1-Naphthaldehyde [C11H8O] by Asch

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284 reactions in Reaxys

2018-02-14 08h:01m:50s (EST)

Search as: As drawn AND (IDE.XRN='386082')

1/112

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Rx-ID: 305254 View in Reaxys 1/284 Yield 100 %

Conditions & References With oxygen, perruthenate modified mesoporous silicate MCM-41 in toluene, Time= 1h, T= 80 °C , Oxidation Bleloch, Andrew; Johnson, Brian F. G.; Ley, Steven V.; Price, Adam J.; Shephard, Douglas S.; Thomas, Andrew W.; Chemical Communications; nb. 18; (1999); p. 1907 - 1908 View in Reaxys

99 %

With C23H35N3O3 (1+)*Br(1-), copper in chlorobenzene, Time= 15h, T= 80 °C Liu, Xiaolong; Xia, Qinqin; Zhang, Yuejiao; Chen, Congyan; Chen, Wanzhi; Journal of Organic Chemistry; vol. 78; nb. 17; (2013); p. 8531 - 8536 View in Reaxys

99 %

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

99 %

With dihydrogen peroxide in water, Time= 6h, T= 100 °C , chemoselective reaction Wu, Suntao; Chen, Liyu; Yin, Biaolin; Li, Yingwei; Chemical Communications; vol. 51; nb. 48; (2015); p. 9884 9887 View in Reaxys

> 99 %

With tert.-butylnitrite, oxygen, acetic acid in toluene, Time= 1.5h, T= 50 °C Karimi, Babak; Vahdati, Saleh; Vali, Hojatollah; RSC Advances; vol. 6; nb. 68; (2016); p. 63717 - 63723 View in Reaxys

> 99 %

4.1.15 : 4.1.2 Typical experimental procedure with HIO3 in the presence of TEMPO (Method B) General procedure: To a solution of 1-(p-bromophenyl)ethanol I-23 (201 mg, 1.0 mmol) in DMF (2.0 mL) was added HIO3 (194 mg, 1.1 mmol) and TEMPO (7.8 mg, 0.05 mmol). The mixture was stirred for 2 h at room temperature under an Ar atmosphere. After the reaction, the reaction mixture was poured into aq Na2S2O3, and extracted with a mixture of Et2O: hexane=1:1 (3*10 mL). Then, the organic layer was poured into satd NaCl (10 mL) and extracted with Et2O (10 mL). The organic layer was dried over Na2SO4. After being filtration and removal of the solvent under reduced pressure, the residue was purified by flash short column chromatography on silica gel (EtOAc-hexane, 1:4) to give p-bromoacetophenone II-23 in 99percent yield. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, iodic acid in N,N-dimethyl-formamide, Time= 2h, T= 20 °C , Inert atmosphere, Reagent/catalyst, Temperature Imai, Sho; Togo, Hideo; Tetrahedron; vol. 72; nb. 44; (2016); p. 6948 - 6954 View in Reaxys

99 %

Aerobic Oxidation of Alcohols 1a–o; Typical Procedure General procedure: Cu-PdNPs/bio-silica catalyst (80 mg) and TEMPO (5 mg, 0.03 mmol)in toluene (3 mL). The reaction flask was purged and filled with oxygen(1 atm) and heated at 110 °C overnight. The reaction mixture was then centrifuged and the supernatant was removed. The solvent was evaporated in vacuo, and the crude product was purified by flash column chromatography (silica gel; hexane/EtOAc). The recovered solid catalyst was washed with toluene (3 × 2 mL) and dried in an oven(100 °C, 4 h) for its reuse. The following known compounds includedin Table

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2 were characterized by comparison of their chromatographicand spectroscopic data (FTIR, 1H NMR, 13C NMR, and MS) with those described previously. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in toluene, T= 110 °C , p= 760.051Torr , Reagent/ catalyst Buxaderas, Eduardo; Graziano-Mayer, Marilyn; Volpe, María Alicia; Radivoy, Gabriel; Synthesis (Germany); vol. 49; nb. 6; (2017); p. 1387 - 1393; Art.No: SS-2016-M0473-OP 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 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

98%

15 : Example 1: General procedure: In a 150 mL thick-walled pressure tube equipped with a magnetic stirrer,In an air atmosphere,To the system was added benzyl alcohol (i.e., R1 in formula (I) H) 1.0 mmol (108.1 mg)Ammonia (1.6 x 10-2 mol / L) 5.0 mL,5 molpercent (9.5 mg) of cuprous iodide,TEMPO 5 molpercent (7.8 mg),100 & lt; 0 & gt; C for 12 h,After the reaction is over,The reaction solution was cooled to room temperature,And extracted with ethyl acetate (3 x 5.0 mL). The organic layers were combined and concentrated in vacuo to remove ethyl acetate to give the crude product. The crude product was purified by column chromatography(Petroleum ether: ethyl acetate = 10: 1) to give the pure desired product.The yield of 97.6 mg was 92percent. With ammonium hydroxide, copper(l) iodide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, Time= 18h, T= 100 °C Patent; Zhejiang University of Technology; Zhang Guofu; Zhao Yiyong; Zhang Guihua; Ding Chengrong; Lv Jinghui; Yu Yidong; (10 pag.); CN106905097; (2017); (A) Chinese View in Reaxys

97 %

With C34H37N4O6Ru2 (1+)*Cl(1-), potassium hydoxide in toluene, Time= 6h, T= 70 °C , Schlenk technique, Inert atmosphere Dutta, Indranil; Sarbajna, Abir; Pandey, Pragati; Rahaman, S. M. Wahidur; Singh, Kuldeep; Bera, Jitendra K.; Organometallics; vol. 35; nb. 10; (2016); p. 1505 - 1513 View in Reaxys

96 %

With sodium perborate tetrahydrate, sulfuric acid, potassium bromide in water, T= 80 °C Han, Mikyoung; Jeong, Ku Sun; Lee, Jong Chan; Bulletin of the Korean Chemical Society; vol. 33; nb. 7; (2012); p. 2405 - 2406 View in Reaxys

96 %

Stage 1: With copper(I) bromide in acetonitrile, Time= 0.05h, T= 20 °C , Inert atmosphere Stage 2: With N,N'-di-tert-butyldiaziridinone in acetonitrile, Time= 5h, T= 60 °C Zhu, Yingguang; Zhao, Baoguo; Shi, Yian; Organic Letters; vol. 15; nb. 5; (2013); p. 992 - 995 View in Reaxys

96 %

With potassium osmate(VI) dihydrate, potassium carbonate, potassium hexacyanoferrate(III) in water, acetonitrile, Time= 0.333333h, T= 60 °C , chemoselective reaction Fernandes, Rodney A.; Bethi, Venkati; RSC Advances; vol. 4; nb. 76; (2014); p. 40561 - 40568 View in Reaxys

95 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, sodium carbonate, L-proline, copper(I) bromide in methanol, Time= 3h, T= 20 °C Zhang, Guofu; Han, Xingwang; Luan, Yuxin; Wang, Yong; Wen, Xin; Ding, Chengrong; Chemical Communications; vol. 49; nb. 72; (2013); p. 7908 - 7910 View in Reaxys

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95 %

Cu/L2/TEMPO-Catalyzed Aerobic Oxidation of Benzylic Alcohols; General Procedure General procedure: A 30-mL Schlenk tube was evacuated and filled with O2, the benzyl alcohol (1 mmol), Cu powder (5percent mol), imidazolium (5percent mol), TEMPO (5percent mol), and H2O (3 mL) was added and stirred at 35 °C under an O2 atmosphere by connecting an O2 balloon. When the reaction was complete, the mixture was extracted with CH2Cl2 (3 × 10 mL). The combined extracts were dried (MgSO4). Then the solvent was removed and the mixture was purified by column chromatography (silica gel) to give the product. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C20H36N5 (3+)*3Br(1-), oxygen, copper in water, Time= 6h, T= 35 °C , Schlenk technique Chen, Congyan; Liu, Bo; Chen, Wanzhi; Synthesis (Germany); vol. 45; nb. 24; (2013); p. 3387 - 3391; Art.No: SS-2013-H0531-OP View in Reaxys

95 %

With 1-methyl-1H-imidazole, copper(l) iodide, C20H25N4O2 in acetonitrile, Time= 2h, T= 25 °C Wang, Lianyue; Bie, Zhixing; Shang, Sensen; Lv, Ying; Li, Guosong; Niu, Jingyang; Gao, Shuang; RSC Advances; vol. 6; nb. 41; (2016); p. 35008 - 35013 View in Reaxys

94 %

With oxygen, potassium carbonate in toluene, Time= 10h, T= 90 °C , p= 760.051Torr Zhang, Lei; Li, Pinhua; Yang, Jin; Wang, Min; Wang, Lei; ChemPlusChem; vol. 79; nb. 2; (2014); p. 217 - 222 View in Reaxys

93 %

With [RhCl2(p-cymene)]2, oxygen, caesium carbonate in 5,5-dimethyl-1,3-cyclohexadiene, Time= 24h, T= 130 °C Zhang, Di; Pan, Changduo; Catalysis Communications; vol. 20; (2012); p. 41 - 45 View in Reaxys

93 %

With hydrogenchloride, platinum, sodium chloride in chloroform, water, T= 30 °C , Electrolysis Bosco, A. John; Lawrence; Christopher; Radhakrishnan; Joseph Rosario, A. Arul; Raja; Vasudevan; Journal of Physical Organic Chemistry; vol. 28; nb. 9; (2015); p. 591 - 595 View in Reaxys

93 %

General procedure for aerobic oxidation of alcohols in water General procedure: To a 48 mL tube, were added Cu(II) or Cu(I) salt (0.05 mmol), PEG-PyTa (0.025 mmol) and H2O (3.0 mL). The mixture was stirred for 30 min at room temperature and a clear dark-blue solution was observed. Then alcohols (1.0 mmol), TEMPO (0.05 mmol), and K2CO3 (0.2 mmol) were sequentially added, followed by connecting a balloon of oxygen. The reaction mixture was stirred at room temperature until the reaction completed based on GC analysis. After that, the reaction mixture was extracted with MTBE (3 mL×3) and the extracts were combined, dried over anhydrous Na2SO4 and concentrated under vacuum. Finally, the residue was purified by flash chromatography on silica to afford the desired aldehydes. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C110H202N8O47, oxygen, copper(II) bis(trifluoromethanesulfonate), potassium carbonate in water, Time= 24h, T= 20 °C , Green chemistry Sun, Nan; Zhang, Xiaonan; Jin, Liqun; Hu, Baoxiang; Shen, Zhenlu; Hu, Xinquan; Catalysis Communications; vol. 101; (2017); p. 5 - 9 View in Reaxys

92 %

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

92 %

With ammonium peroxydisulfate, Montmorillonite K10, silver nitrate in hexane, Time= 2.5h, T= 60 °C Hirano; Kojima; Yakabe; Morimoto; Journal of Chemical Research - Part S; nb. 7; (2001); p. 274 - 276 View in Reaxys

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92 %

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

92 %

With 3-(6-(3,5-dimethyl-1H-pyrazol-1-yl)pyridin-2-yl)-1-(2-((1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)oxy)-2-oxoethyl)-1H-imidazol-3-ium iodide, oxygen, sodium carbonate, copper(I) bromide, Time= 24h, T= 50 °C , Ionic liquid Guo, Bin; Xue, Jiang-Yan; Li, Hong-Xi; Tan, Da-Wei; Lang, Jian-Ping; RSC Advances; vol. 6; nb. 57; (2016); p. 51687 - 51693 View in Reaxys

92 %

With zinc zirconium phosphate, dihydrogen peroxide in neat (no solvent), Time= 0.333333h, T= 60 °C , Green chemistry Karimi, Hirbod; Journal of the Chinese Chemical Society; vol. 62; nb. 7; (2015); p. 604 - 613 View in Reaxys

91 %

With 10 Ru/C, oxygen in toluene, Time= 24h, T= 50 °C , p= 760.051Torr Mori, Shigeki; Takubo, Masato; Makida, Kazuya; Yanase, Takayoshi; Aoyagi, Satoka; Maegawa, Tomohiro; Monguchi, Yasunari; Sajiki, Hironao; Chemical Communications; nb. 34; (2009); p. 5159 - 5161 View in Reaxys

91 %

General Procedures for the Copper-Catalyzed Primary BenzylicAlcohol Oxidation under Air in Water (pMethylbenzylAlcohol) General procedure: A mixture of p-methylbenzyl alcohol (1.0 mmol), N-phenylglycine(0.0076 g, 0.05 mmol), CuBr2 (0.0112 g, 0.05 mmol),Na2CO3 (0.1060 g, 1.0 mmol), TEMPO (0.0078 g, 0.05 mmol),H2O (3.0 mL) were added to a 100 mL Schlenk tube, which wasvigorously stirred in air under reflux for 0.5 h. After the reaction,the product was extracted with CH2Cl2 (3 × 2.0 mL). Thecombined organic phase was washed with H2O (3.0 mL) anddried over anhydrous MgSO4. After concentration undervacuum, the residue was purified by column chromatography toafford pmethylbenzaldehyde.Isolated yield: 0.1080 g (90percent). With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, sodium carbonate, N-Phenylglycine, copper(ll) bromide in water, Time= 2h, Reflux, Schlenk technique Zhang, Guofu; Lei, Jie; Han, Xingwang; Luan, Yuxin; Ding, Chengrong; Shan, Shang; Synlett; vol. 26; nb. 6; (2015); p. 779 - 784 View in Reaxys

91 %

4.2 General procedure for the synthesis of 59 benzylaldehyde General procedure: To a 10mL round bottom flask, the mixture of 12 benzylalcohol 1a (1.0mmol, 0.104mL) and Cu2(ophen)2 (0.05mmol, 26mg,) in 60 CH3CN (4mL), was stirred in oil bath at 60°C under oxygen atmosphere (oxygen ball). The reaction was monitored and conversions were determined by GC–MS. With Cu2(ophen)2, oxygen in acetonitrile, Time= 12h, T= 60 °C , Green chemistry Zhang, Lingjuan; Liu, Jie; Zhang, Fuqiang; Zhang, Xian-Ming; Journal of Catalysis; vol. 354; (2017); p. 78 - 83 View in Reaxys

91 %

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

90 %

With potassium permanganate, Tris(3,6-dioxaheptyl)amine in dichloromethane, Time= 8h, Ambient temperature McKillop, Alexander; Mills, Lester S.; Synthetic Communications; vol. 17; nb. 6; (1987); p. 647 - 656 View in Reaxys

90 %

With hexamethylenebis(N-methylimidazolium) dichlorochromate, Time= 0.5h, T= 80 °C

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Hosseinzadeh, Rahman; Mohadjerani, Maryam; Tajbakhsh, Mahmood; Nouzarian, Mahboobe; Synthetic Communications; vol. 41; nb. 12; (2011); p. 1725 - 1732 View in Reaxys 90 %

With Pyridine-2,6-dicarboxylic acid, dihydrogen peroxide, trifluoroacetic acid, zinc dibromide in tetrahydrofuran, water, Time= 16h, T= 20 °C Wu, Xiao-Feng; Chemistry - A European Journal; vol. 18; nb. 29; (2012); p. 8912 - 8915 View in Reaxys

90 %

General procedure for the oxidation of alcohols with molecular iodine and potassium tertbutoxide General procedure: (Tables 1 and 2, Scheme 1). In a typical run, a reaction flask (25 mL) was chargedwith an indicated amount of I2 (typically, 508 mg, 2 mmol) and potassium tert-butoxide(typically, 470 mg, 4.2 mmol). The mixture was suspended in CH2Cl2 (5 mL) and stirred at 10 oCfor 30 min, then alcohol (1 mmol) was added. The mixture was continually stirred at an indicatedtemperature (typically, at 10 °C) until the consumption of the alcohol (monitoring with TLC,typically, for a few hours), then diluted with CH2Cl2 (10 mL) and washed with saturated aqueoussodium thiosulfate (10 mL). The aqueous phase was extracted with CH2Cl2 (three portions of 10mL each). The combined organic phase was washed with deionized water and saturated aqueousNaCl, dried over anhydrous Na2SO4, and then filtered and concentrated. The crude product waspurified by column chromatography (silica, hexane or hexane/ EtOAc mixture as eluent). Theyields are listed in Tables 1 and 2 as well as Scheme 1.1-Naphthaldehyde (2a).30 A white amorphous solid (111 mg, 90percent yield). 1H NMR (CDCl3, 300MHz): 10.36 (s, 1H), 9.26 (d, J 8.5 Hz, 1H), 8.05 (d, J 8.2 Hz, 1H), 7.94 (d, J 6.9 Hz, 1H), 7.89(d, J 8.2 Hz, 1H), 7.68 (t, J 7.2 Hz, 1H), 7.61−7.54 (m, 2H). 13C NMR (CDCl3, 75 MHz): 193.44, 136.61, 135.15, 133.54, 131.18, 130.33, 128.92, 128.34, 126.81, 124.73. With potassium tert-butylate, iodine in dichloromethane, Time= 1.5h, T= 10 °C , Catalytic behavior, Reagent/catalyst, Temperature, Solvent Luo, Qun-Li; Nan, Wen-Hui; Li, Yu; Chen, Xiang; Arkivoc; vol. 2014; nb. 4; (2014); p. 350 - 361 View in Reaxys

87.3 %

With oxygen, Time= 4h, p= 760.051Torr , Irradiation, Sealed tube, Catalytic behavior, Kinetics, Reagent/catalyst Chen, Yu; Li, Weizun; Wang, Jingyu; Yang, Qian; Hou, Qidong; Ju, Meiting; RSC Advances; vol. 6; nb. 74; (2016); p. 70352 - 70363 View in Reaxys

87 %

General procedure for the oxidation of alcohols General procedure: A mixture of aryl alcohol (1 mmol) and [FemDMMerA]Y (100 mg) in solvent(5 mL) was refluxed in oil bath. After completion of the reaction as monitored byTLC, the reaction mixture was filtered to remove insoluble SILP catalyst.Evaporation of solvent in vacuuo followed by column chromatography over silicagel using petroleum ether/ethyl acetate (95:5 v/v) afforded pure aldehydes. With ferrocene-labeled Merrifield resin-supported ionic liquid ([FemDMMerA]RuO4) in tetrahydrofuran, Time= 5h, Reflux, Green chemistry Kurane, Rajanikant; Bansode, Prakash; Khanapure, Sharanabasappa; Salunkhe, Rajashri; Rashinkar, Gajanan; Research on Chemical Intermediates; vol. 42; nb. 12; (2016); p. 7807 - 7821 View in Reaxys

87 %

25 : Example 25: [Cu6 (pyt) 6]Catalytic dehydrogenation of 1-naphthaldehyde In the glove box, will be 1 - naphthalene methanol (1.0 mmol), [Cu6 (Pyt)6 ] (0.1 mmol), KOH (1.0 mmol) is added to the test tube with the magnetic coil in the has, then adding 2.0 ml dry toluene solvent. After the sealed reaction tube, is taken out of the glove box. Toward the nozzle leads into the small and stable and low production, stable air flow after such as, for 70 °C reaction under 24 h; after the reaction, extracted with ethyl acetate (3 × 5 ml), the combined organic phase, dried with anhydrous sodium sulfate, filtered, concentrated filtrate for rotary evaporator, and then separating and purifying column law silica gel chromatography, to obtain the target product between 1 - naphthalene formaldehyde (yield 87percent). With [Cu6(SC5H4N)6], potassium hydoxide in toluene, Time= 24h, T= 70 °C , Glovebox, Inert atmosphere Patent; Soochow University; Li, Hongxi; Tan, Dawei; Li, Haiyan; Lang, Jianping; (15 pag.); CN106588957; (2017); (A) Chinese View in Reaxys

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86 %

With dmap, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper diacetate in neat (no solvent), Time= 18h, T= 80 °C , Green chemistry Guan, Mingyu; Wang, Chao; Zhang, Jingyu; Zhao, Yingsheng; RSC Advances; vol. 4; nb. 90; (2014); p. 48777 48782 View in Reaxys

85 %

With bis(pentafluorophenyl)borinic acid, magnesium sulfate, pivalaldehyde in toluene, Time= 42h, Ambient temperature Ishihara, Kazuaki; Kurihara, Hideki; Yamamoto, Hisashi; Journal of Organic Chemistry; vol. 62; nb. 17; (1997); p. 5664 - 5665 View in Reaxys

85 %

With hydrogen bromide, potassium nitrate, sodium bromide in dichloromethane, water, Electrochemical reaction Zhang, Li; Zha, Zhenggen; Wang, Zhiyong; Fu, Shengquan; Tetrahedron Letters; vol. 51; nb. 10; (2010); p. 1426 - 1429 View in Reaxys

85 %

With potassium nitrate in water, Time= 3h, T= 20 °C , Electrolysis Zhang, Li; Zha, Zhenggen; Wang, Zhiyong; Synlett; nb. 13; (2010); p. 1915 - 1918 View in Reaxys

85 %

Typical procedure for the formation of aldehydes (3a-q) General procedure: A test tube equipped with a magnetic stirring bar was charged with 1 (5 mg, 0.005 mmol, 0.25 molpercent), TEMPO (16 mg, 0.10 mmol, 5 molpercent), and K2CO3 (69 mg, 0.50 mmol, 25 molpercent). Alcohols (2a-q, 2.0 mmol), H2O (5 mL) and H2O2 (30percent, 1 mL) were added. The mixed light green solution was stirred at 60°C for 12 h, cooled to room temperature, and then extracted by Et2O (3 × 5mL). The organic layers were combined, washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. On elution with petroleum ether and ethyl acetate, the crude product was further purified by column chromatography on silica. All aldehyde products synthesized in this work are known and confirmed by 1H NMR spectra. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C40H54CuN4O5 (2+)*2I(1-), dihydrogen peroxide, potassium carbonate in water, Time= 12h, T= 60 °C Gao, Jun; Ren, Zhi-Gang; Lang, Jian-Ping; Journal of Organometallic Chemistry; vol. 792; (2015); p. 88 - 92; Art.No: 18908 View in Reaxys

84 %

With [Cu6(pyridine-2-thiolate)6], potassium hydoxide in toluene, Time= 24h, T= 70 °C , Schlenk technique, Glovebox, Inert atmosphere Tan, Da-Wei; Li, Hong-Xi; Zhang, Meng-Juan; Yao, Jian-Lin; Lang, Jian-Ping; ChemCatChem; vol. 9; nb. 6; (2017); p. 1113 - 1118 View in Reaxys

83 %

20 : 4.5. General procedure for the aerobic alcohol oxidation General procedure: Under an air atmosphere, a Schlenk tube was charged with MCM-41-bpy-CuI (40 mg, 0.025 mmol), alcohol (0.5 mmol), TEMPO (4 mg, 0.025 mmol), aqueous ammonia (0.5 mmol, 25e28percent, w/w) and EtOH (1.0 mL). The mixture was stirred at 50 °C for 18-48 h. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate (10 mL), and filtered. The MCM-41-bpy-CuI complex was washed with EtOH (2*5 mL), and Et2O (5 mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (petroleum/ethyl acetate=15:1 to 10:1) to provide the desired product. With ammonium hydroxide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in ethanol, Time= 36h, T= 50 °C Zhao, Hong; Chen, Qiurong; Wei, Li; Jiang, Yuanyuan; Cai, Mingzhong; Tetrahedron; vol. 71; nb. 46; (2015); p. 8725 - 8731; Art.No: 27151 View in Reaxys

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83 %

With iron(III) chloride hexahydrate, C17H26N3 (1+)*Br(1-), dihydrogen peroxide in water, Time= 3h, T= 20 °C , chemoselective reaction Yan, Qi; Fang, Ye Chen; Jia, Yun Xue; Duan, Xin Hong; New Journal of Chemistry; vol. 41; nb. 6; (2017); p. 2372 - 2377 View in Reaxys

80 %

With Tributylphosphine oxide, oxygen, sodium acetate, palladium diacetate in toluene, Time= 24h, T= 80 °C , p= 750.075Torr , Molecular sieve, Concentration, Reagent/catalyst Gowrisankar, Saravanan; Neumann, Helfried; Goerdes, Dirk; Thurow, Kerstin; Jiao, Haijun; Beller, Matthias; Chemistry - A European Journal; vol. 19; nb. 47; (2013); p. 15979 - 15984 View in Reaxys

78 %

With iodine, oxygen in acetonitrile, Time= 5h, T= 20 °C , Irradiation Farhadi, Saeid; Zabardasti, Abedien; Babazadeh, Zaynab; Tetrahedron Letters; vol. 47; nb. 50; (2006); p. 8953 8957 View in Reaxys

78 %

With oxygen, potassium carbonate, polymer-incarcerated gold nanocluster catalyst in water, Time= 5h, T= 20 °C , p= 760.051Torr Miyamura, Hiroyuki; Matsubara, Ryosuke; Miyazaki, Yoji; Kobayashi, Shu; Angewandte Chemie - International Edition; vol. 46; nb. 22; (2007); p. 4151 - 4154 View in Reaxys

77 %

With tert.-butylhydroperoxide, titanium(IV) isopropylate in dichloromethane, Time= 24h, T= 20 °C Krohn, Karsten; Khanbabaee, Karamali; Rieger, Hagen; Chemische Berichte; vol. 123; nb. 6; (1990); p. 1357 1364 View in Reaxys

77 %

With mercury(II) oxide in acetonitrile, T= 25 °C , UV-irradiation Habibi; Farhadi; Polish Journal of Chemistry; vol. 78; nb. 5; (2004); p. 741 - 744 View in Reaxys

77 %

2.2 Catalytic reaction General procedure: In a typical experiment, 4-methoxybenzyl alcohol (12μL, 0.1mmol), Cu-FMOF (11.3mg, 10mmol percent), TEMPO (7.8mg, 0.05mmol) and NaCO3 (10.6mg, 0.1mmol) in 1mL of air saturated acetonitrile were taken in a 15-mL three-necked round-bottom flask. The solution was magnetically stirred for 16h at 75°C under air atmosphere. The progress of the reaction was monitored via gas chromatography (Shimadzu GC-2010AF) involving a Chromopak capillary column and flame ionization detector. The products were further confirmed by using gas chromatography–mass spectroscopy (GC–MS) (Shimadzu GCMS-2010). The concentrations of 4-methoxybenzyl alcohol and 4-methoxybenzylaldehyde were calibrated by external standard method with standard samples (see Fig. S1). With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, {[Cu2(1,2-benzenedicarboxylate)2(1,4-bis(1,2,4-triazol-1-ylmethyl)-2,3,5,6-tetrafluorobenzene)2]·3H2O}n, sodium carbonate in acetonitrile, Time= 16h, T= 75 °C Chen, Sheng-Chun; Lu, Sheng-Nan; Tian, Feng; Li, Nan; Qian, Han-Yu; Cui, Ai-Jun; He, Ming-Yang; Chen, Qun; Catalysis Communications; vol. 95; (2017); p. 6 - 11 View in Reaxys

76 %

With oxygen, phosphotungstic acid, silica gel in acetonitrile, Time= 2.5h, T= 20 °C , UV-irradiation Farhadi, Saeid; Afshari, Mozhgan; Maleki, Mansoureh; Babazadeh, Zaynab; Tetrahedron Letters; vol. 46; nb. 49; (2005); p. 8483 - 8486 View in Reaxys

76 %

With oxygen, (nBu4N)4W10O32, silica gel in acetonitrile, Time= 2h, T= 25 °C , UV-irradiation Farhadi, Saeid; Afshari, Mozhgan; Journal of Chemical Research; nb. 3; (2006); p. 188 - 191 View in Reaxys

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76 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, copper 1,3,5-benzenetricarboxylate, oxygen, sodium carbonate in acetonitrile, Time= 16h, T= 75 °C , p= 760.051Torr Qi, Yue; Luan, Yi; Yu, Jie; Peng, Xiong; Wang, Ge; Chemistry - A European Journal; vol. 21; nb. 4; (2015); p. 1589 - 1597 View in Reaxys

75 %

With urea hydrogen peroxide adduct, 1-butyl-3-methylimidazolium Tetrafluoroborate, magnesium bromide, Time= 2h, T= 60 °C Heel, Joong Park; Jong, Chan Lee; Synlett; nb. 1; (2009); p. 79 - 80 View in Reaxys

75 %

General Experimental Procedure for the Oxidation of Alcohols: General procedure: To a solution of the alcohol (1.0 mmol) and hydrogen peroxide(5.0 mmol, 30percent aq) was added BiBr3 (10 molpercent). The reactionmixture was stirred at 70 °C for 10–40 min, and thereaction mixture was extracted with dichloromethane (2 × 5mL). The combined organic layers were washed with saturatedbrine (2 × 5 mL) and dried with anhydrous MgSO4. After evaporationof the solvent, the residue was purified by flash columnchromatography (SiO2; CH2Cl2–hexane, 3:2) to afford the purecarbonyl compound. With bismuth(III) bromide, dihydrogen peroxide in water, Time= 0.166667h, T= 70 °C , Green chemistry Han, Mi-Kyung; Kim, Sohwa; Kim, Sung Tae; Lee, Jong Chan; Synlett; vol. 26; nb. 17; (2015); p. 2434 - 2436; Art.No: ST-2015-U0545-L View in Reaxys

72 %

With 4‐(acetylamino)‐2,2,6,6‐tetramethyl‐1‐oxopiperidinium tetrafluoroborate in water, Time= 24h, Reflux Mamros, Audrey N.; Sharrow, Phillip R.; Weller, William E.; Luderer, Mark R.; Fair, Justin D.; Pazehoski, Kristina O.; Luderer, Matthew R.; Arkivoc; vol. 2011; nb. 5; (2011); p. 23 - 33 View in Reaxys

70 %

4.2. Typical experimental procedure of palladium/NHC-catalyzed tandem benzylic oxidation/oxidative esterification of benzylic alcohols with phenols General procedure: Under oxygen, a reaction tube was charged with phenols (0.2 mmol), benzylic alcohols (0.3 mmol), Pd(OAc)2 (2.2 mg, 5 mol percent), L5 (8.5 mg, 10 mol percent), Na2CO3 (10.6 mg, 0.1 mmol) in dry xylene (2 mL). After the mixture was stirred for 36 h at 130 °C, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product. With oxygen, palladium diacetate, sodium carbonate in 5,5-dimethyl-1,3-cyclohexadiene, Time= 36h, T= 130 °C Luo, Fang; Pan, Changduo; Cheng, Jiang; Chen, Fan; Tetrahedron; vol. 67; nb. 33; (2011); p. 5878 - 5882 View in Reaxys

70 %

Stage 1: With C24H20B(1-)*C5H12NO2 (1+)*C5H11NO2 in acetonitrile, Time= 0.166667h, T= 20 °C , Ley-Griffith Ru Oxidation Stage 2: With tetrapropylammonium perruthennate in acetonitrile, T= 20 °C , Ley-Griffith Ru Oxidation Moore, Peter W.; Mirzayans, Paul M.; Williams, Craig M.; Chemistry - A European Journal; vol. 21; nb. 9; (2015); p. 3567 - 3571 View in Reaxys

68 %

Oppenauer Oxidation of Alcohols Using In(i-OPr)3; General Procedure General procedure: To a screw tube in a glovebox was added In(Oi-Pr)3 (29.2 mg, 0.1 mmol). The tube was then sealed and removed from the glovebox, and CHCl3 (1 mL), alcohol (0.5 mmol), and pivalaldehyde (280 μL, 2.5 mmol) were added under N2 in this order. After stirring the mixture at r.t. for 3 h, H2O (1.0 mL) was added to the reaction mixture, which was then extracted with EtOAc. The organic phase was dried (Na2SO4), and evaporated under reduced pressure. The crude material was purified by silica gel column chromatography (Table 2 and Scheme 2). With indium isopropoxide, pivalaldehyde in chloroform, Time= 3h, T= 20 °C , Glovebox, Sealed tube, Inert atmosphere, Oppenauer Oxidation Ogiwara, Yohei; Ono, Yuji; Sakai, Norio; Synthesis (Germany); vol. 48; nb. 23; (2016); p. 4143 - 4148; Art.No: SS-2016-F0462-OP

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View in Reaxys 68.5 %

Typical procedure for the oxidation of alcohols General procedure: A solution of BTC (0.41 g, 1.39 mmol) in dry CH2Cl2 (5 mL) was cooled in an ice-salt bath under an atmosphere of N2. A solution of I (1.24 g, 4.17 mmol) in dry CH2Cl2 (5 mL) was added dropwise for 0.5 h, at −15 °C. Stirring was continued for 0.5 h, and a solution of benzyl alcohol (0.3 g, 2.78 mmol) in dry CH2Cl2 (5 mL) was added dropwise for 0.5 h, at−15 °C. After stirring for 0.5 h, Et3N (0.84 g, 8.34 mmol) was added slowly while the temperature should be controlled below −15 °C. When the reaction was completed, 10percent HCl solution in water was added dropwise until the pH of the reaction solution reached 2 under ice bath. The mixture was extracted with nhexane or petroleum ether (10 mL x 2),decanted. The product was acquired after organic layer was concentrated and purified by flash chromatography (SiO2; n-hexane). (0.27 g, 92percent). The water layer was used for the recovery of V and the excess I. Stage 1: With bis(trichloromethyl) carbonate, 4-(2-(2-(methylsulfinyl)ethyl)-4-nitrophenyl)morpholine in dichloromethane, Time= 1h, T= -15 °C , Inert atmosphere, Swern Oxidation Stage 2: With triethylamine in dichloromethane, T= -15 °C , Inert atmosphere, Swern Oxidation Ye, Xiaojing; Fu, Hongliang; Ma, Jiahao; Zhong, Weihui; Synthetic Communications; vol. 46; nb. 10; (2016); p. 885 - 892 View in Reaxys

65 %

Stage 1: With C6H13N2O(1+)*C6H12N2O*C24H20B(1-) in acetonitrile, Time= 0.166667h, T= 20 °C , Ley-Griffith Ru Oxidation Stage 2: With tetrapropylammonium perruthennate in acetonitrile, Time= 16h, T= 20 °C , Ley-Griffith Ru Oxidation Moore, Peter W.; Jiao, Yanxiao; Mirzayans, Paul M.; Sheng, Lexter Ng Qi; Hooker, Jordan P.; Williams, Craig M.; European Journal of Organic Chemistry; vol. 2016; nb. 20; (2016); p. 3401 - 3407 View in Reaxys

65 %

General procedure for the oxidation of 1,2-diols, a-hydroxyketones and alcohols to 1,2-diketones and aldehydes/ketones General procedure: In a typical experiment, a mixture of 1,2-diols/a-hydroxyketones/alcohols (1 mmol), sodium bromate (3 mmol),and bmim[HSO4]:H2O 3:1 (v/v) along with a stir bar was placed in a RB flask fitted with a condenser. The reaction mixture was stirred magnetically in an oil-bath maintained at 60 C for an appropriate time as mentioned in Tables 3,4, and 5, respectively. After completion of the reaction, as monitored by TLC using petroleum ether:ethyl acetate(80:20, v/v) as eluent, the reaction mixture was cooled to room temperature and worked up as mentioned above. The product obtained was identified by m.p (wherever applicable), IR and NMR spectra. With 1-butyl-3-methylimidazolium hydrogen sulfate, sodium bromate in water, Time= 0.5h, T= 60 °C , Green chemistry Khurana, Jitender M.; Lumb, Anshika; Chaudhary, Ankita; Monatshefte fur Chemie; vol. 148; nb. 2; (2017); p. 381 - 386 View in Reaxys

60 %

With N-Bromosuccinimide, 1-butyl-3-methylimidazolium Tetrafluoroborate, Time= 2h, 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

55 %

With sodium bismuthate in water, acetic acid, acetone, Time= 10h, Heating, Oxidation Banik, Bimal K.; Ghatak, Anjan; Venkatraman; Becker, Frederick F.; Synthetic Communications; vol. 30; nb. 15; (2000); p. 2701 - 2705 View in Reaxys

52 %

With (carbonyl)chloro(hydrido)tris(triphenylphosphine)ruthenium(II), oxygen in toluene, Time= 18h, T= 90 °C , p= 760.051Torr , Molecular sieve, Sealed tube Ray, Ritwika; Chandra, Shubhadeep; Maiti, Debabrata; Lahiri, Goutam Kumar; Chemistry - A European Journal; vol. 22; nb. 26; (2016); p. 8814 - 8822 View in Reaxys

51 %

Stage 1: in toluene, Time= 0.0833333h, Ultrasonication

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Stage 2: With oxygen in toluene, T= 303 °C , Darkness Tsukamoto, Daijiro; Shiraishi, Yasuhiro; Sugano, Yoshitsune; Ichikawa, Satoshi; Tanaka, Shunsuke; Hirai, Takayuki; Journal of the American Chemical Society; vol. 134; nb. 14; (2012); p. 6309 - 6315 View in Reaxys 46 %

With eosin y in dimethyl sulfoxide, Time= 24h, T= 80 °C , Irradiation Li, Jian; Wang, Hongni; Liu, Li; Sun, Jiangtao; RSC Advances; vol. 4; nb. 91; (2014); p. 49974 - 49978 View in Reaxys

45 %

With tetrakis(pyridine)silver(II) peroxodisulfate in acetonitrile, Time= 3h, Heating Firouzabadi, Habib; Salehi, Peyman; Mohammadpour-Baltork, Iraj; Bulletin of the Chemical Society of Japan; vol. 65; nb. 10; (1992); p. 2878 - 2880 View in Reaxys

43 %

Open air oxidation of alcohols An initial set of experiments was performed by placing CuSO4·5H2O (0.03 mmol from stock solution of 50 mg/mL in H2O) and salicylaldimine (0.06 mmol) into a 100 mL two-neck round-bottom flask fitted with a condenser and a magnetic stirring bar. The reaction mixture was diluted with 5 mL of distilled water and heated at 80 °C for 15 min to ensure the complex formation. After cooling to room temperature, 0.15 mmol of TEMPO was introduced into the solution which was heated at desired temperature for 5 min. Benzyl alcohol (3 mmol) was then added into the solution. The catalysis was carried out for 1.5 h and then the aqueous solution was extracted with ethyl acetate (3 mL * 3 mL). With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, (1-methylethyl)(2-hydroxy-3,5-di(t-butyl)phenyl)methylimine, copper(ll) bromide in water, Time= 12h, T= 80 °C , Green chemistry Ahmad, Jahir Uddin; Raeisaenen, Minna T.; Kemell, Marianna; Heikkilae, Mikko J.; Leskelae, Markku; Repo, Timo; Applied Catalysis A: General; vol. 449; (2012); p. 153 - 162 View in Reaxys With chromium(III) oxide, sulfuric acid West; Journal of the American Chemical Society; vol. 42; (1920); p. 1663 View in Reaxys With dinitrogen tetraoxide Field; Grundy; Journal of the Chemical Society; (1955); p. 1110 View in Reaxys With pyridine, N-bromoacetamide Lecomte; Gault; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 238; (1954); p. 2538 View in Reaxys With N-chloro-succinimide Hebbelynck; Martin; Bulletin des Societes Chimiques Belges; vol. 60; (1951); p. 54,65 View in Reaxys With potassium dichromate, sulfuric acid Bamberger; Lodter; Chemische Berichte; vol. 21; (1888); p. 258 View in Reaxys With dipotassium peroxodisulfate Horii et al.; Yakugaku Zasshi; vol. 76; (1956); p. 1101; ; (1957); p. 3553 View in Reaxys

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61 % Chromat.

With 2-Diazobenzophenon-Kation, 2,4,6-trifluoromethylpyridine, RuL3 (2+) in acetonitrile, Time= 0.333333h, Irradiation Cano-Yelo, Herminia; Deronzier, Alain; Tetrahedron Letters; vol. 25; nb. 48; (1984); p. 5517 - 5520 View in Reaxys

96.0 % Chromat.

With 2,6-dimethylpyridine, β-cyclodextrin with a ferrocene moiety, tetraethylammonium perchlorate in acetonitrile, Time= 12h, electrolytic oxidation; also benzyl alcohol, var. times, var. charge passed, Mechanism, Product distribution Suzuki, Iwao; Chen, Qiang; Kashiwagi, Yoshitomo; Osa, Tetsuo; Ueno, Akihiko; Chemistry Letters; nb. 10; (1993); p. 1719 - 1722 View in Reaxys

92 % Chromat.

With oxygen, Ru-Co-Al-CO3 HT in toluene, Time= 1h, T= 60 °C Matsushita, Tsuyoshi; Ebitani, Kohki; Kaneda, Kiyotomi; Chemical Communications; nb. 3; (1999); p. 265 - 266 View in Reaxys With K10-montmorillonite clay-supported tetrabutylammonium periodate in 2,2,4-trimethylpentane, Time= 4h, Heating, Yield given Venkatachalapathy; Rajarajan; Shayira Banu; Pitchumani; Tetrahedron; vol. 55; nb. 13; (1999); p. 4071 - 4076 View in Reaxys With manganese(IV) oxide in tetrahydrofuran, T= 20 °C Quesada, Ernesto; Taylor, Richard J.K.; Tetrahedron Letters; vol. 46; nb. 38; (2005); p. 6473 - 6476 View in Reaxys With manganese(IV) oxide in tetrahydrofuran, Time= 4h, T= 20 °C Quesada, Ernesto; Raw, Steven A.; Reid, Mark; Roman, Estelle; Taylor, Richard J.K.; Tetrahedron; vol. 62; nb. 28; (2006); p. 6673 - 6680 View in Reaxys

98 % Chromat.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, potassium carbonate, poly(styrene-co-styrene derivatives) incarcerated ruthenium in 1,2-dichloro-ethane, Time= 7h, T= 80 °C , p= 750.075Torr Matsumoto, Tsutomu; Ueno, Masaharu; Kobayashi, Juta; Miyamura, Hiroyuki; Mori, Yuichiro; Kobayashi, Shue; Advanced Synthesis and Catalysis; vol. 349; nb. 4-5; (2007); p. 531 - 534 View in Reaxys Naphthalene-1-carboxylic acid is dissolved in dry THF and 5 equiv. of borane dimethylsulfide complex are added. The mixture obtained is stirred at rt, diluted with EtAc, washed with 1N HCI and 5percent NaHCO3 solution, dried and solvent is evaporated. (Naphthalene-i-yl)-methanol is obtained, which is dissolved in CH2CI2- To the solution obtained 1.5 equiv. of Dess-Martin reagent are added at rt. The mixture obtained is diluted with EtAc, extracted with 1 N HCI and 5percent NaHCO3-solution, dried and solvent is evaporated. Naphthalene-1-carboxaldehyde is obtained and dissolved with 1 equiv. of racemic-Boc-α-phosphonoglycine trimethylester in CH2CI2 and 1.1 equiv. of DBU are added. The mixture obtained is stirred at rt and treated in sequence with 1N HCI and 5percent NaHCO3 solution. The phases obtained are separated, the organic phase obtained is dried and solvent is evaporated. 2-Boc-amino-3(naphthalene-1- yl)-acrylic acid methyl ester (cis/trans mixture) is obtained, is dissolved in MeOH/H2O at pH 6.5 (phosphate buffer) and 20 w/wpercent of 10percent Pd/C are added. The mixture obtained is hydrogenated at rt and 50 bar, the catalyst is filtered off and from the filtrate obtained solvent is evaporated. Racemic naphythylalanine methylester is obtained, dissolved in methanolic NH3 and stirred. The mixture obtained is subjected to extractive work up. Racemic naphythylalanine amide is obtained. With Dess-Martin periodane in dichloromethane, T= 20 °C , Dess-Martin Oxidation Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/111371; (2006); (A1) English View in Reaxys With Ag/hydrotalcite in para-xylene, Time= 40h, T= 130 °C

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Mitsudome, Takato; Mikami, Yusuke; Funai, Hisashi; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Angewandte Chemie - International Edition; vol. 47; nb. 1; (2008); p. 138 - 141 View in Reaxys 5 :Preparation of 1-naphthalenecarboxaldehyde An amount of 3.87 ml. oxalyl chloride (44.24 mmol) was dissolved in 100 ml. DCM. The mixture was cooled to -60° C. An amount of 5.6 ml. DMSO was added dropwise using a syringe. The mixture was stirred for 15 min. A solution of 5g of naphthalene-1 -methanol in 75 ml. DCM was added dropwide. The reaction was continued for 1 h at -600C. An amount of 20 ml. triethylamine was added. The mixture was allowed to attain 15° C. The mixture was transferred to an extraction funnel, washed with water, 1 M HCI, water and brine. The organic layer was then dried over magnesium sulfate and evaporated. The crude product was sufficiently pure to be used without further purification in the next step. With oxalyl dichloride, dimethyl sulfoxide in dichloromethane, Time= 1.25h, T= -60 - 15 °C Patent; EVOLVA SA; WO2008/89461; (2008); (A1) English View in Reaxys 93 %Chromat.

With α,α,α-trifluorotoluene, oxygen in water, Time= 18h, T= 20 °C Miyamura, Hiroyuki; Matsubara, Ryosuke; Kobayashi, Shu; Chemical Communications; nb. 17; (2008); p. 2031 2033 View in Reaxys PREPARATION OF STARTING MATERIALS; NAPHYTHYLALANINE amide (Compound A1) Naphthalene-1-carboxylic acid is dissolved in dry THF and 5 equiv. of borane DIMETHYLSULFIDE complex are added. The mixture obtained is stirred at rt, diluted with EtAc, washed with 1 N HCI and 5percent NAHCOS solution, dried and solvent is evaporated. (Naphthalene-1-yl)-methanol is obtained, which is dissolved in CH2CI2. To the solution obtained 1.5 equiv. of Dess-Martin reagent are added at rt. The mixture obtained is diluted with EtAc, extracted with 1 N HCI and 5percent NAHCOS-SOFUTION, dried and solvent is evaporated. NAPHTHALENE-1-CARBOXALDEHYDE is obtained and dissolved with 1 equiv. of RACEMIC-BOC-A-PHOSPHONOGLYCINE trimethylester in CH2CI2 and 1.1 equiv. of DBU are added. The mixture obtained is stirred at rt and treated in sequence with 1 N HCI and 5percent NAHCO3 solution. The phases obtained are separated, the organic phase obtained is dried and solvent is evaporated. 2-BOC-AMINO-3-(NAPHTHALENE-1- yl)-acrylic acid methyl ester (cis/trans mixture) is obtained, is dissolved in MEOH/H20 at pH 6.5 (phosphate buffer) and 20 w/wpercent of 10percent Pd/C are added. The mixture obtained is hydrogenated at rt and 50 bar, the catalyst is filtered off and from the filtrate obtained solvent is evaporated. Racemic naphythylalanine methylester is obtained, dissolved in METHANOLIC NH3 and stirred. The mixture obtained is subjected to extractive work up. Racemic NAPHYTHYLALANINE amide is obtained. With Dess-Martin periodane in dichloromethane, T= 20 °C Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/65382; (2004); (A1) English View in Reaxys

99 %Chromat.

With tert.-butylnitrite, oxygen in water, Time= 15h, T= 50 °C , p= 760.051Torr Karimi, Babak; Farhangi, Elham; Chemistry - A European Journal; vol. 17; nb. 22; (2011); p. 6056 - 6060 View in Reaxys 5 :An amount of 3.87 mL oxalyl chloride (44.24 mmol) was dissolved in 100 mL DCM. The mixture was cooled to -60° C. An amount of 5.6 mL DMSO was added dropwise using a syringe. The mixture was stirred for 15 min. A solution of 5 g of naphthalene-1-methanol in 75 mL DCM was added dropwide. The reaction was continued for 1 h at -60° C. An amount of 20 mL triethylamine was added. The mixture was allowed to attain 15° C. The mixture was transferred to an extraction funnel, washed with water, 1M HCl, water and brine. The organic layer was then dried over magnesium sulfate and evaporated. The crude product was sufficiently pure to be used without further purification in the next step. With oxalyl dichloride, dimethyl sulfoxide in dichloromethane, Time= 1h, T= -60 °C Patent; EVOLVA SA; US2011/178112; (2011); (A1) English View in Reaxys With copper(ll) sulfate pentahydrate, sulfuric acid, dihydrogen peroxide in water, Time= 0.5h, T= 100 °C Ahmad, Jahir Uddin; Raeisaenen, Minna T.; Leskelae, Markku; Repo, Timo; Applied Catalysis A: General; vol. 411-412; (2012); p. 180 - 187

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View in Reaxys 75 %Chromat.

With oxygen, caesium carbonate in toluene, Time= 6h, T= 20 °C Karimi, Babak; Esfahani, Farhad Kabiri; Advanced Synthesis and Catalysis; vol. 354; nb. 7; (2012); p. 1319 1326 View in Reaxys

95 %Chromat.

With Iron(III) nitrate nonahydrate, sodium chloride in 1,2-dichloro-ethane, Time= 2h, T= 20 °C , p= 760.051Torr Tamura, Naoya; Aoyama, Tadashi; Takido, Toshio; Kodomari, Mitsuo; Synlett; vol. 23; nb. 9; (2012); p. 1397 1401 View in Reaxys

88 %Chromat.

With lithium hydroxide monohydrate, Pd/DNA in water, Time= 12h, T= 60 °C , Inert atmosphere Tang, Lin; Sun, Huayin; Li, Yunfeng; Zha, Zhenggen; Wang, Zhiyong; Green Chemistry; vol. 14; nb. 12; (2012); p. 3423 - 3428 View in Reaxys With oxygen in toluene, Time= 6h, T= 14.84 - 24.84 °C , p= 760.051Torr , UV-irradiation Sugano, Yoshitsune; Shiraishi, Yasuhiro; Tsukamoto, Daijiro; Ichikawa, Satoshi; Tanaka, Shunsuke; Hirai, Takayuki; Angewandte Chemie - International Edition; vol. 52; nb. 20; (2013); p. 5295 - 5299; Angew. Chem.; vol. 125; nb. 20; (2013); p. 5403 - 5407,5 View in Reaxys

95 %Chromat.

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C49H74N4O34, copper(II) acetate monohydrate, sodium carbonate in water, Time= 12h, Reflux, Green chemistry Zhang, Guofu; Han, Xingwang; Luan, Yuxin; Wang, Yong; Wen, Xin; Xu, Li; Ding, Chengrong; Gao, Jianrong; RSC Advances; vol. 3; nb. 42; (2013); p. 19255 - 19258 View in Reaxys

> 99 With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, Ir(4,4'-di-tert-butyl-2,2'-bipyridyl)(2-phenylpyridine)2(PF6), tet%Chromat. rabutyl-ammonium chloride, oxygen, sodium hydrogencarbonate in dichloromethane, water, Time= 48h, T= 20 °C , Irradiation, Green chemistry, Reagent/catalyst, Solvent, chemoselective reaction Liu, Dongwang; Zhou, Hongxia; Gu, Xiangyong; Shen, Xiaoqin; Li, Pixu; Chinese Journal of Chemistry; vol. 32; nb. 2; (2014); p. 117 - 122 View in Reaxys 97 %Spectr.

With tert.-butylnitrite, [Cu(4,7-bis(4-pyridyl)-1,1,3,3-tetramethylisoindolin-2-yloxyl)2(SiF6)], oxygen, Time= 24h, T= 80 °C , Sealed tube Li, Liangchun; Matsuda, Ryotaro; Tanaka, Iku; Sato, Hiroshi; Kanoo, Prakash; Jeon, Hyung Joon; Foo, Maw Lin; Wakamiya, Atsushi; Murata, Yasujiro; Kitagawa, Susumu; Journal of the American Chemical Society; vol. 136; nb. 21; (2014); p. 7543 - 7546 View in Reaxys

92 %Spectr.

General procedure for the oxidation General procedure: DMSO (2 mmol) in DCM was added to a solution of MeSiCl3 (0.5 mmol) in DCM at – 20 °C, after 3 h, low the temperature to – 78 °C, the color of the solution turned milky white, 1 equivalent of alcohol in DCM was slowly added, after being stirred for 3 h, 8 equivalents of Et3N was slowly added, then the reaction mixture was warmed to the room temperature and diluted by DCM, and then the organic solvents was evaporated. The residue was purified by flash chromatography (elution with petroleum ether 30 °C – 60 °C/diethyl ether), with dibromomethane or benzyl methyl ether as internal standard for 1HNMR yield. Stage 1: With Methyltrichlorosilane, dimethyl sulfoxide in dichloromethane, Time= 3h, T= -78 °C , Swern Oxidation Stage 2: With triethylamine in dichloromethane, T= -78 - 20 °C , Swern Oxidation Wang, Yuanxun; Wang, Chao; Sun, Jian; Synthetic Communications; vol. 44; nb. 20; (2014); p. 2961 - 2965 View in Reaxys Catalytic One-Pot Oxidation-Olefination; General Procedure

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General procedure: CuCl (2.5 mg, 0.025 mmol) and 1,10-phenanthroline (4.5 mg, 0.025mmol) were placed in a vessel and toluene (5 mL) was added. The resulting solution was stirred at r.t. until the solution became green and clear (5 to 10 min). Then K2CO3 (138 mg, 1 mmol) and EtO2CNH-NHCO2Et (18.5 mg, 0.125 mmol) were added. The solution was stirred at r.t. for another 10 min. Alcohol (0.60 mmol) was added, the mixture was heated at 90 °C under an O2 atmosphere (O2 balloon) until the reaction was completed (TLC analysis). The vessel was backfilled with N2, Ph3P (157.2 mg, 0.6 mmol), CuI (9.5mg, 0.05 mmol), LiOt-Bu (56.0 mg, 0.7 mmol), and tosylhydrazone (0.5 mmol) were added. The solution was stirred at 90 °C for 10 h. The solvent was removed under reduced pressure and the crude alkene was purified by flash chromatography (silica gel). With 1,10-Phenanthroline, diethyl hydrazodicarboxylate, oxygen, potassium carbonate, copper(l) chloride in toluene, T= 90 °C Sha, Qiang; Wei, Yunyang; Synthesis (Germany); vol. 46; nb. 17; (2014); p. 2353 - 2361; Art.No: SS-2014-H0185OP View in Reaxys General procedure of the catalytic reaction General procedure: 1 mmol benzyl alcohol, 1.375 g catalyst, 20 ml water, and15 ml ether were mixed in a flask (50 ml). A balloon wasused to introduce O2 at ambient pressure, keeping the temperatureat 30 °C for a given time. At the end of the reaction,a few drops of diluted HCl solution (1 mol/L) wereadded to the reaction system, and the pH of water wasadjusted to 3–4. After stirring, the catalyst was transferredinto the water and the upper organic layer was isolated forGC analysis. With oxygen in diethyl ether, water, Time= 15h, T= 30 °C , p= 760.051Torr , chemoselective reaction Zhu, Yaoqin; Xu, Jia; Lu, Ming; Journal of the Iranian Chemical Society; vol. 12; nb. 7; (2015); p. 1213 - 1219; Art.No: 584 View in Reaxys 2.3. Catalytic oxidation of alcohol General procedure: Liquid-phase catalytic oxidation of benzyl alcohol was carriedout in a 25 mL two-neck flask with reflux condenser and magneticallystirred autoclave heated in an oil bath under atmospheric pressure. Dioxygen was bubbled (10 mL/min) through a solutionof acetonitrile (ACN, 8 mL), benzyl alcohol (108 mg, 1 mmol), IBA (216 mg, 3 mmol), and catalyst (1.9 106 mmol, calculated on the intercalated metlloporphyrin) at 60°C. The product samples were drawn at regular time intervals and analyzed with a gas chromatograph(Shimadzu GC-2010AF) having a Chromopak capillarycolumn and FID detector. The products were further confirmedusing GC–MS (Shimadzu GCMS-2010). The conversions of the reactions were calculated with no allowance for the background. After the reaction, the resulting mixture was cooled and the catalyst was separated by centrifugation and washed with solvent. After drying in vacuum, the recycled catalyst can be reused in the next run under the same conditions. The conversion, yield of benzaldehyde, and selectivity presented here are based on the GC calculations using chlorobenzene as the internal standard reference compound. With oxygen, isobutyraldehyde in acetonitrile, Time= 1h, T= 60 °C , p= 760.051Torr , Reflux, Autoclave Zhou, Wei-You; Tian, Peng; Sun, Fu'An; He, Ming-Yang; Chen, Qun; Journal of Catalysis; vol. 335; (2016); p. 105 - 116 View in Reaxys Reaction Steps: 2 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 °C / Inert atmosphere 2: sodium carbonate; tris[2-phenylpyridinato-C2,N]iridium(III); diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / 1,4-dioxane / 3 h / 25 °C / Irradiation; Inert atmosphere With tris[2-phenylpyridinato-C2,N]iridium(III), di-isopropyl azodicarboxylate, diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, sodium carbonate, triphenylphosphine in tetrahydrofuran, 1,4-dioxane Zhang, Jing; Li, Yang; Zhang, Fuyuan; Hu, Chenchen; Chen, Yiyun; Angewandte Chemie - International Edition; vol. 55; nb. 5; (2016); p. 1872 - 1875; Angew. Chem.; vol. 128; nb. 5; (2016); p. 1904 - 1907,4 View in Reaxys 99 %Spectr.

2.3 Procedure for Alcohol Oxidation General procedure: A 15 mL test tube, which was equipped with a magnetic stirbar and charged with catalysts (0.05 equiv., 0.025 mmol) andTEMPO (0.05 equiv., 0.025 mmol), was evacuated andbackfilled with oxygen (this process was repeated a total ofthree times).To this mixture, alcohol (1 equiv., 0.5 mmol) andNMI (0.2 equiv., 0.1 mmol) was added with 1 mL of acetonitrile.Themixturewas stirred for the required time at 70 °C under an O2 balloon. At the end

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of the reaction, the mixturewas diluted by adding ethyl acetate and filtered through silicaplugs. The silica was washed several times with ethyl acetate,and the solvent was evaporated. A yield of the aldehyde productwas determined by integration using an internal standard(1,1,2,2-tetrachloroethane) in the 1H NMR spectrum. With 1-methyl-1H-imidazole, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, T= 70 °C Kim, Bo Ram; Oh, Jung Suk; Kim, Jinho; Lee, Chang Yeon; Catalysis Letters; vol. 146; nb. 4; (2016); p. 734 743 View in Reaxys Reaction Steps: 2 1: 1H-imidazole / dichloromethane / 20 °C 2: 4‐(acetylamino)‐2,2,6,6‐tetramethyl‐1‐oxopiperidinium tetrafluoroborate / acetonitrile / 72 h / 40 °C With 1H-imidazole, 4‐(acetylamino)‐2,2,6,6‐tetramethyl‐1‐oxopiperidinium tetrafluoroborate in dichloromethane, acetonitrile Loman, Jacob J.; Pistritto, Vincent A.; Kelly, Christopher B.; Leadbeater, Nicholas E.; Synlett; vol. 27; nb. 16; (2016); p. 2372 - 2377; Art.No: ST-2016-R0295-L View in Reaxys 65 %Chromat.

With C39H29N5ORu(2+)*2ClO4 (1-), dihydrogen peroxide in water, acetonitrile, Time= 12h, T= 70 °C , Reflux Singha Hazari, Arijit; Ray, Ritwika; Hoque, Md Asmaul; Lahiri, Goutam Kumar; Inorganic Chemistry; vol. 55; nb. 16; (2016); p. 8160 - 8173 View in Reaxys

54 %Spectr.

With 1-methyl-1H-imidazole, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, (x)C2H3N*C12H6N2O4 (2-)*4C16H12O4 (2-)*C

22H16O4

(2-)*Cu(1+)*4HO(1-)*I(1-)*4O(2-)*6Zr(4+)

in acetonitrile, Time= 6h, T= 20 °C , Catalytic behavior, Reagent/

catalyst Yuan, Shuai; Chen, Ying-Pin; Qin, Jun-Sheng; Lu, Weigang; Zou, Lanfang; Zhang, Qiang; Wang, Xuan; Sun, Xing; Zhou, Hong-Cai; Journal of the American Chemical Society; vol. 138; nb. 28; (2016); p. 8912 - 8919 View in Reaxys > 99 With tert.-butylnitrite, oxygen, acetic acid in toluene, Time= 4.5h, T= 50 °C , p= 750.075Torr , Reagent/catalyst %Chromat. Karimi, Babak; Farhangi, Elham; Vali, Hojatollah; Vahdati, Saleh; ChemSusChem; vol. 7; nb. 9; (2014); p. 2735 2741 View in Reaxys Reaction procedure for benzyl alcohol oxidation General procedure: Liquid-phase catalytic oxidation of benzyl alcohol was carriedout in a 25 mL two-neck-flask with reflux condenser and magnet-ically stirred autoclave heated in an oil bath under atmosphericpressure. Dioxygen was bubbled (10 mL/min) through a solution oftoluene (8 mL), benzyl alcohol (216 mg, 2 mmol), and catalyst (1.0 g)at 80C. The product samples were drawn at regular time intervalsand analyzed with a gas chromatography (Shimadzu GC-2010AF)having SE-30 capillary column and FID detector. The products werefurther confirmed using GC–MS (Shimadzu GCMS-2010) with a DB-5MS capillary column. After the reaction, the resulting mixture wascooled with ice bath and the catalyst was separated by centrifuga-tion and washed with solvent. After drying at room temperature invacuum, the recycled catalyst can be reused in the next run underthe same conditions. The conversion, yield of benzaldehyde andselectivity presented here are based on the GC calculations usingchlorobenzene as the internal standard reference compound. With oxygen in toluene, Time= 8h, T= 80 °C , p= 760.051Torr , Autoclave, Heating Zhou, Weiyou; Tao, Qianyun; Pan, Jiugao; Liu, Jie; Qian, Junfeng; He, Mingyang; Chen, Qun; Journal of Molecular Catalysis A: Chemical; vol. 425; (2016); p. 255 - 265 View in Reaxys With water, oxygen in tetrahydrofuran, Time= 48h, T= 25 °C , p= 760.051Torr Cheng, Hong-Gang; Miguélez, Javier; Miyamura, Hiroyuki; Yoo, Woo-Jin; Kobayashi, Shū; Chemical Science; vol. 8; nb. 2; (2017); p. 1356 - 1359 View in Reaxys With oxygen in water, Time= 3h, T= 16 °C , UV-irradiation, Catalytic behavior

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Chen, Yu-Zhen; Wang, Zhiyong U.; Wang, Hengwei; Lu, Junling; Yu, Shu-Hong; Jiang, Hai-Long; Journal of the American Chemical Society; vol. 139; nb. 5; (2017); p. 2035 - 2044 View in Reaxys 2.3. Typical Procedure for Alcohol Oxidation. General procedure: Liquid-phaseoxidation of 1-phenylethanol was performed in glass flaskequipped with a magnetic stirrer, reflux condenser, andthermometer. In a typical experiment, a mixture of the1-phenylethanol (2mmol), toluene (10 mL), and the catalyst(0.3 g) was transferred in a glass three-necked roundbottomedflask (100 mL); the resulting mixture was thenheated to desired temperature with vigorous stirring. Theoxidation experiment was started by bubbling oxygen gas ata flow rate of 20 mL/min into the reaction mixture. After thereaction, the solid catalyst was filtered off by centrifugationand the liquid productswere analyzed by gas chromatographyto determine the conversion of the alcohol and productselectivity by GC, 7890A,Agilent Technologies Inc., equippedwith a flame ionization detector (FID) and a 19019S-001 HPPONAcolumn. With oxygen in toluene, Time= 0.333333h, T= 100 °C Assal, Mohamed E.; Kuniyil, Mufsir; Shaik, Mohammed Rafi; Khan, Mujeeb; Al-Warthan, Abdulrahman; Siddiqui, Mohammed Rafiq H.; Adil, Syed Farooq; Journal of Chemistry; vol. 2017; (2017); Art.No: 2937108 View in Reaxys With manganese(IV) oxide in acetonitrile, Time= 4h Alegre-Requena, Juan V.; Marqués-López, Eugenia; Herrera, Raquel P.; Advanced Synthesis and Catalysis; vol. 360; nb. 1; (2018); p. 124 - 129 View in Reaxys

O OH

Rx-ID: 1745441 View in Reaxys 2/284 Yield 93 %

Conditions & References With 1H-imidazole, sodium periodate in water, acetonitrile, Time= 30h, T= 20 °C Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Mohammadpoor-baltork, Iraj; Sirjanian, Narges; Parand, Somayeh; Bioorganic and Medicinal Chemistry; vol. 17; nb. 9; (2009); p. 3394 - 3398 View in Reaxys

90 %

With 1H-imidazole, sodium periodate, [Mn(III)-salophen]Cl in water, acetonitrile, Time= 0.25h, T= 20 °C Mirkhani, Valiollah; Tangestaninejad, Shahram; Moghadam, Majid; Moghbel, Maryam; Bioorganic and Medicinal Chemistry; vol. 12; nb. 5; (2004); p. 903 - 906 View in Reaxys

89 %

With 1H-imidazole, sodium periodate, {Mn(III)[5,10,15,20-tetrakis(4-H2N-Ph)porphyrin]}polystyrene in acetonitrile, Time= 6h, T= 20 °C Mirkhani, Valiollah; Tangestaninejad, Shahram; Moghadam, Majid; Karimian, Zohreh; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 20; (2003); p. 3433 - 3435 View in Reaxys

88 %

With benzyltriphenylphosphonium peroxodisulfate in acetonitrile, Time= 0.5h, Heating, Oxidation, decarboxylation 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

86 %

With potassium 12-tungstocobaltate(III) in water, acetonitrile, Time= 0.2h, Microwave irradiation Farhadi; Ansari; Journal of the Iranian Chemical Society; vol. 8; nb. 2; (2011); p. 470 - 476 View in Reaxys

83 %

With oxygen, copper diacetate in dimethyl sulfoxide, Time= 18h, T= 120 °C , Sealed tube

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Feng, Qiang; Song, Qiuling; Journal of Organic Chemistry; vol. 79; nb. 4; (2014); p. 1867 - 1871 View in Reaxys 80 %

General Procedure for the preparation of Aldehydes and Ketones from Aryl acetic acids General procedure: In an oven dried tube containing a mixture of 4-methyl phenyl acetic acid 1a (200 mg, 1.33mmol) and potassium persulfate (360 mg, 2.66 mmol), water (2 mL) was added and heated at 90 °C for 12 h. Upon completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature (24°C) and it was extracted with ethyl acetate (3 x 5 mL). The crude product was purified by column chromatography to furnish compound 2a as colorless liquid (136 mg, 85percent yield). With dipotassium peroxodisulfate in water, Time= 12h, T= 90 °C , Green chemistry Mete, Trimbak B.; Khopade, Tushar M.; Bhat, Ramakrishna G.; Tetrahedron Letters; vol. 58; nb. 29; (2017); p. 2822 - 2825 View in Reaxys

74 %

With meso-tetrakis(tetraphenyl)porphyrin iron(III) chloride, tetrabutylammonium periodite in dichloromethane, Time= 4h, Ambient temperature Tangestaninejad, Shahram; Mirkhani, Valiollah; Journal of Chemical Research - Part S; nb. 12; (1998); p. 820 821 View in Reaxys

74 %

With mercury(II) fluoride, oxygen in acetonitrile, Time= 24h, T= 25 °C , Irradiation Farhadi, Saeid; Zaringhadam, Parisa; Sahamieh, Reza Zarei; Tetrahedron Letters; vol. 47; nb. 12; (2006); p. 1965 - 1968 View in Reaxys

70 %

With oxygen, mercury(II) oxide in methanol, acetonitrile, T= 25 °C , UV-irradiation Habibi, Mohammad H.; Farhadi, Saeid; Journal of Chemical Research; nb. 4; (2004); p. 296 - 297 View in Reaxys

60 %

With tetrabutylammonium periodite in 1,4-dioxane, Time= 8h, Heating Santaniello, Enzo; Ponti, Federico; Manzocchi, Ada; Tetrahedron Letters; vol. 21; (1980); p. 2655 - 2656 View in Reaxys

Rx-ID: 2002293 View in Reaxys 3/284 Yield 87 %

Conditions & References Synthesis of aromatic aldehydes General procedure: A 50 mL round-bottomed flask, equipped with a gas inlet tube, a refluxcondenser and a magnetic stirring bar was charged with MCM-41-2PPdCl2 (102 mg, 0.05 mmol Pd), aryl halide (5.0 mmol) and HCOONa(7.5 mmol). The flask was flushed with CO. DMF (5 mL) was addedby syringe and a slow stream of CO was passed into the suspension.The mixture was vigorously stirred at 110–130 °C for 2–20 h, cooledto room temperature and diluted with diethyl ether (50 mL). Thepalladium catalyst was separated from the mixture by filtration,washed with distilled water (2 × 10 mL), ethanol (2 × 10 mL) and ether(2 × 10 mL) and reused in the next run. The ethereal solution waswashed with water (3 × 20 mL), and dried over anhydrous magnesiumsulfate and concentrated under reduced pressure. The residue waspurified by flash column chromatography on silica gel (hexane–ethylacetate = 10 : 1). With sodium formate in N,N-dimethyl-formamide, Time= 5h, T= 110 °C , p= 760.051Torr Jiang, Jianwen; Wang, Pingping; Cai, Mingzhong; Journal of Chemical Research; vol. 38; nb. 4; (2014); p. 218 222 View in Reaxys

86 %

2.3. General procedure for the formylation of aryl iodides or bromides General procedure: A 50mL round-bottomed flask equipped with a gas inlet tube, a reflux condenser, and a magnetic stirring bar was charged with MCM-41-S-PdCl2 (173mg, 0.05 mmol Pd), aryl halide (5.0 mmol) and HCOONa (7.5

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mmol). The flask was flushed with carbon monoxide. DMF (5 mL) was added by syringe and a slow stream of CO was passed into the suspension. The mixture was vigorously stirred at 100–110°C for 4–24h, cooled to room temperature, and diluted with diethyl ether (50 mL). The palladium catalyst was separated from the mixture by filtration, washed with distilled water (2×10 mL), ethanol (2×10 mL) and ether (2×10 mL) and reused in the next run. The ethereal solution was washed with water (3×20mL) and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane–ethyl acetate=10:1). (0008) All formylation products were characterized by comparison of their spectra and physical data with authentic samples. IR spectra were determined on a Perkin-Elmer 683 instrument. 1H NMR (400MHz) and 13C NMR (100MHz) spectra were recorded on a Bruker Avance 400MHz spectrometer with TMS as an internal standard and CDCl3 as solvent. With sodium formate in N,N-dimethyl-formamide, Time= 12h, T= 100 °C , p= 760.051Torr Hao, Wenyan; Ding, Guodong; Cai, Mingzhong; Catalysis Communications; vol. 51; (2014); p. 53 - 57 View in Reaxys 85 %

General Procedure A for reductive carbonylation of aryl iodide to aromatic aldehyde underambient conditions. General procedure: A flask was charged with aryl iodide 1 (0.5 mmol), Pd(OAc)2 (2.4 mg, 0.01mmol), Na2CO3 (53.1 mg. 0.5 mmol), NaHCO3 (42.0 mg, 0.5 mmol), and PEG-400 (2 g) beforestandard cycles evacuation and backfilling with dry and pure carbon monoxide. Triethylsilane(162.8 μl, 1.0 mmol) was added successively. Then, the mixture was stirred at room temperaturefor the indicated time. At the end of the reaction, the reaction mixture was extracted with diethylether (3 × 10 mL). The organic phases were combined, and the volatile components wereevaporated under reduced pressure. The crude product was purified by column chromatography onsilica gel (petroleum ether / diethyl ether). With triethylsilane, palladium diacetate, sodium hydrogencarbonate, sodium carbonate, Time= 36h, T= 20 °C , p= 760.051Torr Han, Wei; Liu, Binbin; Chen, Junjie; Zhou, Qing; Synlett; vol. 28; nb. 7; (2017); p. 835 - 840 View in Reaxys

72 %

General experimental procedure for reductive carbonylation of (hetero)aryl iodides: The reaction was performed in high pressure autoclave of 100 mL capacity manufactured by M/s Amar Industries. Toluene (10 mL), Pd(acac)2 (3 mg, 1 mol percent), and dppm (7.7 mg, 2 mol percent) were added to the autoclave reactor. To this solution iodobenzene (204 mg, 1.0 mmol), n-hexadecane (50 mg, internal GC standard), TMEDA (N,N,N',N'-tetramethylethylenediamine, 1 equiv) were added. The mixture was flushed twice with CO/H2 1:1, then synthetic gas pressure was adjusted to 10 bar and the mixture was heated at 100 °C for 10 h. After completion of reaction, the reaction mixture was cooled to room temperature. The light yellow colored solution was evaporated and residue obtained was purified by column chromatography (silica gel, mesh size 60-120) using pet ether/ethyl acetate (95:05) as eluent to get the desired formylated product. With palladium(II) acetylacetonate, N,N,N,N,-tetramethylethylenediamine, hydrogen, bis-diphenylphosphinomethane in toluene, Time= 10h, T= 100 °C , p= 7500.75Torr , Autoclave Singh, Abhilash S.; Bhanage, Bhalchandra M.; Nagarkar, Jayashree M.; Tetrahedron Letters; vol. 52; nb. 18; (2011); p. 2383 - 2386 View in Reaxys

68 %

With 2,2'-azobis(isobutyronitrile), tri-n-butyl-tin hydride in benzene, Time= 2h, T= 110 °C , p= 66195.7Torr Ryu, Ilhyong; Kusano, Kazuya; Masumi, Norio; Yamazaki, Hirosi; Ogawa, Akiya; Sonoda, Noboru; Tetrahedron Letters; vol. 31; nb. 47; (1990); p. 6887 - 6890 View in Reaxys

Rx-ID: 4730709 View in Reaxys 4/284

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Yield

Conditions & References With silica gel, ferric nitrate in hexane, Time= 0.166667h, T= 50 °C , Yield given Hirano, Masao; Ukawa, Ken; Yakabe, Shigetaka; Morimoto, Takashi; Organic Preparations and Procedures International; vol. 29; nb. 4; (1997); p. 480 - 484 View in Reaxys

108 mg

General procedure for the conversion of aromatic carboxylic acids to aldehydes [Method A] General procedure: To a freshly distilled toluene solution (2.0 mL) in a screw-capped test tube under a N2 atmosphere were successively added a magnetic stirrer bar, carboxylic acid (1.0 mmol), 1,2-ethanedithiol (1.20 mmol, 113 mg), InI3 (0.05 mmol, 23 mg), and TMDS (2.0 mmol, 2.6 x 102 μL). The test tube was sealed with a cap that contained a PTFE septum, and was heated to 60 °C for 2 h. After 2 h, the mixture was quenched using H2O (0.5 mL). And then, H2O2 (30percent aqueous solution, 4 mmol, 0.5 mL) was added and stirred at room temperature for 15 h. The resultant mixture was directly subjected to a column tube filled with a silica gel (hexane as an eluent) to give the corresponding aldehydes, if necessary, further purified by bulb to bulb distillation. With indium (III) iodide, dihydrogen peroxide in water, toluene, Time= 15h, T= 20 °C , Inert atmosphere, Sealed tube Sakai, Norio; Minato, Kohei; Ogiwara, Yohei; Tetrahedron Letters; vol. 58; nb. 48; (2017); p. 4563 - 4567 View in Reaxys

N OH

Rx-ID: 4768451 View in Reaxys 5/284 Yield 97 %

Conditions & References With molybdenum(V) chloride, zinc in acetonitrile, Time= 0.116667h, T= 20 °C Firouzabadi, Habib; Jamalian, Arezu; Karimi, Babak; Bulletin of the Chemical Society of Japan; vol. 75; nb. 8; (2002); p. 1761 - 1764 View in Reaxys

95 %

With ammonium peroxydisulfate, Montmorillonite K10, silver nitrate in hexane, Time= 2.5h, T= 50 °C Hirano; Kojima; Yakabe; Morimoto; Journal of Chemical Research - Part S; nb. 7; (2001); p. 277 - 279 View in Reaxys

93 %

With iodine in acetonitrile, Time= 4h, Heating, deoximation Yadav; Sasmal, Pradip K.; Chand, Pratap K.; Synthetic Communications; vol. 29; nb. 21; (1999); p. 3667 - 3671 View in Reaxys

91 %

With iodic acid in dichloromethane, Time= 13h, T= 20 °C Chandrasekhar, Sosale; Gopalaiah, Kovuru; Tetrahedron Letters; vol. 43; nb. 22; (2002); p. 4023 - 4024 View in Reaxys

90 %

With tris[trinitratocerium(IV)] paraperiodate, Time= 0.583333h, T= 90 °C Shirini; Esm-Hosseini; Hejazi; Mohammadpoor-Baltork; Journal of Chemical Research; nb. 1; (2006); p. 29 - 31 View in Reaxys

80 %

With zirconium hydrogen sulfate, silica gel in hexane, Time= 2.2h, Heating Shirini; Zolfigol; Safari; Mohammadpoor-Baltork; Mirjalili; Tetrahedron Letters; vol. 44; nb. 40; (2003); p. 7463 7465 View in Reaxys

76 %

With ammonium thiosulphate, Time= 0.03h, Irradiation Varma, Rajender S.; Meshram, Harshadas M.; Tetrahedron Letters; vol. 38; nb. 31; (1997); p. 5427 - 5428 View in Reaxys

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Reaction Steps: 2 1.1: Et3N / diethyl ether / 1 h / 0 °C 2.1: Co2(CO)8; Et3N / diethyl ether / 0.25 h / 20 °C 2.2: H2O / methanol / 0.5 h / 20 °C With dicobalt octacarbonyl, triethylamine in diethyl ether, 1.1: Acetylation / 2.1: deoximation / 2.2: Dehydration Mukai, Chisato; Nomura, Izumi; Kataoka, Osamu; Hanaoka, Miyoji; Synthesis; nb. 11; (1999); p. 1872 - 1874 View in Reaxys 89 %Chromat.

With SnO2 nanoclusters embedded on mesoporous Sn(IV) organophosphonate framework in water, acetone, Time= 7h, Reflux Borah, Suchibrata; Bhattacharyya, Bagmita; Deka, Jumi; Borah, Aditya; Devi, Anuchaya; Deka, Dhanapati; Mishra, Shashank; Raidongia, Kalyan; Gogoi, Nayanmoni; Dalton Transactions; vol. 46; nb. 26; (2017); p. 8664 8672 View in Reaxys

O O

Rx-ID: 5198813 View in Reaxys 6/284 Yield 99 %

Conditions & References With bismuth(III) chloride in chloroform, Time= 0.333333h, Heating, deprotection Mohammadpoor-Baltork; Aliyan; Synthetic Communications; vol. 29; nb. 16; (1999); p. 2741 - 2746 View in Reaxys

99 %

With tin(ll) chloride in acetonitrile, Time= 0.0333333h, T= 25 °C , Hydrolysis Mohammadpoor-Baltork; Aliyan; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 38; nb. 10; (1999); p. 1223 - 1225 View in Reaxys

99 %

With H6P2W18O62 in toluene, Time= 0.0833333h, T= 100 °C Romanelli; Autino; Baronetti; Thomas; Synthetic Communications; vol. 34; nb. 21; (2004); p. 3909 - 3914 View in Reaxys

98 %

With caro's acid, silica gel in dichloromethane, Time= 0.116667h, Heating Lakouraj; Tajbakhsh; Khojasteh; Gholami; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 12; (2004); p. 2645 - 2651 View in Reaxys

97 %

With aluminium trichloride in acetonitrile, Time= 0.0833333h, Heating, Deacetylation Mohammadpoor-Baltork, Iraj; Aliyan, Hamid; Journal of Chemical Research - Part S; nb. 4; (1999); p. 272 - 273 View in Reaxys

95 %

With poly(4-vinylpyridine)-supported sulfuric acid in acetonitrile, Time= 1h, T= 50 °C , Green chemistry Dutta, Papia; Sarma, Parishmita; Borah, Ruli; Synthetic Communications; vol. 43; nb. 10; (2013); p. 1378 - 1386 View in Reaxys

92 %

With tetrachlorosilane in dichloromethane, Time= 0.5h, T= 20 °C Firouzabadi, Habib; Iranpoor, Nasser; Hazarkhani, Hassan; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 177; nb. 12; (2002); p. 2847 - 2858 View in Reaxys

90 %

With ammonium cerium(IV) nitrate in acetonitrile, Time= 5h, T= 70 °C

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Roy, Subhas Chandra; Banerjee, Biplab; Synlett; nb. 10; (2002); p. 1677 - 1678 View in Reaxys 90 %

With 2,6-dicarboxypyridinium chlorochromate in acetonitrile, Time= 0.233333h, T= 20 °C Hosseinzadeh, Rahman; Tajbakhsh, Mahmood; Shakoori, Alireza; Niaki, Mohammad Yazdani; Monatshefte fur Chemie; vol. 135; nb. 10; (2004); p. 1243 - 1249 View in Reaxys

92 %Chromat.

General procedure for deprotection of 1,1-diacetates General procedure: To a stirred mixture of aldehyde (1 mmol) and acetic anhydride (1.2 mmol), CMK-5-SO3H (0.023g, 1 molpercent) was added, and the mixture was stirred at room temperature for the appropriate time (table 1). The reaction progress was followed by GC. After completion of the protection reaction, water (3 mL) was added to the reaction mixture to perform the deprotection reaction. After completion of the cleavage reaction, Et2O (20 mL) wasadded and the reaction mixture was filtered to separate the catalyst. The solvent was evaporated under reduced pressure to afford the corresponding aldehydes. With water, Time= 0.583333h, T= 20 °C , Green chemistry Zareyee, Daryoush; Mirzajanzadeh, Ehsan; Khalilzadeh, Mohammad Ali; Journal of Chemical Sciences; vol. 127; nb. 7; (2015); p. 1229 - 1234 View in Reaxys General procedure for deprotection of 1,1-diacetates General procedure: To a stirred mixture of aldehyde (1 mmol) and acetic anhydride (1.5 mmol), MNPs-SA (25 mg) was added, and the mixture was stirred at room temperature for the appropriate time (Table 3). After completion of the protection reaction, water (3 mL) was added to the reaction mixture to perform the deprotection reaction. After completion of the cleavage reaction, Et2O (20 mL) was added and the reaction mixture was filtered to separate the catalyst. The solvent was evaporated under reduced pressure to afford the corresponding aldehydes. With water, T= 20 °C , Green chemistry, chemoselective reaction Sajjadifar, Sami; Nasri, Parastoo; Research on Chemical Intermediates; vol. 43; nb. 11; (2017); p. 6677 - 6689 View in Reaxys

Rx-ID: 41724977 View in Reaxys 7/284 Yield 85 %

Conditions & References With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II), 1,8-diazabicyclo[5.4.0]undec-7-ene in N,N-dimethyl-formamide, Time= 20h, T= 80 °C , p= 7500.75Torr , Autoclave, Green chemistry Yu, Bo; Yang, Zhenzhen; Zhao, Yanfei; Hao, Leiduan; Zhang, Hongye; Gao, Xiang; Han, Buxing; Liu, Zhimin; Chemistry - A European Journal; vol. 22; nb. 3; (2016); p. 1097 - 1102 View in Reaxys

75 %

21 : Example 21 iodobenzobenzene with CO2 and PHMS reaction synthesis of formylbenzobenzene In a 20 ml reactor, place 10 ml acetonitrile, 5mmol iodobenzobenzene, 15mmol PMHS with weight average molecular weight of 2000, 5.5mmol DBU, 0.01mmol palladium carbon catalyst consisting of a mass ratio of 10: 100 palladium nanoparticles and activated carbon carrier. Seal. Heat to 80 °C. Place CO2 to 1MPa. React for 20 hours. The results are as follows: iodobenzobenzene conversion is 100percent; main product is formylbenzobenzene, yield is 75percent. With carbon supported Pd nanoparticles, 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile, Time= 20h, T= 80 °C , p= 7500.75Torr , Sealed tube, Green chemistry Patent; Institute of Chemistry, Chinese Academy of Sciences; Liu, Zhimin; Yu, Bo; Zhang, Hongye; Zhao, Yanfei; Yang, Zhenzhen; Yang, Guanying; (10 pag.); CN104803835; (2017); (B) Chinese View in Reaxys

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OH H

Rx-ID: 42304120 View in Reaxys 8/284 Yield

Conditions & References

72 %

With palladium diacetate, triethylamine, dicyclohexyl-carbodiimide, tricyclohexylphosphine in N,N-dimethyl-formamide, Time= 10h, T= 60 °C , Inert atmosphere, Sealed tube Wu, Fu-Peng; Peng, Jin-Bao; Meng, Ling-Shen; Qi, Xinxin; Wu, Xiao-Feng; ChemCatChem; vol. 9; nb. 16; (2017); p. 3121 - 3124 View in Reaxys

66 %

Stage 1: With palladium diacetate, acetic anhydride, tricyclohexylphosphine in N,N-dimethyl-formamide, Time= 1h, T= 30 °C , Inert atmosphere, Green chemistry Stage 2: With triethylamine in N,N-dimethyl-formamide, Time= 6h, T= 80 °C , Inert atmosphere, Green chemistry Qi, Xinxin; Li, Chong-Liang; Wu, Xiao-Feng; Chemistry - A European Journal; vol. 22; nb. 17; (2016); p. 5835 5838 View in Reaxys

OH Br

Rx-ID: 44765879 View in Reaxys 9/284 Yield

Conditions & References

50 %

With nickel(II) chloride hexahydrate, (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile, caesium carbonate, 4,4'di-tert-butyl-2,2'- bipyridine in N,N-dimethyl-formamide, Time= 24h, T= 20 °C , Schlenk technique, Inert atmosphere, Irradiation Huang, He; Li, Xiangmin; Yu, Chenguang; Zhang, Yueteng; Mariano, Patrick S.; Wang, Wei; Angewandte Chemie - International Edition; vol. 56; nb. 6; (2017); p. 1500 - 1505; Angew. Chem.; vol. 129; nb. 6; (2017); p. 1522 - 1527,6 View in Reaxys

O O

Rx-ID: 45031741 View in Reaxys 10/284 Yield

Conditions & References

58 %, 11 % 4.2. General procedure for addition of 1,3-dicarbonyl compounds to alkenes General procedure: A solution of 1,3-diketone (5 mmol) and olefin (5 mmol) in 20 mL of a glacial acetic acid in a flame-dried flask was heated to 50 °C under nitrogen. Then 10 mmol of Mn(OAc)3*2H2O and 2 mmol of Cu(OAc)2 were added to the solution. The dark brown solution became lighter as the Mn(III) was reduced. When the reaction was complete, the solution was colorless to light blue-green with a variable amount of white precipitate present. Water was added to the reaction mixture and the precipitate was dissolved. The solution was extracted with methylene chloride. The combined organic layers were washed several times with saturated NaHCO3 solution and then water and dried (MgSO4). Evaporation of the solvent gave the crude compound, which was purified by crystallization or column chromatography. With copper(II) acetate dihydrate, manganese(III) triacetate dihydrate in acetic acid, Time= 2h, T= 50 °C , Inert atmosphere Çalışkan, Raşit; Nohut, Neslihan; Yılmaz, Özlem; Sahin, Ertan; Balci, Metin; Tetrahedron; vol. 73; nb. 4; (2017); p. 291 - 297

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View in Reaxys

O O O

Rx-ID: 45031750 View in Reaxys 11/284 Yield

Conditions & References

100 %

With copper(II) acetate dihydrate, manganese(III) triacetate dihydrate in acetic acid, Time= 24h, T= 50 °C , Inert atmosphere Çalışkan, Raşit; Nohut, Neslihan; Yılmaz, Özlem; Sahin, Ertan; Balci, Metin; Tetrahedron; vol. 73; nb. 4; (2017); p. 291 - 297 View in Reaxys

(v4)

S O

– (v1)

C– Zn 2+

(v2)

ClLi

Rx-ID: 45079835 View in Reaxys 12/284 Yield 73 %

Conditions & References With trifuran-2-yl-phosphane, palladium diacetate in tetrahydrofuran, toluene, Time= 2h, T= 0 °C , Schlenk technique Haraguchi, Ryosuke; Tanazawa, Sho-Go; Tokunaga, Naoya; Fukuzawa, Shin-Ichi; Organic Letters; vol. 19; nb. 7; (2017); p. 1646 - 1649 View in Reaxys

Rx-ID: 45079860 View in Reaxys 13/284 Yield

Conditions & References Reaction Steps: 2 1.1: acetic anhydride / 2.5 h / 45 °C / Schlenk technique 1.2: 24 h / 30 °C / Schlenk technique 2.1: palladium diacetate; trifuran-2-yl-phosphane / tetrahydrofuran; toluene / 2 h / 0 °C / Schlenk technique With trifuran-2-yl-phosphane, palladium diacetate, acetic anhydride in tetrahydrofuran, toluene Haraguchi, Ryosuke; Tanazawa, Sho-Go; Tokunaga, Naoya; Fukuzawa, Shin-Ichi; Organic Letters; vol. 19; nb. 7; (2017); p. 1646 - 1649 View in Reaxys

N OH

Rx-ID: 45341720 View in Reaxys 14/284 Yield

Conditions & References With dibenzyl diselenide, dihydrogen peroxide in Petroleum ether, Time= 24h, T= 60 °C , Overall yield = 51 percent Jing, Xiaobi; Yuan, Dandan; Yu, Lei; Advanced Synthesis and Catalysis; vol. 359; nb. 7; (2017); p. 1194 - 1201

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View in Reaxys

O O

Rx-ID: 45615773 View in Reaxys 15/284 Yield

Conditions & References

67 %

With 1,2,3,4-tetrahydroisoquinoline in acetonitrile, Time= 24h, Green chemistry Huang, He; Yu, Chenguang; Li, Xiangmin; Zhang, Yongqiang; Zhang, Yueteng; Chen, Xiaobei; Mariano, Patrick S.; Xie, Hexin; Wang, Wei; Angewandte Chemie - International Edition; vol. 56; nb. 28; (2017); p. 8201 - 8205; Angew. Chem.; vol. 129; nb. 28; (2017); p. 8313 - 8317,5 View in Reaxys

Rx-ID: 45849845 View in Reaxys 16/284 Yield

Conditions & References

58 %

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

Rx-ID: 46421541 View in Reaxys 17/284 Yield

Conditions & References With (.eta.(6)-benzene)chloro[1,2-bis(diphenylphosphino)ethane]ruthenium(II) chloride in benzene, Time= 24h, T= 120 °C , Inert atmosphere, Schlenk technique, Sealed tube Kim, Kicheol; Moeljadi, Adhitya Mangala Putra; Hirao, Hajime; Hong, Soon Hyeok; Advanced Synthesis and Catalysis; vol. 359; nb. 19; (2017); p. 3292 - 3298 View in Reaxys

F F F O

P+ O

O–

O O

Rx-ID: 46723286 View in Reaxys 18/284 Yield 0.085 g

Conditions & References A typical procedure for production of 2,4,6-trimethyl benzaldehyde General procedure: To a solution of TPPD (0.672 g, 1.2 mmol) in EtOH (3 mL), sodium formate (0.068 g, 1mmol) was added and the mixture allowed stirring for 30 min. Then, mesitylene (0.14 mL, 1mmol) was added to this solution and the mixture was stirred for 60 min at room temperature.After 65 min, the solvent was removed under reduced pressure and then the saturated sodiumbicarbonate solution (10 mL) was added. The mixture was extracted with chloroform (3x5mL) and the organic layer washed with water and dried over anhydrous MgSO4. The filtratewas

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evaporated and the crude product purified by silica gel column chromatography usingethyl acetate/n-hexane (3:7) as eluent to afford 2,4,6-trimethylbenzaldehyde (0.134 g, 82percent).The products are all known compounds. in ethanol, Time= 1.25h, T= 20 °C , regioselective reaction Khodaei, Mohammad M.; Alizadeh, Abdolhamid; Hezarkhani, Hadis Afshar; Chemistry Letters; vol. 46; nb. 6; (2017); p. 840 - 843 View in Reaxys

O O

Rx-ID: 46733117 View in Reaxys 19/284 Yield

Conditions & References

20 %, 25 %, 28 %

With oxygen, potassium carbonate in 1,4-dioxane, Time= 48h, T= 60 °C Kumar, Sandeep; Chaudhary, Abha; Bandna; Bhattacherjee, Dhananjay; Thakur, Vandna; Das, Pralay; New Journal of Chemistry; vol. 41; nb. 9; (2017); p. 3242 - 3245 View in Reaxys

Rx-ID: 342287 View in Reaxys 20/284 Yield 88 %

Conditions & References With sodium hydride, sodium iodide in tetrahydrofuran, mineral oil, T= 85 °C , Inert atmosphere, Sealed tube Too, Pei Chui; Chan, Guo Hao; Tnay, Ya Lin; Hirao, Hajime; Chiba, Shunsuke; Angewandte Chemie - International Edition; vol. 55; nb. 11; (2016); p. 3719 - 3723; Angew. Chem.; vol. 128; nb. 11; (2016); p. 3783 - 3787,5 View in Reaxys With LiAlH2(OEt)2 Brown; Tsukamoto; Journal of the American Chemical Society; vol. 81; (1959); p. 502 View in Reaxys

Rx-ID: 656891 View in Reaxys 21/284 Yield 92 %

Conditions & References With carbon tetrabromide, oxygen in acetonitrile, Time= 2h, T= 20 °C , Irradiation, Green chemistry Tripathi, Shubhangi; Singh, Sachchida N.; Yadav, Lal Dhar S.; RSC Advances; vol. 6; nb. 18; (2016); p. 14547 14551 View in Reaxys

26 %

With air, titanium(IV) oxide, silver sulfate in acetonitrile, Time= 5h, Ambient temperature, Irradiation Baciocchi; Rosato; Rol; Sebastiani; Tetrahedron Letters; vol. 33; nb. 37; (1992); p. 5437 - 5440 View in Reaxys With selenium(IV) oxide, T= 200 °C

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Ssultanow; Rodionow; Schemjakin; Zhurnal Obshchei Khimii; vol. 16; (1946); p. 2072,2075; ; (1948); p. 881 View in Reaxys Jensen et al.; Acta Chemica Scandinavica (1947-1973); vol. 6; (1952); p. 180,186 View in Reaxys 16.0 % Spectr.

With cerium(IV) triflate, water, Time= 22h, T= 20 °C Laali, Kenneth K.; Herbert, Mark; Cushnyr, Brad; Bhatt, Anand; Terrano, David; Journal of the Chemical Society. Perkin Transactions 1; nb. 6; (2001); p. 578 - 583 View in Reaxys Reaction Steps: 2 1: N-bromosuccinimide, benzoyl peroxide / benzene / 2 h / Heating 2: MeONa, 2-nitropropane / methanol / 7 h / 20 - 40 °C With N-Bromosuccinimide, Perbenzoic acid, 2-nitropropane, sodium methylate in methanol, benzene Hashizume; Ito; Yamada; Nagashima; Kanao; Tomoda; Sunazuka; Kumagai; Omura; Chemical and pharmaceutical bulletin; vol. 42; nb. 3; (1994); p. 512 - 520 View in Reaxys Reaction Steps: 2 1: bromine 2: hexamethylenetetramine; alcohol With ethanol, hexamethylenetetramine, bromine Mayer,F.; Sieglitz; Chemische Berichte; vol. 55; (1922); p. 1854 View in Reaxys With selenium(IV) oxide in 1,4-dioxane, Reflux Setoguchi, Masaki; Iimura, Shin; Sugimoto, Yuuichi; Yoneda, Yoshiyuki; Chiba, Jun; Watanabe, Toshiyuki; Muro, Fumihito; Iigo, Yutaka; Takayama, Gensuke; Yokoyama, Mika; Taira, Tomoe; Aonuma, Misato; Takashi, Tohru; Nakayama, Atsushi; MacHinaga, Nobuo; Bioorganic and Medicinal Chemistry; vol. 20; nb. 3; (2012); p. 1201 - 1212 View in Reaxys Reaction Steps: 2 1: N-Bromosuccinimide / tetrachloromethane / 4 h / 20 - 30 °C / Irradiation 2: 4-methylmorpholine N-oxide / 14 h / 20 °C / Reflux With N-Bromosuccinimide, 4-methylmorpholine N-oxide in tetrachloromethane Tabata, Masayuki; Moriyama, Katsuhiko; Togo, Hideo; European Journal of Organic Chemistry; vol. 2014; nb. 16; (2014); p. 3402 - 3410 View in Reaxys

Rx-ID: 2018910 View in Reaxys 22/284 Yield 95 %

Conditions & References With Bis(N-methylpiperazinyl) aluminum hydride in tetrahydrofuran, Time= 24h, Heating Hubert, Terrance D.; Eyman, Darrell, P.; Wiemer, David F.; Journal of Organic Chemistry; vol. 49; nb. 12; (1984); p. 2279 - 2281 View in Reaxys

80 %

With 9-borabicyclo[3.3.1]nonane dimer, lithium dihydrido borata-bicyclo[3.3.0]nonane in tetrahydrofuran, Time= 6h, Ambient temperature Cha, Jin Soon; Kim, Jin Euog; Oh, Se Yeon; Kim, Jong Dae; Tetrahedron Letters; vol. 28; nb. 39; (1987); p. 4575 - 4578 View in Reaxys

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With 9-borabicyclo[3.3.1]nonane dimer, tert.-butyl lithium, 1.) THF, room temp.; 2.) THF, pentane, -20 deg C, 10 min and room temp., 6 h, Yield given. Multistep reaction Cha, Jin Soon; Kim, Jin Euog; Yoon, Mal Sook; Kim, Young Shick; Tetrahedron Letters; vol. 28; nb. 49; (1987); p. 6231 - 6234 View in Reaxys With ThxBHO-s-Bu in tetrahydrofuran, Time= 96h, T= 25 °C , Yield given Cha, Jin Soon; Chang, Seok Won; Kim, Jong Mi; Kwon, Oh Oun; Lee, Jae Cheol; Organic Preparations and Procedures International; vol. 29; nb. 6; (1997); p. 665 - 669 View in Reaxys Reaction Steps: 2 1.1: thionyl chloride / N,N-dimethyl-formamide; dichloromethane / 4 h / Reflux 1.2: 12 h / 20 °C 2.1: sodium hydride; sodium iodide / mineral oil; tetrahydrofuran / 85 °C / Inert atmosphere; Sealed tube With thionyl chloride, sodium hydride, sodium iodide in tetrahydrofuran, dichloromethane, N,N-dimethyl-formamide, mineral oil Too, Pei Chui; Chan, Guo Hao; Tnay, Ya Lin; Hirao, Hajime; Chiba, Shunsuke; Angewandte Chemie - International Edition; vol. 55; nb. 11; (2016); p. 3719 - 3723; Angew. Chem.; vol. 128; nb. 11; (2016); p. 3783 - 3787,5 View in Reaxys

N N

Rx-ID: 41615857 View in Reaxys 23/284 Yield

Conditions & References

51 %

With sodium dithionite, spermwhale myoglobin (H64V,V68A) in methanol, aq. phosphate buffer, Time= 24h, T= 20 °C , pH= 7, Catalytic behavior Giovani, Simone; Singh, Ritesh; Fasan, Rudi; Chemical Science; vol. 7; nb. 1; (2015); p. 234 - 239 View in Reaxys With sodium dithionite in methanol, aq. phosphate buffer, Time= 24h, T= 20 °C , pH= 7, Enzymatic reaction, Catalytic behavior Giovani, Simone; Alwaseem, Hanan; Fasan, Rudi; ChemCatChem; vol. 8; nb. 16; (2016); p. 2609 - 2613 View in Reaxys

Rx-ID: 41724965 View in Reaxys 24/284 Yield 76 %

Conditions & References With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II), 1,8-diazabicyclo[5.4.0]undec-7-ene in N,N-dimethyl-formamide, Time= 20h, T= 100 °C , p= 7500.75Torr , Autoclave, Green chemistry Yu, Bo; Yang, Zhenzhen; Zhao, Yanfei; Hao, Leiduan; Zhang, Hongye; Gao, Xiang; Han, Buxing; Liu, Zhimin; Chemistry - A European Journal; vol. 22; nb. 3; (2016); p. 1097 - 1102 View in Reaxys

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O O

O HO

Rx-ID: 41800979 View in Reaxys 25/284 Yield

Conditions & References

50 %, 17 %

With tris[2-phenylpyridinato-C2,N]iridium(III), diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, sodium carbonate in 1,4-dioxane, Time= 3h, T= 25 °C , Irradiation, Inert atmosphere Zhang, Jing; Li, Yang; Zhang, Fuyuan; Hu, Chenchen; Chen, Yiyun; Angewandte Chemie - International Edition; vol. 55; nb. 5; (2016); p. 1872 - 1875; Angew. Chem.; vol. 128; nb. 5; (2016); p. 1904 - 1907,4 View in Reaxys

OH O

Rx-ID: 42249151 View in Reaxys 26/284 Yield 65 %

Conditions & References 6 : Example 6 Following the procedure described in Example 1, was added 10mL round-bottomed flask 1a (0.5mmol, 80mg) and dichloromethane (2mL), followed by dropwise added ICl (1.5mmol, 1.5mL (1MinCH2Cl2)). The reaction was stirred at room temperature for 0.5 hours at room temperature, quenched by the addition of 2 mL of saturated sodium thiosulfate solution, extracted with dichloromethane (5 mL x 3), and the organic phase was washed successively with water and saturated brine, Sodium drying. Filtration, spin-drying and separation by silica gel column (petroleum ether / ethyl acetate = 10/1) gave 1-naphthaldehyde 2a (51 mg, 65percent) as a pale yellow liquid. With Iodine monochloride in dichloromethane, Time= 0.5h, T= 20 °C , Solvent, Temperature Patent; Henan Normal University; Fan, Xuesen; Li, Bin; Zhang, Xinying; Chen, Nana; Guo, Shenghai; (9 pag.); CN105601480; (2016); (A) Chinese View in Reaxys

64 %

Typical procedure for the preparation of 1-naphthaldehyde (2a). To a flask containing a solution of 1-phenylpent-4-yn-2-ol (1a, 80 mg, 0.5 mmol) in dry CH2Cl2 (2 mL) was added ICl (1 mL, 1 M in CH2Cl2) in a dropwise manner. Then, the mixture was stirred at room temperature under an air atmosphere for 0.5 h. The reaction was quenched with aqueous Na2S2O3 solution and extracted with CH2Cl2 (5 mL × 3). The combined organic layers were washed with brine, and then dried over anhydrous Na2SO4. The solvent was evaporated under vacuum and the crude product was purified by column chromatography on silica gel using petroleum ether–ethyl acetate (10:1) as eluent to give 1-naphthaldehyde (2a, 50 mg, 64percent). Substituted 1-naphthaldehydes (2b–2h) were obtained in a similar manner. Details of analytical data of products 2a-2h are presented as follows: 1-Naphthaldehyde (2a)3: 1H NMR (400 MHz, CDCl3) δ: 7.58–7.64 (m, 2H), 7.67–7.72 (m, 1H), 7.92 (d, J = 7.6 Hz, 1H), 7.98–7.99 (m, 1H), 8.10 (d, J = 8.0 Hz, 1H), 9.26 (d, J = 8.0 Hz, 1H), 10.40 (s, 1H); 13C NMR (100 MHz, CDCl3) δ: 124.9, 127.0, 128.5, 129.1, 130.6, 131.4, 133.7, 135.3, 136.7, 193.6; MS: m/z 157 (MH)+. With Iodine monochloride in dichloromethane, Time= 0.5h, T= 20 °C , Mechanism, Reagent/catalyst, Solvent, Temperature Li, Bin; Shen, Nana; Fan, Xuesen; Zhang, Xinying; Tetrahedron Letters; vol. 57; nb. 17; (2016); p. 1843 - 1846 View in Reaxys

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Rx-ID: 42249160 View in Reaxys 27/284 Yield

Conditions & References With Iodine monochloride in dichloromethane, Time= 0.5h, T= 20 °C Li, Bin; Shen, Nana; Fan, Xuesen; Zhang, Xinying; Tetrahedron Letters; vol. 57; nb. 17; (2016); p. 1843 - 1846 View in Reaxys

N O

Rx-ID: 42543849 View in Reaxys 28/284 Yield

Conditions & References

86 %

With tert.-butylhydroperoxide, water, sodium dodecyl-sulfate, copper(II) acetate monohydrate, Time= 3h, T= 120 °C Deb, Mohit L.; Pegu, Choitanya Dev; Borpatra, Paran J.; Baruah, Pranjal K.; RSC Advances; vol. 6; nb. 46; (2016); p. 40552 - 40559 View in Reaxys

Rx-ID: 43202462 View in Reaxys 29/284 Yield 81 %

Conditions & References General Procedure General procedure: To a round bottom flask equipped with a stirbar was added the silyl ether (1 equiv.) and theoxoammonium salt 1 (1 equiv.), followed by acetonitrile (0.2 M in the silyl ether). The solutionwas heated to 40 °C while stirring for 72 hours. After this time, the crude mixture was dilutedwith Et2O (200 mL) and deionized water (200 mL). The phases were separated and the aqueouslayer was extracted with Et2O (3 × 50 mL). The combined organic layers were washed withdeionized water (≈ 100 mL), brine (≈ 100 mL), and dried with Na2SO4. The solvent wasremoved in vacuo by rotary evaporation, and the resulting crude mixture was adhered to silicagel using 1.5 weight equivalents of SiO2 (relative to the theoretical yield). The dry-packedmaterial was gently added atop a silica gel plug, and the pure product was obtained using anappropriate solvent system as determined via TLC With 4‐(acetylamino)‐2,2,6,6‐tetramethyl‐1‐oxopiperidinium tetrafluoroborate in acetonitrile, Time= 72h, T= 40 °C Loman, Jacob J.; Pistritto, Vincent A.; Kelly, Christopher B.; Leadbeater, Nicholas E.; Synlett; vol. 27; nb. 16; (2016); p. 2372 - 2377; Art.No: ST-2016-R0295-L View in Reaxys

Rx-ID: 782845 View in Reaxys 30/284 Yield 96 %

Conditions & References With dihydrogen peroxide in ethanol, Time= 4h, Reflux, Green chemistry Bayat, Ahmad; Shakourian-Fard, Mehdi; Ramezanpour, Shaghayegh; Mahmoodi Hashemi, Mohammad; New Journal of Chemistry; vol. 39; nb. 5; (2015); p. 3845 - 3851 View in Reaxys

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82 %

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

80 %

With sodium periodate in N,N-dimethyl-formamide, Time= 0.583333h, T= 150 °C Das, Sasmita; Panigrahi; Maikap, Golak C.; Tetrahedron Letters; vol. 44; nb. 7; (2003); p. 1375 - 1377 View in Reaxys

75 %

With dihydrogen peroxide, vanadia, Aliquat 336 in water, Time= 20h, Heating Li, Chunbao; Zheng, Pengwu; Li, Jie; Zhang, Hang; Cui, Yi; Shao, Qiyun; Ji, Xiujie; Zhang, Jian; Zhao, Pengying; Xu, Yanli; Angewandte Chemie - International Edition; vol. 42; nb. 41; (2003); p. 5063 - 5066 View in Reaxys With ethanol, hexamethylenetetramine Mayer,F.; Sieglitz; Chemische Berichte; vol. 55; (1922); p. 1854 View in Reaxys With 2-nitropropane, sodium methylate in methanol, Time= 7h, T= 20 - 40 °C Hashizume; Ito; Yamada; Nagashima; Kanao; Tomoda; Sunazuka; Kumagai; Omura; Chemical and pharmaceutical bulletin; vol. 42; nb. 3; (1994); p. 512 - 520 View in Reaxys

259.3 mg

With 4-methylmorpholine N-oxide, Time= 14h, T= 20 °C , Reflux Tabata, Masayuki; Moriyama, Katsuhiko; Togo, Hideo; European Journal of Organic Chemistry; vol. 2014; nb. 16; (2014); p. 3402 - 3410 View in Reaxys Reaction Steps: 2 1: eosin y; oxygen / dimethyl sulfoxide / 12 h / 25 °C / Irradiation 2: eosin y / dimethyl sulfoxide / 24 h / 80 °C / Irradiation With oxygen, eosin y in dimethyl sulfoxide Li, Jian; Wang, Hongni; Liu, Li; Sun, Jiangtao; RSC Advances; vol. 4; nb. 91; (2014); p. 49974 - 49978 View in Reaxys

Rx-ID: 2772206 View in Reaxys 31/284 Yield 96 %

Conditions & References With lithium tetrafluoroborate in acetonitrile, Time= 48h, Ambient temperature Lipshutz, Bruce H.; Harvey, Daniel F.; Synthetic Communications; vol. 12; nb. 4; (1982); p. 267 - 278 View in Reaxys

95 %

With ammonium cerium(IV) nitrate in methanol, water, Time= 0.166667h, T= 20 °C , Ring cleavage Nair, Vijay; Nair, Latha G.; Balagopal, Lakshmi; Rajan, Roshini; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 38; nb. 11; (1999); p. 1234 - 1236 View in Reaxys

90 %

With polyaniline-sulfate salt, water, Time= 2h, Heating Palaniappan, Srinivasan; Narender, Puli; Saravanan, Chandrasekaran; Rao, Vaidya Jayathirtha; Synlett; nb. 12; (2003); p. 1793 - 1796 View in Reaxys

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86 %

With sodium tetrahydroborate, nickel(II) chloride hexahydrate in methanol, Time= 3h, Reflux, chemoselective reaction Khurana, Jitender M.; Dawra, Kiran; Sharma, Purnima; RSC Advances; vol. 5; nb. 16; (2015); p. 12048 - 12051 View in Reaxys

Rx-ID: 36367964 View in Reaxys 32/284 Yield

Conditions & References

51 %Chro- General procedure for the aerobic oxidative esterification reactions mat., 7 General procedure: Alcohol (0.50 mmol), hydrocarbon (10 mmol, 20 equiv), NaH2PO4 (74 mg, 97percent, anhy%Chromat. drous, 0.6mmol, 1.2 equiv), Bu4NI (36.9 mg, 0.10mmol, 20 mol percent), TBHP (70percent aqueous solution, 0.42 mL,3.0 mmol, 6 equiv) and MeCN (2 mL) were added into a Schlenk flask with a high vacuum valve (V = 45 mL) fitting in a Radleys parallel synthesis station.1 The solution was stirred vigorously and heated at 80 oC for 36 hours. After it was cooled down to room temperature, 5 mL of water was added and the products were extracted by 15 mL of chloroform for three times. After dried by anhydrous MgSO4,the solution was diluted with methanol to 25.00 mL for GC test. The ester products for GC standard curves were synthesized independently following the reported procedures.2 With tert.-butylhydroperoxide, sodium dihydrogenphosphate, tetrabutylammomium bromide, toluene in acetonitrile, Time= 36h, T= 80 °C , Schlenk technique Liu, Lianghui; Yun, Lin; Wang, Zikuan; Fu, Xuefeng; Yan, Chun-Hua; Tetrahedron Letters; vol. 54; nb. 39; (2013); p. 5383 - 5386 View in Reaxys 6 %ChroGeneral procedure for the aerobic oxidative esterificationreactions mat., 23 General procedure: Alcohol (0.50 mmol), hydrocarbon (10 mmol, 20 equiv), NaH2PO4 (74 mg, 97percent, anhy%Chromat. drous, 0.6mmol, 1.2 equiv), Bu4NI (36.9 mg, 0.10mmol, 20 mol percent), TBHP (70percent aqueous solution, 0.42 mL,3.0 mmol, 6 equiv) and MeCN (2 mL) were added into a Schlenk flask with a high vacuum valve (V = 45 mL) fitting in a Radleys parallel synthesis station.1 The solution was stirred vigorously and heated at 80 oC for 36 hours. After it was cooled down to room temperature, 5 mL of water was added and the products were extracted by 15 mL of chloroform for three times. After dried by anhydrous MgSO4,the solution was diluted with methanol to 25.00 mL for GC test. The ester products for GC standard curves were synthesized independently following the reported procedures.2 With tert.-butylhydroperoxide, sodium dihydrogenphosphate, iodine, toluene in acetonitrile, Time= 36h, T= 80 °C , Schlenk technique Liu, Lianghui; Yun, Lin; Wang, Zikuan; Fu, Xuefeng; Yan, Chun-Hua; Tetrahedron Letters; vol. 54; nb. 39; (2013); p. 5383 - 5386 View in Reaxys 2.3. Procedure for the catalytic oxidation of benzyl alcohol in acetone General procedure: A 50 mL three-necked glass flask was charged with a mixture ofDPPH (98.6 mmg, 0.25 mmol),WO3/Al2O3 (0.844 g,W: 3 mmol), alcohol(50 mmol), and 30 mL acetone. One neck was connected with awater condenser to reflux. Besides, there must be a deflated balloonon the top of the condenser to collect the evaporated acetone. And anotherneck was connected with a dropping funnel to add acetone.Then an oxygen steel cylinder was used to slowly provide the oxygenfor the reaction through the third neck with an air duct. The ventilationspeed must be adjusted according to the size of the balloon. Moreover,to maintain the airtightness of the whole reaction, the liquid level inthe dropping funnel should be kept in a certain height. Then themixturewas stirred at 80 °C for 4 h. The reaction mixture was subjected to GCanalysis to supervise the reaction process till the oxidation ended. With 2,2-diphenyl-1-picrylhydrazyl, tungusten oxide/alumina, oxygen in acetone, Time= 4h, T= 80 °C Zhu, Yaoqin; Xu, Jian; Lu, Ming; Catalysis Communications; vol. 48; (2014); p. 78 - 84 View in Reaxys

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in N,N-dimethyl-formamide, Time= 6h, T= 120 °C , Inert atmosphere Zhu, Yaoqin; Shen, Mengnan; Xia, Yonggen; Lu, Ming; Applied Organometallic Chemistry; vol. 29; nb. 3; (2015); p. 152 - 156 View in Reaxys

Rx-ID: 39529322 View in Reaxys 33/284 Yield

Conditions & References Reaction Steps: 2 1: sodium formate; palladium diacetate; 1,2-bis-(diphenylphosphino)ethane / dimethyl sulfoxide / Inert atmosphere; Sealed tube 2: water With water, sodium formate, palladium diacetate, 1,2-bis-(diphenylphosphino)ethane in dimethyl sulfoxide Zhang, Ying; Jiang, Xiao; Wang, Jin-Mei; Chen, Jing-Lei; Zhu, Yong-Ming; RSC Advances; vol. 5; nb. 22; (2015); p. 17060 - 17063 View in Reaxys

Rx-ID: 39529387 View in Reaxys 34/284 Yield

Conditions & References With water Zhang, Ying; Jiang, Xiao; Wang, Jin-Mei; Chen, Jing-Lei; Zhu, Yong-Ming; RSC Advances; vol. 5; nb. 22; (2015); p. 17060 - 17063 View in Reaxys

O O

Rx-ID: 39755352 View in Reaxys 35/284 Yield 67 %, 72 %

Conditions & References With sodium azide, copper(II) choride dihydrate, oxygen in N,N-dimethyl-formamide, Time= 10h, T= 100 °C , Schlenk technique, Sealed tube Gu, Lijun; Jin, Cheng; Chemical Communications; vol. 51; nb. 30; (2015); p. 6572 - 6575 View in Reaxys

Rx-ID: 39895726 View in Reaxys 36/284

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Yield

Conditions & References

68 %Chro- With tert.-butylhydroperoxide, 2C21H13N3O6 (2-)*4Co(2+)*HO(1-)*17H2O in neat (no solvent), Time= 4h, T= 50 °C , mat., 10 Green chemistry %Chromat. Kumar, Girijesh; Kumar, Gulshan; Gupta, Rajeev; Inorganic Chemistry; vol. 54; nb. 6; (2015); p. 2603 - 2615 View in Reaxys 55 %Chro- With C24H23MnN5O5S2, oxygen, isovaleraldehyde in acetonitrile, Time= 4h, T= 30 °C mat., 11 %Chromat. Bansal, Deepak; Kumar, Gulshan; Hundal, Geeta; Gupta, Rajeev; Dalton Transactions; vol. 43; nb. 39; (2014); p. 14865 - 14875 View in Reaxys

Rx-ID: 39991852 View in Reaxys 37/284 Yield

Conditions & References

30 %, 60 %

With sodium tetrahydroborate, nickel(II) chloride hexahydrate in methanol, Time= 18h, chemoselective reaction Khurana, Jitender M.; Dawra, Kiran; Sharma, Purnima; RSC Advances; vol. 5; nb. 16; (2015); p. 12048 - 12051 View in Reaxys

Rx-ID: 39991874 View in Reaxys 38/284 Yield

Conditions & References

70 %, 25 %

With sodium tetrahydroborate, nickel(II) chloride hexahydrate in methanol, Time= 8h, Reflux, chemoselective reaction Khurana, Jitender M.; Dawra, Kiran; Sharma, Purnima; RSC Advances; vol. 5; nb. 16; (2015); p. 12048 - 12051 View in Reaxys

(v3)

(v5)

O Fe TB-5 O O

(v3) (v3)

(v3)

Rx-ID: 41220571 View in Reaxys 39/284 Yield 78 %

Conditions & References With triethylamine, palladium dichloride in water, N,N-dimethyl-formamide, Time= 4.5h, T= 110 °C , p= 760.051Torr , Inert atmosphere Iranpoor, Nasser; Firouzabadi, Habib; Etemadi-Davan, Elham; Rostami, Abed; Rajabi Moghadam, Khashayar; Applied Organometallic Chemistry; vol. 29; nb. 11; (2015); p. 719 - 724 View in Reaxys

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(v3)

(v5)

O Fe TB-5 O

(v3) (v3)

(v3)

Rx-ID: 41220583 View in Reaxys 40/284 Yield

Conditions & References

70 %

With potassium carbonate, palladium dichloride in water, N,N-dimethyl-formamide, Time= 17h, T= 110 °C , p= 760.051Torr , Inert atmosphere Iranpoor, Nasser; Firouzabadi, Habib; Etemadi-Davan, Elham; Rostami, Abed; Rajabi Moghadam, Khashayar; Applied Organometallic Chemistry; vol. 29; nb. 11; (2015); p. 719 - 724 View in Reaxys

Rx-ID: 41436918 View in Reaxys 41/284 Yield

Conditions & References

61 %, 16 %

With Polystyrene-supported palladium(0) nanoparticles, Time= 0.75h, T= 130 °C , p= 5171.62Torr , Microwave irradiation, Sealed tube Shil, Arun K.; Kumar, Sandeep; Reddy, C. Bal; Dadhwal, Sumit; Thakur, Vandna; Das, Pralay; Organic Letters; vol. 17; nb. 21; (2015); p. 5352 - 5355 View in Reaxys

Rx-ID: 799086 View in Reaxys 42/284 Yield 97 %

Conditions & References With tri-n-butyl-tin hydride, tetrakis(triphenylphosphine) palladium(0) in benzene, Time= 0.166667h, Ambient temperature Four, P.; Guibe, F.; Journal of Organic Chemistry; vol. 46; nb. 22; (1981); p. 4439 - 4445 View in Reaxys

90 %

With tri-n-butyl-tin hydride in 1-methyl-pyrrolidin-2-one, T= 20 °C , Inert atmosphere Le Menez, Patrick; Hamze, Abdallah; Provot, Olivier; Brion, Jean-Daniel; Alami, Mouad; Synlett; nb. 7; (2010); p. 1101 - 1103 View in Reaxys

86 %

With polymethylhydrosiloxane, trifuran-2-yl-phosphane, tetrabutyl ammonium fluoride, potassium fluoride, tris-(dibenzylideneacetone)dipalladium(0) in tetrahydrofuran, water, Time= 1h, T= 20 °C Lee, Kyoungsoo; Maleczka Jr., Robert E.; Organic Letters; vol. 8; nb. 9; (2006); p. 1887 - 1888 View in Reaxys With Pd-BaSO4, xylene, Hydrogenation Shoesmith; Guthrie; Journal of the Chemical Society; (1928); p. 2332 View in Reaxys With lithium tri-t-butoxyaluminum hydride Brown; Rao; Journal of the American Chemical Society; vol. 80; (1958); p. 5368,5377 View in Reaxys

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With sodium tris(tert-butoxo)aluminium hydride in tetrahydrofuran, diethylene glycol dimethyl ether, Time= 3h, T= -78 °C , Yield given Cha, Jin Soon; Brown, Herbert C.; Journal of Organic Chemistry; vol. 58; nb. 17; (1993); p. 4732 - 4734 View in Reaxys 97 % Spectr.

With tri-n-butyl-tin hydride, tetrakis(triphenylphosphine) palladium(0) in benzene, Time= 2h, Ambient temperature Guibe, Francois; Four, Pierre; Riviere, Henriette; Journal of the Chemical Society, Chemical Communications; nb. 10; (1980); p. 432 - 433 View in Reaxys

98 % Chromat.

Stage 1: With aluminium hydride in tetrahydrofuran, Time= 1h, T= 20 °C , Metallation Stage 2: With pyridinium chlorochromate in tetrahydrofuran, dichloromethane, Time= 3h, T= 20 °C , Oxidation Cha, Jin Soon; Kim, Jong Mi; Chun, Joong Hyun; Kwon, Oh Oun; Kwon, Sang Yong; Han, Sung Wook; Organic Preparations and Procedures International; vol. 31; nb. 2; (1999); p. 204 - 207 View in Reaxys Reaction Steps: 2 1: K2CO3 / CH2Cl2 / 20 °C 2: 85 percent / triethylsilane; PPh3 / Pd(OAc)2 / dimethylformamide / 12 h / 60 °C With triethylsilane, potassium carbonate, triphenylphosphine, palladium diacetate in dichloromethane, N,N-dimethylformamide Nakanishi, Jun; Tatamidani, Hiroto; Fukumoto, Yoshiya; Chatani, Naoto; Synlett; nb. 6; (2006); p. 869 - 872 View in Reaxys

95 %Spectr.

With tert-butyl isocyanide, CpRu(PiPr3)(CH3CN)2PF6, Dimethylphenylsilane in [(2)H6]acetone, Time= 20h, T= 20 °C , chemoselective reaction Gutsulyak, Dmitry V.; Nikonov, Georgii I.; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 607 - 611 View in Reaxys With triethylsilane, bis-triphenylphosphine-palladium(II) chloride, (Z)-N,N-diisopropyl-2-styrylbenzamide in tetrahydrofuran, Time= 24h, T= 65 °C , Inert atmosphere, chemoselective reaction Bai, Xing-Feng; Xu, Li-Wen; Zheng, Long-Sheng; Jiang, Jian-Xiong; Lai, Guo-Qiao; Shang, Jun-Yan; Chemistry - A European Journal; vol. 18; nb. 26; (2012); p. 8174 - 8179 View in Reaxys

95 %Spectr.

I.I : I. General Procedure for Reactions in NMR Tubes General procedure: In a representative procedure, to a solution of acid chloride such as 4-BrC6H4COCl (0.043 g, 0.20 mmol), HSiMe2Ph (0.030 mL, 0.20 mmol), internal standard (tetramethylsilane (TMS) or Cp2Fe), and t-BuCN (0.002-0.004 mL, 10-20 mol percent) in acetone-d6 (0.6 mL) was added [Cp(Pri 3P)Ru(NCMe)2]+[PF6]− (0.005 g, 5 mol percent). The resulting mixture was mixed at room temperature and the progress of the reaction was monitored by NMR spectroscopy. The order of mixing the reagents other than the catalyst can differ as the reagents have not been observed to react with each other in the absence of a catalyst. However, it is useful to add the catalyst as the last reagent because addition of the catalyst before the nitrile has been observed to result in the deactivation of the catalyst. With tert-butyl isocyanide, CpRu(PiPr3)(CH3CN)2PF6, Dimethylphenylsilane in [(2)H6]acetone, Time= 20h, T= 20 °C , chemoselective reaction Patent; Brock Unviersity; Nikonov, Georgii; Gutsulyak, Dmitry; Lee, Sun Hwa; US2014/228579; (2014); (A1) English View in Reaxys

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Rx-ID: 854265 View in Reaxys 43/284 Yield 91 %

Conditions & References With C13H26B(1-)*K(1+) in tetrahydrofuran, Time= 24h, Ambient temperature Cha, Jin Soon; Yoon, Sook; Tetrahedron Letters; vol. 30; nb. 28; (1989); p. 3677 - 3680 View in Reaxys

45 %

General procedure for the reduction of nitriles into aldehydes: General procedure: 40-Methyl-2-biphenylcarbonitrile 1d (Table 2 entry 4). To a nitrogen purged screw-capedvial containing 1d (630 mg, 3.3 mmol, 1.0 equiv) in 500 lL of toluene wereadded TMDS (5.8 mL, 32.8 mmol, 10.0 equiv) and V(O)(OiPr)3 (780 lL,3.3 mmol, 1.0 equiv) at rt. The mixture was then heated at 60 C for 20 h(the colorless solution turned into deep purple) and then cooled to roomtemperature. The clear solution was diluted with toluene (10 mL) and acidifiedusing aqueous H3PO4 85percent (2.0 g diluted in 5.0 ml of water, 5.2 equiv). Theorganic layer was separated, washed with aqueous 1 m HCl (3 10 mL), driedover MgSO4 and concentrated under vacuum (40-methyl-2biphenylcarboxaldehyde 2d was present in 70percent estimated GC yield). Flashcolumn chromatography on silica gel (cyclohexane/ethyl acetate 9:1) afforded2d in 60percent isolated yield With 1,1,3,3-Tetramethyldisiloxane, vanadium(V) oxytriisopropoxide in toluene, Time= 20h, T= 60 °C Laval, Stephane; Dayoub, Wissam; Pehlivan, Leyla; Metay, Estelle; Delbrayelle, Dominique; Mignani, Gerard; Lemaire, Marc; Tetrahedron Letters; vol. 55; nb. 1; (2014); p. 23 - 26 View in Reaxys With hydrogenchloride, ethyl acetate, tin(ll) chloride, T= 0 °C , Erhitzen des Reaktionsprodukts mit Wasserdampf Shoppee; Journal of the Chemical Society; (1933); p. 37,39 View in Reaxys Stephen; Stephen; Journal of the Chemical Society; (1956); p. 4695 View in Reaxys With hydrogenchloride, diethyl ether, tin(ll) chloride, Erwaermen des Reaktionsprodukts mit Wasser Stephen; Journal of the Chemical Society; vol. 127; (1925); p. 1877 View in Reaxys With sodium triethoxyalanate Hesse; Schroedel; Justus Liebigs Annalen der Chemie; vol. 607; (1957); p. 24,30 View in Reaxys With lithium triethoxyaluminum hydride Brown et al.; Tetrahedron Letters; nb. 3; (1959); p. 9 View in Reaxys Brown; Garg; Journal of the American Chemical Society; vol. 86; (1964); p. 1085,1087 View in Reaxys With diisobutylaluminium hydride Scharkin; Chorlina; Doklady Akademii Nauk SSSR; vol. 116; (1957); p. 422; ; 112-117 <1957> 879 View in Reaxys With ethanol, water, nickel, Hydrogenation.weiteres Reagens:Essigester Rupe; Becherer; Helvetica Chimica Acta; vol. 6; (1923); p. 882 View in Reaxys With sodium tris(diethylamino)aluminum hydride in tetrahydrofuran, Time= 1h, T= 25 °C , Yield given Cha, Jin Soon; Jeoung, Min Kyoo; Kim, Jong Mi; Kwon, Oh Oun; Lee, Jae Cheol; Organic Preparations and Procedures International; vol. 26; nb. 5; (1994); p. 583 - 588

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View in Reaxys Stage 1: With lithium tris(dihexylamino)aluminum hydride in tetrahydrofuran, Time= 1h, T= 0 °C , Reduction Stage 2: With hydrogenchloride in tetrahydrofuran, Hydrolysis Cha, Jin Soon; Lee, Sung Eun; Lee, Heung Soo; Organic Preparations and Procedures International; vol. 24; nb. 3; (1992); p. 331 - 334 View in Reaxys Reaction Steps: 2 1: CH2Cl2 / 72 h / Heating 2: 1) Et3SiH, 2) H2O / 1) CH2Cl2, reflux, 2) heating With triethylsilane, water in dichloromethane Fry, James L.; Ott, Roger A.; Journal of Organic Chemistry; vol. 46; nb. 3; (1981); p. 602 - 607 View in Reaxys 91 %Chromat.

With lithium diisobutyl-iso-propoxyaluminium hydride in tetrahydrofuran, hexane, Time= 6h, T= 20 °C Choi, Young Mi; Yoo, Min; An, Duk Keun; Bulletin of the Korean Chemical Society; vol. 31; nb. 2; (2010); p. 473 474 View in Reaxys

Rx-ID: 36722394 View in Reaxys 44/284 Yield

Conditions & References

20 %, 77 %

Typical procedure for formylation of aryl halides catalyzed byPdO/Co3O4(Table 2) General procedure: The suspension of 5 wtpercent PdO/Co3O4(20 mg, 1.6 molpercent Pd atomand 47 molpercent Co to substrate) in dioxane (1 mL) in a stainlessautoclave attached a glass tube was stirred at 120C under H2atmosphere (2 MPa) for 2 h. After cooling to RT, aryl halide 1(0.5 mmol), K2CO3(0.5 mmol) and dioxane (1 mL) were added andstirred at 140C for 20 h under CO:H2= 3:1 atmosphere (4 MPa).The reaction mixture was analyzed by GC using tridecane (30 L,0.1 mmol) as an internal standard after filtration through celite toremove the catalyst. The products 2 and 3 were identified by com-parison of the retention time of GC with the authentic samples. Thealdehydes 2a–f and 2h–k were also characterized by1H and13CNMR after chromatographic purifications. Other aldehydes werefound to be difficult to isolate due to low yields and volatilities. With hydrogen, potassium carbonate in 1,4-dioxane, Time= 20h, T= 120 - 140 °C , p= 30003Torr , Autoclave, Reagent/catalyst Hamasaki, Akiyuki; Yasutake, Yutaro; Norio, Takafumi; Ishida, Tamao; Akita, Tomoki; Ohashi, Hironori; Yokoyama, Takushi; Honma, Tetsuo; Tokunaga, Makoto; Applied Catalysis A: General; vol. 469; (2014); p. 146 152 View in Reaxys

Rx-ID: 37172523 View in Reaxys 45/284 Yield 25 %, 62 %

Conditions & References With palladium on activated charcoal, 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile, Time= 20h, T= 80 °C , Autoclave Yu, Bo; Zhao, Yanfei; Zhang, Hongye; Xu, Jilei; Hao, Leiduan; Gao, Xiang; Liu, Zhimin; Chemical Communications; vol. 50; nb. 18; (2014); p. 2330 - 2333 View in Reaxys

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N O

H 2N

Rx-ID: 37362611 View in Reaxys 46/284 Yield

Conditions & References

72 %, 18 %

With oxygen in neat (no solvent), Time= 5.5h, T= 110 °C , Schlenk technique, Green chemistry, Reagent/catalyst Ahmad, Shahzad; Gopalaiah, Kovuru; Chandrudu, Sankala Naga; Nagarajan, Rajamani; Inorganic Chemistry; vol. 53; nb. 4; (2014); p. 2030 - 2039 View in Reaxys

N I

Rx-ID: 38112133 View in Reaxys 47/284 Yield

Conditions & References

84 %

Stage 1: With triethylsilane, palladium diacetate, sodium carbonate, CyJohnPhos in N,N-dimethyl-formamide, Time= 8h, T= 65 °C , Inert atmosphere, Sealed tube, Green chemistry Stage 2: With water, Green chemistry Jiang, Xiao; Wang, Jin-Mei; Zhang, Ying; Chen, Zhong; Zhu, Yong-Ming; Ji, Shun-Jun; Organic Letters; vol. 16; nb. 13; (2014); p. 3492 - 3495 View in Reaxys

Rx-ID: 38917737 View in Reaxys 48/284 Yield

Conditions & References

66 %

With dihydrogen peroxide, tetra-(n-butyl)ammonium iodide in N,N-dimethyl acetamide, Time= 24h, T= 100 °C , Green chemistry Gong, Jin-Long; Qi, Xinxin; Wei, Duo; Feng, Jian-Bo; Wu, Xiao-Feng; Organic and Biomolecular Chemistry; vol. 12; nb. 38; (2014); p. 7486 - 7488 View in Reaxys

O Br

Rx-ID: 39989067 View in Reaxys 49/284 Yield 54 %

Conditions & References With triethylsilane, dichloro bis(acetonitrile) palladium(II), sodium carbonate, 1,4-di(diphenylphosphino)-butane in N,N-dimethyl-formamide, Time= 20h, T= 20 - 100 °C , p= 15001.5Torr , Inert atmosphere, Autoclave Natte, Kishore; Dumrath, Andreas; Neumann, Helfried; Beller, Matthias; Angewandte Chemie - International Edition; vol. 53; nb. 38; (2014); p. 10090 - 10094; Angew. Chem.; vol. 126; nb. 38; (2015); p. 10254 - 10258,5 View in Reaxys

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Rx-ID: 40269893 View in Reaxys 50/284 Yield

Conditions & References With Al{C4H3N(2-CHNCH2Py)Me2} in chloroform-d1, Inert atmosphere, Meerwein-Ponndorf-Verley Reduction, Reagent/catalyst Hsu, Shu-Ya; Hu, Ching-Han; Tu, Cheng-Yi; Lin, Chia-Her; Chen, Ren-Yung; Datta, Amitabha; Huang, JuiHsien; European Journal of Inorganic Chemistry; vol. 2014; nb. 11; (2014); p. 1965 - 1973 View in Reaxys

Rx-ID: 46451555 View in Reaxys 51/284 Yield

Conditions & References

38 %Chro- With oxygen in cyclohexane, Time= 48h, T= 90 °C , p= 750.075Torr mat., 62 %Chromat. Li, Xinle; Guo, Zhiyong; Xiao, Chaoxian; Goh, Tian Wei; Tesfagaber, Daniel; Huang, Wenyu; ACS Catalysis; vol. 4; nb. 10; (2014); p. 3490 - 3497 View in Reaxys

Rx-ID: 761193 View in Reaxys 52/284 Yield 97 %

Conditions & References With 1-dodecyl-3-methylimidazolium iron chloride, periodic acid, Time= 1.5h, T= 30 °C Hu, Yu Lin; Liu, Qi Fa; Lu, Ting Ting; Lu, Ming; Catalysis Communications; vol. 11; nb. 10; (2010); p. 923 - 927 View in Reaxys

91 %

With 4-methylmorpholine N-oxide, 1-ethyl-3-methyl-1H-imidazol-3-ium chloride, potassium iodide, Time= 0.0333333h, T= 100 °C , Microwave irradiation, Ionic liquid Khumraksa, Bannarak; Phakhodee, Wong; Pattarawarapan, Mookda; Tetrahedron Letters; vol. 54; nb. 15; (2013); p. 1983 - 1986 View in Reaxys

87 %

With sodium nitrate, acetic acid in water, Time= 3h, Reflux Hu, Yu Lin; Wei, Wei; Liu, Qi Fa; Lu, Ming; Bulletin of the Chemical Society of Ethiopia; vol. 24; nb. 2; (2010); p. 277 - 282 View in Reaxys With hydrogenchloride, hexamethylenetetramine, acetic acid Price; Voong; Journal of Organic Chemistry; vol. 14; (1949); p. 111,114 View in Reaxys Badger; Journal of the Chemical Society; (1941); p. 535,537 View in Reaxys Angyal; Tetaz; Wilson; Organic Syntheses; vol. Coll. Vol. IV; (1963); p. 690 View in Reaxys Angyal et al.; Journal of the Chemical Society; (1950); p. 2141,2142,2144 View in Reaxys

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With ethanol, hexamethylenetetramine, acetic acid Rupe; Brentano; Helvetica Chimica Acta; vol. 19; (1936); p. 581,586 View in Reaxys Ruggli; Preuss; Helvetica Chimica Acta; vol. 24; (1941); p. 1345,1354 View in Reaxys With cuprous nitrate Blanc; Bulletin de la Societe Chimique de France; vol. <4> 33; (1923); p. 317; Chem. Zentralbl.; vol. 94; nb. I; (1923); p. 1571 View in Reaxys Reaction Steps: 2 1: 1) tetrabutylammonium chloride, NaOH / 1) benzene, H2O, room temperature, 20 min, 2) benzene, room temperature, 2 days 2: 82 percent / K2CO3 / o-xylene / 10 h / Heating With sodium hydroxide, tetrabutyl-ammonium chloride, potassium carbonate in o-xylene Trost, Barry M.; Liu, Guang-jian; Journal of Organic Chemistry; vol. 46; nb. 22; (1981); p. 4617 - 4620 View in Reaxys

Br–

P O

P+

Rx-ID: 35261743 View in Reaxys 53/284 Yield 84 %

Conditions & References in dichloromethane, Time= 0.0833333h, T= 50 °C , Microwave irradiation, Sealed tube Ramanathan, Mani; Hou, Duen-Ren; Arkivoc; vol. 2013; nb. 3; (2013); p. 98 - 108 View in Reaxys

O O N S Br

Rx-ID: 36051538 View in Reaxys 54/284 Yield 66 %

Conditions & References With triethylsilane, palladium diacetate, sodium carbonate, 1,4-di(diphenylphosphino)-butane in N,N-dimethyl-formamide, T= 90 °C , Inert atmosphere, Sealed tube Ueda, Tsuyoshi; Konishi, Hideyuki; Manabe, Kei; Angewandte Chemie - International Edition; vol. 52; nb. 33; (2013); p. 8611 - 8615; Angew. Chem.; vol. 125; nb. 33; (2013); p. 8773 - 8777,5 View in Reaxys

O HO

Rx-ID: 36367945 View in Reaxys 55/284 Yield 41 %Chromat., 11

Conditions & References General procedure for the aerobic oxidative esterificationreactions

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%ChroGeneral procedure: Alcohol (0.50 mmol), hydrocarbon (10 mmol, 20 equiv), NaH2PO4 (74 mg, 97percent, anhymat., 9 drous, 0.6mmol, 1.2 equiv), Bu4NI (36.9 mg, 0.10mmol, 20 mol percent), TBHP (70percent aqueous solution, 0.42 %Chromat. mL,3.0 mmol, 6 equiv) and MeCN (2 mL) were added into a Schlenk flask with a high vacuum valve (V = 45 mL) fitting in a Radleys parallel synthesis station.1 The solution was stirred vigorously and heated at 80 oC for 36 hours. After it was cooled down to room temperature, 5 mL of water was added and the products were extracted by 15 mL of chloroform for three times. After dried by anhydrous MgSO4,the solution was diluted with methanol to 25.00 mL for GC test. The ester products for GC standard curves were synthesized independently following the reported procedures.2 With tert.-butylhydroperoxide, sodium dihydrogenphosphate, potassium iodide in acetonitrile, Time= 36h, T= 80 °C , Schlenk technique Liu, Lianghui; Yun, Lin; Wang, Zikuan; Fu, Xuefeng; Yan, Chun-Hua; Tetrahedron Letters; vol. 54; nb. 39; (2013); p. 5383 - 5386 View in Reaxys

H N

HCl

N F O

Rx-ID: 36471979 View in Reaxys 56/284 Yield

Conditions & References 4.5.30 (S)-1-(4-tert-Butylphenyl)-2-fluoro-N-methyl-N-(naphthalen-1-ylmethyl)ethanamine hydrochloride ((S)-5) (S)-1-(4-tert-Butylphenyl)-2-fluoro-N-(naphthalen-1-ylmethyl)ethanamine hydrochloride ((S)-17a) (56mg, 0.150mmol) and N,N-diisopropylethylamine (58mg, 0.450mmol) were dissolved in dry DMF (9mL) in an Ace Pressure tube (15mL). MeI (2M in methyl tert-butyl ether, 300μL, 0.600mmol) was added while flushing the tube with N2. The tube was sealed and the reaction was stirred at 100°C for 24h. After cooling to rt, the mixture was diluted with diethyl ether (50mL) and then washed with brine (5×25mL). The combined organic phases were dried over Na2SO4, filtered, and the solvent was removed. The crude product was purified by silica-gel column chromatography (pentane:EtOAc, 8:2, Rf=0.78), by-product 1-naphthylaldehyde (Rf=0.47). The solvent was removed, and ether (5mL) was added before the product was precipitated by adding sat. hydrochloric acid in ether (0.5mL) drop wise. The white solid was washed several times with pentane. This gave 46mg (0.119mmol, 79percent) of a white solid; mp. 129–131°C; purity >98percent (HPLC, 280nm); ee: 97percent (HPLC, Phenomenex Lux Cellulose-1); [α]20D=+18.1[α]D20=+18.1 (c 1.00, MeOH); 1H NMR (CDCl3, 400MHz) δ: 1.32 (s, 9H), 2.22 (s, 3H), 3.95 (ddd, J=19.3Hz, 6.8Hz, 4.6Hz, 1H), 4.03 (s, 2H), 4.71–5.02 (m, 2H), 7.29–7.51 (m, 8H), 7.73–7.78 (m, 1H), 7.82–7.86 (m, 1H), 8.19–8.23 (m, 1H); 13C NMR (CDCl3, 100MHz) δ: 31.4 (3C), 34.6, 38.7 (d, J=1.4Hz), 57.8 (d, J=1.4Hz), 67.5 (d, J=18.3Hz), 84.2 (d, J=174.5Hz), 124.6, 125.2, 125.3 (2C), 125.6, 125.7, 127.3, 127.8, 128.2 (2C), 128.4, 132.4, 133.9, 134.8 (d, J=6.6Hz), 134.9, 150.1. 19F NMR (CDCl3, 564MHz) δ:−221.1 (d t, J=47.8, 19.8, Hz); IR (neat, cm−1): 3048, 2961, 2867, 2360, 1691, 1509, 1363, 1269, 1004, 775, 575; HRMS (EI): 349.2200 (calcd. 349.2200, M+) With N-ethyl-N,N-diisopropylamine in tert-butyl methyl ether, N,N-dimethyl-formamide, Time= 24h, T= 100 °C , Inert atmosphere, Sealed tube Krane Thvedt, Thor H.; Kaasa, Kristin; Sundby, Eirik; Charnock, Colin; Hoff, Bard Helge; European Journal of Medicinal Chemistry; vol. 68; (2013); p. 482 - 496 View in Reaxys

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NH 2 F N F Cl

Rx-ID: 36472183 View in Reaxys 57/284 Yield

Conditions & References Reaction Steps: 2 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 24 h / 50 °C 1.2: Saturated solution 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide; tert-butyl methyl ether / 24 h / 100 °C / Inert atmosphere; Sealed tube With N-ethyl-N,N-diisopropylamine in tert-butyl methyl ether, N,N-dimethyl-formamide, acetonitrile Krane Thvedt, Thor H.; Kaasa, Kristin; Sundby, Eirik; Charnock, Colin; Hoff, Bard Helge; European Journal of Medicinal Chemistry; vol. 68; (2013); p. 482 - 496 View in Reaxys

Rx-ID: 36505283 View in Reaxys 58/284 Yield

Conditions & References

92 %

With copper(l) iodide, oxygen in dimethyl sulfoxide, Time= 15h, T= 120 °C , Reagent/catalyst, Solvent, chemoselective reaction Zhang, Lin; Bi, Xihe; Guan, Xiaoxue; Li, Xingqi; Liu, Qun; Barry, Badru-Deen; Liao, Peiqiu; Angewandte Chemie - International Edition; vol. 52; nb. 43; (2013); p. 11303 - 11307; Angew. Chem.; vol. 125; nb. 43; (2013); p. 11513 - 11517,5 View in Reaxys

Cl SiH

Si O Cl

Rx-ID: 37034403 View in Reaxys 59/284 Yield

Conditions & References With bis(1,5-cyclooctadiene)dichloro[1,3-bis(1′-butylbenzimidazol-2′-yliden-3′-yl)benzene]dirhodium(I) in benzened6, Time= 0.08h, T= 100 °C , Catalytic behavior, Time, Reagent/catalyst, Overall yield = > 99 percent Huckaba, Aron J.; Hollis, T. Keith; Reilly, Sean W.; Organometallics; vol. 32; nb. 21; (2013); p. 6248 - 6256 View in Reaxys

Rx-ID: 1051097 View in Reaxys 60/284

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Yield 86 %

Conditions & References With N,N,N,N,-tetramethylethylenediamine, di-(1-adamantyl)-n-butylphosphine, hydrogen, palladium diacetate in toluene, Time= 20h, T= 100 °C , p= 3750.38Torr , Inert atmosphere Neumann, Helfried; Kadyrov, Renat; Wu, Xiao-Feng; Beller, Matthias; Chemistry - An Asian Journal; vol. 7; nb. 10; (2012); p. 2213 - 2216 View in Reaxys With tributyl-amine, hydrogen, bis(triphenylphosphine)palladium dibromide, p= 63350.6Torr Schoenberg,A.; Heck,R.F.; Journal of the American Chemical Society; vol. 96; nb. 25; (1974); p. 7761 - 7764 View in Reaxys

86 % Chromat.

With 4-methoxy-N'-tetramethylethylenediamine, hydrogen, catacxium A, palladium diacetate in toluene, Time= 16h, T= 100 °C , p= 3750.3Torr Klaus, Stefan; Neumann, Helfried; Zapf, Alexander; Struebing, Dirk; Huebner, Sandra; Almena, Juan; Riermeier, Thomas; Gross, Peter; Sarich, Martin; Krahnert, Wolf-Ruediger; Rossen, Kai; Beller, Matthias; Angewandte Chemie - International Edition; vol. 45; nb. 1; (2006); p. 154 - 158 View in Reaxys

61 % Chromat.

With tribenzylamine, tetrakis(triphenylphosphine) palladium(0) in acetonitrile, Time= 18h, T= 125 °C , p= 2585.7Torr Pri-Bar, I.; Buchman, O.; Journal of Organic Chemistry; vol. 49; nb. 21; (1984); p. 4009 - 4011 View in Reaxys

86 % Chromat.

With N,N,N,N,-tetramethylethylenediamine, hydrogen, catacxium A, palladium diacetate in toluene, Time= 16h, T= 100 °C , p= 3750.38Torr Brennfuehrer, Anne; Neumann, Helfried; Klaus, Stefan; Riermeier, Thomas; Almena, Juan; Beller, Matthias; Tetrahedron; vol. 63; nb. 27; (2007); p. 6252 - 6258 View in Reaxys

92 %Chromat.

With N,N,N,N,-tetramethylethylenediamine, hydrogen, palladium diacetate, catacxium A in toluene, T= 20 - 100 °C , p= 3750.38Torr , Autoclave Sergeev, Alexey G.; Neumann, Helfried; Spannenberg, Anke; Beller, Matthias; Organometallics; vol. 29; nb. 15; (2010); p. 3368 - 3373 View in Reaxys

O O

Rx-ID: 33465239 View in Reaxys 61/284 Yield 32 %, 32 %

Conditions & References 4.2. Typical procedure for one-pot conversion of aromatic bromides into aromatic ethyl esters with ethyl formate General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of pbromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I2 (1523 mg, 6 mmol), K2CO3 (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide ethyl 4-chlorobenzoate in 77percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil. Stage 1: With n-butyllithium in tetrahydrofuran, hexane, Time= 0.5h, T= -78 °C Stage 2: in tetrahydrofuran, hexane, Time= 3h, T= -78 °C Stage 3: With ethanol, iodine, potassium carbonate in hexane, Time= 18h, T= -78 - 20 °C

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Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 68; nb. 24; (2012); p. 4701 - 4709 View in Reaxys

E O

(-)-enantiomer,rel-configuration

(+)-enantiomer,rel-configuration

Rx-ID: 33925315 View in Reaxys 62/284 Yield

Conditions & References

36 %

With N,N'-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene silver chloride, iodosylbenzene, C42H30Cl2FeN3O2, sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate in dichloromethane, Time= 1h, T= 0 °C , optical yield given as percent ee, enantioselective reaction Niwa, Takashi; Nakada, Masahisa; Journal of the American Chemical Society; vol. 134; nb. 33; (2012); p. 13538 13541 View in Reaxys

E O

(+)-enantiomer,rel-configuration

(-)-enantiomer,rel-configuration

Rx-ID: 33925326 View in Reaxys 63/284 Yield

Conditions & References Reaction Steps: 2 1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 1.2: 24 h / 20 °C 2.1: N,N'-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene silver chloride; C42H30Cl2FeN3O2; iodosylbenzene; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 1 h / 0 °C With N,N'-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene silver chloride, iodosylbenzene, C42H30Cl2FeN3O2, tetra-(n-butyl)ammonium iodide, sodium hydride, sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate in tetrahydrofuran, dichloromethane Niwa, Takashi; Nakada, Masahisa; Journal of the American Chemical Society; vol. 134; nb. 33; (2012); p. 13538 13541 View in Reaxys

N S

S S

Rx-ID: 33963517 View in Reaxys 64/284 Yield 95 %

Conditions & References With nitric acid in water, T= 20 °C Ziyaei Halimehjani, Azim; Hajiloo Shayegan, Mojtaba; Hashemi, Mohammad Mahmoodi; Notash, Behrooz; Organic Letters; vol. 14; nb. 15; (2012); p. 3838 - 3841 View in Reaxys

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O E

O racemate

racemate

Rx-ID: 34033366 View in Reaxys 65/284 Yield

Conditions & References

45 %

General procedure for the synthesis of compound 4#10;#10;#10;#10;#10; General procedure: Solution of endoperoxides 3a-e (200 mg) in thiophene free dry benzene (250 mL) in an immersion well type Pyrex glass, water-cooled photoreactor were irradiated with UV light from a 125-Watt medium pressure Hg arc placed coaxially inside the reactor, in the presence of oxygen (continuously bubbled) for 20-25min. The resulting photolysates were concentrated under reduced pressure and their column chromatographic resolution over silica gel packed in hexane, using hexane–chloroform (7:3) as eluent, afforded compound 4 and aldehydes 5#10;#10;#10;#10;#10;#10; With oxygen, mercury in thiophene, benzene, Time= 0.25h, UV-irradiation Sharma, Vishal; Gupta, Vivek; Anthal, Sumati; Saxena, Ajit K.; Ishar, Mohan Paul S.; Tetrahedron Letters; vol. 53; nb. 42; (2012); p. 5649 - 5651 View in Reaxys

OH N

O O

Rx-ID: 34134648 View in Reaxys 66/284 Yield

Conditions & References With tris(acetonitrile)(.eta.5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate in ethanol, Time= 3h, T= 80 °C , Inert atmosphere Chen, Kang; Li, Hu; Lei, Zhi-Quan; Li, Yang; Ye, Wen-He; Zhang, Li-Sheng; Sun, Jian; Shi, Zhang-Jie; Angewandte Chemie - International Edition; vol. 51; nb. 39; (2012); p. 9851 - 9855 View in Reaxys

Rx-ID: 34226903 View in Reaxys 67/284 Yield 57 %, 10 %

Conditions & References 1 Stage 1: With iodine pentafluoride–pyridine–hydrogen fluoride in dichloromethane, Time= 24h, T= 20 °C Stage 2: With water Hara, Shoji; Monoi, Miki; Umemura, Ryosuke; Fuse, Chiaki; Tetrahedron; vol. 68; nb. 49; (2012); p. 10145 10150,6 View in Reaxys

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O O

Rx-ID: 29368084 View in Reaxys 68/284 Yield

Conditions & References

90 %

With Schwartz's reagent in tetrahydrofuran, Time= 0.5h, T= 20 °C Leighty, Matthew W.; Spletstoser, Jared T.; Georg, Gunda I.; Organic Syntheses; vol. 88; (2011); p. 427 - 437 View in Reaxys

75 %

With titanium(IV) isopropylate, 1,1,3,3-Tetramethyldisiloxane in methyl cyclohexane, Time= 24h, T= 20 °C , Inert atmosphere Laval, Stephane; Dayoub, Wissam; Favre-Reguillon, Alain; Demonchaux, Patrice; Mignani, Gerard; Lemaire, Marc; Tetrahedron Letters; vol. 51; nb. 16; (2010); p. 2092 - 2094 View in Reaxys

H 2N

Rx-ID: 332394 View in Reaxys 69/284 Yield

Conditions & References

70 %

With dihydrogen peroxide, vanadia in water, Time= 12h, T= 50 °C Chu, Guobiao; Li, Chunbao; Organic and Biomolecular Chemistry; vol. 8; nb. 20; (2010); p. 4716 - 4719 View in Reaxys With water, indole-2,3-dione Angyal et al.; Journal of the Chemical Society; (1949); p. 2704 View in Reaxys With oxalic acid, dimethyl sulfoxide, O-phenyl phosphorodichloridate, triethylamine, 1.) -10 deg C, 15 min, CH2Cl2, 2.) -10 deg C to 20 deg C, 45 min, 3.) 20 deg C, 30 min, Yield given. Multistep reaction Liu, Hsing-Jang; Nyangulu, James M.; Synthetic Communications; vol. 19; nb. 19; (1989); p. 3407 - 3412 View in Reaxys

N N

O O

Rx-ID: 29111547 View in Reaxys 70/284 Yield 76 %, 11 %, 52 %

Conditions & References With 2,2'-azobis(isobutyronitrile), tri-n-butyl-tin hydride in benzene, Time= 2h, T= 80 °C , Mechanism Kim, Taehoon; Kim, Kyongtae; Tetrahedron Letters; vol. 51; nb. 5; (2010); p. 868 - 871 View in Reaxys

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N O

Rx-ID: 28860970 View in Reaxys 71/284 Yield

Conditions & References

90 %

With hydrogenchloride, water, Time= 1h, T= 20 °C Denmark, Scott E.; Eklov, Brian M.; Yao, Peter J.; Eastgate, Martin D.; Journal of the American Chemical Society; vol. 131; nb. 33; (2009); p. 11770 - 11787 View in Reaxys

Rx-ID: 29222501 View in Reaxys 72/284 Yield

Conditions & References With benzophenone in acetonitrile, T= 20 °C , Inert atmosphere, UV-irradiation, Photolysis, Quantum yield, Reagent/ catalyst, Solvent Watanabe, Asako; Matsushita, Maya; Masuda, Aya; Igarashi, Tetsutaro; Sakurai, Tadamitsu; Heterocycles; vol. 78; nb. 10; (2009); p. 2431 - 2437 View in Reaxys

Rx-ID: 10510396 View in Reaxys 73/284 Yield

Conditions & References

85 %

With perchloric acid in methanol, water, Time= 0.25h, T= 25 - 30 °C Kumar, Raj; Kumar, Dinesh; Chakraborti, Asit K.; Synthesis; nb. 2; (2007); p. 299 - 303 View in Reaxys

85 %

With water in methanol, Time= 0.333333h, T= 25 - 30 °C Kumar, Dinesh; Kumar, Raj; Chakraborti, Asit K.; Synthesis; nb. 8; (2008); p. 1249 - 1256 View in Reaxys

O ZN

O N O

Rx-ID: 25975581 View in Reaxys 74/284 Yield

Conditions & References With trifluoroacetic acid, Time= 0.416667h, T= 75 °C

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Augustine, John Kallikat; Naik, Yanjerappa Arthoba; Mandal, Ashis Baran; Kundapur, Umesha; Journal of Organic Chemistry; vol. 73; nb. 3; (2008); p. 1176 - 1179 View in Reaxys

Rx-ID: 26047601 View in Reaxys 75/284 Yield

Conditions & References

12 %

With cesium pivalate, bis-diphenylphosphinomethane, palladium diacetate in N,N-dimethyl-formamide, Time= 12h, T= 120 °C Kesharwani, Tanay; Larock, Richard C.; Tetrahedron; vol. 64; nb. 26; (2008); p. 6090 - 6102 View in Reaxys

Rx-ID: 26047612 View in Reaxys 76/284 Yield

Conditions & References

71 %

With cesium pivalate, bis-diphenylphosphinomethane, palladium diacetate in N,N-dimethyl-formamide, Time= 2h, T= 120 °C Kesharwani, Tanay; Larock, Richard C.; Tetrahedron; vol. 64; nb. 26; (2008); p. 6090 - 6102 View in Reaxys

Rx-ID: 26047627 View in Reaxys 77/284 Yield 73 %

Conditions & References With cesium pivalate, bis-diphenylphosphinomethane, palladium diacetate in N,N-dimethyl-formamide, Time= 2h, T= 120 °C Kesharwani, Tanay; Larock, Richard C.; Tetrahedron; vol. 64; nb. 26; (2008); p. 6090 - 6102 View in Reaxys

N O

O O O

Rx-ID: 28202332 View in Reaxys 78/284 Yield 15 %

Conditions & References With aluminum (III) chloride in chlorobenzene, Time= 22h, T= -12 - 18 °C Kantlehner, Willi; Anders, Ernst; Mezger, Jochen; Stoyanov, Edmont V.; Kress, Ralf; Wermann, Kurt; Frey, Wolfgang; Goerls, Helmar; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 63; nb. 4; (2008); p. 395 - 406 View in Reaxys

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O S

O F

Rx-ID: 9193346 View in Reaxys 79/284 Yield

Conditions & References

59 %

With palladium diacetate, hydrogen, triphenylphosphine, 2,4,6-trimethyl-pyridine, tributyl-amine in acetonitrile, Time= 18h, T= 120 °C , p= 22501.8Torr Holzapfel, Cedric W.; Ferreira, Alta C.; Marais, Wilhelmina; Journal of Chemical Research - Part S; nb. 5; (2002); p. 218 - 220 View in Reaxys

50 %

With pyridine, hydrogen, palladium diacetate, 1,3-bis-(diphenylphosphino)propane in N,N-dimethyl-formamide, Time= 24h, T= 80 °C , p= 15001.5Torr Brennfuhrer, Anne; Neumann, Helfried; Beller, Matthias; Synlett; nb. 16; (2007); p. 2537 - 2540 View in Reaxys

OH HO

Rx-ID: 11000942 View in Reaxys 80/284 Yield

Conditions & References

2 %, 84 %

With sodium hypochlorite in acetonitrile, Time= 0.25h, T= 20 °C Khurana; Sharma; Gogia; Kandpal; Organic Preparations and Procedures International; vol. 39; nb. 2; (2007); p. 185 - 189 View in Reaxys

N NH O

Rx-ID: 11150086 View in Reaxys 81/284 Yield 83 %

Conditions & References With aluminum oxide, HMTAB, Time= 0.05h, microwave irradiation Heravi, Majid M.; Sabaghiani, Ali J.; Bakavoli, Mehdi; Ghassemzadeh, Mitra; Bakhtiari, Khadijeh; Journal of the Chinese Chemical Society; vol. 54; nb. 1; (2007); p. 123 - 126 View in Reaxys

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O NH

O O

N Z

NH 2 O

Rx-ID: 11185476 View in Reaxys 82/284 Yield

Conditions & References in acetonitrile, T= 25 - 30 °C , Irradiation Igarashi, Tetsutaro; Shimokawa, Masaru; Iwasaki, Miyuki; Nagata, Kensaku; Fujii, Masato; Sakurai, Tadamitsu; Synlett; nb. 9; (2007); p. 1436 - 1440 View in Reaxys

O NH O N Z

H 2N O

Rx-ID: 11185477 View in Reaxys 83/284 Yield

O NH O N Z O

H 2N

Rx-ID: 11185478 View in Reaxys 84/284 Yield

O NH

H 2N

O N Z

Rx-ID: 11185479 View in Reaxys 85/284 Yield

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View in Reaxys O

O NH O

NH 2

N Z O

Rx-ID: 11185480 View in Reaxys 86/284 Yield

O NH

H 2N

O N Z O

Rx-ID: 11185481 View in Reaxys 87/284 Yield

Conditions & References

5% Spectr., 95 % Spectr.

in acetonitrile, T= 25 - 30 °C , Irradiation Igarashi, Tetsutaro; Shimokawa, Masaru; Iwasaki, Miyuki; Nagata, Kensaku; Fujii, Masato; Sakurai, Tadamitsu; Synlett; nb. 9; (2007); p. 1436 - 1440 View in Reaxys O

O NH

NH 2

O N Z

O O

Rx-ID: 11185482 View in Reaxys 88/284 Yield

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O NH O

H 2N

N Z

Rx-ID: 11185483 View in Reaxys 89/284 Yield

O NH O

NH 2

N Z O

Rx-ID: 11185484 View in Reaxys 90/284 Yield

H 2N

O NH O N Z

Rx-ID: 11185485 View in Reaxys 91/284 Yield

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O O NH

H 2N

N Z

Rx-ID: 11185486 View in Reaxys 92/284 Yield

O O NH

H 2N

O O

N Z

H O O

Rx-ID: 11185487 View in Reaxys 93/284 Yield

O O NH

O H 2N

N Z

O H O

Rx-ID: 11185488 View in Reaxys 94/284 Yield

O O NH O

H 2N

N Z

Rx-ID: 11185489 View in Reaxys 95/284

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Yield

O NH

H 2N

H O

N Z

Rx-ID: 11185490 View in Reaxys 96/284 Yield

S O O

H NH

NH 2

O S

N Z

Rx-ID: 11185491 View in Reaxys 97/284 Yield

O N

NH O

Rx-ID: 11312308 View in Reaxys 98/284 Yield

Conditions & References Reaction Steps: 2 1: Et3N / CH2Cl2 / 20 °C 2: acetonitrile / 25 - 30 °C / Irradiation With triethylamine in dichloromethane, acetonitrile

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Igarashi, Tetsutaro; Shimokawa, Masaru; Iwasaki, Miyuki; Nagata, Kensaku; Fujii, Masato; Sakurai, Tadamitsu; Synlett; nb. 9; (2007); p. 1436 - 1440 View in Reaxys

OH ZN O

Rx-ID: 11339270 View in Reaxys 99/284 Yield

Conditions & References Reaction Steps: 2 1: Et3N / CH2Cl2 / 20 °C 2: acetonitrile / 25 - 30 °C / Irradiation With triethylamine in dichloromethane, acetonitrile Igarashi, Tetsutaro; Shimokawa, Masaru; Iwasaki, Miyuki; Nagata, Kensaku; Fujii, Masato; Sakurai, Tadamitsu; Synlett; nb. 9; (2007); p. 1436 - 1440 View in Reaxys Reaction Steps: 2 1: Et3N / CH2Cl2 / 20 °C 2: acetonitrile / 25 - 30 °C / Irradiation With triethylamine in dichloromethane, acetonitrile Igarashi, Tetsutaro; Shimokawa, Masaru; Iwasaki, Miyuki; Nagata, Kensaku; Fujii, Masato; Sakurai, Tadamitsu; Synlett; nb. 9; (2007); p. 1436 - 1440 View in Reaxys Reaction Steps: 2 1: 80 percent / Et3N / CH2Cl2 / 1 h / 20 °C 2: 5 percent Spectr. / acetonitrile / 25 - 30 °C / Irradiation With triethylamine in dichloromethane, acetonitrile Igarashi, Tetsutaro; Shimokawa, Masaru; Iwasaki, Miyuki; Nagata, Kensaku; Fujii, Masato; Sakurai, Tadamitsu; Synlett; nb. 9; (2007); p. 1436 - 1440 View in Reaxys Reaction Steps: 2 1: Et3N / CH2Cl2 / 20 °C 2: acetonitrile / 25 - 30 °C / Irradiation With triethylamine in dichloromethane, acetonitrile Igarashi, Tetsutaro; Shimokawa, Masaru; Iwasaki, Miyuki; Nagata, Kensaku; Fujii, Masato; Sakurai, Tadamitsu; Synlett; nb. 9; (2007); p. 1436 - 1440 View in Reaxys

O O

Rx-ID: 10078477 View in Reaxys 100/284 Yield 40 %

Conditions & References With cyclohexa-1,4-diene in chlorobenzene, Heating Zeidan, Tarek A.; Kovalenko, Serguei V.; Manoharan, Mariappan; Alabugin, Igor V.; Journal of Organic Chemistry; vol. 71; nb. 3; (2006); p. 962 - 975 View in Reaxys With cyclohexa-1,4-diene in chlorobenzene, T= 140 °C , Bergman cyclization, Kinetics, Further Variations: Temperatures

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Zeidan, Tarek A.; Kovalenko, Serguei V.; Manoharan, Mariappan; Alabugin, Igor V.; Journal of Organic Chemistry; vol. 71; nb. 3; (2006); p. 962 - 975 View in Reaxys

Rx-ID: 10162157 View in Reaxys 101/284 Yield

Conditions & References

85 %

With triethylsilane, triphenylphosphine, palladium diacetate in N,N-dimethyl-formamide, Time= 12h, T= 60 °C Nakanishi, Jun; Tatamidani, Hiroto; Fukumoto, Yoshiya; Chatani, Naoto; Synlett; nb. 6; (2006); p. 869 - 872 View in Reaxys

N O

N N

Rx-ID: 9802785 View in Reaxys 102/284 Yield

Conditions & References

4 % Turn- With oxygen, Time= 0.166667h, UV-irradiation, Product distribution, Quantum yield, Further Variations: wavelength ov., 6 % dependence Turnov., 85 % Turnov. Inui, Hiroshi; Murata, Shigeru; Journal of the American Chemical Society; vol. 127; nb. 8; (2005); p. 2628 - 2636 View in Reaxys

N N

Rx-ID: 10079048 View in Reaxys 103/284 Yield

Conditions & References With Pd[(-)-sparteine](OAc)2 in toluene, Time= 36h, Heating Sayyed, Iliyas Ali; Kumar, N.S.C. Ramesh; Sudalai; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 44; nb. 7; (2005); p. 1533 - 1535 View in Reaxys

O S O

O O

Rx-ID: 10334381 View in Reaxys 104/284 Yield 29 % Spectr., 61 % Spectr.,

Conditions & References With 2,6-dimethylpyridine, water in various solvent(s), T= 25 °C , Kinetics Creary, Xavier; Willis, Elizabeth D.; Gagnon, Madeleine; Journal of the American Chemical Society; vol. 127; nb. 51; (2005); p. 18114 - 18120 View in Reaxys

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10 % Spectr.

O racemate

racemate

Rx-ID: 9530615 View in Reaxys 105/284 Yield

Conditions & References

4% Spectr., 10 % Spectr., 86 % Spectr.

With tetrabutylammonium Oxone in acetonitrile, Time= 0.333333h, T= 20 °C , Title compound not separated from byproducts. Mohajer, Daryoush; Iranpoor, Nasser; Rezaeifard, Abdolreza; Tetrahedron Letters; vol. 45; nb. 3; (2004); p. 631 634 View in Reaxys

N H 2N

Rx-ID: 9006849 View in Reaxys 106/284 Yield 92 %

Conditions & References With magnesium hydrogen sulfate, water, silica gel in hexane, Time= 0.5h, T= 20 °C Shirini; Zolfigol; Mallakpour; Hajipour; Baltork; Tetrahedron Letters; vol. 43; nb. 8; (2002); p. 1555 - 1556 View in Reaxys

92 %

With tetrachlorosilane, silica gel in hexane, water, Time= 2h, Heating Shirini; Zolfigol; Khaleghi; Mohammadpour-Baltork; Synthetic Communications; vol. 33; nb. 11; (2003); p. 1839 1844 View in Reaxys

85 %

With ammonium dichromate(VI), water, silica gel, zirconium(IV) chloride, Time= 1.08333h, T= 80 °C Shirini; Zolfigol; Pourhabib; Synthetic Communications; vol. 32; nb. 18; (2002); p. 2837 - 2841 View in Reaxys

78 %

With potassium permanganate, silica gel in water, Time= 0.25h, T= 20 °C Hajipour, Abdol R.; Adibi, Hadi; Ruoho, Arnold E.; Journal of Organic Chemistry; vol. 68; nb. 11; (2003); p. 4553 - 4555 View in Reaxys With sulfuric acid, silica gel in hexane, Time= 0.166667h Zolfigol, Mohammad Ali; Poor-Baltork, Iraj Mohammad; Mirjalili, Bibi Fatemeh; Shirini, Farhad; Salehzadeh, Sadegh; Keypour, Hassan; Ghorbani-Choghamarani, Arash; Zebarjadian, Mohammad Hassan; Mohammadi, Kamal; Hazar, Azizeh; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 178; nb. 12; (2003); p. 2735 2743 View in Reaxys

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S O

Rx-ID: 9302372 View in Reaxys 107/284 Yield

Conditions & References

83 %

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

Rx-ID: 9338381 View in Reaxys 108/284 Yield

Conditions & References

85 %, 10 %

With N,N,N,N,N,N-hexamethylphosphoric triamide, iron(II) oxalate dihydrate, Time= 0.833333h, T= 155 - 160 °C , Product distribution, Further Variations: Reagents, time 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: 9340967 View in Reaxys 109/284 Yield

Conditions & References

65 %, 30 %

With N,N,N,N,N,N-hexamethylphosphoric triamide, iron(II) oxalate dihydrate, Time= 0.166667h, T= 155 - 160 °C , Product distribution, Further Variations: Reagents, time Khurana, Jitender M.; Chauhan, Sushma; Maikap, Golak C.; Organic and Biomolecular Chemistry; vol. 1; nb. 10; (2003); p. 1737 - 1740 View in Reaxys

2H 2H 2H

O 2H

S O

F O

O O –O

S F

F F

2H 2H 2H

S+ O

2H 2H

Rx-ID: 9511756 View in Reaxys 110/284

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Yield

Conditions & References Time= 67h, T= 25 - 60 °C , Kinetics Creary, Xavier; Miller, Kevin; Journal of Organic Chemistry; vol. 68; nb. 22; (2003); p. 8683 - 8692 View in Reaxys

O O

O N

Rx-ID: 9218391 View in Reaxys 111/284 Yield

Conditions & References

74 % Chromat., 35 % Chromat., 14 % Chromat., 42 % Chromat.

in water, acetonitrile, Time= 0.00416667h, UV-irradiation, Quantum yield Bushan, K. Mani; Xu, Hua; Ruane, Patrick H.; D'Sa, Raechelle A.; Pavlos, Christopher M.; Smith, Joseph A.; Celius, Tevye C.; Toscano, John P.; Journal of the American Chemical Society; vol. 124; nb. 43; (2002); p. 12640 12641 View in Reaxys

Rx-ID: 9312277 View in Reaxys 112/284 Yield

Conditions & References

39 %

With tetrabutylammomium bromide, palladium dichloride, Time= 72h, T= 120 °C Ganchegui, Benjamin; Bouquillon, Sandrine; Henin, Francoise; Muzart, Jacques; Tetrahedron Letters; vol. 43; nb. 37; (2002); p. 6641 - 6644 View in Reaxys

O O

Rx-ID: 5199551 View in Reaxys 113/284 Yield 80 %

Conditions & References With N -hydroxyphthalimide, nitrogen(II) oxide in acetonitrile, Time= 10h, T= 60 °C Eikawa, Masahiro; Sakaguchi, Satoshi; Ishii, Yasutaka; Journal of Organic Chemistry; vol. 64; nb. 13; (1999); p. 4676 - 4679 View in Reaxys

80%

15 : EXAMPLE 15 EXAMPLE 15 The procedure of Example 9 was repeated, except that 1 mmol of 1-t-butoxymethylnaphthalene was used instead of 4-methoxymethyltoluene. As a result, 1-t-butoxymethylnaphthalene was converted, at a rate of 87percent, into 1-naphthylaldehyde (yield: 80percent). Patent; Daicel Chemical Industries, Ltd.; US6201156; (2001); (B1) English

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View in Reaxys

H 2N

NH 2

Rx-ID: 8752691 View in Reaxys 114/284 Yield

Conditions & References

45 %

With pyridine, trimethylamine-N-oxide, water, osmium(VIII) oxide in tetrahydrofuran, Time= 12h, T= 20 °C Gao; Herzig; Wang; Synthesis; nb. 4; (2001); p. 544 - 546 View in Reaxys

Rx-ID: 8816160 View in Reaxys 115/284 Yield

Conditions & References

20 %

With C2H2Cl2F3O2V, oxygen in tert-butyl alcohol, Time= 72h, T= 70 °C Hirao, Toshikazu; Morimoto, Chihiro; Takada, Takashi; Sakurai, Hidehiro; Tetrahedron; vol. 57; nb. 24; (2001); p. 5073 - 5079 View in Reaxys

Sn HO

Rx-ID: 8848192 View in Reaxys 116/284 Yield

Conditions & References

38 %, 58 %

With C2H2Cl2F3O2V, oxygen in tert-butyl alcohol, Time= 24h, T= 50 °C Hirao, Toshikazu; Morimoto, Chihiro; Takada, Takashi; Sakurai, Hidehiro; Tetrahedron Letters; vol. 42; nb. 10; (2001); p. 1961 - 1963 View in Reaxys

28 %, 5 %, With C2H2Cl2F3O2V, oxygen in tert-butyl alcohol, Time= 24h, T= 50 °C 58 %, 4 % Hirao, Toshikazu; Morimoto, Chihiro; Takada, Takashi; Sakurai, Hidehiro; Tetrahedron; vol. 57; nb. 24; (2001); p. 5073 - 5079 View in Reaxys

Rx-ID: 8940563 View in Reaxys 117/284 Yield 27 % Chromat.,

Conditions & References With hydrogen, 2,2-dimethylpropanoic anhydride, tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, Time= 24h, T= 80 °C , p= 22501.8Torr Nagayama; Shimizu; Yamamoto; Bulletin of the Chemical Society of Japan; vol. 74; nb. 10; (2001); p. 1803 - 1815

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50 % Spectr.

View in Reaxys

N O

Rx-ID: 8957412 View in Reaxys 118/284 Yield

Conditions & References

61 %, 57 %

With oxygen in acetonitrile, T= 20 °C , Irradiation, long-wavelenght light (366 nm) Inui, Hiroshi; Murata, Shigeru; Chemistry Letters; nb. 8; (2001); p. 832 - 833 View in Reaxys

N N N N

Rx-ID: 8957413 View in Reaxys 119/284 Yield

Conditions & References

3 %, 82 %

in acetonitrile, T= 20 °C , Irradiation, short-wavelenght light (>300 nm) Inui, Hiroshi; Murata, Shigeru; Chemistry Letters; nb. 8; (2001); p. 832 - 833 View in Reaxys

Rx-ID: 5589729 View in Reaxys 120/284 Yield 87.5%

Conditions & References 4.d : d As described in Example 1b, 21.15 g of the compound prepared according to Example 4c were reacted with 14.3 ml of phosphorus oxychloride and 20.9 ml of dimethylformamide. After chromatography with petroleum ether/diethyl ether (2:1), 19.35 g 87.5percent of the theoretical yield) of the naphthaldehyde were obtained in the form of colorless crystals melting at 62°-64° C. 1 H-NMR (CDCl ): 3 0.96-1.01 (t, 3H, CH3); 1.44-1.56 (m, 2H, CH2); 1.71-1.82 (s, 2H, CH2); 2.52-2.57 (m, 2H, CH2); 2.81-2.87 (m, 2H, CH2); 3.97-4.01 (t, 2H, OCH2); 6.75-6.78 (m, 2H, aromat.,olefin.); Patent; Gruenenthal GmbH; US5254731; (1993); (A1) English View in Reaxys

61%

2.e : e e (-)-(6S,7S)-5,6,7,8-Tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphthalenecarbaldehyde Operating as indicated in Helv. Chim. Acta, op. cit., the compound obtained under letter d) was oxidized by means of Ce(NH4)2 (NO3)6. To this end, the reaction took place in methanol at 50°.

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The product obtained was purified by column chromatography (SiO2), eluding with pentane:ether (97:3), to provide 2.0 g of naphthalenecarbaldehyde in 61percent yield. A sample was recrystallized in ethyl alcohol. [α]20 D=-39° (c=0.85; CHCl3); about 77percent ee Operating in a similar manner, there was obtained the corresponding (+) compound [α]20 D=+42° (c=1.08; CHCl3); about 82percent ee. Patent; Firmenich S.A.; US5521151; (1996); (A1) English View in Reaxys Herstellung von <α-14 C><1>Naphthaldehyd Evans; Journal of the Chemical Society; (1957); p. 2790,2794 View in Reaxys Gross,H.; Matthey,G.; Chemische Berichte; vol. 97; (1964); p. 2606 - 2613 View in Reaxys Olah,G.A.; Kuhn,S.J.; Journal of the American Chemical Society; vol. 82; (1960); p. 2380 - 2382 View in Reaxys Stiles,M.; Sisti,A.J.; Journal of Organic Chemistry; vol. 25; nb. 10; (1960); p. 1691 - 1693 View in Reaxys Paquette,L.A. et al.; Synthetic Communications; vol. 6; (1976); p. 575 - 581 View in Reaxys Periasamy,M.; Bhatt,M.V.; Synthesis; (1977); p. 330 - 332 View in Reaxys Comins; Meyers; Synthesis; (1978); p. 403 View in Reaxys Rieche et al.; Chemische Berichte; vol. 93; (1960); p. 88,90 View in Reaxys Backeberg; Staskun; Journal of the Chemical Society; (1962); p. 3961 View in Reaxys Oda; Hayashi; Nippon Kagaku Zasshi; vol. 87; (1966); p. 291,292 View in Reaxys Ertel; Friedrich; Chemische Berichte; vol. 110; (1977); p. 86,95 View in Reaxys van Es; Staskun; Journal of the Chemical Society; (1965); p. 5775 View in Reaxys Staskun; Backeberg; Journal of the Chemical Society; (1964); p. 5880 View in Reaxys Brown; Tsukamoto; Journal of the American Chemical Society; vol. 86; (1964); p. 1089,1092 View in Reaxys Sacharkin et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); (1964); p. 1415; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1964); p. 1511 View in Reaxys Patent; Univ. of Delaware; US3960932; (1976); ; vol. 85; nb. 108421 View in Reaxys Watkins; Phytochemistry (Elsevier); vol. 8; (1969); p. 979,981 View in Reaxys Oda et al.; Nippon Kagaku Zasshi; vol. 87; (1966); p. 978 View in Reaxys Brown; Garg; Journal of the American Chemical Society; vol. 86; (1964); p. 1085,1087 View in Reaxys Periasamy; Bhatt; Tetrahedron Letters; (1978); p. 4561 View in Reaxys Kremlev et al.; Voprosy Khimii i Khimicheskoi Tekhnologii; vol. 25; (1972); p. 32,33-36; ; vol. 78; nb. 110775z; Chem. Zentralbl.; Ref.Zh.Khim. No 16 <1972> Zh 217 View in Reaxys Kaberia; Vickery; Journal of the Chemical Society, Chemical Communications; (1978); p. 459 View in Reaxys Costa et al.; Journal of Heterocyclic Chemistry; vol. 11; (1974); p. 943,947,948 View in Reaxys Wege; Wilkinson; Australian Journal of Chemistry; vol. 26; (1973); p. 1751,1755,1756,1762 View in Reaxys

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Barton et al.; Tetrahedron Letters; (1979); p. 3331,3333 View in Reaxys Patent; Jagupolskij et al.; SU387962; (1973); Ref. Zh., Khim.; vol. 15; nb. N175P; (1974) View in Reaxys Sitkin et al.; Zhurnal Organicheskoi Khimii; vol. 11; (1975); p. 452,443 View in Reaxys Prot; Roczniki Chemii; vol. 45; (1971); p. 247 View in Reaxys Kreutzberger; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 304; (1971); p. 362,363, 365 View in Reaxys Gaiffe; Pallaud; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 252; (1961); p. 1339,1340 View in Reaxys The remaining teabags of amino acid on resin were each reacted as above in separate reactions with the following 94 aldehydes such that all combinations of 4-carboxy disubstituted dihydroisoquinolones were formed as indicated in the following (R2) list: 2-hydroxybenzaldehyde (salicylaldehyde), 1-methyl-2-pyrrolecarboxaldehyde, 1-naphthaldehyde, 2,3,4-trifluorobenzaldehyde, 2,3,5-trichlorobenzaldehyde, 2,3-(methylenedioxy)benzaldehyde, 2,3-difluorobenzaldehyde, 2,4-dichlorobenzaldehyde, 2,6-difluorobenzaldehyde, 2-bromobenzaldehyde, 2-chloro-5-nitrobenzaldehyde, 2-chloro-6-fluorobenzaldehyde, 2-cyanobenzaldehyde, 2-fluorobenzaldehyde, 2-furaldehyde, ... Patent; Basu; Amaresh; Gahman; Timothy C.; Girten; Beverly E.; Griffith; Michael C.; Hecht; Curtis C.; Kiely; John S.; Slivka; Sandra R.; US6127381; (2000); (A1) English View in Reaxys Typical examples of aldehyde and polyamines employed in preparing these Schiff bases include the following: ALDEHYDES Benzaldehyde ... 2-methoxybenzaldehyde 4-methoxybenzaldehyde 2-naphthaldehyde 1-naphthaldehyde 4-phenylbenzaldehyde Propionaldehyde n-Butyraldehyde ... Patent; Petrolite Corporation; US4311841; (1982); (A1) English View in Reaxys A few illustrative examples of preferred aldehydes include ... 2-methoxy-1-naphthaldehyde 4-methoxy-1-naphthaldehyde 3-methyl-p-anisaldehyde 10-methylanthracene-9-carboxaldehyde 1-naphthaldehyde 2-naphthaldehyde pentafluorobenzaldehyde phenanthrene-9-carboxaldehyde ... Patent; Ethyl Corporation; US4837327; (1989); (A1) English View in Reaxys

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As examples of aldehydes of VII and VIII there may be mentioned the following: benzaldehyde 1-naphthaldehyde 2-hydroxy-1-naphthaldehyde 4-formyl pyridine 1-phenyl-3-methyl-4-formyl pyrazol-5-one Patent; Ciba-Geigy Corporation; US3987023; (1976); (A1) English View in Reaxys Substitution of the following aldehydes: (a) Naphthalene-1-carboxaldehyde (b) Naphthalene-2-carboxaldehyde (c) 2,3-Dihydro-1,4-benzodioxin-6-carboxaldehyde (d) 1,3-Benzodioxole-5-carboxaldehyde (e) 3-Methylbenzaldehyde ... Patent; Smith Kline and French Laboratories Limited; US4185103; (1980); (A1) English View in Reaxys

O O

Rx-ID: 8550061 View in Reaxys 121/284 Yield

Conditions & References

18 %

With aluminium trichloride in chlorobenzene, Time= 22h, T= 10 - 20 °C , Formylation Kantlehner, Willi; Vettel, Markus; Gissel, Alexander; Haug, Erwin; Ziegler, Georg; Ciesielski, Michael; Scherr, Oliver; Haas, Richard; Advanced Synthesis and Catalysis; vol. 342; nb. 3; (2000); p. 297 - 310 View in Reaxys

N NH O

Rx-ID: 8604953 View in Reaxys 122/284 Yield

Conditions & References

93 %

With caro's acid, silica gel, Time= 0.0416667h, Irradiation, Oxidation Bose, D. Subhas; Venkat Narsaiah; Lakshminarayana; Synthetic Communications; vol. 30; nb. 17; (2000); p. 3121 - 3125 View in Reaxys

HO N

O O

Rx-ID: 24346565 View in Reaxys 123/284 Yield

Conditions & References 13.A : A. A. 1-Naphthalenecarboxaldehyde

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To a cold (-78° C.) solution of oxalyl chloride (6.9 mL, 0.079 mol) in dry CH2 Cl2 (200 mL) was added dropwise dry DMSO (11.2 mL, 0.158 mol). The mixture was stirred for 10 min, and then a solution of 1-naphthalenemethanol (10.0 g, 0.063 mol) in dry CH2 Cl2 (40 mL) was added over 15 min. The mixture was stirred for 10 min, and then Et3 N (44 mL, 0.316 mol) was added slowly. The reaction mixture was allowed to warm to room temperature. After 3.5 h, to the pale yellow heterogeneous mixture was added 10percent aqueous citric acid (30 mL) and water (100 mL). The organic phase was washed with water (100 mL) and saturated aqueous NaCl (100 mL), dried (anhydrous MgSO4), filtered, and concentrated. Ether-hexane (1:1) was added, and the mixture was filtered. Concentration provided a pale orange oil (9.7 g). in dichloromethane, water, dimethyl sulfoxide Patent; LeukoSite, Inc.; US6083903; (2000); (A1) English View in Reaxys 13.A : A. A. 1-naphthalenecarboxaldehyde To a cold (-78° C.) solution of oxalyl chloride (6.9 mL, 0.079 mol) in dry CH2 Cl2 (200 mL) was added dropwise dry DMSO (11.2 mL, 0.158 mol). The mixture was stirred for 10 min, and then a solution of 1-naphthalenemethanol (10.0 g, 0.063 mol) in dry CH2 Cl2 (40 mL) was added over 15 min. The mixture was stirred for 10 min, and then Et3 N (44 mL, 0.316 mol) was added slowly. The reaction mixture was allowed to warm to room temperature. After 3.5 h, to the pale yellow heterogeneous mixture was added 10percent aqueous citric acid (30 mL) and water (100 mL). The organic phase was washed with water (100 mL) and saturated aqueous NaCl (100 mL), dried (anhydrous MgSO4), filtered, and concentrated. Ether-hexane (1:1) was added and the mixture was filtered. Concentration provided a pale orange oil (9.7 g). in dichloromethane, water, dimethyl sulfoxide Patent; ProScript, Inc.; US5780454; (1998); (A1) English View in Reaxys

N O O

Rx-ID: 5110540 View in Reaxys 124/284 Yield

Conditions & References With sodium, 1.) THF, 25 deg C, 2 h, 2.) room temperature, 8 h, Yield given, Multistep reaction Periasamy, Mariappan; Rama Reddy, Malladi; Bharathi, Pandi; Synthetic Communications; vol. 29; nb. 4; (1999); p. 677 - 683 View in Reaxys

O O

Rx-ID: 5132097 View in Reaxys 125/284 Yield 55 %

Conditions & References With sodium in tetrahydrofuran, Ambient temperature, acylation and formylation of polycyclic aromatic hydrocarbons; formation of radical anions, their acylation with carboxylic acid esters and formylation with N,N-dialkylformamides, Product distribution

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Periasamy, Mariappan; Rama Reddy, Malladi; Bharathi, Pandi; Synthetic Communications; vol. 29; nb. 4; (1999); p. 677 - 683 View in Reaxys With sodium, 1.) THF, 25 deg C, 2 h, 2.) room temperature, 8 h, Yield given, Multistep reaction Periasamy, Mariappan; Rama Reddy, Malladi; Bharathi, Pandi; Synthetic Communications; vol. 29; nb. 4; (1999); p. 677 - 683 View in Reaxys

Rx-ID: 5151416 View in Reaxys 126/284 Yield

Conditions & References T= 650 °C , p= 0.05 - 0.1Torr , Yield given, Further byproducts given. Yields of byproduct given Engler, Thomas A.; Shechter, Harold; Journal of Organic Chemistry; vol. 64; nb. 12; (1999); p. 4247 - 4254 View in Reaxys

Rx-ID: 5151455 View in Reaxys 127/284 Yield

Conditions & References

29 %

T= 510 °C , p= 0.05 - 0.1Torr , Further byproducts given. Yields of byproduct given Engler, Thomas A.; Shechter, Harold; Journal of Organic Chemistry; vol. 64; nb. 12; (1999); p. 4247 - 4254 View in Reaxys

N N O

Rx-ID: 5257978 View in Reaxys 128/284 Yield 76 %

Conditions & References With ammonium cerium(IV) nitrate in water, acetonitrile, Time= 20h, T= 20 °C , Oxidation Giurg, Miroslaw; Mlochowski, Jacek; Synthetic Communications; vol. 29; nb. 24; (1999); p. 4307 - 4313 View in Reaxys

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PH O

(v5)

P O

Rx-ID: 5298247 View in Reaxys 129/284 Yield

Conditions & References

60 %

in acetonitrile, Time= 5h, Irradiation, Decomposition Zhao, Ningning; Strehmel, Bernd; Gorman, Anthony A.; Hamblett, Ian; Neckers, Douglas C.; Journal of Physical Chemistry A; vol. 103; nb. 39; (1999); p. 7757 - 7765 View in Reaxys

N O

Rx-ID: 8539802 View in Reaxys 130/284 Yield

Conditions & References Stage 1: With dicobalt octacarbonyl, triethylamine in diethyl ether, Time= 0.25h, T= 20 °C , deoximation Stage 2: With water in methanol, Time= 0.5h, T= 20 °C , Dehydration, Title compound not separated from byproducts Mukai, Chisato; Nomura, Izumi; Kataoka, Osamu; Hanaoka, Miyoji; Synthesis; nb. 11; (1999); p. 1872 - 1874 View in Reaxys

Rx-ID: 16393303 View in Reaxys 131/284 Yield

Conditions & References Reaction Steps: 2 1: 1.) t-BuLi, TMEDA / 1.) Et2O, pentane, -70 deg C, 20 deg C, 2.) -70 deg C to room temperature 2: 650 °C / 0.05 - 0.1 Torr With N,N,N,N,-tetramethylethylenediamine, tert.-butyl lithium Engler, Thomas A.; Shechter, Harold; Journal of Organic Chemistry; vol. 64; nb. 12; (1999); p. 4247 - 4254 View in Reaxys Reaction Steps: 2 1: buthyllithium / 1.)tetramethylethylenediamine, ethyl ether, -78 deg C 2: 9 percent / 650 °C / 0.05 - 0.1 Torr With n-butyllithium Engler, T. A.; Shechter, H.; Tetrahedron Letters; vol. 23; nb. 27; (1982); p. 2715 - 2718 View in Reaxys

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Rx-ID: 16396761 View in Reaxys 132/284 Yield

Conditions & References Reaction Steps: 3 1: 510 °C / 0.05 - 0.1 Torr 2: 1.) t-BuLi, TMEDA / 1.) Et2O, pentane, -70 deg C, 20 deg C, 2.) -70 deg C to room temperature 3: 650 °C / 0.05 - 0.1 Torr With N,N,N,N,-tetramethylethylenediamine, tert.-butyl lithium Engler, Thomas A.; Shechter, Harold; Journal of Organic Chemistry; vol. 64; nb. 12; (1999); p. 4247 - 4254 View in Reaxys

Rx-ID: 16398207 View in Reaxys 133/284 Yield

Conditions & References Reaction Steps: 4 1: 1.) t-BuLi, TMEDA / 1.) Et2O, pentane, -70 deg C, 20 deg C, 2.) -70 deg C to room temperature 2: 510 °C / 0.05 - 0.1 Torr 3: 1.) t-BuLi, TMEDA / 1.) Et2O, pentane, -70 deg C, 20 deg C, 2.) -70 deg C to room temperature 4: 650 °C / 0.05 - 0.1 Torr With N,N,N,N,-tetramethylethylenediamine, tert.-butyl lithium Engler, Thomas A.; Shechter, Harold; Journal of Organic Chemistry; vol. 64; nb. 12; (1999); p. 4247 - 4254 View in Reaxys Reaction Steps: 2 1: 1.) t-BuLi, TMEDA / 1.) Et2O, pentane, -70 deg C, 20 deg C, 2.) -70 deg C to room temperature 2: 510 °C / 0.05 - 0.1 Torr With N,N,N,N,-tetramethylethylenediamine, tert.-butyl lithium Engler, Thomas A.; Shechter, Harold; Journal of Organic Chemistry; vol. 64; nb. 12; (1999); p. 4247 - 4254 View in Reaxys

N O

NH 2

Rx-ID: 25355109 View in Reaxys 134/284 Yield 87 mg (80%)

Conditions & References Reductive Amination Of An Aldehyde And A Primary Amine: 1-naphthaldehyde (51 mg, 0.33 mmol) and 4-amino-1-benzylpiperidine (93 mg, 0.5 mmol) yielded 87 mg (80percent) MS (m/e): 331 (M+1) Patent; ELI LILLY AND COMPANY; EP818431; (1998); (A1) English View in Reaxys

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H 2N O

Rx-ID: 25355110 View in Reaxys 135/284 Yield

Conditions & References

62 mg (72%)

Reductive Amination Of An Aldehyde And A Primary Amine: 1-naphthaldehyde (51 mg, 0.33 mmol) and α-methyl benzylamine (60 mg, 0.5 mmol) yielded 62 mg (72percent) MS (m/e): 262 (M+1) Patent; ELI LILLY AND COMPANY; EP818431; (1998); (A1) English View in Reaxys

O NH 2 O

Rx-ID: 25355111 View in Reaxys 136/284 Yield

Conditions & References

63 mg (79%)

Reductive Amination Of An Aldehyde And A Primary Amine: 1-naphthaldehyde (51 mg, 0.33 mmol) and tetrahydrofurfurylamine (51 mg, 0.5 mmol) yielded 63 mg (79percent) MS (m/e): 242 (M+1) Patent; ELI LILLY AND COMPANY; EP818431; (1998); (A1) English View in Reaxys

H 2N

Rx-ID: 25355112 View in Reaxys 137/284 Yield 104 mg (82%)

Conditions & References Reductive Amination Of An Aldehyde And A Primary Amine: 1-naphthaldehyde (51 mg, 0.33 mmol) and 2-[(2-aminomethyl)phenylthio]benzyl alcohol (122 mg, 0.5 mmol) yielded 104 mg (82percent) MS (m/e): 386 (M+1) Patent; ELI LILLY AND COMPANY; EP818431; (1998); (A1) English View in Reaxys

NH 2

Rx-ID: 25355113 View in Reaxys 138/284 Yield 69 mg (70%)

Conditions & References Reductive Amination Of An Aldehyde And A Primary Amine: 1-naphthaldehyde (51 mg, 0.33 mmol) and tryptamine (122 mg, 0.5 mmol) yielded 69 mg (70percent) MS (m/e): 301 (M+1) Patent; ELI LILLY AND COMPANY; EP818431; (1998); (A1) English View in Reaxys

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OH O

O O HO

Rx-ID: 4832124 View in Reaxys 139/284 Yield

Conditions & References With oxygen, vanadium(V) oxide, antimony(III) oxide, titanium(IV) oxide in water, T= 330 °C , p= 750.06Torr , other temperatures, Product distribution Antol, Marcel; Cvengrosova, Zuzana; Vrabel, Imrich; Lesko, Jan; Hronec, Milan; Collection of Czechoslovak Chemical Communications; vol. 62; nb. 9; (1997); p. 1481 - 1490 View in Reaxys

S OH

Rx-ID: 4902200 View in Reaxys 140/284 Yield

Conditions & References

52 %

With toluene-4-sulfonic acid in acetonitrile, Time= 0.333333h, T= 90 °C Naka, Hiroyuki; Sato, Soichi; Horn, Ernst; Furukawa, Naomichi; Heterocycles; vol. 46; nb. 1; (1997); p. 177 184 View in Reaxys

O O

Rx-ID: 5095278 View in Reaxys 141/284 Yield

Conditions & References

3 %, 12 %, T= 600 °C , p= 0.01Torr 27 %, 1 % Chen, Ping-Shu; Chou, Chin-Hsing; Tetrahedron; vol. 53; nb. 50; (1997); p. 17115 - 17126 View in Reaxys 3 %, 12 %, T= 600 °C , p= 0.01Torr 12 %, 1 % Chen, Ping-Shu; Chou, Chin-Hsing; Tetrahedron; vol. 53; nb. 50; (1997); p. 17115 - 17126 View in Reaxys

O Sn

Cl O

Rx-ID: 4343127 View in Reaxys 142/284 Yield 80 %

Conditions & References With aluminium trichloride in dichloromethane, Time= 4h, T= -78 °C

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Niestroj, Michael; Neumann, Wilhelm P.; Chemische Berichte; vol. 129; nb. 1; (1996); p. 45 - 51 View in Reaxys

O HO

Rx-ID: 4424621 View in Reaxys 143/284 Yield

Conditions & References

4 %, 2 %, 2%

With methyltrioxorhenium(VII) in benzene, Time= 48h, Ambient temperature Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 61; nb. 1; (1996); p. 324 - 328 View in Reaxys

N N

O N

Rx-ID: 4453093 View in Reaxys 144/284 Yield

Conditions & References Time= 24h, T= 15 °C , Irradiation, other irradiation wavelength, other temperatures; also in solution (MeCN), Product distribution, Quantum yield Koshima, Hideko; Ding, Kuiling; Chisaka, Yosuke; Matsuura, Teruo; Ohashi, Yuji; Mukasa, Manabu; Journal of Organic Chemistry; vol. 61; nb. 7; (1996); p. 2352 - 2357 View in Reaxys

H 2N O

Rx-ID: 4557379 View in Reaxys 145/284 Yield

Conditions & References With sodium methylate in tetrahydrofuran, 0 deg C, 30 min, r.t., 2 h, Yield given. Yields of byproduct given Baudin, Jean-Bernard; Commenil, Marie-Gabrielle; Julia, Sylvestre A.; Lome, Robert; Ruel, Odile; Bulletin de la Societe Chimique de France; vol. 133; nb. 11; (1996); p. 1127 - 1141 View in Reaxys

S O

O S O

Rx-ID: 4572775 View in Reaxys 146/284

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Yield

Conditions & References

3 %, 42 %, With lithium methanolate in tetrahydrofuran, Time= 18h, T= 18 °C 4% Spectr., 24 Baudin, Jean-Bernard; Commenil, Marie-Gabrielle; Julia, Sylvestre A.; Lome, Robert; Ruel, Odile; Bulletin de la Societe Chimique de France; vol. 133; nb. 11; (1996); p. 1127 - 1141 % Spectr. View in Reaxys

S O

Rx-ID: 4572776 View in Reaxys 147/284 Yield

Conditions & References

73 %, 5 % Spectr.

With sodium methylate in tetrahydrofuran, Time= 4.5h, T= 0 °C Baudin, Jean-Bernard; Commenil, Marie-Gabrielle; Julia, Sylvestre A.; Lome, Robert; Ruel, Odile; Bulletin de la Societe Chimique de France; vol. 133; nb. 11; (1996); p. 1127 - 1141 View in Reaxys

12-methoxy-16-oxo-15-nor-pimara-8,11,13trien-19-oic acid methyl ester

S S O

Rx-ID: 17592413 View in Reaxys 148/284 Yield

Conditions & References Reaction Steps: 2 1: 81 percent / N-bromosuccinimide / CH2Cl2 / 0 deg C, 20 min, r.t., 1 h 2: sodium methoxide / tetrahydrofuran / 0 deg C, 30 min, r.t., 2 h With N-Bromosuccinimide, sodium methylate in tetrahydrofuran, dichloromethane Baudin, Jean-Bernard; Commenil, Marie-Gabrielle; Julia, Sylvestre A.; Lome, Robert; Ruel, Odile; Bulletin de la Societe Chimique de France; vol. 133; nb. 11; (1996); p. 1127 - 1141 View in Reaxys Reaction Steps: 2 1: 81 percent / N-bromosuccinimide / CH2Cl2 / 0 deg C, 20 min, r.t., 1 h 2: 42 percent / LiOCH3 / tetrahydrofuran / 18 h / 18 °C With N-Bromosuccinimide, lithium methanolate in tetrahydrofuran, dichloromethane Baudin, Jean-Bernard; Commenil, Marie-Gabrielle; Julia, Sylvestre A.; Lome, Robert; Ruel, Odile; Bulletin de la Societe Chimique de France; vol. 133; nb. 11; (1996); p. 1127 - 1141 View in Reaxys Reaction Steps: 2 1: 81 percent / N-bromosuccinimide / CH2Cl2 / 0 deg C, 20 min, r.t., 1 h 2: 73 percent / NaOCH3 / tetrahydrofuran / 4.5 h / 0 °C With N-Bromosuccinimide, sodium methylate in tetrahydrofuran, dichloromethane Baudin, Jean-Bernard; Commenil, Marie-Gabrielle; Julia, Sylvestre A.; Lome, Robert; Ruel, Odile; Bulletin de la Societe Chimique de France; vol. 133; nb. 11; (1996); p. 1127 - 1141 View in Reaxys

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12-methoxy-16-oxo-15-nor-pimara-8,11,13trien-19-oic acid methyl ester S OH

Rx-ID: 17610111 View in Reaxys 149/284 Yield

Conditions & References Reaction Steps: 3 1: 89 percent / Br2, aq.KHCO3 2: 81 percent / N-bromosuccinimide / CH2Cl2 / 0 deg C, 20 min, r.t., 1 h 3: sodium methoxide / tetrahydrofuran / 0 deg C, 30 min, r.t., 2 h With N-Bromosuccinimide, bromine, sodium methylate, potassium hydrogencarbonate in tetrahydrofuran, dichloromethane Baudin, Jean-Bernard; Commenil, Marie-Gabrielle; Julia, Sylvestre A.; Lome, Robert; Ruel, Odile; Bulletin de la Societe Chimique de France; vol. 133; nb. 11; (1996); p. 1127 - 1141 View in Reaxys Reaction Steps: 3 1: 89 percent / Br2, aq.KHCO3 2: 81 percent / N-bromosuccinimide / CH2Cl2 / 0 deg C, 20 min, r.t., 1 h 3: 42 percent / LiOCH3 / tetrahydrofuran / 18 h / 18 °C With N-Bromosuccinimide, lithium methanolate, bromine, potassium hydrogencarbonate in tetrahydrofuran, dichloromethane Baudin, Jean-Bernard; Commenil, Marie-Gabrielle; Julia, Sylvestre A.; Lome, Robert; Ruel, Odile; Bulletin de la Societe Chimique de France; vol. 133; nb. 11; (1996); p. 1127 - 1141 View in Reaxys Reaction Steps: 3 1: 89 percent / Br2, aq.KHCO3 2: 81 percent / N-bromosuccinimide / CH2Cl2 / 0 deg C, 20 min, r.t., 1 h 3: 73 percent / NaOCH3 / tetrahydrofuran / 4.5 h / 0 °C With N-Bromosuccinimide, bromine, sodium methylate, potassium hydrogencarbonate in tetrahydrofuran, dichloromethane Baudin, Jean-Bernard; Commenil, Marie-Gabrielle; Julia, Sylvestre A.; Lome, Robert; Ruel, Odile; Bulletin de la Societe Chimique de France; vol. 133; nb. 11; (1996); p. 1127 - 1141 View in Reaxys

3-[methyl]-6,7,8-tri-[methoxy]-1-[2'-(naphth-1''-yl)ethenyl] -isoquinoline O

Rx-ID: 25412731 View in Reaxys 150/284 Yield 54%

Conditions & References 35 : 3-[Methyl]-6,7,8-tri-[methoxy]-1-[2'-(naphth-1''-yl)-ethenyl]-isoquinoline Example 35 3-[Methyl]-6,7,8-tri-[methoxy]-1-[2'-(naphth-1''-yl)-ethenyl]-isoquinoline According to the method of Example 1 3-[methyl]-6,7,8-tri-[methoxy]-1-[2'-(naphth-1''-yl)-ethenyl] -isoquinoline is prepared from 1,3-di-[methyl]-6,7,8-tri- [methoxy]-isoquinoline with naphth-1-yl-aldehyde Yield: 54percent. M.p.: 99 to 106.5°C (methanol) Patent; EGIS GYOGYSZERGYAR RT.; EP680953; (1995); (A1) English View in Reaxys

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O H

Rx-ID: 2126863 View in Reaxys 151/284 Yield

Conditions & References in acetonitrile, Time= 17h, Irradiation, radiolysis by 1.4 mR of radiation from a 60Co source; with/without Et3N reagent, Product distribution, Rate constant Guthrie, Robert D.; Patwardhan, Manjiri; Chateauneuf, John E.; Journal of Physical Organic Chemistry; vol. 7; nb. 3; (1994); p. 147 - 152 View in Reaxys O

Rx-ID: 2935305 View in Reaxys 152/284 Yield

Conditions & References

40 %, 10 %

With manganese(III) sulfate, sulfuric acid in acetonitrile, Time= 10h, T= 25 °C Bhatt, M. Vivekananda; Periasamy, Mariappan; Tetrahedron; vol. 50; nb. 11; (1994); p. 3575 - 3586 View in Reaxys

30 %, 20 %

With cerium(IV) ammonium sulphate, sulfuric acid in acetonitrile, Time= 24h, T= 25 °C , CAS oxidation of various 1substituted naphthalenes and other reagent, Product distribution, Mechanism Bhatt, M. Vivekananda; Periasamy, Mariappan; Tetrahedron; vol. 50; nb. 11; (1994); p. 3575 - 3586 View in Reaxys

30 %, 20 %

With cerium(IV) ammonium sulphate, sulfuric acid in acetonitrile, Time= 24h, T= 25 °C Bhatt, M. Vivekananda; Periasamy, Mariappan; Tetrahedron; vol. 50; nb. 11; (1994); p. 3575 - 3586 View in Reaxys

N O

Rx-ID: 3680352 View in Reaxys 153/284 Yield

Conditions & References With 3-chloro-benzenecarboperoxoic acid in dichloromethane, T= 25 °C , Yield given. Yields of byproduct given Sakanishi, Katsumasa; Nugroho, Mohamed Bambang; Kato, Yoshiyuki; Yamazaki, Natsuki; Tetrahedron Letters; vol. 35; nb. 21; (1994); p. 3559 - 3562 View in Reaxys 1

-1

-1 O

O O

Rx-ID: 2017093 View in Reaxys 154/284

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Yield

Conditions & References p= 3 - 6Torr , -ΔG1 0 (150 deg C), ΔH1 0, ΔS1 0 of electron transfer at 1 atm, other temperatures, Equilibrium constant, Thermodynamic data Heinis, Thomas; Chowdhury, Swapan; Kebarle, Paul; Organic Mass Spectrometry; vol. 28; nb. 4; (1993); p. 358 365 View in Reaxys p= 3 - 6Torr , temperature range: 345 to 500 K, Equilibrium constant Heinis, Thomas; Chowdhury, Swapan; Kebarle, Paul; Organic Mass Spectrometry; vol. 28; nb. 4; (1993); p. 358 365 View in Reaxys

O O

-1

-1 O

N O

Rx-ID: 2066876 View in Reaxys 155/284 Yield

O OH

Rx-ID: 2935296 View in Reaxys 156/284 Yield 35 %, 6 %

Conditions & References With silica gel, T= -196.1 °C , Irradiation Barbas, John T.; Sigman, Michael E.; Buchanan, A.C.; Chevis, Eddie A.; Photochemistry and Photobiology; vol. 58; nb. 2; (1993); p. 155 - 158 View in Reaxys

35 %, 6 %

With methylene blue, silica gel, T= -196.1 °C , Irradiation, also on Al2O3, Rate constant Barbas, John T.; Sigman, Michael E.; Buchanan, A.C.; Chevis, Eddie A.; Photochemistry and Photobiology; vol. 58; nb. 2; (1993); p. 155 - 158 View in Reaxys

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O O O

OH HO

Rx-ID: 3101093 View in Reaxys 157/284 Yield

Conditions & References in tetrahydrofuran, T= 60 °C , E(act.), ΔH(excit.), ΔS(excit.); var. solvents, Rate constant, Thermodynamic data Fomin, V. A.; Etlis, I. V.; Kurskii, Yu. A.; Nozrina, F. D.; Chervyakova, G. N.; Shmuilovich, S. M.; Russian Journal of Organic Chemistry; vol. 29; nb. 5.2; (1993); p. 811 - 819; Zhurnal Organicheskoi Khimii; vol. 29; nb. 5; (1993); p. 982 - 993 View in Reaxys

Rx-ID: 3709024 View in Reaxys 158/284 Yield

Conditions & References in chlorobenzene, T= 120 °C , Ea, ΔH(excit.), ΔS(excit.), ΔG(excit.); var. solvents, var. temp., Kinetics, Thermodynamic data Etlis, I. V.; Fomin, V. A.; Nozrina, F. D.; Kurskii, Yu. A.; Shmuilovich, S. M.; Russian Journal of Organic Chemistry; vol. 29; nb. 5.2; (1993); p. 820 - 825; Zhurnal Organicheskoi Khimii; vol. 29; nb. 5; (1993); p. 994 - 1000 View in Reaxys

O H O

Rx-ID: 1738652 View in Reaxys 159/284 Yield

Conditions & References T= 18.9 - 21.9 °C , Irradiation, further solvents and temperatures; lifetimes of transients, temperature dependence of ylide lifetimes; quenching reactions; also triplet sensitation, Mechanism Clark, K. B.; Bhattacharyya, K.; Das, P. K.; Scaiano, J. C.; Schaap, A. P.; Journal of Organic Chemistry; vol. 57; nb. 13; (1992); p. 3706 - 3712 View in Reaxys

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racemate

Rx-ID: 1999447 View in Reaxys 160/284 Yield

Conditions & References T= 18.9 - 21.9 °C , Irradiation, other solvents and temperatures; lifetimes of transients, temperature dependence of ylide lifetimes; quenching reactions; also triplet sensitation, Mechanism Clark, K. B.; Bhattacharyya, K.; Das, P. K.; Scaiano, J. C.; Schaap, A. P.; Journal of Organic Chemistry; vol. 57; nb. 13; (1992); p. 3706 - 3712 View in Reaxys

Rx-ID: 2182832 View in Reaxys 161/284 Yield

Conditions & References

20 %, 31 %

With 9,10-Dicyanoanthracene, oxygen in benzene, Time= 24h, Irradiation Tamai, Toshiyuki; Mizuno, Kazuhiko; Hashida, Isao; Otsuji, Yoshio; Chemistry Letters; nb. 5; (1992); p. 781 784 View in Reaxys

29 %, 13 %

With 9,10-Dicyanoanthracene, oxygen in acetonitrile, Time= 1.5h, Irradiation Tamai, Toshiyuki; Mizuno, Kazuhiko; Hashida, Isao; Otsuji, Yoshio; Chemistry Letters; nb. 5; (1992); p. 781 784 View in Reaxys

N O O

Rx-ID: 2370406 View in Reaxys 162/284 Yield

Conditions & References

71 % Chromat., 72 % Chromat.

With oxygen, copper(l) chloride in acetonitrile, Time= 20h, T= 60 °C , p= 760Torr

71 % Chromat., 72 % Chromat.

With oxygen, copper(l) chloride in acetonitrile, Time= 20h, T= 60 °C , p= 760Torr

Murata, Satoru; Suzuki, Kaoru; Tamatani, Akira; Miura, Masahiro; Nomura, Masakatsu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 11; (1992); p. 1387 - 1392 View in Reaxys

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O O

O HO

Rx-ID: 2935304 View in Reaxys 163/284 Yield

Conditions & References With n-hexadecane peroxidized at 160 deg C, Time= 1.55556h, T= 160 °C , other naphthalenes, Product distribution, Mechanism Igarashi; Jensen; Lusztyk; Korcek; Ingold; Journal of the American Chemical Society; vol. 114; nb. 20; (1992); p. 7727 - 7736 View in Reaxys

N O

Cl –

H 2N

N+

Cl –

N H O

N+

Rx-ID: 3223970 View in Reaxys 164/284 Yield

Conditions & References in water, T= 25 °C , Equilibrium constant Stachissini, Antonia Sonia; Amaral, Antonia T. do; Amaral, Luciano do; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 11; (1992); p. 1929 - 1931 View in Reaxys

O O O

Rx-ID: 5253195 View in Reaxys 165/284 Yield

Conditions & References With pyridine, lithium-tris(diethylamino)hydridoaluminate in tetrahydrofuran, Time= 0.5h, T= 0 °C , Reduction Cha, Jin Soon; Lee, Jae Cheol Lee; Lee, Sung Eun; Organic Preparations and Procedures International; vol. 24; nb. 3; (1992); p. 327 - 330 View in Reaxys

aminoacyl chlorotrityl resin HO

Rx-ID: 16172311 View in Reaxys 166/284 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran / 20 °C 2: Li(Et2N)3AlH; pyridine / tetrahydrofuran / 0.5 h / 0 °C With pyridine, lithium-tris(diethylamino)hydridoaluminate in tetrahydrofuran, 1: Substitution / 2: Reduction

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Cha, Jin Soon; Lee, Jae Cheol Lee; Lee, Sung Eun; Organic Preparations and Procedures International; vol. 24; nb. 3; (1992); p. 327 - 330 View in Reaxys

O O

Rx-ID: 1784018 View in Reaxys 167/284 Yield

Conditions & References With hydrogen fluoride, antimony pentafluoride, Time= 3h, T= 0 °C , p= 15200Torr , other polynuclear aromatic compounds; var reaction conditions, Product distribution Tanaka; Souma; Journal of the Chemical Society - Series Chemical Communications; nb. 21; (1991); p. 1551 - 1553 View in Reaxys

O OH

Rx-ID: 2749651 View in Reaxys 168/284 Yield

Conditions & References With oxygen, dichloro-acetic acid, Paraquat, iron(II) chloride, Ambient temperature, Irradiation, other conditions: absence of catalysts, other times, Product distribution Santamaria, Jean; Jroundi, Rachid; Tetrahedron Letters; vol. 32; nb. 34; (1991); p. 4291 - 4294 View in Reaxys

Rx-ID: 2935298 View in Reaxys 169/284 Yield 14 %, 69 %

Conditions & References 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

14 %, 69 %

With oxygen, dichloro-acetic acid, Paraquat, iron(II) chloride in methanol, acetonitrile, Time= 4h, Ambient temperature, Irradiation, Mechanism Santamaria, Jean; Jroundi, Rachid; Tetrahedron Letters; vol. 32; nb. 34; (1991); p. 4291 - 4294 View in Reaxys With potassium permanganate in water, acetic acid, T= 30 °C , ΔH(act.), ΔS(act.), ΔG(act.); effect of acetic acid; effect of Mn(II) ions; effect of different anions;, Kinetics, Thermodynamic data, Mechanism Gopalan, R.; Ekambaram, K.; Journal of the Indian Chemical Society; vol. 63; (1986); p. 696 - 698 View in Reaxys

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O– F

O S

O F

N+ O

Rx-ID: 1784065 View in Reaxys 170/284 Yield

Conditions & References

50 %

Time= 48h, T= 130 °C Martinez, Antonio Garcia; Alvarez, Roberto Martinez; Barcina, Jose Osio; Cerero, S. Moya de la; Vilar, E. Teso; et al.; Journal of the Chemical Society, Chemical Communications; nb. 22; (1990); p. 1571 - 1572 View in Reaxys O– Cl 1O OO

1 S N

N O

Rx-ID: 2036941 View in Reaxys 171/284 Yield

Conditions & References in acetonitrile, also in the presence of 2,6-di-tert-butyl-4-methylpyridine, Product distribution, Mechanism Chiou, Shishue; Hoque, A. K. M. M.; Shine, Henry J.; Journal of Organic Chemistry; vol. 55; nb. 10; (1990); p. 3227 - 3232 View in Reaxys

Rx-ID: 3761042 View in Reaxys 172/284 Yield

Conditions & References

59 %, 31 %

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

Rx-ID: 24894559 View in Reaxys 173/284 Yield

Conditions & References 7 : Reduction of naphthoic acid to naphthaldehyde EXAMPLE 7 Reduction of naphthoic acid to naphthaldehyde The reactant was 20 wt percent naphthoic acid dissolved in triglyme. The acid feed was 0.07 LHSV per hour and the hydrogen flow rate was 650 GHSV per hour. At 350° C. 41percent of the naphthoic acid was reduced to the naphthaldehyde with 80percent selectivity to the aldehyde and 17percent selectivity to methyl naphthoate.

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At 365° C. conversion of the acid was 37percent with 75percent selectivity to the naphthaldehyde and 21percent selectivity to methyl naphthoate. in Triethylene glycol dimethyl ether Patent; Ethyl Corporation; US4950799; (1990); (A1) English View in Reaxys

Rx-ID: 2935300 View in Reaxys 174/284 Yield

Conditions & References

6% Spectr., 93 % Spectr.

With dichloro-acetic acid, oxygen in methanol, acetonitrile, Time= 3h, T= 20 °C , Irradiation

6% Spectr., 93 % Spectr.

With dichloro-acetic acid, oxygen in methanol, acetonitrile, Time= 3h, T= 20 °C , Irradiation, var. alkylaromatic compd., Mechanism, Product distribution

Santamaria, J.; Jroundi, R.; Rigaudy, J.; Tetrahedron Letters; vol. 30; nb. 35; (1989); p. 4677 - 4680 View in Reaxys

O O

Rx-ID: 2935301 View in Reaxys 175/284 Yield

Conditions & References

3 %, 95 %

With ammonium cerium(IV) nitrate in water, acetic acid, Time= 2h, T= 85 °C Sydnes, Leiv K.; Burkow, Ivan C.; Hansen, Sissel H.; Tetrahedron; vol. 41; nb. 23; (1985); p. 5703 - 5706 View in Reaxys

35 %, 39 %

With lt;Mn3O(OAc)6(OAc)(HOAc)gt;*5H2O, lithium chloride in acetic acid, Time= 27h, T= 100 °C Futami; Hishino; Kurosawa; Bulletin of the Chemical Society of Japan; vol. 62; nb. 11; (1989); p. 3567 - 3571 View in Reaxys

H S

O O N

H N H

N O

O O

racemate

Rx-ID: 3009282 View in Reaxys 176/284 Yield

Conditions & References With hydrogenchloride in tetrahydrofuran, Time= 24h, T= 45 °C Gupta, Ram B.; Franck, Richard W.; Onan, Kay D.; Soll, Clifford E.; Journal of Organic Chemistry; vol. 54; nb. 5; (1989); p. 1097 - 1101 View in Reaxys

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O O O

N N

N O racemate

Rx-ID: 3012567 View in Reaxys 177/284 Yield

Conditions & References With amberlyst-15, potassium carbonate, 1.) THF, H2O, 40 deg C, 24 h, 2.) THF, methanol, water, 50-60 deg C, 3 min, Yield given. Multistep reaction Gupta, Ram B.; Franck, Richard W.; Onan, Kay D.; Soll, Clifford E.; Journal of Organic Chemistry; vol. 54; nb. 5; (1989); p. 1097 - 1101 View in Reaxys

O (v2) – (v3) O Mn3+ (v2)

O–

(v2)

O O

Rx-ID: 3983930 View in Reaxys 178/284 Yield

Conditions & References

35 %, 39 %

O Cl –

ammonium carbonate

N+ O

Rx-ID: 20475622 View in Reaxys 179/284 Yield

Conditions & References Reaction Steps: 2 1: CaCO3 / methanol / 72 h / 25 - 40 °C 2: 3 N aq. HCl / tetrahydrofuran / 24 h / 45 °C With hydrogenchloride, calcium carbonate in tetrahydrofuran, methanol Gupta, Ram B.; Franck, Richard W.; Onan, Kay D.; Soll, Clifford E.; Journal of Organic Chemistry; vol. 54; nb. 5; (1989); p. 1097 - 1101 View in Reaxys Reaction Steps: 2 1: 95 percent / CaCO3 / methanol / 72 h / 25 - 40 °C 2: 1.) Amberlyst-15, 2.) K2CO3 / 1.) THF, H2O, 40 deg C, 24 h, 2.) THF, methanol, water, 50-60 deg C, 3 min With amberlyst-15, potassium carbonate, calcium carbonate in methanol Gupta, Ram B.; Franck, Richard W.; Onan, Kay D.; Soll, Clifford E.; Journal of Organic Chemistry; vol. 54; nb. 5; (1989); p. 1097 - 1101 View in Reaxys

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O O

Rx-ID: 3479934 View in Reaxys 180/284 Yield

Conditions & References With perchloric acid in acetic acid, Time= 96h, Yield given. Yields of byproduct given Linde; Cramer; Archiv der Pharmazie; vol. 321; nb. 4; (1988); p. 237 - 240 View in Reaxys

O O O O

Rx-ID: 19147772 View in Reaxys 181/284 Yield

Conditions & References Reaction Steps: 3 1: 53 percent / i-pentyl nitrite / 1,2-dimethoxy-ethane 2: 96 percent / H2 / 5percent Pd/C / methanol 3: 70percent HClO4 / acetic acid / 96 h With perchloric acid, hydrogen, isopentyl nitrite, palladium on activated charcoal in methanol, 1,2-dimethoxyethane, acetic acid Linde; Cramer; Archiv der Pharmazie; vol. 321; nb. 4; (1988); p. 237 - 240 View in Reaxys

H 2N O

4-amino-2.6-dioxy-pyridine

HO O

Rx-ID: 19161603 View in Reaxys 182/284 Yield

O O

Rx-ID: 19169783 View in Reaxys 183/284 Yield

Conditions & References Reaction Steps: 2 1: 96 percent / H2 / 5percent Pd/C / methanol 2: 70percent HClO4 / acetic acid / 96 h With perchloric acid, hydrogen, palladium on activated charcoal in methanol, acetic acid

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Linde; Cramer; Archiv der Pharmazie; vol. 321; nb. 4; (1988); p. 237 - 240 View in Reaxys

Rx-ID: 1999429 View in Reaxys 184/284 Yield

Conditions & References

7 %, 10 %, in 2,2,4-trimethylpentane, Time= 2h, Ambient temperature, Irradiation 71 %, 2.3 Griffin, G. William; Horn, Keith A.; Journal of the American Chemical Society; vol. 109; nb. 16; (1987); p. 4919 % 4926 View in Reaxys in 2,2,4-trimethylpentane, Ambient temperature, Irradiation, activation energy, Rate constant, Thermodynamic data Griffin, G. William; Horn, Keith A.; Journal of the American Chemical Society; vol. 109; nb. 16; (1987); p. 4919 4926 View in Reaxys

Co2(CO)8

I Br

O O

Rx-ID: 6680298 View in Reaxys 185/284 Yield 54 %, 20 %, 2 %, 3 %

Conditions & References With sodium hydroxide, carbon monoxide, cetyltrimethylammonim bromide in water, benzene, Time= 20h, T= 20 °C , p= 760Torr Miura, Masahiro; Akase, Fumiaki; Shinohara, Masato; Nomura, Masakatsu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1987); p. 1021 - 1026 View in Reaxys

O O

Z O

O racemate

Rx-ID: 2056930 View in Reaxys 186/284 Yield 3 %, 39 %

Conditions & References With tetraphenylporphyrine, oxygen in tetrachloromethane, Time= 13h, Ambient temperature, Irradiation, Yield given Atasoy, Basri; Balci, Metin; Tetrahedron; vol. 42; nb. 5; (1986); p. 1461 - 1468 View in Reaxys

3 %, 39 %

With tetraphenylporphyrine, oxygen in tetrachloromethane, Time= 13h, Ambient temperature, Irradiation, Yield given. Title compound not separated from byproducts Atasoy, Basri; Balci, Metin; Tetrahedron; vol. 42; nb. 5; (1986); p. 1461 - 1468 View in Reaxys

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3 %, 39 %

With tetraphenylporphyrine, oxygen in tetrachloromethane, Time= 13h, Ambient temperature, Irradiation, Yields of byproduct given Atasoy, Basri; Balci, Metin; Tetrahedron; vol. 42; nb. 5; (1986); p. 1461 - 1468 View in Reaxys O

O O N

O N O

N O

Rx-ID: 2331341 View in Reaxys 187/284 Yield

Conditions & References T= 37 °C , Equilibrium constant Seal, B. K.; Mukherjee, A. K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 25; nb. 5; (1986); p. 413 - 415 View in Reaxys

Rx-ID: 2656154 View in Reaxys 188/284 Yield

Conditions & References

0.5 %, 34 %, 23 %

With oxygen in cyclohexane, T= 24.9 °C , p= 760Torr Barcus, R. L.; Hadel, L. M.; Johnston, L. J.; Platz, M. S.; Savino, T. G.; Scaiano, J. C.; Journal of the American Chemical Society; vol. 108; nb. 14; (1986); p. 3928 - 3937 View in Reaxys

O Z O

Rx-ID: 2816649 View in Reaxys 189/284 Yield

Conditions & References With triethylamine in dichloromethane, Time= 0.5h, Ambient temperature, Yield given Atasoy, Basri; Balci, Metin; Tetrahedron; vol. 42; nb. 5; (1986); p. 1461 - 1468 View in Reaxys

Rx-ID: 2935302 View in Reaxys 190/284 Yield

Conditions & References With oxygen, 2,6,9,10-tetracyanoanthracene in acetonitrile, T= 22 °C , Irradiation, photooxidation, other sensitizers, solvents and products, Product distribution, Mechanism, Quantum yield Albini, Angelo; Spreti, Silvia; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 41; nb. 10; (1986); p. 1286 - 1292

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View in Reaxys

O Br

Rx-ID: 3886502 View in Reaxys 191/284 Yield 54 %, 20 %, 2 %, 3 %

Conditions & References With sodium hydroxide, dicobalt octacarbonyl, cetyltrimethylammonim bromide in benzene, Time= 20h, T= 20 °C , p= 760Torr Miura, Masahiro; Akase, Fumiaki; Nomura, Masakatsu; Journal of the Chemical Society, Chemical Communications; nb. 3; (1986); p. 241 - 242 View in Reaxys

4 %, 20 %, With sodium hydroxide, dicobalt octacarbonyl, cetyltrimethylammonim bromide in benzene, Time= 20h, T= 20 °C , 2 %, 3 % p= 760Torr Miura, Masahiro; Akase, Fumiaki; Nomura, Masakatsu; Journal of the Chemical Society, Chemical Communications; nb. 3; (1986); p. 241 - 242 View in Reaxys

Rx-ID: 20788883 View in Reaxys 192/284 Yield

Conditions & References Reaction Steps: 2 1: O2, tetraphenylporphyrine / CCl4 / 13 h / Ambient temperature; Irradiation 2: Et3N / CH2Cl2 / 0.5 h / Ambient temperature With tetraphenylporphyrine, oxygen, triethylamine in tetrachloromethane, dichloromethane Atasoy, Basri; Balci, Metin; Tetrahedron; vol. 42; nb. 5; (1986); p. 1461 - 1468 View in Reaxys

Rx-ID: 20789333 View in Reaxys 193/284 Yield

Conditions & References Reaction Steps: 2 1: 1.) butyllithium; 2.) H2O / 1.) hexane, THF, -70 deg C, 45 min, then -20 deg C, 1 h; 2.) -70 deg C 2: O2, tetraphenylporphyrine / CCl4 / 13 h / Ambient temperature; Irradiation With n-butyllithium, tetraphenylporphyrine, water, oxygen in tetrachloromethane Atasoy, Basri; Balci, Metin; Tetrahedron; vol. 42; nb. 5; (1986); p. 1461 - 1468 View in Reaxys Reaction Steps: 3 1: 1.) butyllithium; 2.) H2O / 1.) hexane, THF, -70 deg C, 45 min, then -20 deg C, 1 h; 2.) -70 deg C 2: O2, tetraphenylporphyrine / CCl4 / 13 h / Ambient temperature; Irradiation 3: Et3N / CH2Cl2 / 0.5 h / Ambient temperature With n-butyllithium, tetraphenylporphyrine, water, oxygen, triethylamine in tetrachloromethane, dichloromethane Atasoy, Basri; Balci, Metin; Tetrahedron; vol. 42; nb. 5; (1986); p. 1461 - 1468

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View in Reaxys

O O

O O O

Rx-ID: 2191209 View in Reaxys 194/284 Yield

Conditions & References in benzene-d6, T= 35 °C , Irradiation, Quantum yield Holden, David A.; Gray, J. Bradley; McEwan, Ian; Journal of Organic Chemistry; vol. 50; nb. 6; (1985); p. 866 873 View in Reaxys

O O

Rx-ID: 2882634 View in Reaxys 195/284 Yield

Conditions & References

3 %, 95 %

With ammonium cerium(IV) nitrate in water, Time= 2h, T= 85 °C Sydnes, Leiv K.; Burkow, Ivan C.; Hansen, Sissel H.; Tetrahedron; vol. 41; nb. 23; (1985); p. 5703 - 5706 View in Reaxys

O O

Rx-ID: 3133440 View in Reaxys 196/284 Yield

Rx-ID: 3593889 View in Reaxys 197/284

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Yield

Conditions & References

84 %

in benzene, Time= 3.5h, Irradiation Gravel, Denis; Murray, Stevens; Ladouceur, Gaetan; Journal of the Chemical Society, Chemical Communications; nb. 24; (1985); p. 1828 - 1829 View in Reaxys

HO O

Rx-ID: 1581940 View in Reaxys 198/284 Yield

Conditions & References With oxygen, Irradiation, Product distribution, Quantum yield, Mechanism Slocum, Gregory H.; Schuster, Gary B.; Journal of Organic Chemistry; vol. 49; nb. 12; (1984); p. 2177 - 2185 View in Reaxys

O N Mg

Rx-ID: 1630825 View in Reaxys 199/284 Yield 92 %

Conditions & References in diethyl ether, Time= 0.5h, Ambient temperature Olah, George A.; Ohannesian, Lena; Arvanaghi, Massoud; Journal of Organic Chemistry; vol. 49; nb. 20; (1984); p. 3856 - 3857 View in Reaxys

Rx-ID: 1999360 View in Reaxys 200/284 Yield

O O HO

Rx-ID: 2935299 View in Reaxys 201/284 Yield

Conditions & References

55 % Chromat., 20 % Chromat., 20 % Chromat.

With 9,10-Dicyanoanthracene, oxygen in acetonitrile, Irradiation

55 % Chromat.,

With 9,10-Dicyanoanthracene in acetonitrile, Irradiation, photooxygenation depending on the solvent polarity investigated; other naphtalenic compounds; other solvent: CH2Cl2, Mechanism

Santamaria, J.; Gabillet, P.; Bokobza, L.; Tetrahedron Letters; vol. 25; nb. 20; (1984); p. 2139 - 2142 View in Reaxys

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20 % Chromat., 20 % Chromat.

Santamaria, J.; Gabillet, P.; Bokobza, L.; Tetrahedron Letters; vol. 25; nb. 20; (1984); p. 2139 - 2142 View in Reaxys

O Mg O

Rx-ID: 3345626 View in Reaxys 202/284 Yield

Conditions & References With hydrogenchloride, 1.) ether, 1 h, room temp., Yield given. Multistep reaction Olah, George A.; Surya Prakash, G. K.; Arvanaghi, Massoud; Synthesis; nb. 3; (1984); p. 228 - 230 View in Reaxys

HO O

Rx-ID: 3560232 View in Reaxys 203/284 Yield

Rx-ID: 3560249 View in Reaxys 204/284 Yield

–O

Li+ Mg Br

Rx-ID: 3563625 View in Reaxys 205/284 Yield 78 %

Conditions & References in tetrahydrofuran, Time= 2h, Heating Bogavac, M.; Arsenijevic, L.; Pavlov, S.; Arsenijevic, V.; Tetrahedron Letters; vol. 25; nb. 17; (1984); p. 1843 1844 View in Reaxys

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HO O

Rx-ID: 3761005 View in Reaxys 206/284 Yield

Rx-ID: 3761008 View in Reaxys 207/284 Yield

I N

Rx-ID: 3893732 View in Reaxys 208/284 Yield

Conditions & References 1.) metalation, 2.) alkylation, 3.) hydrolysis, Yield given. Multistep reaction. Yields of byproduct given Comins, Daniel L.; Brown, Jack D.; Journal of Organic Chemistry; vol. 49; nb. 6; (1984); p. 1078 - 1083 View in Reaxys

–O

Na +

O O

Rx-ID: 2037263 View in Reaxys 209/284 Yield

Conditions & References

18 %

in methanol, Time= 50h, Heating, Yield given Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys

18 % Turn- in methanol, Time= 50h, Heating, Yields of byproduct given ov. Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys

– Ag+ O

S O

O O

S O

Rx-ID: 2037265 View in Reaxys 210/284

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Yield

Conditions & References

60 % Turn- in N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 50h, T= 75 °C ov., 17 % Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 Turnov. View in Reaxys

Rx-ID: 2037270 View in Reaxys 211/284 Yield

Conditions & References

60 %

With sodium methylate in N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 40h, T= 75 °C , further reagents Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys

Rx-ID: 2045020 View in Reaxys 212/284 Yield

Conditions & References

70 %

With potassium carbonate in ethanol, Time= 6h, T= 20 - 25 °C , further reagents Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys

Rx-ID: 2045021 View in Reaxys 213/284 Yield

Conditions & References With hydrogenchloride in methanol Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys

–

Ag+ O

O O

Rx-ID: 2114062 View in Reaxys 214/284 Yield

Conditions & References

65 % Turn- in acetic acid, Time= 39h, T= 75 °C ov., 35 % Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 Turnov. View in Reaxys

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O O

Rx-ID: 2114064 View in Reaxys 215/284 Yield

Conditions & References

65 % Turn- With silver(I) acetate in acetic acid, Time= 39h, T= 75 °C ov., 35 % Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 Turnov. View in Reaxys

O O

O S

Rx-ID: 2881082 View in Reaxys 216/284 Yield

Conditions & References Time= 120h, T= 75 °C , influence of reaction time, Product distribution Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys

ammonium carbonate

Rx-ID: 19884437 View in Reaxys 217/284 Yield

Conditions & References Reaction Steps: 2 1: 93 percent Turnov. / sodium acetate / hexamethylphosphoric acid triamide / 24 h / 75 °C 2: 70 percent / potassium carbonate / ethanol / 6 h / 20 - 25 °C / further reagents With sodium acetate, potassium carbonate in N,N,N,N,N,N-hexamethylphosphoric triamide, ethanol Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 2 1: 60 percent / 0.75 h 2: 35 percent Turnov. / acetic acid / 39 h / 75 °C in acetic acid Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 3 1: magnesium / tetrahydrofuran / Heating 2: 15 percent / tetrahydrofuran / 48 h / Heating 3: 35 percent Turnov. / acetic acid / 39 h / 75 °C With magnesium in tetrahydrofuran, acetic acid Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 3 1: magnesium / tetrahydrofuran / Heating 2: 15 percent / chlorotrimethylsilane / tetrahydrofuran / 48 h / Heating 3: 35 percent Turnov. / acetic acid / 39 h / 75 °C With chloro-trimethyl-silane, magnesium in tetrahydrofuran, acetic acid

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Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 3 1: magnesium / tetrahydrofuran / Heating 2: tetrahydrofuran / 48 h / Heating 3: 35 percent Turnov. / acetic acid / 39 h / 75 °C With magnesium in tetrahydrofuran, acetic acid Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys

ammonium carbonate O

Rx-ID: 19886295 View in Reaxys 218/284 Yield

Conditions & References Reaction Steps: 2 1: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 2: methanol / 50 h / Heating With N-Bromosuccinimide, Perbenzoic acid in methanol, tetrachloromethane Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 3 1: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 2: 93 percent Turnov. / sodium acetate / hexamethylphosphoric acid triamide / 24 h / 75 °C 3: 70 percent / potassium carbonate / ethanol / 6 h / 20 - 25 °C / further reagents With N-Bromosuccinimide, Perbenzoic acid, sodium acetate, potassium carbonate in tetrachloromethane, N,N,N,N,N,N-hexamethylphosphoric triamide, ethanol Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 2 1: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 2: 17 percent Turnov. / hexamethylphosphoric acid triamide / 50 h / 75 °C With N-Bromosuccinimide, Perbenzoic acid in tetrachloromethane, N,N,N,N,N,N-hexamethylphosphoric triamide Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 2 1: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 2: 60 percent / sodium methoxide / hexamethylphosphoric acid triamide / 40 h / 75 °C / further reagents With N-Bromosuccinimide, Perbenzoic acid, sodium methylate in tetrachloromethane, N,N,N,N,N,N-hexamethylphosphoric triamide Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys

ammonium carbonate

Rx-ID: 19897209 View in Reaxys 219/284 Yield

Conditions & References Reaction Steps: 2 1: 25 mg / tetrahydrofuran / 0.17 h / -78 °C

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2: 35 percent Turnov. / acetic acid / 39 h / 75 °C in tetrahydrofuran, acetic acid Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 3 1: 25 mg / tetrahydrofuran / 0.17 h / -78 °C 2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: methanol / 50 h / Heating With N-Bromosuccinimide, Perbenzoic acid in tetrahydrofuran, methanol, tetrachloromethane Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 4 1: 25 mg / tetrahydrofuran / 0.17 h / -78 °C 2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: 93 percent Turnov. / sodium acetate / hexamethylphosphoric acid triamide / 24 h / 75 °C 4: 70 percent / potassium carbonate / ethanol / 6 h / 20 - 25 °C / further reagents With N-Bromosuccinimide, Perbenzoic acid, sodium acetate, potassium carbonate in tetrahydrofuran, tetrachloromethane, N,N,N,N,N,N-hexamethylphosphoric triamide, ethanol Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 3 1: 25 mg / tetrahydrofuran / 0.17 h / -78 °C 2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: 17 percent Turnov. / hexamethylphosphoric acid triamide / 50 h / 75 °C With N-Bromosuccinimide, Perbenzoic acid in tetrahydrofuran, tetrachloromethane, N,N,N,N,N,N-hexamethylphosphoric triamide Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 3 1: 25 mg / tetrahydrofuran / 0.17 h / -78 °C 2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: 60 percent / sodium methoxide / hexamethylphosphoric acid triamide / 40 h / 75 °C / further reagents With N-Bromosuccinimide, Perbenzoic acid, sodium methylate in tetrahydrofuran, tetrachloromethane, N,N,N,N,N,N-hexamethylphosphoric triamide Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys

ammonium carbonate

Mg Br

Rx-ID: 19911570 View in Reaxys 220/284 Yield

Conditions & References Reaction Steps: 2 1: 15 percent / tetrahydrofuran / 48 h / Heating 2: 35 percent Turnov. / acetic acid / 39 h / 75 °C in tetrahydrofuran, acetic acid Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 3 1: 15 percent / tetrahydrofuran / 48 h / Heating

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2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: methanol / 50 h / Heating With N-Bromosuccinimide, Perbenzoic acid in tetrahydrofuran, methanol, tetrachloromethane Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 4 1: 15 percent / tetrahydrofuran / 48 h / Heating 2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: 93 percent Turnov. / sodium acetate / hexamethylphosphoric acid triamide / 24 h / 75 °C 4: 70 percent / potassium carbonate / ethanol / 6 h / 20 - 25 °C / further reagents With N-Bromosuccinimide, Perbenzoic acid, sodium acetate, potassium carbonate in tetrahydrofuran, tetrachloromethane, N,N,N,N,N,N-hexamethylphosphoric triamide, ethanol Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 3 1: 15 percent / tetrahydrofuran / 48 h / Heating 2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: 17 percent Turnov. / hexamethylphosphoric acid triamide / 50 h / 75 °C With N-Bromosuccinimide, Perbenzoic acid in tetrahydrofuran, tetrachloromethane, N,N,N,N,N,N-hexamethylphosphoric triamide Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 3 1: 15 percent / tetrahydrofuran / 48 h / Heating 2: 40 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 4.5 h / Heating 3: 60 percent / sodium methoxide / hexamethylphosphoric acid triamide / 40 h / 75 °C / further reagents With N-Bromosuccinimide, Perbenzoic acid, sodium methylate in tetrahydrofuran, tetrachloromethane, N,N,N,N,N,N-hexamethylphosphoric triamide Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 2 1: 15 percent / chlorotrimethylsilane / tetrahydrofuran / 48 h / Heating 2: 35 percent Turnov. / acetic acid / 39 h / 75 °C With chloro-trimethyl-silane in tetrahydrofuran, acetic acid Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran / 48 h / Heating 2: 35 percent Turnov. / acetic acid / 39 h / 75 °C in tetrahydrofuran, acetic acid Card,P.J.; Friedli,F.E.; Shechter,H.; Journal of the American Chemical Society; vol. 105; (1983); p. 6104 View in Reaxys

O O O

H O

O O

H O

O racemate

Rx-ID: 1538239 View in Reaxys 221/284

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Yield

Conditions & References

13 % Chromat., 40 % Chromat., 36 % Chromat. 13 % Chromat., 40 % Chromat., 36 % Chromat.

in acetonitrile, Time= 2h, Irradiation, with other α-epoxyketones, also with other aldehyde, dipolarophile; var. of irradiation time, solvent, Product distribution Hallet, Philippe; Muzart, Jacques; Pete, Jean-Pierre; Bulletin de la Societe Chimique de France; vol. 2; nb. 7-8; (1982); p. 262 - 264 View in Reaxys in acetonitrile, Time= 2h, Irradiation Hallet, Philippe; Muzart, Jacques; Pete, Jean-Pierre; Bulletin de la Societe Chimique de France; vol. 2; nb. 7-8; (1982); p. 262 - 264 View in Reaxys

H O

O O

H O

O racemate

Rx-ID: 1828497 View in Reaxys 222/284 Yield

Conditions & References

13 % Chromat., 40 % Chromat., 36 % Chromat.

With maleic anhydride in acetonitrile, Time= 2h, Irradiation Hallet, Philippe; Muzart, Jacques; Pete, Jean-Pierre; Bulletin de la Societe Chimique de France; vol. 2; nb. 7-8; (1982); p. 262 - 264 View in Reaxys

Rx-ID: 2551082 View in Reaxys 223/284 Yield

Conditions & References

39 %, 7 %, T= 650 °C , p= 0.05 - 0.1Torr , Further byproducts given 8 %, 9 % Engler, T. A.; Shechter, H.; Tetrahedron Letters; vol. 23; nb. 27; (1982); p. 2715 - 2718 View in Reaxys

Rx-ID: 2551083 View in Reaxys 224/284

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Yield

Conditions & References

5 %, 39 %, T= 650 °C , p= 0.05 - 0.1Torr , Mechanism 7 %, 8 %, Engler, T. A.; Shechter, H.; Tetrahedron Letters; vol. 23; nb. 27; (1982); p. 2715 - 2718 9 %, 3 % View in Reaxys -1 F (v4)

B FF

O C+ H

Rx-ID: 2627866 View in Reaxys 225/284 Yield

Conditions & References

2 %, 13 %, With dihydrogen peroxide in tetrahydrofuran, Further byproducts given 11 %, 17 % Pomerantz, Martin; Swei, Gwo-Shin; Tetrahedron Letters; vol. 23; nb. 30; (1982); p. 3027 - 3030 View in Reaxys -1 F (v4)

B FF

O C+ H

Rx-ID: 2627867 View in Reaxys 226/284 Yield

Conditions & References

2 %, 11 %, 17 %, 4 %

With dihydrogen peroxide in tetrahydrofuran, Further byproducts given Pomerantz, Martin; Swei, Gwo-Shin; Tetrahedron Letters; vol. 23; nb. 30; (1982); p. 3027 - 3030 View in Reaxys

O O O

O O

racemate

Rx-ID: 3416174 View in Reaxys 227/284 Yield

Conditions & References

55 % Chromat., 12 % Chromat., 32 % Chromat.

in acetonitrile, Time= 0.5h, Irradiation Hallet, Philippe; Muzart, Jacques; Pete, Jean-Pierre; Bulletin de la Societe Chimique de France; vol. 2; nb. 7-8; (1982); p. 262 - 264 View in Reaxys

O O

Rx-ID: 3805729 View in Reaxys 228/284

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Yield

Conditions & References

46 % Chromat., 80 % Chromat.

in acetonitrile, Time= 0.3h, Irradiation Hallet, Philippe; Muzart, Jacques; Pete, Jean-Pierre; Bulletin de la Societe Chimique de France; vol. 2; nb. 7-8; (1982); p. 262 - 264 View in Reaxys

O Se

O O

O Se

Se Se

Rx-ID: 3983929 View in Reaxys 229/284 Yield 6 %, 6 %, 6 %, 19 %

Conditions & References Time= 11.75h, T= 120 °C Barton, Derek H. R.; Hui, Raymond A. H. F.; Ley, Steven V.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 9; (1982); p. 2179 - 2186 View in Reaxys

O Se

Se Se

Rx-ID: 3983931 View in Reaxys 230/284 Yield 6 %, 6 %, 6 %, 19 %

Conditions & References With benzeneseleninic anhydride, Time= 11.75h, T= 120 °C Barton, Derek H. R.; Hui, Raymond A. H. F.; Ley, Steven V.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 9; (1982); p. 2179 - 2186 View in Reaxys

O Cl

Rx-ID: 1456558 View in Reaxys 231/284 Yield 45 %

Conditions & References With potassium tert-butylate, Time= 12h, T= 0 °C Billups, W. E.; Reed, Larry E.; Casserly, Edward W.; Lin, L. P.; Journal of Organic Chemistry; vol. 46; nb. 7; (1981); p. 1326 - 1333 View in Reaxys

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O N Mg O

Rx-ID: 1560756 View in Reaxys 232/284 Yield

Conditions & References

94 %

in diethyl ether, Time= 0.25h, Ambient temperature Olah, George A.; Arvanaghi, Massoud; Angewandte Chemie; vol. 93; nb. 10; (1981); p. 925 - 926 View in Reaxys

Z O

Rx-ID: 1828496 View in Reaxys 233/284 Yield

Conditions & References

17 %, 16 %

in benzene, Time= 0.5h, Ambient temperature, Irradiation, other solvents, Product distribution, Mechanism Hallet, Philippe; Muzart, Jacques; Pete, Jean-Piere; Journal of Organic Chemistry; vol. 46; nb. 21; (1981); p. 4275 - 4279 View in Reaxys

O Cl

Rx-ID: 2092336 View in Reaxys 234/284 Yield 10 %, 18 %

Conditions & References With tetrahydrofuran, potassium tert-butylate, Time= 12h, T= 0 °C Billups, W. E.; Reed, Larry E.; Casserly, Edward W.; Lin, L. P.; Journal of Organic Chemistry; vol. 46; nb. 7; (1981); p. 1326 - 1333 View in Reaxys

Rx-ID: 2125164 View in Reaxys 235/284 Yield

Conditions & References With methanol, oxygen, Ambient temperature, Irradiation Slocum, Gregory H.; Kaufmann, Kenneth; Schuster, Gary B.; Journal of the American Chemical Society; vol. 103; nb. 15; (1981); p. 4625 - 4627 View in Reaxys

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-1 F (v4)

B FF

N+

Rx-ID: 2632638 View in Reaxys 236/284 Yield

Conditions & References With triethylsilane, water, 1) CH2Cl2, reflux, 2) heating, Yield given. Multistep reaction Fry, James L.; Ott, Roger A.; Journal of Organic Chemistry; vol. 46; nb. 3; (1981); p. 602 - 607 View in Reaxys

O Br

Rx-ID: 2882633 View in Reaxys 237/284 Yield

Conditions & References

12 %, 39 %, 18 %

With copper diacetate, cobalt(II) acetate, sodium bromide, Time= 1h, T= 150 °C , p= 30400Torr Okada, Toshihiko; Kamiya, Yoshio; Bulletin of the Chemical Society of Japan; vol. 54; nb. 9; (1981); p. 2724 2727 View in Reaxys

O Br

Rx-ID: 2935297 View in Reaxys 238/284 Yield

Conditions & References

12 %, 39 %, 18 %

With copper diacetate, cobalt(II) acetate, acetic acid, sodium bromide, Time= 1h, T= 150 °C , p= 30400Torr Okada, Toshihiko; Kamiya, Yoshio; Bulletin of the Chemical Society of Japan; vol. 54; nb. 9; (1981); p. 2724 2727 View in Reaxys

N O

S O

Rx-ID: 3487052 View in Reaxys 239/284 Yield 82 %

Conditions & References With potassium carbonate in o-xylene, Time= 10h, Heating Trost, Barry M.; Liu, Guang-jian; Journal of Organic Chemistry; vol. 46; nb. 22; (1981); p. 4617 - 4620 View in Reaxys

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N O

Rx-ID: 3490562 View in Reaxys 240/284 Yield

Conditions & References

89 %

With potassium carbonate in o-xylene, Time= 6h, Heating Trost, Barry M.; Liu, Guang-jian; Journal of Organic Chemistry; vol. 46; nb. 22; (1981); p. 4617 - 4620 View in Reaxys

NZ N+

Cl – Mg Br

Rx-ID: 3995490 View in Reaxys 241/284 Yield 82 %

Conditions & References in diethyl ether, Ambient temperature Gupton, John T.; Polk, Dale E.; Synthetic Communications; vol. 11; nb. 7; (1981); p. 571 - 578 View in Reaxys

HN O

Rx-ID: 19156435 View in Reaxys 242/284 Yield

Conditions & References Reaction Steps: 2 1: 75 percent / Et3N / diethyl ether / 3 h / Ambient temperature 2: 82 percent / K2CO3 / o-xylene / 10 h / Heating With potassium carbonate, triethylamine in diethyl ether, o-xylene Trost, Barry M.; Liu, Guang-jian; Journal of Organic Chemistry; vol. 46; nb. 22; (1981); p. 4617 - 4620 View in Reaxys Reaction Steps: 2 1: 73 percent / Et3N / CH2Cl2 / 3 h / Ambient temperature 2: 89 percent / K2CO3 / o-xylene / 6 h / Heating With potassium carbonate, triethylamine in dichloromethane, o-xylene Trost, Barry M.; Liu, Guang-jian; Journal of Organic Chemistry; vol. 46; nb. 22; (1981); p. 4617 - 4620 View in Reaxys

Cl Cl O

Rx-ID: 21282171 View in Reaxys 243/284

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Yield

Conditions & References Reaction Steps: 2 1: 73 percent / N-bromosuccinimide (NBS), benzoyl peroxide / CCl4 / 5 h / Heating 2: t-BuOK / 12 h / 0 °C With N-Bromosuccinimide, Perbenzoic acid, potassium tert-butylate in tetrachloromethane Billups, W. E.; Reed, Larry E.; Casserly, Edward W.; Lin, L. P.; Journal of Organic Chemistry; vol. 46; nb. 7; (1981); p. 1326 - 1333 View in Reaxys Reaction Steps: 2 1: 73 percent / N-bromosuccinimide (NBS), benzoyl peroxide / CCl4 / 5 h / Heating 2: 10 percent / t-BuOK, THF / 12 h / 0 °C With tetrahydrofuran, N-Bromosuccinimide, Perbenzoic acid, potassium tert-butylate in tetrachloromethane Billups, W. E.; Reed, Larry E.; Casserly, Edward W.; Lin, L. P.; Journal of Organic Chemistry; vol. 46; nb. 7; (1981); p. 1326 - 1333 View in Reaxys

O O

Rx-ID: 2935280 View in Reaxys 244/284 Yield

Conditions & References

3 %, 30 %, With sodium persulfate, sulfuric acid, silver nitrate in water, Time= 0.5h, T= 60 °C 30 % Citterio, Attilio; Gazzetta Chimica Italiana; vol. 110; nb. 4; (1980); p. 253 - 258 View in Reaxys

O HO

Rx-ID: 2935303 View in Reaxys 245/284 Yield

Conditions & References

3 %, 30 %, With sodium persulfate, sulfuric acid, silver nitrate, p-benzoquinone in water, Time= 0.5h, T= 60 °C 30 % Citterio, Attilio; Gazzetta Chimica Italiana; vol. 110; nb. 4; (1980); p. 253 - 258 View in Reaxys

N O

1-naphthylmagnesiumhalogenide O

Rx-ID: 5589730 View in Reaxys 246/284 Yield 36 %

Conditions & References in diethyl ether, 1.) -70 deg C, 10 min; 2.) 0 deg C Walther, H.; Haase, L.; Gross, H.; Costisella, B.; Keitel, I.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 6; (1980); p. 902 - 908 View in Reaxys

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1-naphthylmagnesiumhalogenide

N S

Rx-ID: 5589731 View in Reaxys 247/284 Yield

Conditions & References

24 %

in diethyl ether, 1.) -70 deg C, 10 min; 2.) 0 deg C Walther, H.; Haase, L.; Gross, H.; Costisella, B.; Keitel, I.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 6; (1980); p. 902 - 908 View in Reaxys

O Li

Rx-ID: 698746 View in Reaxys 248/284 Yield

Conditions & References Evans; Chemistry and Industry (London, United Kingdom); (1957); p. 1596 View in Reaxys

O O

Rx-ID: 419817 View in Reaxys 249/284 Yield

Conditions & References With lithium aluminium tetrahydride Weygand et al.; Angewandte Chemie; vol. 65; (1953); p. 525,529 View in Reaxys

O Se

O O

Rx-ID: 5818198 View in Reaxys 250/284 Yield

Conditions & References T= 240 °C Ssultanow; Rodionow; Schemjakin; Zhurnal Obshchei Khimii; vol. 16; (1946); p. 2072,2075; ; (1948); p. 881 View in Reaxys Jensen et al.; Acta Chemica Scandinavica (1947-1973); vol. 6; (1952); p. 180,186 View in Reaxys

N N

Rx-ID: 301005 View in Reaxys 251/284 Yield

Conditions & References Bertin; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 229; (1949); p. 660; Annales de Chimie (Cachan, France); vol. <12> 8; (1953); p. 296,314

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View in Reaxys

NH H

O O

H 2N

Rx-ID: 7441945 View in Reaxys 252/284 Yield

Conditions & References Angyal et al.; Journal of the Chemical Society; (1949); p. 2704 View in Reaxys

C O O

Rx-ID: 5589733 View in Reaxys 253/284 Yield

Conditions & References With tetrafluoroboric acid, T= -30 - 20 °C , p= 57000 - 551000Torr Patent; Du Pont de Nemours and Co.; US2485237; (1946) View in Reaxys

O O Mg O

Rx-ID: 699986 View in Reaxys 254/284 Yield

Conditions & References With toluene, T= 100 °C , Kochen des gebildeten Acetals mit wss. HCl Schlenk; Bergmann; Justus Liebigs Annalen der Chemie; vol. 479; (1930); p. 58,74 View in Reaxys Zersetzung des Reaktionsproduktes mit Salzsaeure Bodroux; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 138; (1904); p. 701; Bulletin de la Societe Chimique de France; vol. <3> 31; (1904); p. 587 View in Reaxys Kikkoji; Biochemische Zeitschrift; vol. 35; (1911); p. 67 View in Reaxys Bodroux; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 138; (1904); p. 701; Bulletin de la Societe Chimique de France; vol. <3> 31; (1904); p. 587 View in Reaxys With toluene, T= 115 - 125 °C , Kochen des gebildeten Acetals mit wss. H2SO4 Friedmann; Biochemische Zeitschrift; vol. 242; (1931); p. 266,273 View in Reaxys Buu-Hoi; Cagniant; ; vol. 80; (1942); p. 384 View in Reaxys

N N

Rx-ID: 301075 View in Reaxys 255/284

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Yield

Conditions & References Anderson; Short; Journal of the Chemical Society; (1933); p. 485 View in Reaxys Rupe; Brentano; Helvetica Chimica Acta; vol. 19; (1936); p. 581,586 View in Reaxys Ruggli; Preuss; Helvetica Chimica Acta; vol. 24; (1941); p. 1345,1354 View in Reaxys

Rx-ID: 22032668 View in Reaxys 256/284 Yield

Conditions & References Reaction Steps: 2 1: concentrated aqueous HCl; acetic acid; H2SO4 2: hexamethylenetetramine; aqueous acetic acid; aqueous ethanol With hydrogenchloride, ethanol, hexamethylenetetramine, sulfuric acid, acetic acid Ruggli; Preuss; Helvetica Chimica Acta; vol. 24; (1941); p. 1345,1354 View in Reaxys Reaction Steps: 2 1: petroleum ether; zinc chloride; hydrogen chloride 2: copper nitrate With hydrogenchloride, cuprous nitrate, zinc(II) chloride, Petroleum ether Blanc; Bulletin de la Societe Chimique de France; vol. <4> 33; (1923); p. 317; Chem. Zentralbl.; vol. 94; nb. I; (1923); p. 1571 View in Reaxys Reaction Steps: 3 1: carbon disulfide solution; AlCl3 2: NaOH-solution 3: aniline / Spaltung des so entstandenen Anils mit Schwefelsaeure With carbon disulfide, sodium hydroxide, aluminium trichloride, aniline Rousset; Bulletin de la Societe Chimique de France; vol. <3> 17; (1897); p. 309 View in Reaxys

Rx-ID: 490877 View in Reaxys 257/284 Yield

Conditions & References With hydrogenchloride Patent; Kroehnke; DE755943; (1938); View in Reaxys

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Rx-ID: 139797 View in Reaxys 258/284 Yield

Conditions & References With hydrogenchloride, aluminium trichloride, chlorobenzene, T= 70 °C , anschliessendes Behandeln mit wss. HCl Hinkel; Ayling; Beynon; Journal of the Chemical Society; (1936); p. 339,342 View in Reaxys

Cl HN

Z O

Rx-ID: 139834 View in Reaxys 259/284 Yield

Conditions & References With aluminium trichloride, 1,1,2,2-tetrachloroethane, T= 70 °C , anschliessendes Behandeln mit wss. HCl Hinkel; Ayling; Beynon; Journal of the Chemical Society; (1936); p. 339,342 View in Reaxys

Cl Al

Z O

Rx-ID: 6680295 View in Reaxys 260/284 Yield

Conditions & References T= 70 °C Hinkel; Ayling; Beynon; Journal of the Chemical Society; (1936); p. 339,342 View in Reaxys

Rx-ID: 6680296 View in Reaxys 261/284 Yield

Conditions & References T= 20 - 70 °C Hinkel; Ayling; Beynon; Journal of the Chemical Society; (1936); p. 339,342 View in Reaxys

naphthaldehyde-(1)-semicarbazone O

Rx-ID: 5589734 View in Reaxys 262/284 Yield

Conditions & References With hydrogenchloride, carbon dioxide, steam Wuyts; Berman; Lacourt; Bulletin des Societes Chimiques Belges; vol. 40; (1931); p. 665,669 View in Reaxys

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palladium Cl

barium sulfate

Rx-ID: 5818200 View in Reaxys 263/284 Yield

Conditions & References Hydrogenation Shoesmith; Guthrie; Journal of the Chemical Society; (1928); p. 2332 View in Reaxys

Rx-ID: 311362 View in Reaxys 264/284 Yield

Conditions & References With hydrogen, zinc(II) oxide, T= 400 °C Patent; I.G. Farbenind.; DE526482; (1926); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 775 View in Reaxys

O O

Rx-ID: 395549 View in Reaxys 265/284 Yield

Conditions & References With phosphorus pentachloride, 1,1,2,2-tetrachloroethane, T= 140 - 150 °C , Eintragen des Reaktionsprodukts in eine mit Chlorwasserstoff gesaettigte aetherische Loesung von Zinn(II)-chlorid und Destillieren mit Wasserdampf Gibson et al.; Journal of the Chemical Society; (1926); p. 2253 View in Reaxys

tin (II)-chloride

Rx-ID: 6680297 View in Reaxys 266/284 Yield

Conditions & References Erwaermen des Reaktionsprodukts mit Wasser Stephen; Journal of the Chemical Society; vol. 127; (1925); p. 1877 View in Reaxys

copper nitrate Cl

Rx-ID: 5818199 View in Reaxys 267/284

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Yield

Conditions & References Blanc; Bulletin de la Societe Chimique de France; vol. <4> 33; (1923); p. 317; Chem. Zentralbl.; vol. 94; nb. I; (1923); p. 1571 View in Reaxys

nickel O

<α-naphthyl-methyl>-amine

bis-<α-naphthyl-methyl>-amine Rx-ID: 6726427 View in Reaxys 268/284

Yield

Conditions & References Hydrogenation Rupe; Becherer; Helvetica Chimica Acta; vol. 6; (1923); p. 882 View in Reaxys Patent; Rupe; DE429042; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 328 View in Reaxys

N N

Rx-ID: 301100 View in Reaxys 269/284 Yield

Conditions & References Mayer,F.; Sieglitz; Chemische Berichte; vol. 55; (1922); p. 1854 View in Reaxys

Rx-ID: 322059 View in Reaxys 270/284 Yield

Conditions & References With phosphoric acid, lead dioxide, acetic acid Hebert; Bulletin de la Societe Chimique de France; vol. <4> 27; (1920); p. 50 View in Reaxys

NH 2

Rx-ID: 22128849 View in Reaxys 271/284 Yield

Conditions & References Reaction Steps: 2 1: sodium amalgam; alcoholic aqueous hydrochloric acid 2: Cr2O3-H2SO4 With hydrogenchloride, chromium(III) oxide, sodium amalgam, sulfuric acid West; Journal of the American Chemical Society; vol. 42; (1920); p. 1663 View in Reaxys

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Cl OH

Rx-ID: 22130664 View in Reaxys 272/284 Yield

Conditions & References Reaction Steps: 2 1: sodium carbonate 2: lead dioxide; glacial acetic acid; phosphoric acid With phosphoric acid, sodium carbonate, lead dioxide, acetic acid Hebert; Bulletin de la Societe Chimique de France; vol. <4> 27; (1920); p. 50 View in Reaxys

Mg O

Rx-ID: 22151264 View in Reaxys 273/284 Yield

Conditions & References Reaction Steps: 3 2: sodium carbonate 3: lead dioxide; glacial acetic acid; phosphoric acid With phosphoric acid, sodium carbonate, lead dioxide, acetic acid Hebert; Bulletin de la Societe Chimique de France; vol. <4> 27; (1920); p. 50 View in Reaxys

Br Br Cl

OH O

Rx-ID: 7916197 View in Reaxys 274/284 Yield

Conditions & References T= 25 °C Kohler,Patch; Journal of the American Chemical Society; vol. 38; (1916); p. 1208 View in Reaxys

Rx-ID: 416198 View in Reaxys 275/284 Yield

Conditions & References bei der Ozonspaltung, β-methyl-α-<naphthyl-(1)>-α.γ-pentadiene Bjelouss; Chemische Berichte; vol. 45; (1912); p. 627 View in Reaxys

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Mg O

Rx-ID: 762633 View in Reaxys 276/284 Yield

Conditions & References Zersetzung des Reaktionsproduktes mit Salzsaeure Monier-Williams; Journal of the Chemical Society; vol. 89; (1906); p. 275 View in Reaxys Gattermann; Justus Liebigs Annalen der Chemie; vol. 393; (1912); p. 224 View in Reaxys Monier-Williams; Journal of the Chemical Society; vol. 89; (1906); p. 275 View in Reaxys

Br– Mg+

Rx-ID: 796102 View in Reaxys 277/284 Yield

Conditions & References Monier-Williams; Journal of the Chemical Society; vol. 89; (1906); p. 275 View in Reaxys

O O

Br– Mg+

Rx-ID: 699940 View in Reaxys 278/284 Yield

Conditions & References und Kochen des Reaktionsproduktes mit verd.Schwefelsaeure Bodroux; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 138; (1904); p. 701; Bulletin de la Societe Chimique de France; vol. <3> 31; (1904); p. 587 View in Reaxys

Br–

Mg+

Rx-ID: 825549 View in Reaxys 279/284 Yield

Conditions & References Gattermann; Maffezzoli; Chemische Berichte; vol. 36; (1903); p. 4153 View in Reaxys

O OH

Rx-ID: 378178 View in Reaxys 280/284 Yield

Conditions & References With aniline, Spaltung des so entstandenen Anils mit Schwefelsaeure Rousset; Bulletin de la Societe Chimique de France; vol. <3> 17; (1897); p. 309

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View in Reaxys

O O

Rx-ID: 22130688 View in Reaxys 281/284 Yield

Conditions & References Reaction Steps: 2 1: NaOH-solution 2: aniline / Spaltung des so entstandenen Anils mit Schwefelsaeure With sodium hydroxide, aniline Rousset; Bulletin de la Societe Chimique de France; vol. <3> 17; (1897); p. 309 View in Reaxys

2 –O

O Ca 2+

α-naphthoate of calcium O

Rx-ID: 5589732 View in Reaxys 282/284 Yield

Conditions & References durch Destillation Lugli; Gazzetta Chimica Italiana; vol. 11; (1881); p. 394 View in Reaxys

OH HN O

S O

Rx-ID: 521029 View in Reaxys 283/284 Yield

Conditions & References With chromium(III) oxide, sulfuric acid Patent; I. G. Farbenind.; DE482837; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 424 View in Reaxys

OH HN O

Cr2O3-H2SO4

S O

Rx-ID: 8236692 View in Reaxys 284/284 Yield

Conditions & References Patent; I. G. Farbenind.; DE482837; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 424 View in Reaxys

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