaparambil M.; Kamat, Prashant V.; George, Manapurathu V.; Canadian Journal of Chemistry; vol. 65; (1987); p. 2039 - 2049 View in Reaxys

28 %

With oxygen, potassium in tetrahydrofuran, Time= 10h Ashok, Konda; Scaria, Pallikkaparambil M.; Kamat, Prashant V.; George, Manapurathu V.; Canadian Journal of Chemistry; vol. 65; (1987); p. 2039 - 2049 View in Reaxys

O O O O

O O

Rx-ID: 2077256 View in Reaxys 442/827

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Yield

Conditions & References

16 %, 5 %, 30 %, 30 %

With C8K in tetrahydrofuran, T= 25 °C Tamarkin, Dov; Rabinovitz, Mordecai; Journal of Organic Chemistry; vol. 52; nb. 15; (1987); p. 3472 - 3474 View in Reaxys

27 %, 4 %, 19 %, 13 %

With C8K in 1,2-dimethoxyethane, T= 25 °C Tamarkin, Dov; Rabinovitz, Mordecai; Journal of Organic Chemistry; vol. 52; nb. 15; (1987); p. 3472 - 3474 View in Reaxys

O HO O

Rx-ID: 2092129 View in Reaxys 443/827 Yield

Conditions & References

1 % Spectr., With potassium hydroxide in 1,2-dimethoxyethane, Time= 1h, T= 20 °C 99 % Solov'yanov, A. A.; El-Said, Ahmed Ali Ahmed; Beletskaya, I. P.; Reutov, O. A.; Journal of Organic Chemistry USSR (EngSpectr. lish Translation); vol. 23; nb. 7; (1987); p. 1232 - 1243; Zhurnal Organicheskoi Khimii; vol. 23; nb. 7; (1987); p. 1365 - 1377 View in Reaxys 5 % Spectr., With potassium hydroxide, 18-crown-6 ether in benzene, Time= 1h, T= 20 °C , var. phase-transfer catalysts, oth. solvent, oth. 95 % temperature, oth. time, absence of catalyst, oth. bases, Product distribution, Mechanism Spectr. Solov'yanov, A. A.; El-Said, Ahmed Ali Ahmed; Beletskaya, I. P.; Reutov, O. A.; Journal of Organic Chemistry USSR (English Translation); vol. 23; nb. 7; (1987); p. 1232 - 1243; Zhurnal Organicheskoi Khimii; vol. 23; nb. 7; (1987); p. 1365 - 1377 View in Reaxys

Rx-ID: 2106556 View in Reaxys 444/827 Yield

Conditions & References

99 % Chromat.

With potassium hydroxide, 18-crown-6 ether in benzene, Time= 34h, T= 80 °C Solov'yanov, A. A.; El-Said, Ahmed Ali Ahmed; Beletskaya, I. P.; Reutov, O. A.; Journal of Organic Chemistry USSR (English Translation); vol. 23; nb. 7; (1987); p. 1232 - 1243; Zhurnal Organicheskoi Khimii; vol. 23; nb. 7; (1987); p. 1365 - 1377 View in Reaxys

Rx-ID: 2106557 View in Reaxys 445/827 Yield 17 % Chromat., 81 % Chromat.

Conditions & References With potassium hydroxide, 18-crown-6 ether in benzene, Time= 34h, T= 80 °C , oth. phase-transfer catalyst, oth. solvent, oth. time, oth. base, Product distribution, Mechanism

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Solov'yanov, A. A.; El-Said, Ahmed Ali Ahmed; Beletskaya, I. P.; Reutov, O. A.; Journal of Organic Chemistry USSR (English Translation); vol. 23; nb. 7; (1987); p. 1232 - 1243; Zhurnal Organicheskoi Khimii; vol. 23; nb. 7; (1987); p. 1365 - 1377 View in Reaxys

HO O

Rx-ID: 2153701 View in Reaxys 446/827 Yield

Conditions & References

5 % Spectr., With potassium carbonate, 18-crown-6 ether in benzene, Time= 52h, T= 80 °C 95 % Solov'yanov, A. A.; El-Said, Ahmed Ali Ahmed; Beletskaya, I. P.; Reutov, O. A.; Journal of Organic Chemistry USSR (EngSpectr. lish Translation); vol. 23; nb. 7; (1987); p. 1232 - 1243; Zhurnal Organicheskoi Khimii; vol. 23; nb. 7; (1987); p. 1365 - 1377 View in Reaxys 50 % Spectr., 50 % Spectr.

With sodium hydroxide, 18-crown-6 ether in benzene, Time= 1h, T= 20 °C , var. phase-transfer catalysts, oth. solvents, oth. temperature, oth. time, absence of catalyst, oth. bases, Product distribution, Mechanism Solov'yanov, A. A.; El-Said, Ahmed Ali Ahmed; Beletskaya, I. P.; Reutov, O. A.; Journal of Organic Chemistry USSR (English Translation); vol. 23; nb. 7; (1987); p. 1232 - 1243; Zhurnal Organicheskoi Khimii; vol. 23; nb. 7; (1987); p. 1365 - 1377 View in Reaxys

O P N

Rx-ID: 2171679 View in Reaxys 447/827 Yield 55.0 %, 10.8 %, 81 %

55 %, 10.8 %, 81.0 %

Conditions & References With lead dioxide in dichloromethane, Time= 1.33333h, T= 30 °C Handoo, Kishan L.; Gadru, Kanchan; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 26; nb. 1-12; (1987); p. 412 - 417 View in Reaxys With lead dioxide in dichloromethane, trifluoroacetic acid, Time= 0.5h, T= 28 - 30 °C Handoo, Kishan L.; Gadru, Kanchan; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 26; nb. 1-12; (1987); p. 412 - 417 View in Reaxys

55.0 %, 10.8 %, 81.0 %

With lead dioxide in dichloromethane, trifluoroacetic acid, Time= 1.33333h, T= 30 °C , Mechanism, Product distribution Handoo, Kishan L.; Gadru, Kanchan; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 26; nb. 1-12; (1987); p. 412 - 417 View in Reaxys

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5.5 %, 65.6 %, 72.0 %

With tris(4-bromophenyl)ammonium perchlorate in dichloromethane, Time= 1.33333h, T= 30 °C Handoo, Kishan L.; Gadru, Kanchan; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 26; nb. 1-12; (1987); p. 412 - 417 View in Reaxys

5.5 %, 65.6 %, 72.0 %

With tris(4-bromophenyl)ammonium perchlorate in dichloromethane, Time= 1.33333h, T= 30 °C , Mechanism, Product distribution Handoo, Kishan L.; Gadru, Kanchan; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 26; nb. 1-12; (1987); p. 412 - 417 View in Reaxys

7.5 %, 62.5 %, 69.0 %

With antimonypentachloride in dichloromethane, Time= 1.33333h, T= 30 °C , Mechanism, Product distribution Handoo, Kishan L.; Gadru, Kanchan; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 26; nb. 1-12; (1987); p. 412 - 417 View in Reaxys N N

Rx-ID: 2523131 View in Reaxys 448/827 Yield 60 %, 23 %

Conditions & References With 2,3-cis-epoxybutane, Irradiation, Further byproducts given Shields, Charles J.; Schuster, Gary B.; Tetrahedron Letters; vol. 28; nb. 8; (1987); p. 853 - 856 View in Reaxys

60 %, 23 %

With epoxy-2,3 butane, Irradiation, Further byproducts given Shields, Charles J.; Schuster, Gary B.; Tetrahedron Letters; vol. 28; nb. 8; (1987); p. 853 - 856 View in Reaxys O

O O

O O O

Rx-ID: 2830416 View in Reaxys 449/827 Yield 38 %, 36 %

Conditions & References With dihydrogen peroxide, bis(o-nitrophenyl) diselenide in dichloromethane, Time= 42h, Ambient temperature Syper, Ludwik; Tetrahedron; vol. 43; nb. 12; (1987); p. 2853 - 2872 View in Reaxys

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O HO

Rx-ID: 2940880 View in Reaxys 450/827 Yield

Conditions & References

0.18 g, 0.56 g

With sodium tetrahydroborate in tetrahydrofuran, ethanol, Time= 3h, Ambient temperature Chung, Ying-Sheng; Kruk, Henry; Barizo, Ophelia M.; Katz, Morris; Lee-Ruff, Edward; Journal of Organic Chemistry; vol. 52; nb. 7; (1987); p. 1284 - 1288 View in Reaxys

Rx-ID: 2940881 View in Reaxys 451/827 Yield

Conditions & References

100 mg, 820 With methanesulfonic acid in chloroform, Time= 4.5h, T= 0 °C mg Chung, Ying-Sheng; Kruk, Henry; Barizo, Ophelia M.; Katz, Morris; Lee-Ruff, Edward; Journal of Organic Chemistry; vol. 52; nb. 7; (1987); p. 1284 - 1288 View in Reaxys N N O

Rx-ID: 3814143 View in Reaxys 452/827 Yield 60 %, 23 %

Conditions & References Irradiation, Further byproducts given Shields, Charles J.; Schuster, Gary B.; Tetrahedron Letters; vol. 28; nb. 8; (1987); p. 853 - 856 View in Reaxys

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N N O

Rx-ID: 3814144 View in Reaxys 453/827 Yield

Conditions & References

60 %, 23 %

Irradiation, Further byproducts given Shields, Charles J.; Schuster, Gary B.; Tetrahedron Letters; vol. 28; nb. 8; (1987); p. 853 - 856 View in Reaxys

O O

Rx-ID: 3814167 View in Reaxys 454/827 Yield

Conditions & References

60 %, 23 %

With 9-diazofluorenone, Irradiation, Further byproducts given Shields, Charles J.; Schuster, Gary B.; Tetrahedron Letters; vol. 28; nb. 8; (1987); p. 853 - 856 View in Reaxys

9-bromo-anthrone

Rx-ID: 20469489 View in Reaxys 455/827 Yield

Conditions & References Reaction Steps: 2 1: 3.70 g / triethylamine / benzene / 0.33 h / Heating 2: 100 mg / methanesulfonic acid / CHCl3 / 4.5 h / 0 °C With methanesulfonic acid, triethylamine in chloroform, benzene Chung, Ying-Sheng; Kruk, Henry; Barizo, Ophelia M.; Katz, Morris; Lee-Ruff, Edward; Journal of Organic Chemistry; vol. 52; nb. 7; (1987); p. 1284 - 1288 View in Reaxys

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O (v5) (v5)(v5) (v5)

(v5)(v5) (v5) (v5)

Mn O O

(v8)

O O

(v3)

(v8)

O (v3)

Rx-ID: 26507099 View in Reaxys 456/827 Yield

Conditions & References

29 %, 10 %

With aluminium trichloride, acetyl chloride in dichloromethane, 20°C, 1h; pouring mixt. into H2O, sepn. of org. layer, washing, drying, evapn.; chromy. (Fluorisil), elution of Mn-complex with CH2Cl2, repeated chromy. with petroleum ether/ether=1:1; recrystn. (CH2Cl2/pentane), elem. anal. Lobanova, I. A.; Zdanovich, V. I.; Petrovskii, P. V.; Vasyukova, N. I.; Kolobova, N. E.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; (1987); p. 1278 - 1282; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 36; (1987); p. 1384 - 1388 ; (from Gmelin) View in Reaxys

O Br

Rx-ID: 1581390 View in Reaxys 457/827 Yield

Conditions & References With oxygen, sodium methylate, Irradiation, different wavelength, Quantum yield, Mechanism Verbeek, J. M.; Cornelisse, J.; Lodder, G.; Tetrahedron; vol. 42; nb. 20; (1986); p. 5679 - 5684 View in Reaxys OH

(v2) –

O– (v2)

Mn3+ (v3)

O–

(v2)

O O

O Cl

Rx-ID: 2044767 View in Reaxys 458/827 Yield

Conditions & References

12 %, 49 %, With lithium chloride in acetic acid, Time= 3.83333h, Heating, Mechanism 37 % Yonemura, Hiroshi; Nishino, Hiroshi; Kurosawa, Kazu; Bulletin of the Chemical Society of Japan; vol. 59; (1986); p. 3153 3160 View in Reaxys 12 %, 49 %, With lithium chloride in acetic acid, Time= 3.83333h, Heating 37 % Yonemura, Hiroshi; Nishino, Hiroshi; Kurosawa, Kazu; Bulletin of the Chemical Society of Japan; vol. 59; (1986); p. 3153 3160 View in Reaxys

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O Cl

Rx-ID: 2044768 View in Reaxys 459/827 Yield

Conditions & References

12 %, 49 %, With manganese triacetate, lithium chloride in acetic acid, Time= 3.83333h, Heating 37 % Yonemura, Hiroshi; Nishino, Hiroshi; Kurosawa, Kazu; Bulletin of the Chemical Society of Japan; vol. 59; (1986); p. 3153 3160 View in Reaxys

O S

Rx-ID: 2565061 View in Reaxys 460/827 Yield

Conditions & References With toluene-4-sulfonic acid in d(4)-methanol, T= 100 °C Nakanishi, Waro; Kusuyama, Yoshiaki; Ikeda, Yoshitsugu; Oki, Michinori; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1986); p. 799 - 804 View in Reaxys

Cl N

NH O

Rx-ID: 2574826 View in Reaxys 461/827 Yield

Conditions & References With hydrogenchloride, potassium tert-butylate in dimethyl sulfoxide, Time= 15h, Ambient temperature

52 %

Boyd, Derek R.; McCombe, Kenneth M.; Sharma, Narain D.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 867 - 872 View in Reaxys

Cl O

Rx-ID: 2587985 View in Reaxys 462/827

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Yield 59 %

Conditions & References With hydrogenchloride, potassium tert-butylate in dimethyl sulfoxide, Time= 15h, Ambient temperature Boyd, Derek R.; McCombe, Kenneth M.; Sharma, Narain D.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 867 - 872 View in Reaxys

N O

Rx-ID: 2597846 View in Reaxys 463/827 Yield 90 %

Conditions & References With potassium tert-butylate in tetrahydrofuran, Time= 15h, Ambient temperature Boyd, Derek R.; McCombe, Kenneth M.; Sharma, Narain D.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 867 - 872 View in Reaxys With potassium tert-butylate in tetrahydrofuran, Time= 8h, Ambient temperature, Yield given Boyd, Derek R.; McCombe, Kenneth M.; Sharma, Narain D.; Tetrahedron Letters; vol. 23; nb. 28; (1982); p. 2907 - 2908 View in Reaxys

N O

Rx-ID: 2601897 View in Reaxys 464/827 Yield 88 %

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O O O

Rx-ID: 2845258 View in Reaxys 465/827 Yield

Conditions & References With tert.-butylhydroperoxide, 2,4-dimethylpentane-2,4-diol cyclic chromate in tetrachloromethane, dichloromethane, Time= 8h, T= 0 °C , Yield given Muzart, Jacques; Tetrahedron Letters; vol. 27; nb. 27; (1986); p. 3139 - 3142 View in Reaxys

N O N

Rx-ID: 3935871 View in Reaxys 466/827 Yield

Conditions & References T= 25 °C , Irradiation, effect of concentration, solvent and radical inhibitors, Product distribution Savino, T. G.; Senthilnathan, V. P.; Platz, M. S.; Tetrahedron; vol. 42; nb. 8; (1986); p. 2167 - 2180 View in Reaxys

Rx-ID: 20830394 View in Reaxys 467/827 Yield

Conditions & References Reaction Steps: 2 1: MCPBA / CH2Cl2 / 5 °C 2: t-BuOK, HCl / dimethylsulfoxide / 15 h / Ambient temperature With hydrogenchloride, potassium tert-butylate, 3-chloro-benzenecarboperoxoic acid in dichloromethane, dimethyl sulfoxide Boyd, Derek R.; McCombe, Kenneth M.; Sharma, Narain D.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 867 - 872 View in Reaxys

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Rx-ID: 20831577 View in Reaxys 468/827 Yield

Conditions & References Reaction Steps: 2 1: MCPBA / CH2Cl2 / 5 °C 2: t-BuOK / tetrahydrofuran / 15 h / Ambient temperature With potassium tert-butylate, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, dichloromethane Boyd, Derek R.; McCombe, Kenneth M.; Sharma, Narain D.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 867 - 872 View in Reaxys

Rx-ID: 20831814 View in Reaxys 469/827 Yield

O N

Rx-ID: 20842108 View in Reaxys 470/827 Yield

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View in Reaxys

O O

NH 2

H 2N O

NH 2

Rx-ID: 1945504 View in Reaxys 471/827 Yield

Conditions & References

5 %, 48 %

With manganese triacetate, acetic acid, Time= 0.00166667h, Heating Nishino, Hiroshi; Bulletin of the Chemical Society of Japan; vol. 58; (1985); p. 217 - 222 View in Reaxys

O N

Rx-ID: 2047027 View in Reaxys 472/827 Yield

Conditions & References With sodium hydroxide in 1,4-dioxane, water, T= 25 °C , further nucleophil partner; molecular stacking effect on the kinetic order of the reaction Hoz, Shmaryahu; Gross, Zeev; Speizman, Dov; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1985); p. 1143 - 1146 View in Reaxys

O O

O N

Rx-ID: 2050348 View in Reaxys 473/827 Yield

Conditions & References With sodium hydroxide in 1,4-dioxane, water, T= 25 °C , molecular stacking effect on the kinetic order of the reaction, Rate constant Hoz, Shmaryahu; Gross, Zeev; Speizman, Dov; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1985); p. 1143 - 1146 View in Reaxys

O H

Rx-ID: 2070739 View in Reaxys 474/827

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Yield

Conditions & References

86 %, 85 %

With Celite, pyridinium chlorochromate in dichloromethane, Time= 28h, Heating, highly selective oxidative cleavage Narasimmhan, Vikram; Rathore, Rajendra; Chandrasekaran, S.; Synthetic Communications; vol. 15; nb. 9; (1985); p. 769 774 View in Reaxys

O H I

Rx-ID: 2070740 View in Reaxys 475/827 Yield

Conditions & References

50 %, 92 %, With 4-tButyl iodoxybenzene in chlorobenzene, Time= 7h, T= 130 - 140 °C 45 % Ranganathan, S.; Ranganathan, D.; Singh, S. K.; Tetrahedron Letters; vol. 26; nb. 40; (1985); p. 4955 - 4956 View in Reaxys O

OH N

O O N

N O O

Rx-ID: 2119934 View in Reaxys 476/827 Yield 1.02 g, 0.44 g, 0.12 g, 0.08 g

Conditions & References in methanol, Time= 1.5h, Irradiation Grant, Richard D.; Pinhey, John T.; Rizzardo, Ezio; Smith, Geoffrey C.; Australian Journal of Chemistry; vol. 38; nb. 10; (1985); p. 1505 - 1519 View in Reaxys O

N O

O N

Rx-ID: 2153382 View in Reaxys 477/827 Yield

Conditions & References With sodium hydroxide in 1,4-dioxane, water, T= 25 °C , molecular stacking effect on the kinetic order of the reaction

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Hoz, Shmaryahu; Gross, Zeev; Speizman, Dov; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1985); p. 1143 - 1146 View in Reaxys

O N

N+ Br–

Rx-ID: 2326921 View in Reaxys 478/827 Yield

Conditions & References Heating, Mechanism, Product distribution Donau, Ralf; Alder, Lutz; Thurner, Joern-Uwe; Lieberenz, Michael; Tomaschewski, Guenther; Stoesser, Reinhard; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 25; nb. 12; (1985); p. 438 View in Reaxys

Br–

N+

Rx-ID: 2327003 View in Reaxys 479/827

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Yield

Br–

N+

Rx-ID: 2327298 View in Reaxys 480/827 Yield

H N

N O

Rx-ID: 2845043 View in Reaxys 481/827 Yield

Conditions & References With 1,4-diaza-bicyclo[2.2.2]octane, chloroform-d1, Yield given Boyd, Derek R.; Coulter, Peter B.; Hamilton, Robert; Thompson, Norris T.; Sharma, Narain D.; Stubbs, Michael E.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2123 2128 View in Reaxys

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N O

H N

O N

Rx-ID: 2845044 View in Reaxys 482/827 Yield

Conditions & References Ambient temperature, 2-3 days, Yield given. Yields of byproduct given Boyd, Derek R.; Coulter, Peter B.; Hamilton, Robert; Thompson, Norris T.; Sharma, Narain D.; Stubbs, Michael E.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2123 2128 View in Reaxys

N O

H N N HN

Rx-ID: 2847799 View in Reaxys 483/827 Yield

Conditions & References With 1,4-diaza-bicyclo[2.2.2]octane in chloroform-d1, Time= 1h, Ambient temperature, Yield given. Further byproducts given. Yields of byproduct given Boyd, Derek R.; Coulter, Peter B.; Hamilton, Robert; Thompson, Norris T.; Sharma, Narain D.; Stubbs, Michael E.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2123 2128 View in Reaxys

H N

N O

Rx-ID: 2847800 View in Reaxys 484/827 Yield

Conditions & References With 2,6-dichloro-benzonitrile in chloroform-d1, Yield given

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N O

H N N HN

Rx-ID: 2847801 View in Reaxys 485/827 Yield

O N N

N O

Rx-ID: 2888323 View in Reaxys 486/827 Yield

Conditions & References Ambient temperature, 2-3 weeks, Yield given Boyd, Derek R.; Coulter, Peter B.; Hamilton, Robert; Thompson, Norris T.; Sharma, Narain D.; Stubbs, Michael E.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2123 2128 View in Reaxys

O N N

N O

Rx-ID: 2888324 View in Reaxys 487/827

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Yield

N O

O H

Rx-ID: 2941361 View in Reaxys 488/827 Yield

Conditions & References With DBN in chloroform-d1, Yield given. Yields of byproduct given Boyd, Derek R.; Coulter, Peter B.; Hamilton, Robert; Thompson, Norris T.; Sharma, Narain D.; Stubbs, Michael E.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2123 2128 View in Reaxys

O H

N N

N O

Rx-ID: 2941362 View in Reaxys 489/827 Yield

Conditions & References Time= 12h, Ambient temperature, Yield given. Yields of byproduct given Boyd, Derek R.; Coulter, Peter B.; Hamilton, Robert; Thompson, Norris T.; Sharma, Narain D.; Stubbs, Michael E.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2123 2128 View in Reaxys

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H N

O HN

N O

Rx-ID: 3044855 View in Reaxys 490/827 Yield

Conditions & References With 1,4-diaza-bicyclo[2.2.2]octane in chloroform-d1, Time= 1h, Ambient temperature, Yield given. Yields of byproduct given Boyd, Derek R.; Coulter, Peter B.; Hamilton, Robert; Thompson, Norris T.; Sharma, Narain D.; Stubbs, Michael E.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2123 2128 View in Reaxys Ambient temperature, 1-2 days, Yield given. Yields of byproduct given Boyd, Derek R.; Coulter, Peter B.; Hamilton, Robert; Thompson, Norris T.; Sharma, Narain D.; Stubbs, Michael E.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2123 2128 View in Reaxys

Rx-ID: 3141270 View in Reaxys 491/827 Yield

Conditions & References in benzene, Time= 20h, T= 60.5 °C , other 3,3-(2,2'-biphenyldiyl)-4-methyl-4-aryl-1,2-dioxetanes; Ea, Rate constant, Mechanism, Thermodynamic data Richardson, William H.; Thomson, Stephen A.; Journal of Organic Chemistry; vol. 50; nb. 11; (1985); p. 1803 - 1810 View in Reaxys

O O

Rx-ID: 3143628 View in Reaxys 492/827 Yield

Conditions & References in benzene, T= 60.5 °C , Ea, Rate constant, Thermodynamic data Richardson, William H.; Thomson, Stephen A.; Journal of Organic Chemistry; vol. 50; nb. 11; (1985); p. 1803 - 1810 View in Reaxys

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Rx-ID: 3146342 View in Reaxys 493/827 Yield

O Br

O O

Rx-ID: 3146547 View in Reaxys 494/827 Yield

O O

Rx-ID: 3146587 View in Reaxys 495/827 Yield

O O

Rx-ID: 3147974 View in Reaxys 496/827 Yield

241/345

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O O O

O O

Rx-ID: 3149123 View in Reaxys 497/827 Yield

O O O

Rx-ID: 3154897 View in Reaxys 498/827 Yield

O N

N+ Cl –

Rx-ID: 3280722 View in Reaxys 499/827

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Yield

N O N

Rx-ID: 3935866 View in Reaxys 500/827 Yield

Conditions & References With oxygen, Time= 0.166667h, T= -261.2 °C , Irradiation Dunkin, Ian R.; Bell, Gordon A.; Tetrahedron; vol. 41; (1985); p. 339 - 348 View in Reaxys With oxygen, Time= 0.166667h, T= -261.2 °C , Irradiation, Mechanism Dunkin, Ian R.; Bell, Gordon A.; Tetrahedron; vol. 41; (1985); p. 339 - 348 View in Reaxys

F F O

F F F

Rx-ID: 8450526 View in Reaxys 501/827 Yield

Rx-ID: 20716587 View in Reaxys 502/827 Yield

Conditions & References Reaction Steps: 2 1: m-chloroperbenzoic acid / methanol / 0 °C / 1-2 h 2: 1,5-diazabicyclo<4.3.0>non-5-ene / CDCl3 With DBN, 3-chloro-benzenecarboperoxoic acid in methanol, chloroform-d1

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Boyd, Derek R.; Coulter, Peter B.; Hamilton, Robert; Thompson, Norris T.; Sharma, Narain D.; Stubbs, Michael E.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2123 2128 View in Reaxys Reaction Steps: 2 1: m-chloroperbenzoic acid / methanol / 0 °C / 1-2 h 2: 12 h / Ambient temperature With 3-chloro-benzenecarboperoxoic acid in methanol Boyd, Derek R.; Coulter, Peter B.; Hamilton, Robert; Thompson, Norris T.; Sharma, Narain D.; Stubbs, Michael E.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2123 2128 View in Reaxys

O N O

O N

Rx-ID: 1570527 View in Reaxys 503/827 Yield

Conditions & References

92 %

With sulfuric acid in methanol, Time= 8h, Heating Evans, Andrew R.; Hafiz, Mushtaq; Taylor, Giles A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 6; (1984); p. 1241 - 1246 View in Reaxys

O HO

HO OH

Rx-ID: 1748224 View in Reaxys 504/827 Yield 4 %, 95 %, 1%

Conditions & References With copper(I) oxide in acetonitrile, T= 50 °C Toussaint, Olivier; Capdevielle, Patrice; Maumy, Michel; Tetrahedron; vol. 40; nb. 17; (1984); p. 3229 - 3234 View in Reaxys

HO OH

Rx-ID: 1991124 View in Reaxys 505/827 Yield 8 %, 2 %

Conditions & References With sodium hydride in acetonitrile, Time= 0.25h, T= 50 °C Toussaint, Olivier; Capdevielle, Patrice; Maumy, Michel; Tetrahedron; vol. 40; nb. 17; (1984); p. 3229 - 3234

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View in Reaxys O

Rx-ID: 2040856 View in Reaxys 506/827 Yield

Conditions & References With palladium diacetate, sodium carbonate in N,N-dimethyl acetamide, Time= 4h, T= 170 °C , Yield given Ames, D.E.; Opalko, A.; Tetrahedron; vol. 40; nb. 10; (1984); p. 1919 - 1926 View in Reaxys

Rx-ID: 2090426 View in Reaxys 507/827 Yield

Conditions & References

101 %, 1.4 %, 91 %

in N,N-dimethyl-formamide, electrolytical reduction; other concentrations, addition of bases, add. of DEM, Product distribution, Mechanism Nuntnarumit, C.; Null, W. Edward; Hawley, M. Dale; Journal of Organic Chemistry; vol. 49; nb. 25; (1984); p. 4827 - 4833 View in Reaxys O

O O

Rx-ID: 2142654 View in Reaxys 508/827 Yield

Conditions & References

25 %, 15 %, With palladium diacetate, triethylamine in N,N-dimethyl acetamide, Time= 15h, T= 150 °C , other reagents, other solvents, 60 % Product distribution Ames, D.E.; Opalko, A.; Tetrahedron; vol. 40; nb. 10; (1984); p. 1919 - 1926 View in Reaxys

O O

N S Mg Br

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O O

H 2N

S N

O O

O S HN

Rx-ID: 2211948 View in Reaxys 509/827 Yield

Conditions & References

18 %, 2 %, in diethyl ether, Time= 2.5h, T= -15 °C , Product distribution, Mechanism 62 %, 10 %, Saito, Takao; Nakane, Michio; Motoki, Shinichi; Bulletin of the Chemical Society of Japan; vol. 57; nb. 5; (1984); p. 1429 24 % 1430 View in Reaxys

O S

N S Mg Br

O O

H 2N

O S

Rx-ID: 2254002 View in Reaxys 510/827 Yield

Conditions & References

12 %, 29 %, in diethyl ether, Time= 2.5h, T= -15 °C , THF, 1 h, 0 deg C, Product distribution, Mechanism 48 %, 2 %, Saito, Takao; Nakane, Michio; Motoki, Shinichi; Bulletin of the Chemical Society of Japan; vol. 57; nb. 5; (1984); p. 1429 17 % 1430 View in Reaxys

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O S

N S

O S

H 2N

N O

Rx-ID: 2255642 View in Reaxys 511/827 Yield

Conditions & References

28 %, 18 %, in diethyl ether, Time= 3.5h, T= -15 °C , Product distribution, Mechanism 32 %, 15 %, Saito, Takao; Nakane, Michio; Motoki, Shinichi; Bulletin of the Chemical Society of Japan; vol. 57; nb. 5; (1984); p. 1429 23 % 1430 View in Reaxys

O O

Rx-ID: 2551044 View in Reaxys 512/827 Yield 60 %, 1.8 %, 1.3 %, 63 %

Conditions & References in N,N-dimethyl-formamide, electrolytical reduction, Product distribution, Mechanism Nuntnarumit, C.; Null, W. Edward; Hawley, M. Dale; Journal of Organic Chemistry; vol. 49; nb. 25; (1984); p. 4827 - 4833 View in Reaxys

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Rx-ID: 2579428 View in Reaxys 513/827 Yield

Conditions & References

72 %

With oxygen, Irradiation Vedejs, E.; Perry, D. A.; Journal of Organic Chemistry; vol. 49; nb. 3; (1984); p. 573 - 575 View in Reaxys

O S S

Rx-ID: 2606252 View in Reaxys 514/827 Yield

Conditions & References With thionyl chloride, Time= 2h, Heating El-Barbary, A. A.; Hammouda, H. A.; El-Borai, M.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 23; nb. 8; (1984); p. 770 - 773 View in Reaxys

O S S

Rx-ID: 2606253 View in Reaxys 515/827 Yield

Conditions & References With sulfur El-Barbary, A. A.; Hammouda, H. A.; El-Borai, M.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 23; nb. 8; (1984); p. 770 - 773 View in Reaxys

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N N H

Rx-ID: 2841693 View in Reaxys 516/827 Yield

Conditions & References in methanol, Time= 2h, Irradiation, Yields of byproduct given Couture, A.; Dubiez, R.; Lablanche-Combier, A.; Tetrahedron; vol. 40; nb. 10; (1984); p. 1835 - 1844 View in Reaxys N O O O

O O

O OH

O O

Rx-ID: 2883411 View in Reaxys 517/827 Yield

Conditions & References

56 %, 63 %

in chloroform, Time= 12h, Heating Burgert, Wolfgang; Rewicki, Dieter; Chemische Berichte; vol. 117; nb. 7; (1984); p. 2409 - 2421 View in Reaxys

O N

N H

Rx-ID: 2955213 View in Reaxys 518/827 Yield

Conditions & References in methanol, Time= 2h, Irradiation Couture, A.; Dubiez, R.; Lablanche-Combier, A.; Tetrahedron; vol. 40; nb. 10; (1984); p. 1835 - 1844 View in Reaxys

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Rx-ID: 2994948 View in Reaxys 519/827 Yield

Conditions & References

98 %

O S

N S

O O

S O

H 2N

NH O

Rx-ID: 3555828 View in Reaxys 520/827 Yield

Conditions & References

54 %, 2 %, in diethyl ether, Time= 1h, T= -15 °C , THF, 1 h, 0 deg C, Product distribution, Mechanism 35 %, 16 %, Saito, Takao; Nakane, Michio; Motoki, Shinichi; Bulletin of the Chemical Society of Japan; vol. 57; nb. 5; (1984); p. 1429 6% 1430 View in Reaxys N N

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N N

Rx-ID: 3855425 View in Reaxys 521/827 Yield

Conditions & References

11.4 mg, 58 mg, 72.2 mg, 32.8 %

With zinc(II) chloride in diethyl ether, Time= 1h, Ambient temperature Anjaneyulu, P. S. R.; Lala, Anil K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 23; nb. 9; (1984); p. 802 - 807 View in Reaxys N N

Rx-ID: 3935749 View in Reaxys 522/827 Yield 22 mg, 22 mg, 55 mg

Conditions & References in cyclohexane, Time= 5h, Irradiation, Product distribution Anjaneyulu, P. S. R.; Lala, Anil K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 23; nb. 9; (1984); p. 802 - 807 View in Reaxys N O N

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N N

Rx-ID: 3935803 View in Reaxys 523/827 Yield

Conditions & References

100 mg, 30 Time= 15h, T= 25 °C , Irradiation, Product distribution mg, 60 mg, 220 mg, 110 Anjaneyulu, P. S. R.; Lala, Anil K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemismg, 345 mg try; vol. 23; nb. 9; (1984); p. 802 - 807 View in Reaxys N N

Rx-ID: 3935804 View in Reaxys 524/827 Yield

Conditions & References

100 mg, 30 %, 60 mg, 345 mg

Time= 15h, T= 25 °C , Irradiation, Further byproducts given Anjaneyulu, P. S. R.; Lala, Anil K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 23; nb. 9; (1984); p. 802 - 807 View in Reaxys N N

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NH 2

N N

Rx-ID: 3935863 View in Reaxys 525/827 Yield

Conditions & References

0.6 %, 8 %, 73 %, 14 %

With tetrabutylammonium perchlorate, diethyl malonate in N,N-dimethyl-formamide, T= 20 - 23 °C , interm. anion radicals, Mechanism Triebe, F. M.; Hawley, M. Dale; McDonald, Richard N.; Journal of the Chemical Society, Chemical Communications; nb. 12; (1980); p. 574 - 575 View in Reaxys

0.6 %, 8 %, 73 %, 14 %

With tetrabutylammonium perchlorate, diethyl malonate in N,N-dimethyl-formamide, T= 20 - 23 °C , Pt-cathode Triebe, F. M.; Hawley, M. Dale; McDonald, Richard N.; Journal of the Chemical Society, Chemical Communications; nb. 12; (1980); p. 574 - 575 View in Reaxys

0.27 % Chromat., 0.30 % Chromat., 98.8 % Chromat., 0.39 % Chromat.

With tetramethylammonium tetrafluoroborate in acetonitrile, T= 30 °C , decomposition under the conditions of constant-current electrolysis (c.c.e.) and N2 atmosphere, Product distribution Bethell, Donald; McDowall, Linda J.; Parker, Vernon D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1984); p. 1531 - 1536 View in Reaxys

N N

Rx-ID: 3935868 View in Reaxys 526/827 Yield 1.3 % Chromat., 87.4 % Chromat., 10.9 % Chromat.

Conditions & References With tetramethylammonium tetrafluoroborate in acetonitrile, T= 30 °C , electrochemical reaction, Further byproducts given. Title compound not separated from byproducts Ahmad, Iftikhar; Bethell, Donald; Parker, Vernon D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1984); p. 1527 - 1530 View in Reaxys

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1.2 % Chromat., 34.6 % Chromat., 63.8 % Chromat.

With tris(p-bromophenylammoniumyl) hexachloroantimonate in acetonitrile, T= 30 °C , Further byproducts given. Title compound not separated from byproducts Ahmad, Iftikhar; Bethell, Donald; Parker, Vernon D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1984); p. 1527 - 1530 View in Reaxys N O N

HO OH

Rx-ID: 3935869 View in Reaxys 527/827 Yield

Conditions & References

2.1 % Chromat., 62.8 % Chromat., 33.5 % Chromat.

With copper(II) bis(tetrafluoroborate) in acetonitrile, T= 30 °C , decomposition under electrochemical conditions or by various chemical oxidants with their various concentration, Product distribution, Rate constant

1.2 % Chromat., 34.6 % Chromat., 63.8 % Chromat.

With tris(p-bromophenylammoniumyl) hexachloroantimonate in acetonitrile, T= 30 °C , variation of catalyst concentration, Product distribution, Rate constant

Ahmad, Iftikhar; Bethell, Donald; Parker, Vernon D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1984); p. 1527 - 1530 View in Reaxys

N O

N N

Rx-ID: 3935870 View in Reaxys 528/827 Yield 0.29 % Chromat., 0.25 % Chromat., 92.5 % Chromat.

Conditions & References With tetramethylammonium tetrafluoroborate in acetonitrile, Time= 0.0666667h, T= 30 °C , decomposition under the conditions of interrupted constant-current electrolysis (i.c.c.e.), the effect of air, oxygen and other additives (diethyl malonate, tetralin), Product distribution, Rate constant, Mechanism Bethell, Donald; McDowall, Linda J.; Parker, Vernon D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1984); p. 1531 - 1536 View in Reaxys

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With tetramethylammonium tetrafluoroborate in [D3]acetonitrile, Time= 0.0666667h, T= 30 °C , decomposition under the conditions of interrupted constant-current electrolysis (i.c.c.e.), Rate constant Bethell, Donald; McDowall, Linda J.; Parker, Vernon D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1984); p. 1531 - 1536 View in Reaxys

O O O

9-bromo-anthrone

N N

Rx-ID: 19975039 View in Reaxys 529/827 Yield

Conditions & References Reaction Steps: 2 1: 56 percent / dimethylsulfoxide / 1.17 h 2: 56 percent / CHCl3 / 12 h / Heating in chloroform, dimethyl sulfoxide Burgert, Wolfgang; Rewicki, Dieter; Chemische Berichte; vol. 117; nb. 7; (1984); p. 2409 - 2421 View in Reaxys

O O N

9-bromo-anthrone

Rx-ID: 20552489 View in Reaxys 530/827 Yield

Conditions & References Reaction Steps: 2 1: 60 percent / benzene / 8 h / Ambient temperature 2: 98 percent / H2SO4 / methanol / 8 h / Heating With sulfuric acid in methanol, benzene Evans, Andrew R.; Hafiz, Mushtaq; Taylor, Giles A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 6; (1984); p. 1241 - 1246 View in Reaxys O (v5) (v5) (v5) (v5)

(v5)

(v5) (v9)

O (v3)

(v3)

Cr O O

(v9)

O (v3)

(v5) (v5) (v5) (v5) (v5)

(v3)

O (v3)

Rx-ID: 26824933 View in Reaxys 531/827 Yield 8.5 %, 47 %, 27 %

Conditions & References in N,N-dimethyl-formamide, Electrochem. Process; electrochemical generation of O2(1-) from O2 supplied to the cathode compartment (H-cell, DMF, supporting electrolyte (C4H9)4NPF6); pouring catholyte (with excess O2(1-)) into a flask containing flourene; bubbling O2, 10min, dark;; diln. of catholyte with H2O; extn. with diethyl ether; drying; removal of solvent, vac.; column chromy. (silica gel; eluent: hexane/CH2Cl2 (50percent)); Degrand, C.; Gautheron, B.; Bikrani, M.; Gasquez, F.; Compagnon, P.-L.; Journal of Organometallic Chemistry; vol. 273; nb. 3; (1984); p. 319 - 322 ; (from Gmelin) View in Reaxys

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18 %, 26 %, in N,N-dimethyl-formamide, Electrochem. Process; electrochemical generation of O2(1-) from O2 supplied to the cathode com46 % partment (H-cell, DMF, supporting electrolyte (C4H9)4NPF6); pouring catholyte into a flask containing flourene (O2(1-)/fluorene = 1:1); bubbling O2, 10min, dark;; diln. of catholyte with H2O; extn. with diethyl ether; drying; removal of solvent, vac.; column chromy. (silica gel; eluent: hexane/CH2Cl2 (50percent)); Degrand, C.; Gautheron, B.; Bikrani, M.; Gasquez, F.; Compagnon, P.-L.; Journal of Organometallic Chemistry; vol. 273; nb. 3; (1984); p. 319 - 322 ; (from Gmelin) View in Reaxys 27 %, 9 %, 23 %

in N,N-dimethyl-formamide, Electrochem. Process; electrochemical redn. of fluorene in the dark, Ar; introduction of a stream of O2 for 10min after consumption of 0.9F/mol;; diln. with H2O; extn. with diethyl ether; drying; removal of solvent, vac.; column chromy. (silica gel; eluent: hexane/CH2Cl2 (50percent)); yield up to 46percent; Degrand, C.; Gautheron, B.; Bikrani, M.; Gasquez, F.; Compagnon, P.-L.; Journal of Organometallic Chemistry; vol. 273; nb. 3; (1984); p. 319 - 322 ; (from Gmelin) View in Reaxys

8 %, 25 %, 26.5 %

in N,N-dimethyl-formamide, Electrochem. Process; electrochemical generation of O2(1-) from O2 supplied to the cathode compartment (H-cell, DMF, supporting electrolyte (C4H9)4NPF6); pouring catholyte into a flask containing excess flourene; bubbling O2, 10min, dark;; diln. of catholyte with H2O; extn. with diethyl ether; drying; removal of solvent, vac.; column chromy. (silica gel; eluent: hexane/CH2Cl2 (50percent)); Degrand, C.; Gautheron, B.; Bikrani, M.; Gasquez, F.; Compagnon, P.-L.; Journal of Organometallic Chemistry; vol. 273; nb. 3; (1984); p. 319 - 322 ; (from Gmelin) View in Reaxys

NH 2 N

N N

Rx-ID: 2021075 View in Reaxys 532/827 Yield

Conditions & References

8.5 %, 80 % With potassium hydroxide, oxygen in methanol, dimethyl sulfoxide, Mechanism Handoo, Kishan L.; Gadru, Kanchan; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 22; nb. 9; (1983); p. 839 - 840 View in Reaxys 8.5 %, 80 % With potassium hydroxide, oxygen in methanol, dimethyl sulfoxide, Time= 0.25h Handoo, Kishan L.; Gadru, Kanchan; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 22; nb. 9; (1983); p. 839 - 840 View in Reaxys

N N

Rx-ID: 2027612 View in Reaxys 533/827

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Yield

Conditions & References With potassium hydroxide in methanol, dimethyl sulfoxide, Time= 1h, reaction with and without oxygen, Mechanism Handoo, Kishan L.; Gadru, Kanchan; Jain, C. K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 22; nb. 6; (1983); p. 526 - 530 View in Reaxys

Rx-ID: 2106554 View in Reaxys 534/827 Yield

Conditions & References in benzene, Time= 0.666667h, Irradiation, Yield given. Yields of byproduct given Tomioka, Hideo; Nakamura, Hiroyuki; Izawa, Yasuji; Journal of the Chemical Society, Chemical Communications; nb. 19; (1983); p. 1070 - 1071 View in Reaxys in benzene, Time= 0.333333h, Irradiation, var. time, Product distribution Tomioka, Hideo; Nakamura, Hiroyuki; Izawa, Yasuji; Journal of the Chemical Society, Chemical Communications; nb. 19; (1983); p. 1070 - 1071 View in Reaxys

O O

Rx-ID: 2148285 View in Reaxys 535/827 Yield

O P N N

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NH 2

N N

Rx-ID: 2171676 View in Reaxys 536/827 Yield

Conditions & References With tetrabutylammonium perchlorate in N,N-dimethyl-formamide, Product distribution Herbranson, Dale E.; Theisen, F. J.; Hawley, M. Dale; McDonald, Richard N.; Journal of the American Chemical Society; vol. 105; nb. 9; (1983); p. 2544 - 2549 View in Reaxys

Rx-ID: 2196232 View in Reaxys 537/827 Yield

Conditions & References in diethyl ether, Irradiation Smith, William B.; Harris, Michael C.; Journal of Organic Chemistry; vol. 48; nb. 25; (1983); p. 4957 - 4962 View in Reaxys With oxygen in diethyl ether, Irradiation, Mechanism Smith, William B.; Harris, Michael C.; Journal of Organic Chemistry; vol. 48; nb. 25; (1983); p. 4957 - 4962 View in Reaxys

S S

Rx-ID: 2210509 View in Reaxys 538/827 Yield 100 %

Conditions & References With tert-butylhypochlorite in tetrachloromethane, Time= 1h, Ambient temperature, other reagent El-Wassimy, M.T.M.; Joergensen, K.A.; Lawesson S.-O.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1983); p. 2201 - 2204 View in Reaxys

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O O

O–

O O

C K+

S O

Rx-ID: 2229016 View in Reaxys 539/827 Yield

Conditions & References in tetrahydrofuran, T= 23 °C , Rate constant Nishi, Shin-ichi; Matsuda, Minoru; Phosphorus and Sulfur and the Related Elements; vol. 16; (1983); p. 181 - 186 View in Reaxys

O O

O–

C Li+

O O

S C–

Li+

Rx-ID: 2229017 View in Reaxys 540/827 Yield

Conditions & References in tetrahydrofuran, T= 23 °C , Rate constant Nishi, Shin-ichi; Matsuda, Minoru; Phosphorus and Sulfur and the Related Elements; vol. 16; (1983); p. 181 - 186 View in Reaxys

O O

O–

C Na +

O O

S C–

Na +

Rx-ID: 2229018 View in Reaxys 541/827 Yield

Conditions & References in tetrahydrofuran, T= 23 °C , Rate constant Nishi, Shin-ichi; Matsuda, Minoru; Phosphorus and Sulfur and the Related Elements; vol. 16; (1983); p. 181 - 186 View in Reaxys

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–

S K

Rx-ID: 2229019 View in Reaxys 542/827 Yield

Conditions & References in N,N,N,N,N,N-hexamethylphosphoric triamide, T= 23 °C , other solvent; other alkali cations, Rate constant Nishi, Shin-ichi; Matsuda, Minoru; Phosphorus and Sulfur and the Related Elements; vol. 16; (1983); p. 181 - 186 View in Reaxys

O O

Rx-ID: 2602519 View in Reaxys 543/827 Yield

Conditions & References Heating, ΔG*, ΔH*, ΔS*, Thermodynamic data Adam, Waldemar; Encarnacion, Luis A. Arias; Zinner, Klaus; Chemische Berichte; vol. 116; nb. 3; (1983); p. 839 - 846 View in Reaxys

O O

Rx-ID: 2832919 View in Reaxys 544/827 Yield

Conditions & References in benzene, Time= 20h, Irradiation, Yield given. Yields of byproduct given Tomioka, Hideo; Nakamura, Hiroyuki; Izawa, Yasuji; Journal of the Chemical Society, Chemical Communications; nb. 19; (1983); p. 1070 - 1071 View in Reaxys

S O O

Rx-ID: 2833438 View in Reaxys 545/827 Yield

Conditions & References

5 mg

T= 700 °C , p= 0.01Torr Schank, Kurt; Werner, Frank; Liebigs Annalen der Chemie; nb. 10; (1983); p. 1739 - 1743

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View in Reaxys

O O

Rx-ID: 3042579 View in Reaxys 546/827 Yield

O O

O O O

Rx-ID: 3156991 View in Reaxys 547/827 Yield

O O

Rx-ID: 3517194 View in Reaxys 548/827 Yield

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View in Reaxys Time= 0.666667h, T= 10 °C , Irradiation, Yield given. Yields of byproduct given Tomioka, Hideo; Nakamura, Hiroyuki; Izawa, Yasuji; Journal of the Chemical Society, Chemical Communications; nb. 19; (1983); p. 1070 - 1071 View in Reaxys O

I+

O I

I– I

Rx-ID: 3594827 View in Reaxys 549/827 Yield

Conditions & References

77 %

Time= 0.166667h, T= 180 °C Tolstaya, T. P.; Egorova, L. D.; Lisichkina, I. N.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 32; nb. 12; (1983); p. 2495 - 2501; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1983); p. 2781 - 2787 View in Reaxys 2H

2H 2H

Rx-ID: 3697136 View in Reaxys 550/827 Yield

Conditions & References in benzene, Time= 40h, Irradiation, Yield given. Yields of byproduct given Tomioka, Hideo; Nakamura, Hiroyuki; Izawa, Yasuji; Journal of the Chemical Society, Chemical Communications; nb. 19; (1983); p. 1070 - 1071 View in Reaxys Cl

H 2N

O N

H 2N N

Rx-ID: 3738500 View in Reaxys 551/827

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Yield 9 %, 40.5 %, 25.5 %, 19 %

Conditions & References With Azobenzene, electrochemical reduction Degrand, Chantal; Belot, Gerard; Compagnon, Paul-Louis; Gasquez, Francoise; Canadian Journal of Chemistry; vol. 61; (1983); p. 2581 - 2589 View in Reaxys N N

O H O

Rx-ID: 3840109 View in Reaxys 552/827 Yield

Conditions & References Time= 0.333333h, T= 10 °C , Irradiation, Yield given. Yields of byproduct given Tomioka, Hideo; Nakamura, Hiroyuki; Izawa, Yasuji; Journal of the Chemical Society, Chemical Communications; nb. 19; (1983); p. 1070 - 1071 View in Reaxys N N

O O

Rx-ID: 3853362 View in Reaxys 553/827 Yield

Conditions & References Time= 0.333333h, T= 10 °C , Irradiation, var. time, Product distribution Tomioka, Hideo; Nakamura, Hiroyuki; Izawa, Yasuji; Journal of the Chemical Society, Chemical Communications; nb. 19; (1983); p. 1070 - 1071 View in Reaxys Time= 0.666667h, T= 10 °C , Irradiation, Yield given. Yields of byproduct given Tomioka, Hideo; Nakamura, Hiroyuki; Izawa, Yasuji; Journal of the Chemical Society, Chemical Communications; nb. 19; (1983); p. 1070 - 1071 View in Reaxys

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N N

Rx-ID: 3935746 View in Reaxys 554/827 Yield

O O

Rx-ID: 3935772 View in Reaxys 555/827 Yield

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O O O

H 2N

Na +

N–

S O

Rx-ID: 4074040 View in Reaxys 556/827 Yield 91 %

Conditions & References With acetic acid, Time= 24h Gunasekaran, S.; Venkatasubramanian, N.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical; vol. 22; nb. 9; (1983); p. 774 - 777 View in Reaxys With acetic acid, T= 30 °C , E(activ.), ΔH(activ.), ΔS(activ.), β(activ.), Kinetics, Mechanism, Thermodynamic data Gunasekaran, S.; Venkatasubramanian, N.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical; vol. 22; nb. 9; (1983); p. 774 - 777 View in Reaxys

O S O

O N

O S

SO2

Rx-ID: 7086622 View in Reaxys 557/827 Yield 3 %, 10.5 %, 25 %, 83.6 %

Conditions & References in benzene, Time= 0.5h, Heating Bonini, Bianca F.; Maccagnani, Gaetano; Mazzanti, Germana; Pedrini, Paola; Lammerink, Ben H. M.; Zwanenburg, Binne; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1983); p. 2097 - 2101 View in Reaxys

9-bromo-anthrone O

S O

Rx-ID: 20585458 View in Reaxys 558/827 Yield

Conditions & References Reaction Steps: 4 1: 1) KOtBu / 1) THF, 2) THF, 30 min, reflux 2: 76 percent / acetonitrile / 12 h / Ambient temperature 3: 54 percent / tetracyanoethylene, O3 / CH2Cl2; ethyl acetate / 0.17 h / Ambient temperature 4: 5 mg / 700 °C / 0.01 Torr With potassium tert-butylate, ozone, ethenetetracarbonitrile in dichloromethane, ethyl acetate, acetonitrile

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Schank, Kurt; Werner, Frank; Liebigs Annalen der Chemie; nb. 10; (1983); p. 1739 - 1743 View in Reaxys

9-bromo-anthrone

O O

Rx-ID: 20604720 View in Reaxys 559/827 Yield

Conditions & References Reaction Steps: 2 1: 54 percent / tetracyanoethylene, O3 / CH2Cl2; ethyl acetate / 0.17 h / Ambient temperature 2: 5 mg / 700 °C / 0.01 Torr With ozone, ethenetetracarbonitrile in dichloromethane, ethyl acetate Schank, Kurt; Werner, Frank; Liebigs Annalen der Chemie; nb. 10; (1983); p. 1739 - 1743 View in Reaxys

9-bromo-anthrone

K+

O –O

Rx-ID: 20612923 View in Reaxys 560/827 Yield

Conditions & References Reaction Steps: 3 1: 76 percent / acetonitrile / 12 h / Ambient temperature 2: 54 percent / tetracyanoethylene, O3 / CH2Cl2; ethyl acetate / 0.17 h / Ambient temperature 3: 5 mg / 700 °C / 0.01 Torr With ozone, ethenetetracarbonitrile in dichloromethane, ethyl acetate, acetonitrile Schank, Kurt; Werner, Frank; Liebigs Annalen der Chemie; nb. 10; (1983); p. 1739 - 1743 View in Reaxys Cl

Rx-ID: 21115072 View in Reaxys 561/827 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether 2: O2 / diethyl ether / Irradiation With oxygen in diethyl ether Smith, William B.; Harris, Michael C.; Journal of Organic Chemistry; vol. 48; nb. 25; (1983); p. 4957 - 4962 View in Reaxys

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Rx-ID: 21118764 View in Reaxys 562/827 Yield

Conditions & References Reaction Steps: 2 1: 1.) n-BuLi, 2.) 2,3-dibromo-2,3-dimethylbutane / 1.) THF, hexane, 2.) 10 min 2: O2 / diethyl ether / Irradiation With n-butyllithium, 2,3-dibromo-2,3-dimethylbutane, oxygen in diethyl ether Smith, William B.; Harris, Michael C.; Journal of Organic Chemistry; vol. 48; nb. 25; (1983); p. 4957 - 4962 View in Reaxys 2H

Na +

O–

O 2H 2H

Rx-ID: 1767464 View in Reaxys 563/827 Yield

Conditions & References

6.0 % Chromat., 0.5 % Chromat., 5.9 % Chromat.

Ambient temperature, electrolyses in undivided cell, Pt electrodes, c.p.e. at 1.7 V, further conditions, Product distribution, Mechanism Eberson, Lennart; Webber, Andrew; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 36; nb. 1; (1982); p. 53 - 58 View in Reaxys 2H

H O

Rx-ID: 1767465 View in Reaxys 564/827 Yield

Conditions & References

4.8 % Chro- With tetrabutylammonium tetrafluoroborate, Ambient temperature, electrolyses in undivided cell, Pt electrodes, c.c.e. at 0.5 mA mat., 0.9 % cm-2, Product distribution, Mechanism

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Chromat., Eberson, Lennart; Webber, Andrew; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 36; nb. 2.9 % Chro- 1; (1982); p. 53 - 58 mat. View in Reaxys

O N

(v2)

Rx-ID: 1946522 View in Reaxys 565/827 Yield

Conditions & References

47 %, 33 %

With 18-crown-6 ether, potassium carbonate in acetonitrile, Time= 3h, T= 40 °C Jawdosiuk, Mikolaj; Uminski, Maciej; Journal of the Chemical Society, Chemical Communications; nb. 17; (1982); p. 979 980 View in Reaxys

O P N

Rx-ID: 2171678 View in Reaxys 566/827 Yield 100 %

Conditions & References With oxygen, methylene blue in dichloromethane, Time= 0.0833333h, T= -78 °C , Irradiation, other reagent Suzuki, Nobutaka; Wakatsuki, Satoshi; Izawa, Yasuji; Tetrahedron Letters; vol. 21; nb. 24; (1980); p. 2313 - 2314 View in Reaxys With oxygen, methylene blue in dichloromethane, Irradiation, Quantum yield Suzuki, Nobutaka; Sano, Kaniti; Wakatsuki, Satoshi; Izawa, Yasuji; Bulletin of the Chemical Society of Japan; vol. 55; nb. 3; (1982); p. 842 - 844 View in Reaxys

Rx-ID: 2574825 View in Reaxys 567/827 Yield

Conditions & References With potassium tert-butylate in tetrahydrofuran, Time= 8h, Yield given Boyd, Derek R.; McCombe, Kenneth M.; Sharma, Narain D.; Tetrahedron Letters; vol. 23; nb. 28; (1982); p. 2907 - 2908

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View in Reaxys

N O

Rx-ID: 2587984 View in Reaxys 568/827 Yield

Conditions & References With potassium tert-butylate in tetrahydrofuran, Time= 8h, Ambient temperature, Yield given Boyd, Derek R.; McCombe, Kenneth M.; Sharma, Narain D.; Tetrahedron Letters; vol. 23; nb. 28; (1982); p. 2907 - 2908 View in Reaxys O O

OH O

O N

Rx-ID: 2600555 View in Reaxys 569/827 Yield

Conditions & References With water in 1,4-dioxane, T= 25 °C , pH range: 3 - 12, Rate constant Hoz, Shmaryahu; Perach, Sara Sima; Journal of Organic Chemistry; vol. 47; nb. 21; (1982); p. 4056 - 4059 View in Reaxys O O

O O

O N

Rx-ID: 2602338 View in Reaxys 570/827 Yield

F O

O F

N O

O N

Rx-ID: 2616330 View in Reaxys 571/827 Yield

Conditions & References With water in 1,4-dioxane, T= 25 °C , pH range: 3 - 12, Rate constant

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Hoz, Shmaryahu; Perach, Sara Sima; Journal of Organic Chemistry; vol. 47; nb. 21; (1982); p. 4056 - 4059 View in Reaxys O O

O N

O O

O N

Rx-ID: 2670285 View in Reaxys 572/827 Yield

Conditions & References With water in 1,4-dioxane, T= 25 °C , pH range: 3 - 12, other 9-alkoxyfluorenes, Rate constant, Mechanism Hoz, Shmaryahu; Perach, Sara Sima; Journal of Organic Chemistry; vol. 47; nb. 21; (1982); p. 4056 - 4059 View in Reaxys

O O O

Rx-ID: 2987334 View in Reaxys 573/827 Yield

Conditions & References With sodium methylate in methanol, T= 25 °C , Rate constant Carey, Edwin; O'Ferrall, Rory A. More; Vernon, Nicholas M.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1982); p. 1581 - 1586 View in Reaxys

Rx-ID: 1763861 View in Reaxys 574/827 Yield 82 % Spectr.

Conditions & References in acetonitrile, T= 23 °C , reaction stereoselectivity; in the presence of methanol, Rate constant, Product distribution Zupancic, Joseph J.; Grasse, Peter B.; Schuster, Gary B.; Journal of the American Chemical Society; vol. 103; nb. 9; (1981); p. 2423 - 2425 View in Reaxys

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Rx-ID: 1841947 View in Reaxys 575/827 Yield

Conditions & References

With thiophene, T= 500 °C , p= 1 - 5Torr , Further byproducts given. Yields of byproduct given Reinecke, Manfred G.; Newsom, James G.; Chen, Lao-Jer; Journal of the American Chemical Society; vol. 103; nb. 10; (1981); p. 2760 - 2769 View in Reaxys O C

Rx-ID: 2005187 View in Reaxys 576/827 Yield

Conditions & References

45 % Spectr., 39 % Spectr.

in acetonitrile, T= 23 °C , reaction stereoselectivity; other solvent, other concentrations; in the presence of methanol, Rate constant, Product distribution Zupancic, Joseph J.; Grasse, Peter B.; Schuster, Gary B.; Journal of the American Chemical Society; vol. 103; nb. 9; (1981); p. 2423 - 2425 View in Reaxys

O O

O Cl

Cl Cl

Rx-ID: 2049735 View in Reaxys 577/827 Yield

Conditions & References T= 600 °C , p= 1Torr Mehta, Goverdhan; Reddy, A. Veera; Srikrishna, A.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 20; nb. 8; (1981); p. 698 - 699 View in Reaxys

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Cl Cl

Rx-ID: 2050561 View in Reaxys 578/827 Yield

Rx-ID: 2118396 View in Reaxys 579/827 Yield

Conditions & References With hydrogenchloride in ethanol Horsewood, Peter; Kirby, Gordon W.; Sharma, Ram Prakash; Sweeny, James; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 1802 - 1806 View in Reaxys

H 2N

NH N

Rx-ID: 2581957 View in Reaxys 580/827 Yield

Conditions & References With PPA, T= 170 °C , Yield given Fusco, R.; Sannicolo, F.; Journal of Organic Chemistry; vol. 46; nb. 1; (1981); p. 83 - 89 View in Reaxys

S N

N N

Rx-ID: 2987148 View in Reaxys 581/827

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Yield

Conditions & References

14.7 %, 65.8 %

With 3-chloro-benzenecarboperoxoic acid in diethyl ether, Time= 144h, T= 0 °C Bonini, Bianca F.; Maccagnani, Gaetano; Mazzanti, Germana; Rosini, Goffredo; Foresti, Elisabetta; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2322 - 2327 View in Reaxys

O N

S O

Rx-ID: 2999536 View in Reaxys 582/827 Yield

Conditions & References

25.2 %, 46.7 %

With 3-chloro-benzenecarboperoxoic acid in diethyl ether, Time= 72h, T= 0 °C Bonini, Bianca F.; Maccagnani, Gaetano; Mazzanti, Germana; Rosini, Goffredo; Foresti, Elisabetta; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2322 - 2327 View in Reaxys

O N

N N

S O

Rx-ID: 3002888 View in Reaxys 583/827 Yield

Conditions & References

30.2 %, 45.7 %

With 3-chloro-benzenecarboperoxoic acid in chloroform, Time= 12h, T= 0 °C Bonini, Bianca F.; Maccagnani, Gaetano; Mazzanti, Germana; Rosini, Goffredo; Foresti, Elisabetta; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2322 - 2327 View in Reaxys

O O

Rx-ID: 3126889 View in Reaxys 584/827 Yield

Conditions & References With water, acetic acid, potassium iodide in methanol, T= 50 °C Sawaki, Yasuhiko; Kato, Hiroshi; Ogata, Yoshiro; Journal of the American Chemical Society; vol. 103; nb. 13; (1981); p. 3832 - 3837 View in Reaxys

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Na + 1

-1

S –S

Na +

Rx-ID: 3574090 View in Reaxys 585/827 Yield

Conditions & References in tetrahydrofuran, T= 23 °C , Rate constant Tagaya, Hideyuki; Aruga, Tamotsu; Ito, Osamu; Matsuda, Minoru; Journal of the American Chemical Society; vol. 103; nb. 18; (1981); p. 5484 - 5489 View in Reaxys S

N N

N S

Rx-ID: 3932191 View in Reaxys 586/827 Yield 8.9 %, 82.9 %

Conditions & References in benzene, Time= 5h, Ambient temperature Bonini, Bianca F.; Maccagnani, Gaetano; Mazzanti, Germana; Rosini, Goffredo; Foresti, Elisabetta; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2322 - 2327 View in Reaxys

N N

S N N

Rx-ID: 3932218 View in Reaxys 587/827 Yield 39.1 %, 31.8 %

Conditions & References in benzene, Time= 48h, Ambient temperature Bonini, Bianca F.; Maccagnani, Gaetano; Mazzanti, Germana; Rosini, Goffredo; Foresti, Elisabetta; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2322 - 2327 View in Reaxys

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S N N

S O

N N

Rx-ID: 3932219 View in Reaxys 588/827 Yield 23 %, 27.3 %, 17 %

Conditions & References in chloroform, Time= 168h, Ambient temperature Bonini, Bianca F.; Maccagnani, Gaetano; Mazzanti, Germana; Rosini, Goffredo; Foresti, Elisabetta; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2322 - 2327 View in Reaxys N N

Rx-ID: 3935747 View in Reaxys 589/827 Yield 9 % Spectr., 10 % Spectr., 62 % Spectr., 1 % Spectr.

Conditions & References With oxygen in dichloromethane, Time= 0.5h, T= 0 °C , Irradiation, Product distribution, Mechanism Sawaki, Yasuhiko; Kato, Hiroshi; Ogata, Yoshiro; Journal of the American Chemical Society; vol. 103; nb. 13; (1981); p. 3832 - 3837 View in Reaxys N N

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N N

Rx-ID: 3935757 View in Reaxys 590/827 Yield

Conditions & References With potassium tert-butylate, oxygen in N,N,N,N,N,N-hexamethylphosphoric triamide, tert-butyl alcohol, T= 25 °C , Mechanism

86 %, 6 %

Handoo, Kishan L.; Bahadur, Yogender; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 20; nb. 5; (1981); p. 412 - 414 View in Reaxys N

N O

N O N

Rx-ID: 3935796 View in Reaxys 591/827 Yield

Conditions & References

570 mg, 224 in dichloromethane, T= -30 °C mg Horsewood, Peter; Kirby, Gordon W.; Sharma, Ram Prakash; Sweeny, James; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 1802 - 1806 View in Reaxys

N O O

S N H

Rx-ID: 3935821 View in Reaxys 592/827 Yield

Conditions & References With triethylamine in tetrahydrofuran, Time= 15h Quast, Helmut; Kees, Frieder; Chemische Berichte; vol. 114; nb. 2; (1981); p. 774 - 786 View in Reaxys

N N

O N

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N O N

Rx-ID: 3935845 View in Reaxys 593/827 Yield

Conditions & References

92 mg, 11 %

in benzene, Time= 24h, Heating Horsewood, Peter; Kirby, Gordon W.; Sharma, Ram Prakash; Sweeny, James; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 1802 - 1806 View in Reaxys

N O N

Rx-ID: 3935872 View in Reaxys 594/827 Yield

Conditions & References With tert-butylsulfamyl chloride, triethylamine in tetrahydrofuran, Time= 15h Quast, Helmut; Kees, Frieder; Chemische Berichte; vol. 114; nb. 2; (1981); p. 774 - 786 View in Reaxys O C

CH-insertion product - 18 percent Spectr.

Rx-ID: 7451937 View in Reaxys 595/827 Yield 65 % Spectr.

O C

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CH-insertion product - 6percent Spectr.

Rx-ID: 7451938 View in Reaxys 596/827 Yield

Conditions & References

33 % Spectr., 53 % Spectr.

in acetonitrile, T= 23 °C , reaction stereoselectivity; in the presence of methanol, Rate constant, Product distribution Zupancic, Joseph J.; Grasse, Peter B.; Schuster, Gary B.; Journal of the American Chemical Society; vol. 103; nb. 9; (1981); p. 2423 - 2425 View in Reaxys O

9-bromo-anthrone

Rx-ID: 20549959 View in Reaxys 597/827 Yield

Conditions & References Reaction Steps: 2 1: 82.9 percent / benzene / 5 h / Ambient temperature 2: 25.2 percent / m-chloroperbenzoic acid / diethyl ether / 72 h / 0 °C With 3-chloro-benzenecarboperoxoic acid in diethyl ether, benzene Bonini, Bianca F.; Maccagnani, Gaetano; Mazzanti, Germana; Rosini, Goffredo; Foresti, Elisabetta; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2322 - 2327 View in Reaxys

O N N

9-bromo-anthrone

Rx-ID: 20550021 View in Reaxys 598/827 Yield

Conditions & References Reaction Steps: 2 1: 91 percent / benzene / 5 h / Ambient temperature 2: 30.2 percent / m-chloroperbenzoic acid / CHCl3 / 12 h / 0 °C With 3-chloro-benzenecarboperoxoic acid in chloroform, benzene Bonini, Bianca F.; Maccagnani, Gaetano; Mazzanti, Germana; Rosini, Goffredo; Foresti, Elisabetta; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2322 - 2327 View in Reaxys

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9-bromo-anthrone

Rx-ID: 20567154 View in Reaxys 599/827 Yield

Conditions & References Reaction Steps: 3 1: 62 percent / benzene / 0.17 h / Ambient temperature 2: 82.9 percent / benzene / 5 h / Ambient temperature 3: 25.2 percent / m-chloroperbenzoic acid / diethyl ether / 72 h / 0 °C With 3-chloro-benzenecarboperoxoic acid in diethyl ether, benzene Bonini, Bianca F.; Maccagnani, Gaetano; Mazzanti, Germana; Rosini, Goffredo; Foresti, Elisabetta; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2322 - 2327 View in Reaxys N O N

9-bromo-anthrone

Rx-ID: 20583508 View in Reaxys 600/827 Yield

Conditions & References Reaction Steps: 2 1: 224 mg / CH2Cl2 / -30 °C 2: hydrochloric acid / ethanol With hydrogenchloride in ethanol, dichloromethane Horsewood, Peter; Kirby, Gordon W.; Sharma, Ram Prakash; Sweeny, James; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 1802 - 1806 View in Reaxys Reaction Steps: 2 1: 11 percent / benzene / 24 h / Heating 2: hydrochloric acid / ethanol With hydrogenchloride in ethanol, benzene Horsewood, Peter; Kirby, Gordon W.; Sharma, Ram Prakash; Sweeny, James; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 1802 - 1806 View in Reaxys OH O

Rx-ID: 293624 View in Reaxys 601/827 Yield

Conditions & References With iron(II) sulfate Hock et al.; Chemische Berichte; vol. 83; (1950); p. 227,234 View in Reaxys With N-benzyl-trimethylammonium hydroxide

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Sprinzak; Journal of the American Chemical Society; vol. 80; (1958); p. 5449,5452 View in Reaxys With KO2 in benzene Lee-Ruff, Edward; Timms, Neil; Canadian Journal of Chemistry; vol. 58; nb. 20; (1980); p. 2138 - 2141 View in Reaxys

HO N O

Rx-ID: 1592768 View in Reaxys 602/827 Yield

Conditions & References

100 %

With sulfuric acid, Time= 8h, Heating, other characteristic reaction (with hydroxylamine) Hafiz, Mushtag; Taylor, Giles A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1700 - 1705 View in Reaxys

F O

Rx-ID: 1813158 View in Reaxys 603/827 Yield 5 %, 31 %, 33 %

Conditions & References in various solvent(s), T= -78 °C Patrick, Timothy B.; Cantrell, Gary L.; Inga, Sandra M.; Journal of Organic Chemistry; vol. 45; nb. 8; (1980); p. 1409 1413 View in Reaxys

O F I HO

F O

Rx-ID: 2061446 View in Reaxys 604/827 Yield

Conditions & References Patrick, Timothy B.; Scheibel, Jeffrey J.; Hall, Warren E.; Lee, Young H.; Journal of Organic Chemistry; vol. <22> 45; (1980); p. 4492 - 4494 View in Reaxys

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O S

O N

N S

NH S N

Rx-ID: 2163827 View in Reaxys 605/827 Yield

Conditions & References

37 %

in 1,2-dichloro-ethane, Time= 0.5h, Ambient temperature Saito, Takao; Oikawa, Isao; Motoki, Shinichi; Bulletin of the Chemical Society of Japan; vol. 53; nb. 9; (1980); p. 2582 2585 View in Reaxys

O S

N S

NH S N

Rx-ID: 2180379 View in Reaxys 606/827 Yield 29 %

Conditions & References in 1,2-dichloro-ethane, Time= 0.5h, Ambient temperature Saito, Takao; Oikawa, Isao; Motoki, Shinichi; Bulletin of the Chemical Society of Japan; vol. 53; nb. 9; (1980); p. 2582 2585 View in Reaxys

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O S

N S Cl

N N H

S O

Rx-ID: 2180383 View in Reaxys 607/827 Yield

Conditions & References

27 %

in 1,2-dichloro-ethane, Time= 15h, Ambient temperature Saito, Takao; Oikawa, Isao; Motoki, Shinichi; Bulletin of the Chemical Society of Japan; vol. 53; nb. 9; (1980); p. 2582 2585 View in Reaxys

O S

NH N

Rx-ID: 2180394 View in Reaxys 608/827 Yield

Conditions & References

90 %

With copper(II) sulfate in tetrahydrofuran, methanol, water, Time= 48h, Heating Attanasi, Orazio; Gasperoni, Simonetta; Carletti, Claudio; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 6; (1980); p. 1063 - 1066 View in Reaxys

O HN

Rx-ID: 2442539 View in Reaxys 609/827

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Yield

Conditions & References

12 %, 34 %, With nitronium tetrafluoborate, air in acetonitrile, Time= 0.5h, Further byproducts given 4 %, 30 % Kashin, A. N.; Bumagin, N. A.; Bessonova, M. P.; Beletskaya, I. P.; Reutov, O. A.; Journal of Organic Chemistry USSR (English Translation); vol. 16; nb. 7; (1980); p. 1153 - 1159; Zhurnal Organicheskoi Khimii; vol. 16; nb. 7; (1980); p. 1345 1352 View in Reaxys

O S

N S

S N

Rx-ID: 2681032 View in Reaxys 610/827 Yield

Conditions & References

98 % Chromat., 23 %

in 1,2-dichloro-ethane, Time= 144h, Ambient temperature, var. aldehydes, aldimines, oximes, azines, and thiones, Product distribution Saito, Takao; Oikawa, Isao; Motoki, Shinichi; Bulletin of the Chemical Society of Japan; vol. 53; nb. 4; (1980); p. 1023 1027 View in Reaxys

S O N O

O N

N S

S N O

Rx-ID: 2747443 View in Reaxys 611/827 Yield

Conditions & References

68 %, 27 %, With air in dichloromethane, Time= 0.166667h, T= 20 °C , Product distribution, Mechanism 7% Kashin, A. N.; Bumagin, N. A.; Beletskaya, I. P.; Reutov, O. A.; Journal of Organic Chemistry USSR (English Translation); vol. 16; nb. 12; (1980); p. 2190 - 2195; Zhurnal Organicheskoi Khimii; vol. 16; nb. 12; (1980); p. 2561 - 2566 View in Reaxys

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S S

Rx-ID: 2844263 View in Reaxys 612/827 Yield

Conditions & References

19 %, 20 %, With tetrasulphure tetranitride in tetrahydrofuran, Ambient temperature, Further byproducts given 32 %, 33 % Mataka, Shuntaro; Takahashi, Kazufumi; Yamamoto, Hajime; Tashiro, Masashi; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 2417 - 2421 View in Reaxys

Rx-ID: 2846752 View in Reaxys 613/827 Yield

Conditions & References T= 170 °C Jemison, Robert W.; Ollis, W. David; Sutherland, Ian O.; Tannock, James; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1462 - 1472 View in Reaxys

O 2

Rx-ID: 2846753 View in Reaxys 614/827 Yield

Conditions & References With water-d2, 1.) CDCl3, 2.) 170 deg C, Multistep reaction

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Jemison, Robert W.; Ollis, W. David; Sutherland, Ian O.; Tannock, James; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1462 - 1472 View in Reaxys

O O

Rx-ID: 3001421 View in Reaxys 615/827 Yield

Conditions & References With sulfuric acid, acetic acid, multistep reaction; pyrolysis; no expected triphenylmethanol detection Hafiz, Mushtag; Taylor, Giles A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1700 - 1705 View in Reaxys

Rx-ID: 3178345 View in Reaxys 616/827 Yield 98 %, 90 %

Conditions & References With antimonypentachloride, Time= 0.666667h, T= 20 °C , other reagent, time, Product distribution Miura, Masahiro; Nojima, Masamoto; Kusabayashi, Shigekazu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1950 - 1954 View in Reaxys

98 %, 90 %

With antimonypentachloride in dichloromethane, Time= 0.666667h, T= 20 °C Miura, Masahiro; Nojima, Masamoto; Kusabayashi, Shigekazu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1950 - 1954 View in Reaxys

S N

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S O N

Rx-ID: 3669837 View in Reaxys 617/827 Yield

Conditions & References

7.5 %, 59 %, 31 %

With 3-chloro-benzenecarboperoxoic acid in chloroform, Time= 60h, T= 0 °C Mazzanti, Germana; Maccagnani, Gaetano; Bonini, Bianca F.; Pedrini, Paola; Zwanenburg, Binne; Gazzetta Chimica Italiana; vol. 110; nb. 2/3; (1980); p. 163 - 166 View in Reaxys

7.5 %, 59 %, 31 %

With 3-chloro-benzenecarboperoxoic acid in chloroform, Time= 60h, T= 0 °C , other quantity of oxidizer, other reaction time, Product distribution Mazzanti, Germana; Maccagnani, Gaetano; Bonini, Bianca F.; Pedrini, Paola; Zwanenburg, Binne; Gazzetta Chimica Italiana; vol. 110; nb. 2/3; (1980); p. 163 - 166 View in Reaxys S

O N

S O

Rx-ID: 3932183 View in Reaxys 618/827 Yield

Conditions & References

20 %, 13 %, in benzene, Time= 96h, Ambient temperature, Product distribution, Mechanism 7.5 %, 7.5 Mazzanti, Germana; Maccagnani, Gaetano; Bonini, Bianca F.; Pedrini, Paola; Zwanenburg, Binne; Gazzetta Chimica Ital% iana; vol. 110; nb. 2/3; (1980); p. 163 - 166 View in Reaxys

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S N O

N H

S N

Rx-ID: 3932199 View in Reaxys 619/827 Yield

Conditions & References

13 %, 17 %

in benzene, Time= 168h, Ambient temperature, Further byproducts given Mazzanti, Germana; Maccagnani, Gaetano; Bonini, Bianca F.; Pedrini, Paola; Zwanenburg, Binne; Gazzetta Chimica Italiana; vol. 110; nb. 2/3; (1980); p. 163 - 166 View in Reaxys

N O N

N N

Rx-ID: 3935864 View in Reaxys 620/827 Yield

Conditions & References

1.0 %, 0.5 %, 97 %

With tetrabutylammonium perchlorate in N,N-dimethyl-formamide, T= 20 - 23 °C , Pt-cathode Triebe, F. M.; Hawley, M. Dale; McDonald, Richard N.; Journal of the Chemical Society, Chemical Communications; nb. 12; (1980); p. 574 - 575 View in Reaxys S

N O

O N H

thiofluorenone dimer (51percent) O

S N

Rx-ID: 6731752 View in Reaxys 621/827

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Yield

Conditions & References

13 %, 17 %

in benzene, Time= 168h, Ambient temperature, Product distribution, Mechanism Mazzanti, Germana; Maccagnani, Gaetano; Bonini, Bianca F.; Pedrini, Paola; Zwanenburg, Binne; Gazzetta Chimica Italiana; vol. 110; nb. 2/3; (1980); p. 163 - 166 View in Reaxys O

5β -cyclopentadienyl-(triphenylphosphino)-cobaltafluorene

Rx-ID: 6871118 View in Reaxys 622/827 Yield

Conditions & References

43 %

in benzene, Time= 5h, T= 150 °C , p= 33097.9Torr Wakatsuki, Yasuo; Nomura, Okio; Tone, Hiroatsu; Yamazaki, Hiroshi; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 1344 - 1349 View in Reaxys O

fluorene-Cr(CO)3

Rx-ID: 6871130 View in Reaxys 623/827 Yield

Conditions & References

45 %

With KO2 in dimethyl sulfoxide Top, Siden; Jaouen, Gerard; McGlinchey, Michael; Journal of the Chemical Society, Chemical Communications; nb. 14; (1980); p. 643 - 644 View in Reaxys

9-bromo-anthrone O

Rx-ID: 20554691 View in Reaxys 624/827 Yield

Conditions & References Reaction Steps: 2 1: 81 percent / BuLi / diethyl ether / 3 h / -76 °C 2: 170 °C With n-butyllithium in diethyl ether Jemison, Robert W.; Ollis, W. David; Sutherland, Ian O.; Tannock, James; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1462 - 1472 View in Reaxys Reaction Steps: 2 1: 81 percent / BuLi / diethyl ether / 3 h / -76 °C

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2: 1.) D2O / 1.) CDCl3, 2.) 170 deg C With n-butyllithium, water-d2 in diethyl ether Jemison, Robert W.; Ollis, W. David; Sutherland, Ian O.; Tannock, James; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1462 - 1472 View in Reaxys O

HN O

O N

N NH

Rx-ID: 25273404 View in Reaxys 625/827 Yield

Conditions & References 3.B : B. B. Preparation of 2,7-Di(5-tetrazolyl)fluorenone A mixture of 2,7-dicyanofluorenone (4.6 g) sodium azide (2.62 g) and ammonium chloride (2.6 g) in dimethylformamide (25 ml) was stirred and heated to 100°C for 10 hours. The mixture was cooled, treated with an excess of 2N hydrochloric acid and the solid was filtered, washed with water, dried in vacuo and recrystallized from a mixture of dimethylformamide and water. This product was dissolved in an excess of 0.1N aqueous sodium hydroxide, the solution was filtered and acidified with hydrochloric acid. The resulting precipitate was filtered, washed with water and dried in vacuo to give 2,7-di-(5-tetrazolyl)fluorenone, m.p. above 300°C. With hydrogenchloride, ammonium chloride in N-methyl-acetamide, sodium hydroxide Patent; Burroughs Wellcome Co.; US3939173; (1976); (A) English View in Reaxys

(v3)

(v3) (v3)

(v6)

(v3)

O (v3)

(v3)

Rx-ID: 26174037 View in Reaxys 626/827 Yield

Conditions & References at 225 °C Atkinson, E. R.; Levins, P. L.; Dickelman, T. E.; Chemistry and Industry (London, United Kingdom); (1964); p. 934 ; (from Gmelin) View in Reaxys at 225 °C vol. Cr: Org.Verb.; 1.1.2.1.5.2, page 66 - 70 ; (from Gmelin) View in Reaxys

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H2S

water

Cl 2Hg

Rx-ID: 8426797 View in Reaxys 627/827 Yield

Conditions & References Schoenberg,A. et al.; Chemische Berichte; vol. 95; (1962); p. 1910 - 1916 View in Reaxys

O O N

Rx-ID: 4312707 View in Reaxys 628/827 Yield

Conditions & References With hydrogenchloride Masaki,M.; Ohta,M.; Bulletin of the Chemical Society of Japan; vol. 34; nb. 9; (1961); p. 1257 - 1260 View in Reaxys

O N+

O– Cl O OO

Rx-ID: 22621881 View in Reaxys 629/827 Yield

Conditions & References Reaction Steps: 2 1: aq. NaOH, Py 2: aq. HCl With pyridine, hydrogenchloride, sodium hydroxide Masaki,M.; Ohta,M.; Bulletin of the Chemical Society of Japan; vol. 34; nb. 9; (1961); p. 1257 - 1260 View in Reaxys

O O

Cl (v4)

Rx-ID: 6674346 View in Reaxys 630/827 Yield

Conditions & References Copeland et al.; Journal of the Chemical Society; (1960); p. 3230,3233 View in Reaxys

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air oxygen

aqueous NaOH

Rx-ID: 6671919 View in Reaxys 631/827 Yield

Conditions & References T= 95 °C Kinoshita et al.; Nippon Kagaku Zasshi; vol. 80; (1959); p. 206; ; (1961); p. 4449 View in Reaxys Cl

Cl Al

solvent

Rx-ID: 7155612 View in Reaxys 632/827 Yield

Conditions & References H/D-Isotopeneffekt Denney; Klemchuk; Journal of the American Chemical Society; vol. 80; (1958); p. 6014 View in Reaxys Cl

O Cl Cl

Sn ClCl

solvent

Rx-ID: 7155613 View in Reaxys 633/827 Yield

Conditions & References H/D-Isotopeneffekt Denney; Klemchuk; Journal of the American Chemical Society; vol. 80; (1958); p. 6014 View in Reaxys Cl

ZnCl2

solvent

Rx-ID: 7155617 View in Reaxys 634/827 Yield

Conditions & References H/D-Isotopeneffekt Denney; Klemchuk; Journal of the American Chemical Society; vol. 80; (1958); p. 6014 View in Reaxys

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OH O OH HO

P OH O 2H

Rx-ID: 7978086 View in Reaxys 635/827 Yield

Conditions & References H/D-Isotopeneffekt Denney; Klemchuk; Journal of the American Chemical Society; vol. 80; (1958); p. 3285,3287 View in Reaxys O

OH O OH HO

S OO 2H

Rx-ID: 7978087 View in Reaxys 636/827 Yield

Conditions & References H/D-Isotopeneffekt Denney; Klemchuk; Journal of the American Chemical Society; vol. 80; (1958); p. 3285,3287 View in Reaxys O

OH O

Rx-ID: 7978088 View in Reaxys 637/827 Yield

Conditions & References H/D-Isotopeneffekt Denney; Klemchuk; Journal of the American Chemical Society; vol. 80; (1958); p. 3285,3287 View in Reaxys O

O O

(+-)-fluoren-9-yl-fluoren-9-ylidene-succinic acid-anhydride

Rx-ID: 8167374 View in Reaxys 638/827 Yield

Conditions & References With ozone, ethyl acetate, anschliessendes Hydrieren an Palladium Goldschmidt et al.; Justus Liebigs Annalen der Chemie; vol. 604; (1957); p. 121,126 View in Reaxys O

N+ –O

Rx-ID: 131970 View in Reaxys 639/827

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Yield

Conditions & References With tetrachloromethane, Aufbewahren im Tageslicht Greenhow et al.; Journal of the Chemical Society; (1954); p. 3116,3119 View in Reaxys NH 2

Cl O

Rx-ID: 172661 View in Reaxys 640/827 Yield

Conditions & References With diethyl ether, Erhitzen des Reaktionsprodukts mit aethanol. Natriumaethylat und anschliessend mit wss. H2SO4 Bachmann et al.; Journal of the American Chemical Society; vol. 76; (1954); p. 5554 View in Reaxys -1

F (v4)

B FF

O N

S OO

N+

Rx-ID: 7978105 View in Reaxys 641/827 Yield

Conditions & References T= 25 - 55 °C , Kinetics De Tar; Relyea; Journal of the American Chemical Society; vol. 76; (1954); p. 1680,1683 View in Reaxys O

F F F

Rx-ID: 22043032 View in Reaxys 642/827 Yield

Conditions & References Reaction Steps: 3 1: Raney nickel; dioxane / 180 °C / 14710.2 Torr / Hydrogenation 2: aqueous HCl; sodium acetate; H2O / Diazotization 3: H2SO4 With 1,4-dioxane, hydrogenchloride, sulfuric acid, water, sodium acetate, nickel Pettit; Tatlow; Journal of the Chemical Society; (1954); p. 1071,1073 View in Reaxys

O N O F NH 2

F F

Rx-ID: 22046442 View in Reaxys 643/827 Yield

Conditions & References Reaction Steps: 4 1: acetic acid; sulfuric acid; aqueous sodium nitrite solution / Reagens 4: wss. Phosphinsaeure

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2: Raney nickel; dioxane / 180 °C / 14710.2 Torr / Hydrogenation 3: aqueous HCl; sodium acetate; H2O / Diazotization 4: H2SO4 With 1,4-dioxane, hydrogenchloride, sulfuric acid, water, sodium acetate, nickel, acetic acid, sodium nitrite Pettit; Tatlow; Journal of the Chemical Society; (1954); p. 1071,1073 View in Reaxys O H 2N F F F

Rx-ID: 22071304 View in Reaxys 644/827 Yield

Conditions & References Reaction Steps: 2 1: aqueous HCl; sodium acetate; H2O / Diazotization 2: H2SO4 With hydrogenchloride, sulfuric acid, water, sodium acetate Pettit; Tatlow; Journal of the Chemical Society; (1954); p. 1071,1073 View in Reaxys N N

Rx-ID: 294645 View in Reaxys 645/827 Yield

Conditions & References bei laengerem Aufbewahren oder beim Erhitzen ueber den Schmelzpunkt Arcus; Mesley; Journal of the Chemical Society; (1953); p. 178,180 View in Reaxys

N+

O– Cl O OO

aq.-ethanolic NaOH-solution

air

Rx-ID: 7978092 View in Reaxys 646/827 Yield

Conditions & References Kroehnke; Chemische Berichte; vol. 83; (1951); p. 253,257 View in Reaxys

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N O N

Rx-ID: 848912 View in Reaxys 647/827 Yield

Conditions & References Schoenberg; Awad; Nature (London, United Kingdom); vol. 166; (1950); p. 788 View in Reaxys OH

oxygen

Rx-ID: 6675442 View in Reaxys 648/827 Yield

Conditions & References T= 115 °C , Quecksilberdampflampe.Irradiation Hock et al.; Chemische Berichte; vol. 83; (1950); p. 227,234 View in Reaxys O O

Rx-ID: 103273 View in Reaxys 649/827 Yield

Conditions & References T= 0 °C Roitt; Waters; Journal of the Chemical Society; (1949); p. 3060 View in Reaxys

Rx-ID: 329097 View in Reaxys 650/827 Yield

Conditions & References T= 300 °C Wittig; Doeser; Lorenz; Justus Liebigs Annalen der Chemie; vol. 562; (1949); p. 192,202 View in Reaxys

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Rx-ID: 350085 View in Reaxys 651/827 Yield

Conditions & References T= 300 °C Wittig; Doeser; Lorenz; Justus Liebigs Annalen der Chemie; vol. 562; (1949); p. 192,202 View in Reaxys

Rx-ID: 369142 View in Reaxys 652/827 Yield

Conditions & References T= 270 - 320 °C Wittig; Doeser; Lorenz; Justus Liebigs Annalen der Chemie; vol. 562; (1949); p. 192,202 View in Reaxys

Rx-ID: 369280 View in Reaxys 653/827 Yield

Conditions & References T= 260 - 300 °C Wittig; Doeser; Lorenz; Justus Liebigs Annalen der Chemie; vol. 562; (1949); p. 192,202 View in Reaxys O –

Pb4+

Rx-ID: 638982 View in Reaxys 654/827 Yield

Conditions & References Cavill; Robertson; Whalley; Journal of the Chemical Society; (1949); p. 1567,1570 View in Reaxys

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OH O –O

Pb4+

Rx-ID: 641799 View in Reaxys 655/827 Yield

Conditions & References Criegee; Schnorrenberg; Becke; Justus Liebigs Annalen der Chemie; vol. 565; (1949); p. 7,17 View in Reaxys O

Cl (v4)

Rx-ID: 6671914 View in Reaxys 656/827 Yield

Conditions & References Cavill; Robertson; Whalley; Journal of the Chemical Society; (1949); p. 1567,1570 View in Reaxys

O O

ethanolic KOH

Rx-ID: 6871128 View in Reaxys 657/827 Yield

Conditions & References Einleiten von Sauerstoff Rigaudy; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 228; (1949); p. 253,255 View in Reaxys

O O

CrO3

Rx-ID: 7978093 View in Reaxys 658/827 Yield

Conditions & References Tucker; Whalley; Journal of the Chemical Society; (1949); p. 50,53 View in Reaxys

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O O

Na2Cr2O7 HO

Rx-ID: 8259427 View in Reaxys 659/827 Yield

Conditions & References Tucker; Whalley; Journal of the Chemical Society; (1949); p. 50,53 View in Reaxys OH O O

bis-<9-hydroperoxy-fluorenyl-(9)>-peroxide

Rx-ID: 8269822 View in Reaxys 660/827 Yield

Conditions & References T= 85 - 90 °C , p= 0.01Torr Criegee; Schnorrenberg; Becke; Justus Liebigs Annalen der Chemie; vol. 565; (1949); p. 7,17 View in Reaxys O

Rx-ID: 554194 View in Reaxys 661/827 Yield

Conditions & References With nickel, toluene Kleiderer; Kornfeld; Journal of Organic Chemistry; vol. 13; (1948); p. 455,457 View in Reaxys O

aqueous KOCl solution

Rx-ID: 6671918 View in Reaxys 662/827 Yield

Conditions & References Schiessler; Eldred; Journal of the American Chemical Society; vol. 70; (1948); p. 3958 View in Reaxys

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OH Al3+ 3

oxygen –O

Rx-ID: 6871134 View in Reaxys 663/827 Yield

Conditions & References T= 25 - 30 °C , weitere Verb.: Kupfer(II)-oleat Baker; Stanonis; Journal of the American Chemical Society; vol. 70; (1948); p. 2594 View in Reaxys O

Raney nickel

Rx-ID: 6871136 View in Reaxys 664/827 Yield

Conditions & References Kleiderer; Kornfeld; Journal of Organic Chemistry; vol. 13; (1948); p. 455,457 View in Reaxys

O H

Rx-ID: 598615 View in Reaxys 665/827 Yield

Conditions & References Gluehlampenlicht.Irradiation Wittig; Pieper; Justus Liebigs Annalen der Chemie; vol. 558; (1947); p. 218,227 View in Reaxys

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O H

oxygen

light

Rx-ID: 7155610 View in Reaxys 666/827 Yield

Conditions & References Wittig; Pieper; Justus Liebigs Annalen der Chemie; vol. 558; (1947); p. 218,227 View in Reaxys Cl

sunlight

Cl Cl

fluorenone-(9)-imine hydrochloride

di-<fluorenylidene-(9)>-hydrazine

Rx-ID: 7923063 View in Reaxys 667/827 Yield

Conditions & References Pinck; Hilbert; Journal of the American Chemical Society; vol. 69; (1947); p. 470 View in Reaxys

O–

Na +

Rx-ID: 271426 View in Reaxys 668/827 Yield

Conditions & References T= 20 °C Pinck; Hilbert; Journal of the American Chemical Society; vol. 68; (1946); p. 2739,2740 View in Reaxys Pinck; Hilbert; Journal of the American Chemical Society; vol. 54; (1932); p. 710,713; Journal of the American Chemical Society; vol. 68; (1946); p. 2739

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View in Reaxys N OH N

O–

Na +

Rx-ID: 856285 View in Reaxys 669/827 Yield

Conditions & References T= 60 - 70 °C Pinck; Hilbert; Journal of the American Chemical Society; vol. 68; (1946); p. 867 View in Reaxys N OH N

O–

Na +

Rx-ID: 856290 View in Reaxys 670/827 Yield

Conditions & References Pinck; Hilbert; Journal of the American Chemical Society; vol. 68; (1946); p. 867 View in Reaxys N Cl N

di-<fluorenylidene-(9)>-hydrazine

Rx-ID: 6727716 View in Reaxys 671/827 Yield

Conditions & References Pinck; Hilbert; Journal of the American Chemical Society; vol. 68; (1946); p. 867 View in Reaxys

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N NH 2 N H

H N H

di-<fluorenylidene-(9)>-hydrazine

Rx-ID: 6727717 View in Reaxys 672/827 Yield

Conditions & References Pinck; Hilbert; Journal of the American Chemical Society; vol. 68; (1946); p. 867 View in Reaxys

N N H

H N H

di-<fluorenylidene-(9)>-hydrazine

Rx-ID: 6727718 View in Reaxys 673/827 Yield

Conditions & References Pinck; Hilbert; Journal of the American Chemical Society; vol. 68; (1946); p. 867 View in Reaxys

OH H

H N H

Rx-ID: 7044537 View in Reaxys 674/827 Yield

Conditions & References T= 20 °C Pinck; Hilbert; Journal of the American Chemical Society; vol. 68; (1946); p. 2739,2740

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View in Reaxys Pinck; Hilbert; Journal of the American Chemical Society; vol. 54; (1932); p. 710,713; Journal of the American Chemical Society; vol. 68; (1946); p. 2739 View in Reaxys N H 2N

O H

O O

sodium carbonate

fluorenecarboxamide-(9)

Rx-ID: 7923062 View in Reaxys 675/827 Yield

Conditions & References Harris; Harriman; Wheeler; Journal of the American Chemical Society; vol. 68; (1946); p. 846 View in Reaxys Cl

O O

Na2Cr2O7

Rx-ID: 7978096 View in Reaxys 676/827 Yield

Conditions & References France; Tucker; Forrest; Journal of the Chemical Society; (1945); p. 7,9 View in Reaxys

O O

HO OH

Rx-ID: 743978 View in Reaxys 677/827 Yield

Conditions & References Einwirkung von Sonnenlicht Schoenberg; Mustafa; Journal of the Chemical Society; (1944); p. 67,70; Journal of the Chemical Society; (1945); p. 657,660 View in Reaxys Br

copper-powder O

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O H

Rx-ID: 5810324 View in Reaxys 678/827 Yield

Conditions & References T= 220 - 260 °C Uyeo; Okajima; Yakugaku Zasshi; vol. 64; (1944); p. 133; ; (1951); p. 2918 View in Reaxys

oxygen

O O

Rx-ID: 5956791 View in Reaxys 679/827 Yield

Conditions & References T= 400 - 500 °C Tonomura; Rikagaku Kenkyusho Iho; vol. 23; (1944); p. Chem. Tl. S. 81, 85; ; (1949); p. 7916 View in Reaxys O Br

biphenyl-carbaldehyde-(2) O

Rx-ID: 7069590 View in Reaxys 680/827 Yield

Conditions & References With iodobenzene, copper, T= 220 - 260 °C Uyeo; Okajima; Yakugaku Zasshi; vol. 64; (1944); p. 133; ; (1951); p. 2918 View in Reaxys O

biphenyl-carbaldehyde-(2)

Rx-ID: 7069591 View in Reaxys 681/827 Yield

Conditions & References With copper, T= 300 °C Uyeo; Okajima; Yakugaku Zasshi; vol. 64; (1944); p. 133; ; (1951); p. 2918 View in Reaxys

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copper-powder

Rx-ID: 7155607 View in Reaxys 682/827 Yield

Conditions & References T= 300 °C Uyeo; Okajima; Yakugaku Zasshi; vol. 64; (1944); p. 133; ; (1951); p. 2918 View in Reaxys NH 2

Cl H 2N

(v4)

Rx-ID: 7917970 View in Reaxys 683/827 Yield

Conditions & References Erhitzen des Reaktionsprodukts mit Wasser Von; Wagner; Journal of Organic Chemistry; vol. 9; (1944); p. 155,167 View in Reaxys O

H O

Rx-ID: 6671913 View in Reaxys 684/827 Yield

Conditions & References T= 230 - 240 °C Badger; Journal of the Chemical Society; (1941); p. 535,537 View in Reaxys O

Rx-ID: 271329 View in Reaxys 685/827 Yield

Conditions & References With sodium carbonate, T= 300 °C Patent; I.G. Farbenind.; FR629806; (1926) View in Reaxys Patent; Gen. Aniline Works; US1803205; (1926) View in Reaxys With sodium hydroxide, copper(II) oxide, T= 240 - 250 °C Patent; Dow Chem. Co.; US2377751; (1940) View in Reaxys With sodium hydroxide, iron, T= 240 - 250 °C Patent; Dow Chem. Co.; US2377751; (1940)

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View in Reaxys O O

Rx-ID: 743356 View in Reaxys 686/827 Yield

Conditions & References laengere Einwirkung von Sonnenlicht Oliveri-Mandala; Deleo; Gazzetta Chimica Italiana; vol. 70; (1940); p. 186,189 View in Reaxys O

aqueous NaOH

Cu2O

Rx-ID: 6871125 View in Reaxys 687/827 Yield

Conditions & References T= 240 °C , im Eisen-Autoklaven Patent; Dow Chem. Co.; US2377751; (1940) View in Reaxys OH

O O

OH HO

S OO

O O

Rx-ID: 7978100 View in Reaxys 688/827 Yield

Conditions & References Wittig; Pieper; Chemische Berichte; vol. 73; (1940); p. 295 View in Reaxys OH O

O O

oxygen

Rx-ID: 8284444 View in Reaxys 689/827 Yield

Conditions & References T= 130 °C Wittig; Pieper; Chemische Berichte; vol. 73; (1940); p. 295 View in Reaxys

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O OH O

O H

O O O

Rx-ID: 275479 View in Reaxys 690/827 Yield

Conditions & References T= 200 °C , unter vermindertem Druck Schoenberg; Moubacher; Journal of the Chemical Society; (1939); p. 1430 View in Reaxys O

lead (II)-salt of/the/ 9-hydroxy-fluorene-carboxylic acid-(9)

Rx-ID: 6871132 View in Reaxys 691/827 Yield

Conditions & References Kenner; Wain; Chemische Berichte; vol. 72; (1939); p. 456,457 View in Reaxys

O O

Rx-ID: 103439 View in Reaxys 692/827 Yield

Conditions & References With chloroform Wittig; Lange; Justus Liebigs Annalen der Chemie; vol. 536; (1938); p. 266,269, 272, 278, 282 View in Reaxys

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Rx-ID: 284590 View in Reaxys 693/827 Yield

Conditions & References With tetrachloromethane, oxygen, benzaldehyde Wittig; Lange; Justus Liebigs Annalen der Chemie; vol. 536; (1938); p. 266,269, 272, 278, 282 View in Reaxys With chromic acid Graebe; v. Mantz; Justus Liebigs Annalen der Chemie; vol. 290; (1896); p. 244 View in Reaxys T= 360 - 400 °C , Leiten im Gemisch mit Luft ueber V2O5 Patent; Selden Co.; US1868531; (1928) View in Reaxys bei der Ozonspaltung Klinger; Lonnes; Chemische Berichte; vol. 29; (1896); p. 2159 View in Reaxys Graebe; v. Mantz; Justus Liebigs Annalen der Chemie; vol. 290; (1896); p. 244 View in Reaxys Fischer,H.; Mueller; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 148; (1925); p. 175 View in Reaxys O

1.2.3.4.4a.9a-hexahydro-fluorenone-(9)

Rx-ID: 6671924 View in Reaxys 694/827 Yield

Conditions & References With selenium, T= 280 - 310 °C Fujise; Chemische Berichte; vol. 71; (1938); p. 2461,2468 View in Reaxys

alkaline aqueous KMnO4-solution

O O

OH OH

Rx-ID: 6683051 View in Reaxys 695/827

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Yield

Conditions & References Randall; Benger; Groocock; Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences; vol. 165; (1938); p. 439; Chem. Zentralbl.; vol. 110; nb. I; (1939); p. 911 View in Reaxys Bone et al.; Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences; vol. 148; (1935); p. 492,497 View in Reaxys O

selenium H

Rx-ID: 7978099 View in Reaxys 696/827 Yield

Conditions & References T= 280 - 310 °C Fujise; Chemische Berichte; vol. 71; (1938); p. 2461,2468 View in Reaxys

Rx-ID: 305862 View in Reaxys 697/827 Yield

Conditions & References Aufbewahren France; Maitland; Tucker; Journal of the Chemical Society; (1937); p. 1739,1741 View in Reaxys O

biphenyl-tetracarboxylic acid-(2.6.2'.6')

Rx-ID: 6871121 View in Reaxys 698/827 Yield

Conditions & References Vollmann et al.; Justus Liebigs Annalen der Chemie; vol. 531; (1937); p. 1,68, 150 View in Reaxys With copper (I) acetate Vollmann et al.; Justus Liebigs Annalen der Chemie; vol. 531; (1937); p. 1,68, 150 View in Reaxys With soda lime Vollmann et al.; Justus Liebigs Annalen der Chemie; vol. 531; (1937); p. 1,68, 150 View in Reaxys O

fluorene-carboxylic acid-(9(

Rx-ID: 6871129 View in Reaxys 699/827

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Yield

Conditions & References With chromium(VI) oxide, acetic acid Jeanes; Adams; Journal of the American Chemical Society; vol. 59; (1937); p. 2608,2619 View in Reaxys O

O O

chromium (VI)-oxide

Rx-ID: 7155606 View in Reaxys 700/827 Yield

Conditions & References Jeanes; Adams; Journal of the American Chemical Society; vol. 59; (1937); p. 2608,2619 View in Reaxys O

Cl O

oxygen Cl

Rx-ID: 7155618 View in Reaxys 701/827 Yield

Conditions & References Wieland; Probst; Justus Liebigs Annalen der Chemie; vol. 530; (1937); p. 274,289 View in Reaxys O O O

oxygen HO

Rx-ID: 7155619 View in Reaxys 702/827 Yield

Conditions & References Wieland; Probst; Justus Liebigs Annalen der Chemie; vol. 530; (1937); p. 274,289 View in Reaxys O

air

Rx-ID: 7155620 View in Reaxys 703/827 Yield

Conditions & References Jeanes; Adams; Journal of the American Chemical Society; vol. 59; (1937); p. 2608,2619 View in Reaxys

O O

Na2Cr2O7

Rx-ID: 7978095 View in Reaxys 704/827

310/345

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Yield

Conditions & References France; Maitland; Tucker; Journal of the Chemical Society; (1937); p. 1739,1741 View in Reaxys O

Rx-ID: 22348513 View in Reaxys 705/827 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether / Einleiten von Kohlendioxyd in das Reaktionsgemisch 2: aq. NaOH solution; air With sodium hydroxide, air, diethyl ether Jeanes; Adams; Journal of the American Chemical Society; vol. 59; (1937); p. 2608,2619 View in Reaxys O–

Na +

HO OH

Rx-ID: 628888 View in Reaxys 706/827 Yield

Conditions & References Mechanismus.Hydrolysis Bachmann; Journal of the American Chemical Society; vol. 55; (1933); p. 1185,2827, 2829 View in Reaxys Bent; Irwin; Journal of the American Chemical Society; vol. 58; (1936); p. 2072 View in Reaxys O N

2'-nitro-biphenyl-carboxylic acid-(2)

Rx-ID: 6871116 View in Reaxys 707/827 Yield

Conditions & References With copper oxide-chromium oxide, T= 210 - 240 °C Finzi; Bellavita; Gazzetta Chimica Italiana; vol. 66; (1936); p. 421,428 View in Reaxys

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O N

copper oxide-chromium oxide HO

Rx-ID: 6871123 View in Reaxys 708/827 Yield

Conditions & References T= 210 - 240 °C Finzi; Bellavita; Gazzetta Chimica Italiana; vol. 66; (1936); p. 421,428 View in Reaxys

O–

Na +

Rx-ID: 847019 View in Reaxys 709/827 Yield

Conditions & References unter Luftausschluss Bachmann; Journal of the American Chemical Society; vol. 55; (1933); p. 355,358 View in Reaxys

HO O

chromium (VI)-oxide

Rx-ID: 7364611 View in Reaxys 710/827 Yield

Conditions & References Erhitzen des Reaktionsprodukts unter vermindertem Druck auf 300grad v. Braun; Manz; Justus Liebigs Annalen der Chemie; vol. 496; (1932); p. 170,186 View in Reaxys

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O H

CrO3

O O

Rx-ID: 7446977 View in Reaxys 711/827 Yield

Conditions & References Koelsch; Journal of the American Chemical Society; vol. 54; (1932); p. 4744,4747 View in Reaxys O

Rx-ID: 186146 View in Reaxys 712/827 Yield

Conditions & References T= 360 °C Huntress; Hershberg; Cliff; Journal of the American Chemical Society; vol. 53; (1931); p. 2720,2724 View in Reaxys

Rx-ID: 312124 View in Reaxys 713/827 Yield

Conditions & References T= 360 °C Huntress; Hershberg; Cliff; Journal of the American Chemical Society; vol. 53; (1931); p. 2720,2724 View in Reaxys With calcium carbonate, calcium oxide Kerp; Chemische Berichte; vol. 29; (1896); p. 230 View in Reaxys Fittig; Ostermayer; Justus Liebigs Annalen der Chemie; vol. 166; (1873); p. 363 View in Reaxys With calcium oxide Fittig; Schmitz; Justus Liebigs Annalen der Chemie; vol. 193; (1878); p. 117 View in Reaxys T= 360 °C Huntress; Hershberg; Cliff; Journal of the American Chemical Society; vol. 53; (1931); p. 2720,2724

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View in Reaxys Reaction Steps: 2 1: concentrated sulfuric acid / 150 °C 2: beim Gluehen With sulfuric acid Graebe; Mensching; Chemische Berichte; vol. 13; (1880); p. 1303 View in Reaxys Graebe; Aubin; Chemische Berichte; vol. 20; (1887); p. 845; Justus Liebigs Annalen der Chemie; vol. 247; (1888); p. 275 View in Reaxys O

O HO

Rx-ID: 384174 View in Reaxys 714/827 Yield

Conditions & References T= 360 °C Huntress; Hershberg; Cliff; Journal of the American Chemical Society; vol. 53; (1931); p. 2720,2724 View in Reaxys beim Gluehen Graebe; Mensching; Chemische Berichte; vol. 13; (1880); p. 1303 View in Reaxys Graebe; Aubin; Chemische Berichte; vol. 20; (1887); p. 845; Justus Liebigs Annalen der Chemie; vol. 247; (1888); p. 275 View in Reaxys

OH Cl

Rx-ID: 713150 View in Reaxys 715/827 Yield

Conditions & References Bergmann; Schuchardt; Justus Liebigs Annalen der Chemie; vol. 487; (1931); p. 225,262 View in Reaxys

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O N O

S O

N Cl

S S Cl

S N O

N O

Rx-ID: 61252 View in Reaxys 716/827 Yield

Conditions & References Erhitzen auf Siedetemperatur Schoenberg; Stolpp; Justus Liebigs Annalen der Chemie; vol. 483; (1930); p. 90,105; Chemische Berichte; vol. 63; (1930); p. 3102,3111 View in Reaxys

O Cl

Cl O

Rx-ID: 211557 View in Reaxys 717/827 Yield

Conditions & References Ozonolyse Kliegl; Weng; Wiest; Chemische Berichte; vol. 63; (1930); p. 1262,1268 View in Reaxys

O N

O O

O Cl

Rx-ID: 424981 View in Reaxys 718/827 Yield

Conditions & References With water Schoenberg; Stolpp; Chemische Berichte; vol. 63; (1930); p. 3102,3116 View in Reaxys

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O N

O N S

O N O

Rx-ID: 526468 View in Reaxys 719/827 Yield

Conditions & References T= 200 °C , Erhitzen im Hochvakuum Schoenberg; Stolpp; Justus Liebigs Annalen der Chemie; vol. 483; (1930); p. 90,105; Chemische Berichte; vol. 63; (1930); p. 3102,3111 View in Reaxys O N O

S O

S S

S N O

N O

Rx-ID: 528994 View in Reaxys 720/827 Yield

Conditions & References T= 170 °C Schoenberg; Stolpp; Justus Liebigs Annalen der Chemie; vol. 483; (1930); p. 90,105; Chemische Berichte; vol. 63; (1930); p. 3102,3111 View in Reaxys

O O

O Cl

N H

Rx-ID: 8203106 View in Reaxys 721/827 Yield

Conditions & References Schoenberg; Stolpp; Chemische Berichte; vol. 63; (1930); p. 3102,3116 View in Reaxys

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Cr2O3-H2SO4

Rx-ID: 7155608 View in Reaxys 722/827 Yield

Conditions & References T= 95 - 97 °C Courtot; Pierron; Bulletin de la Societe Chimique de France; vol. <4>45; (1929); p. 290 View in Reaxys

alcoholic alkali

Rx-ID: 7156386 View in Reaxys 723/827 Yield

Conditions & References Kliegl; Chemische Berichte; vol. 62; (1929); p. 1330; Chemische Berichte; vol. 64; (1931); p. 2422 View in Reaxys

O O

sunlight

Rx-ID: 7164658 View in Reaxys 724/827 Yield

Conditions & References Eckert; Journal fuer Praktische Chemie (Leipzig); vol. <2> 121; (1929); p. 276 View in Reaxys

O O

O OH

Cl O

Rx-ID: 61134 View in Reaxys 725/827 Yield

Conditions & References beim Ozonisieren und Erwaermen des Ozonids mit Wasser Kuhn; Levy; Chemische Berichte; vol. 61; (1928); p. 2243 View in Reaxys

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Rx-ID: 419208 View in Reaxys 726/827 Yield

Conditions & References bei der Ozonspaltung Kuhn; Winterstein; Helvetica Chimica Acta; vol. 11; (1928); p. 113; Helvetica Chimica Acta; vol. 12; (1929); p. 493 View in Reaxys OH

Cl S O

Rx-ID: 6671915 View in Reaxys 727/827 Yield

Conditions & References beim Destillieren; im Vakuum Ranedo; Leon; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 24; p. 555; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 1267 View in Reaxys Bell; Journal of the Chemical Society; (1928); p. 3248 View in Reaxys

air

vanadium containing catalysts

Rx-ID: 6671922 View in Reaxys 728/827 Yield

Conditions & References T= 350 - 500 °C Patent; Selden Co.; US1892768; (1928) View in Reaxys

air

steam

vanadium containing catalysts

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Rx-ID: 6671923 View in Reaxys 729/827 Yield

Conditions & References T= 350 - 500 °C Patent; Selden Co.; US1892768; (1928) View in Reaxys O

diphenyl-carboxylic acid-(2)-chloride

Rx-ID: 6871126 View in Reaxys 730/827 Yield

Conditions & References With aluminium trichloride, benzene Schlenk; Bergmann; Justus Liebigs Annalen der Chemie; vol. 464; (1928); p. 28 View in Reaxys Cl

Cl Al

Rx-ID: 7155604 View in Reaxys 731/827 Yield

Conditions & References Schlenk; Bergmann; Justus Liebigs Annalen der Chemie; vol. 464; (1928); p. 28 View in Reaxys

air

V2O5 upon pumice stone

steam

Rx-ID: 7155615 View in Reaxys 732/827 Yield

Conditions & References T= 360 - 400 °C Patent; Selden Co.; US1868531; (1928) View in Reaxys

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V2O5

Rx-ID: 7155616 View in Reaxys 733/827 Yield

Conditions & References T= 360 - 400 °C , Oxydation Patent; Selden Co.; US1868531; (1928) View in Reaxys OH

Cl PCl Cl Cl

Rx-ID: 6671916 View in Reaxys 734/827 Yield

Conditions & References Bachmann; Clarke; Journal of the American Chemical Society; vol. 49; (1927); p. 2093 View in Reaxys NH 2

air

H N

tetra-fluorenyl-(9)-hydrazine

Rx-ID: 7458304 View in Reaxys 735/827 Yield

Conditions & References mit Sonnenlicht oder auch mit ultravioletten Licht.Irradiation Goldschmidt; Beuschel; Justus Liebigs Annalen der Chemie; vol. 447; (1926); p. 203 View in Reaxys Goldschmidt; Reichel; Justus Liebigs Annalen der Chemie; vol. 456; (1927); p. 165 View in Reaxys

O Br N

H O

Br Br

Rx-ID: 7541961 View in Reaxys 736/827

320/345

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Yield

Conditions & References Goldschmidt; Reichel; Justus Liebigs Annalen der Chemie; vol. 456; (1927); p. 165 View in Reaxys O

O HN

tetrafluorenyl-(9)-hydrazine

Rx-ID: 7816159 View in Reaxys 737/827 Yield

Conditions & References With acetic acid Goldschmidt; Reichel; Justus Liebigs Annalen der Chemie; vol. 456; (1927); p. 165 View in Reaxys

O O

O N

H O

N O

Rx-ID: 7978089 View in Reaxys 738/827 Yield

Conditions & References Goldschmidt; Reichel; Justus Liebigs Annalen der Chemie; vol. 456; (1927); p. 165 View in Reaxys

O O

O N

O O

Rx-ID: 7978090 View in Reaxys 739/827 Yield

Conditions & References Goldschmidt; Reichel; Justus Liebigs Annalen der Chemie; vol. 456; (1927); p. 165 View in Reaxys

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OH NH 2

Rx-ID: 549605 View in Reaxys 740/827 Yield

Conditions & References Zersetzung bei laengerem Aufbewahren Kliegl; Wuensch; Weigele; Chemische Berichte; vol. 59; (1926); p. 640 View in Reaxys O

Na2CO3 Cl

Rx-ID: 6871133 View in Reaxys 741/827 Yield

Conditions & References T= 300 °C Patent; I.G. Farbenind.; FR629806; (1926) View in Reaxys Patent; Gen. Aniline Works; US1803205; (1926) View in Reaxys O

O O

Rx-ID: 347151 View in Reaxys 742/827 Yield

Conditions & References bei der Kalischmelze Eckert; Chemische Berichte; vol. 58; (1925); p. 320; Chem. Zentralbl.; vol. 95; nb. I; (1924); p. 1713 View in Reaxys O

O OH

NH 2

O HO

OH O

Rx-ID: 384653 View in Reaxys 743/827

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2018-06-21 23:31:28

Yield

Conditions & References Behandeln der Diazoloesung mit verd. Schwefelsaeure, zuletzt bei 80grad.Diazotization Sieglitz; Chemische Berichte; vol. 57; (1924); p. 317 View in Reaxys O

Rx-ID: 303491 View in Reaxys 744/827 Yield

Conditions & References Erhitzen unter Luftzutritt Wieland; Reindel; Ferrer; Chemische Berichte; vol. 55; (1922); p. 3315 View in Reaxys

H 2N

Rx-ID: 7448041 View in Reaxys 745/827 Yield

Conditions & References Reddelien; Chemische Berichte; vol. 54; (1921); p. 3130 View in Reaxys

NH 2

Rx-ID: 7916209 View in Reaxys 746/827 Yield

Conditions & References Reddelien; Chemische Berichte; vol. 54; (1921); p. 3130 View in Reaxys

O O

NH N

H 2N

Rx-ID: 8252016 View in Reaxys 747/827 Yield

Conditions & References Reddelien; Chemische Berichte; vol. 54; (1921); p. 3130

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View in Reaxys O

diluted acid

O O NH 2 O

Rx-ID: 8262508 View in Reaxys 748/827 Yield

Conditions & References Reddelien; Danilof; Chemische Berichte; vol. 54; (1921); p. 3136 View in Reaxys

O HO

Yield

Conditions & References

Rx-ID: 355158 View in Reaxys 749/827 With calcium oxide Meyer,R.; Meyer,W.; Taeger; Chemische Berichte; vol. 53; (1920); p. 2041 View in Reaxys

O HO

Yield

Conditions & References

calcium oxide

Rx-ID: 7541963 View in Reaxys 750/827 Meyer,R.; Meyer,W.; Taeger; Chemische Berichte; vol. 53; (1920); p. 2041 View in Reaxys

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O O N

H 2N

Rx-ID: 848070 View in Reaxys 751/827 Yield

Conditions & References T= 250 °C Staudinger; Miescher; Helvetica Chimica Acta; vol. 2; (1919); p. 580 View in Reaxys

O H N

H 2N

Rx-ID: 7920209 View in Reaxys 752/827 Yield

Conditions & References Staudinger; Gaule; Chemische Berichte; vol. 49; (1916); p. 1965 View in Reaxys

O H N

O N Cl

H 2N

Rx-ID: 7920210 View in Reaxys 753/827 Yield

Conditions & References Staudinger; Gaule; Chemische Berichte; vol. 49; (1916); p. 1965 View in Reaxys

O O

CrO3

Rx-ID: 7155609 View in Reaxys 754/827

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Yield

Conditions & References Wislicenus; Chemische Berichte; vol. 48; (1915); p. 622 View in Reaxys

H 2N

Rx-ID: 7918760 View in Reaxys 755/827 Yield

Conditions & References Reddelien; Chemische Berichte; vol. 47; (1914); p. 1362 View in Reaxys

H 2N

diluted mineral acid

Rx-ID: 7918761 View in Reaxys 756/827 Yield

Conditions & References Reddelien; Chemische Berichte; vol. 47; (1914); p. 1362 View in Reaxys O

O O

Rx-ID: 297907 View in Reaxys 757/827 Yield

Conditions & References beim Erhitzen ueber den Schmelzpunkt Wieland; Reisenegger; Justus Liebigs Annalen der Chemie; vol. 401; (1913); p. 247 View in Reaxys O

diphenylenacetate_of sodium

Rx-ID: 6871127 View in Reaxys 758/827 Yield

Conditions & References With water, oxygen Wislicenus; Ruthing; Chemische Berichte; vol. 46; (1913); p. 2770 View in Reaxys

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potassium compound of 9-isonitro-fluorene

Rx-ID: 6871135 View in Reaxys 759/827 Yield

Conditions & References With potassium permanganate Nametkin; Posdnjakowa; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 45; (1913); p. 1422; Chem. Zentralbl.; vol. 85; nb. I; (1914); p. 757 View in Reaxys OH

H N

nitrogen H

N O

Rx-ID: 7083100 View in Reaxys 760/827 Yield

Conditions & References beim Erhitzen auf den Schmelzpunkt Angeli; Alessandri; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 22 I; (1913); p. 744 View in Reaxys NH 2

O H

O O

Rx-ID: 7541962 View in Reaxys 761/827 Yield

Conditions & References Stolle; Muenzel; Wolf; Chemische Berichte; vol. 46; (1913); p. 2348 View in Reaxys

Rx-ID: 312125 View in Reaxys 762/827 Yield

Conditions & References With calcium oxide, durch Destillation Kerp; Chemische Berichte; vol. 29; (1896); p. 230 View in Reaxys Fittig; Ostermayer; Justus Liebigs Annalen der Chemie; vol. 166; (1873); p. 363 View in Reaxys Pummerer; Chemische Berichte; vol. 45; (1912); p. 294 View in Reaxys Stobbe; Chemische Berichte; vol. 44; (1911); p. 1481 View in Reaxys

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Fittig; Schmitz; Justus Liebigs Annalen der Chemie; vol. 193; (1878); p. 117 View in Reaxys

calcium oxide HO

Rx-ID: 7164776 View in Reaxys 763/827 Yield

Conditions & References Kerp; Chemische Berichte; vol. 29; (1896); p. 230 View in Reaxys Fittig; Ostermayer; Justus Liebigs Annalen der Chemie; vol. 166; (1873); p. 363 View in Reaxys Stobbe; Chemische Berichte; vol. 44; (1911); p. 1481 View in Reaxys Fittig; Schmitz; Justus Liebigs Annalen der Chemie; vol. 193; (1878); p. 117 View in Reaxys Pummerer; Chemische Berichte; vol. 45; (1912); p. 295 View in Reaxys

burnt/baked lime/chalk/ HO

pseudodiphenylene ketone

Rx-ID: 7457461 View in Reaxys 764/827 Yield

Conditions & References bei der Destillation Kerp; Chemische Berichte; vol. 29; (1896); p. 230 View in Reaxys Fittig; Ostermayer; Justus Liebigs Annalen der Chemie; vol. 166; (1873); p. 363 View in Reaxys Pummerer; Chemische Berichte; vol. 45; (1912); p. 294 View in Reaxys Fittig; Schmitz; Justus Liebigs Annalen der Chemie; vol. 193; (1878); p. 117 View in Reaxys

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ZnCl2

Cl 2Zn

Rx-ID: 8428253 View in Reaxys 765/827 Yield

Conditions & References Reddelien; Justus Liebigs Annalen der Chemie; vol. 388; (1912); p. 186; Chemische Berichte; vol. 46; (1913); p. 2716 View in Reaxys O

ZnCl2

water

Cl 2Zn

Rx-ID: 8428254 View in Reaxys 766/827 Yield

Conditions & References Reddelien; Justus Liebigs Annalen der Chemie; vol. 388; (1912); p. 186; Chemische Berichte; vol. 46; (1913); p. 2716 View in Reaxys O O

natrium carbonate containing solution

potassium permanganate

Rx-ID: 5455785 View in Reaxys 767/827 Yield

Conditions & References Stobbe; Justus Liebigs Annalen der Chemie; vol. 380; (1911); p. 126 View in Reaxys

O OH

potassium permanganate

natrium carbonate

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Rx-ID: 5455786 View in Reaxys 768/827 Yield

Conditions & References Stobbe; Justus Liebigs Annalen der Chemie; vol. 380; (1911); p. 126 View in Reaxys

Rx-ID: 171320 View in Reaxys 769/827 Yield

Conditions & References Schmidt,J.; Wagner; Chemische Berichte; vol. 43; (1910); p. 1800; Justus Liebigs Annalen der Chemie; vol. 387; (1912); p. 159 View in Reaxys Cl

Rx-ID: 189723 View in Reaxys 770/827 Yield

Conditions & References Schmidt,J.; Wagner; Chemische Berichte; vol. 43; (1910); p. 1800; Justus Liebigs Annalen der Chemie; vol. 387; (1912); p. 159 View in Reaxys Cl

H O

Rx-ID: 6871117 View in Reaxys 771/827 Yield

Conditions & References Schmidt,J.; Wagner; Chemische Berichte; vol. 43; (1910); p. 1800; Justus Liebigs Annalen der Chemie; vol. 387; (1912); p. 159 View in Reaxys N

O O

KOH-solution

Rx-ID: 6871131 View in Reaxys 772/827 Yield

Conditions & References Wislicenus; Russ; Chemische Berichte; vol. 43; (1910); p. 2729 View in Reaxys

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O O

potassium permanganate

Rx-ID: 7155611 View in Reaxys 773/827 Yield

Conditions & References Wislicenus; Russ; Chemische Berichte; vol. 43; (1910); p. 2729 View in Reaxys NH

O H H

H N

H O

Rx-ID: 7441455 View in Reaxys 774/827 Yield

Conditions & References Kliegl; Chemische Berichte; vol. 43; (1910); p. 2492 View in Reaxys

diluted mineral acid

H 2N

Rx-ID: 7917233 View in Reaxys 775/827 Yield

Conditions & References Reddelien; Chemische Berichte; vol. 43; (1910); p. 2478; Justus Liebigs Annalen der Chemie; vol. 388; (1912); p. 185 View in Reaxys N HO

O O

alkali

Rx-ID: 7978091 View in Reaxys 776/827 Yield

Conditions & References Wislicenus; Russ; Chemische Berichte; vol. 43; (1910); p. 2729 View in Reaxys

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O O H

H O

Cl OO

Rx-ID: 7978097 View in Reaxys 777/827 Yield

Conditions & References Hofmann; Metzler; Lecher; Chemische Berichte; vol. 43; (1910); p. 180 View in Reaxys O

Rx-ID: 368747 View in Reaxys 778/827 Yield

Conditions & References beim Erhitzen ueber den Schmelzpunkt Wislicenus; Waldmueller; Chemische Berichte; vol. 41; (1908); p. 3338 View in Reaxys beim Erhitzen ueber den Schmelzpunkt Wislicenus; Waldmueller; Chemische Berichte; vol. 41; (1908); p. 3338 View in Reaxys O O Br

Rx-ID: 481685 View in Reaxys 779/827 Yield

Conditions & References beim Erhitzen ueber den Schmelzpunkt Wislicenus; Waldmueller; Chemische Berichte; vol. 41; (1908); p. 3338 View in Reaxys O

9-isonitro-fluorene potassium

Rx-ID: 6871119 View in Reaxys 780/827 Yield

Conditions & References With air, ethanol Wislicenus; Waldmueller; Chemische Berichte; vol. 41; (1908); p. 3338 View in Reaxys

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9-isonitro-fluorene

Rx-ID: 6871120 View in Reaxys 781/827 Yield

Conditions & References beim Erhitzen ueber den Schmelzpunkt Wislicenus; Waldmueller; Chemische Berichte; vol. 41; (1908); p. 3338 View in Reaxys O

OH N

potassium salt

air

KNO2

Rx-ID: 7454944 View in Reaxys 782/827 Yield

Conditions & References Wislicenus; Waldmueller; Chemische Berichte; vol. 41; (1908); p. 3338 View in Reaxys O

OH N

potassium salt

air

KNO2

Rx-ID: 7454945 View in Reaxys 783/827 Yield

Conditions & References Wislicenus; Waldmueller; Chemische Berichte; vol. 41; (1908); p. 3338 View in Reaxys O

OH N

nitrogen oxides

Rx-ID: 7456098 View in Reaxys 784/827 Yield

Conditions & References beim Erhitzen ueber den Schmelzpunkt Wislicenus; Waldmueller; Chemische Berichte; vol. 41; (1908); p. 3338 View in Reaxys

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O O Br

O Br

nitrogen oxides

Rx-ID: 8282404 View in Reaxys 785/827 Yield

Conditions & References beim Erhitzen auf den Schmelzpunkt Wislicenus; Waldmueller; Chemische Berichte; vol. 41; (1908); p. 3338 View in Reaxys O

OH N

Rx-ID: 22087862 View in Reaxys 786/827 Yield

Conditions & References Reaction Steps: 2 1: alcohol 2: beim Erhitzen ueber den Schmelzpunkt With ethanol Wislicenus; Waldmueller; Chemische Berichte; vol. 41; (1908); p. 3338 View in Reaxys

air oxygen

Rx-ID: 7444834 View in Reaxys 787/827 Yield

Conditions & References unter intermediaerer Bildung eines Ozonids Daufresne; Bulletin de la Societe Chimique de France; vol. <4> 1; (1907); p. 1236 View in Reaxys

Rx-ID: 284591 View in Reaxys 788/827 Yield

Conditions & References With acetic acid Hantzsch; Glover; Chemische Berichte; vol. 39; (1906); p. 4169; Chemische Berichte; vol. 40; (1907); p. 4346 View in Reaxys

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Rx-ID: 672618 View in Reaxys 789/827 Yield

Conditions & References With oxygen Staudinger; Chemische Berichte; vol. 39; (1906); p. 3065 View in Reaxys

O O

Rx-ID: 672621 View in Reaxys 790/827 Yield

Conditions & References With diethyl ether, zinc(II) chloride, bei der Einw. von Luft; Behandeln mit Petrolaether Staudinger; Chemische Berichte; vol. 39; (1906); p. 3065 View in Reaxys

O O

sunlight

Rx-ID: 7155614 View in Reaxys 791/827 Yield

Conditions & References Hantzsch; Glover; Chemische Berichte; vol. 39; (1906); p. 4169; Chemische Berichte; vol. 40; (1907); p. 4346 View in Reaxys

Br O

chromic acid

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O Br O

Rx-ID: 7987731 View in Reaxys 792/827 Yield

Conditions & References 9-<β.β-dibromo-β-phenyl-propylidene>-fluorene Thiele; Henle; Justus Liebigs Annalen der Chemie; vol. 347; (1906); p. 304 View in Reaxys

O O

Rx-ID: 640506 View in Reaxys 793/827 Yield

Conditions & References Smedley; Journal of the Chemical Society; vol. 87; (1905); p. 1251 View in Reaxys

O O

mineral acid

Rx-ID: 7978094 View in Reaxys 794/827 Yield

Conditions & References Smedley; Journal of the Chemical Society; vol. 87; (1905); p. 1251 View in Reaxys O

O O H

OH N

Rx-ID: 8213904 View in Reaxys 795/827 Yield

Conditions & References Schmidt,J.; Bauer; Chemische Berichte; vol. 38; (1905); p. 3760 View in Reaxys O

O O

OH N

air O

Rx-ID: 8213905 View in Reaxys 796/827 Yield

Conditions & References Schmidt,J.; Bauer; Chemische Berichte; vol. 38; (1905); p. 3760 View in Reaxys

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O OH HO

S OO

Rx-ID: 6671917 View in Reaxys 797/827 Yield

Conditions & References Behandeln mit Wasser Weger; Doering; Chemische Berichte; vol. 36; (1903); p. 878 View in Reaxys O

H C–

CrO3

K+

Rx-ID: 8316872 View in Reaxys 798/827 Yield

Conditions & References Fanto; Monatshefte fuer Chemie; vol. 19; (1898); p. 584 View in Reaxys Graebe; Rateanu; Justus Liebigs Annalen der Chemie; vol. 279; (1894); p. 258 View in Reaxys Fittig; Schmitz; Justus Liebigs Annalen der Chemie; vol. 193; (1878); p. 135 View in Reaxys O O

ethanolic KOH-solution

O HO

Rx-ID: 5567390 View in Reaxys 799/827 Yield

Conditions & References Klinger; Lonnes; Chemische Berichte; vol. 29; (1896); p. 734 View in Reaxys

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chromic acid mixture

Rx-ID: 7155605 View in Reaxys 800/827 Yield

Conditions & References Graebe; v. Mantz; Justus Liebigs Annalen der Chemie; vol. 290; (1896); p. 241 View in Reaxys

alcoholic potash

O O

Rx-ID: 7156387 View in Reaxys 801/827 Yield

Conditions & References Klinger; Lonnes; Chemische Berichte; vol. 29; (1896); p. 2159 View in Reaxys

chromic acid mixture

Rx-ID: 7326871 View in Reaxys 802/827 Yield

Conditions & References Klinger; Lonnes; Chemische Berichte; vol. 29; (1896); p. 2159 View in Reaxys

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dibiphenylenethene O

Rx-ID: 7326872 View in Reaxys 803/827 Yield

Conditions & References bei der Oxydation Klinger; Lonnes; Chemische Berichte; vol. 29; (1896); p. 2159 View in Reaxys

permanganate

alkali

β.β-diphenyl-β-diphenylen-ethylene

Rx-ID: 7978098 View in Reaxys 804/827 Yield

Conditions & References Klinger; Lonnes; Chemische Berichte; vol. 29; (1896); p. 734 View in Reaxys

O HO

soda lime O

β.β-diphenyl-β-diphenylen-ethylene

Rx-ID: 7981089 View in Reaxys 805/827 Yield

Conditions & References bei der Destillation Klinger; Lonnes; Chemische Berichte; vol. 29; (1896); p. 734 View in Reaxys

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chromic acid

compound C39H28O3

Rx-ID: 8272846 View in Reaxys 806/827 Yield

Conditions & References Klinger; Lonnes; Chemische Berichte; vol. 29; (1896); p. 734 View in Reaxys O

O HO

OH H 2N 2 O

Rx-ID: 186147 View in Reaxys 807/827 Yield

Conditions & References Zerfaellt bei hoeherer Temperatur Graebe; Aubin; Justus Liebigs Annalen der Chemie; vol. 247; (1888); p. 261 View in Reaxys O

CS2

Rx-ID: 6871124 View in Reaxys 808/827 Yield

Conditions & References With copper Carnelley; Dunn; Chemische Berichte; vol. 21; (1888); p. 2005 View in Reaxys O– O

O O

O– 2

Ag+

Rx-ID: 544904 View in Reaxys 809/827 Yield

Conditions & References bei trockener Destillation Bamberger; Hooker; Justus Liebigs Annalen der Chemie; vol. 229; (1885); p. 142

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View in Reaxys O

silver salt of/the/ fluorenone-dicarboxylic acid-(1.7)

Rx-ID: 6871137 View in Reaxys 810/827 Yield

Conditions & References Bamberger; Hooker; Justus Liebigs Annalen der Chemie; vol. 229; (1885); p. 142 View in Reaxys O

O O

silver salt of/the/ fluorenone-dicarboxylic acid-(1.7) HO

Rx-ID: 7367653 View in Reaxys 811/827 Yield

Conditions & References beim trockenen Erhitzen; Behandeln des Destillats mit Ammoniak und Faellen der Loesung mit Salzsaeure Bamberger; Hooker; Justus Liebigs Annalen der Chemie; vol. 229; (1885); p. 142 View in Reaxys

lead oxide O O

Rx-ID: 5802761 View in Reaxys 812/827 Yield

Conditions & References Wittenberg; Meyer,V.; Chemische Berichte; vol. 16; (1883); p. 502 View in Reaxys

burnt/baked lime/chalk/ O O

Rx-ID: 5802763 View in Reaxys 813/827 Yield

Conditions & References beim Gluehen Anschuetz; Schultz; Justus Liebigs Annalen der Chemie; vol. 196; (1879); p. 48 View in Reaxys

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barytes solution O O O

O HO

Rx-ID: 5806413 View in Reaxys 814/827 Yield

Conditions & References Anschuetz; Schultz; Justus Liebigs Annalen der Chemie; vol. 196; (1879); p. 48 View in Reaxys

KOH-solution O O O

O HO

Rx-ID: 5806414 View in Reaxys 815/827 Yield

Conditions & References Anschuetz; Schultz; Justus Liebigs Annalen der Chemie; vol. 196; (1879); p. 48 View in Reaxys O

Rx-ID: 131977 View in Reaxys 816/827 Yield

Conditions & References With chromium(VI) oxide, acetic acid, Behandeln mit Wasser; Reinigung durch Umkrystallisieren aus Benzol und Alkohol Fittig; Schmitz; Justus Liebigs Annalen der Chemie; vol. 193; (1878); p. 135 View in Reaxys O

Rx-ID: 353190 View in Reaxys 817/827

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Yield

Conditions & References beim Gluehen Fittig; Gebhard; Justus Liebigs Annalen der Chemie; vol. 193; (1878); p. 148 View in Reaxys

O HO

O O

Rx-ID: 736410 View in Reaxys 818/827 Yield

Conditions & References Anschuetz; Japp; Chemische Berichte; vol. 11; (1878); p. 213 View in Reaxys

O Cl

potassium permanganate Cl

Cl O O

Rx-ID: 5802762 View in Reaxys 819/827 Yield

Conditions & References Anschuetz; Japp; Chemische Berichte; vol. 11; (1878); p. 213 View in Reaxys

CaO O

Rx-ID: 7156859 View in Reaxys 820/827 Yield

Conditions & References beim Gluehen Fittig; Gebhard; Justus Liebigs Annalen der Chemie; vol. 193; (1878); p. 148 View in Reaxys O

Rx-ID: 22080488 View in Reaxys 821/827 Yield

Conditions & References Reaction Steps: 2 1: CrO3; acetic acid 2: beim Gluehen With chromium(VI) oxide, acetic acid Fittig; Gebhard; Justus Liebigs Annalen der Chemie; vol. 193; (1878); p. 148 View in Reaxys

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O HO

chromic acid mixture

Rx-ID: 6671921 View in Reaxys 822/827 Yield

Conditions & References Friedlaender; Chemische Berichte; vol. 10; (1877); p. 534 View in Reaxys Baeyer; Friedlaender; Chemische Berichte; vol. 10; (1877); p. 126 View in Reaxys O

Rx-ID: 7542603 View in Reaxys 823/827 Yield

Conditions & References beim Gluehen Fittig; Gebhard; Chemische Berichte; vol. 10; (1877); p. 2141; Justus Liebigs Annalen der Chemie; vol. 193; (1878); p. 142 View in Reaxys OH

chromic acid

Rx-ID: 6871122 View in Reaxys 824/827 Yield

Conditions & References Barbier; Chemische Berichte; vol. 7; (1874); p. 1649; Chemische Berichte; vol. 8; (1875); p. 829 View in Reaxys Barbier; Annales de Chimie (Cachan, France); vol. <5> 7; (1876); p. 510; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1876); p. 418 View in Reaxys OH

CaO

Rx-ID: 6671920 View in Reaxys 825/827 Yield

Conditions & References Fittig; Ostermayer; Justus Liebigs Annalen der Chemie; vol. 166; (1873); p. 363 View in Reaxys O –O

O Ca 2+

Ca(OH)2

H O

Rx-ID: 7978101 View in Reaxys 826/827

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Yield

Conditions & References Fittig; Ostermayer; Justus Liebigs Annalen der Chemie; vol. 166; (1873); p. 363 View in Reaxys

air oxygen

cobalt naphthenate

Rx-ID: 6675217 View in Reaxys 827/827 Yield

Conditions & References T= 135 - 145 °C , Dehydrierung I.G. Farbenind.; zit. bei Schenck in K. Ziegler; View in Reaxys

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