1-Phenyl-2-propyn-1-one (Benzoylacetylene) by Asch

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43 reactions in Reaxys

2017-08-01 05h:05m:37s (EST)

43 reactions in Reaxys

2017-08-01 05h:09m:51s (EST)

1. Query

Search as: As drawn 2. Query

(1. Query) AND NOT itemno in (7,8,9,10)

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Rx-ID: 277705 View in Reaxys 1/43 Yield

Conditions & References With tetrachloromethane, di-tert-butyl chromate, acetic acid, Reagens 4: Acetanhydrid Iwai; Okajima; Yakugaku Zasshi; vol. 78; (1958); p. 1252,1254; ; (1959); p. 5191 View in Reaxys With selenium(IV) oxide, ethanol Iwai; Okajima; Yakugaku Zasshi; vol. 78; (1958); p. 1252,1254; ; (1959); p. 5191 View in Reaxys O

Cr O (v6) O

Rx-ID: 570604 View in Reaxys 2/43 Yield

Conditions & References Iwai; Okajima; Yakugaku Zasshi; vol. 78; (1958); p. 1252,1254; ; (1959); p. 5191 View in Reaxys

Rx-ID: 782370 View in Reaxys 3/43 Yield 99 %

Conditions & References With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide, Time= 5h, T= 20 °C Bagley, Mark C.; Brace, Christian; Dale, James W.; Ohnesorge, Maren; Phillips, Nathan G.; Xiong, Xin; Bower, Justin; Journal of the Chemical Society. Perkin Transactions 1; nb. 14; (2002); p. 1663 - 1671 View in Reaxys

97 %

With silica gel, Bobbitt's oxidant in dichloromethane Bobbitt, James M.; Journal of Organic Chemistry; vol. 63; nb. 25; (1998); p. 9367 - 9374 View in Reaxys

97 %

With polystyrene-2-iodoxybenzamide in N,N-dimethyl-formamide, T= 20 °C , chemoselective reaction Diz, Paula M.; Coelho, Alberto; El Maatougui, Abdelaziz; Azuaje, Jhonny; Caamano, Olga; Gil, Alvaro; Sotelo, Eddy; Journal of Organic Chemistry; vol. 78; nb. 13; (2013); p. 6540 - 6549 View in Reaxys

96 %

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran, dimethyl sulfoxide, Time= 3h, T= 0 - 20 °C Lu, Jin-Yong; Arndt, Hans-Dieter; Journal of Organic Chemistry; vol. 72; nb. 11; (2007); p. 4205 - 4212 View in Reaxys

94 %

With periodic acid, .LAMBDA.-(+)-tris(acetylacetonato)chromium(III) in acetonitrile, Time= 1h, T= 20 °C Xu, Liang; Trudell, Mark L.; Tetrahedron Letters; vol. 44; nb. 12; (2003); p. 2553 - 2555 View in Reaxys

94 %

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in ethyl acetate, T= 80 °C Chassaing, Stefan; Kueny-Stotz, Marie; Isorez, Geraldine; Brouillard, Raymond; European Journal of Organic Chemistry; nb. 15; (2007); p. 2438 - 2448 View in Reaxys

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94 %

With dihydrogen peroxide in water, acetone, Time= 3h, T= 56 °C , chemoselective reaction Kikukawa, Yuji; Yamaguchi, Kazuya; Mizuno, Noritaka; Angewandte Chemie - International Edition; vol. 49; nb. 35; (2010); p. 6096 - 6100 View in Reaxys

94 %

With [bis(acetoxy)iodo]benzene, magnesium sulfate in 1,2-dichloro-ethane, Time= 5h, T= 45 °C Rahaman, Hasimur; Laha, Radha M.; Maiti, Dilip K.; Ghosh, Sujit Kumar; RSC Advances; vol. 5; nb. 43; (2015); p. 33923 - 33929 View in Reaxys

92 %

With chromium(VI) oxide, tert.-butylhydroperoxide in dichloromethane, Time= 24h, Ambient temperature Muzart; N'Ait Ajjou; Synthesis; nb. 8; (1993); p. 785 - 787 View in Reaxys

92 %

With Iron(III) nitrate nonahydrate, 2,2,6,6-tetramethyl-piperidine-N-oxyl, oxygen, sodium chloride in toluene, Time= 6.8h, T= 20 °C Liu, Jinxian; Xie, Xi; Ma, Shengming; Synthesis; vol. 44; nb. 10; (2012); p. 1569 - 1576 View in Reaxys

91 %

With chromium(VI) oxide, sulfuric acid Kundu, Nitya G.; Pal, Manojit; Chowdhury, Chinmay; Journal of Chemical Research, Miniprint; nb. 1; (1995); p. 101 - 123 View in Reaxys

90 %

With calcium hypochlorite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 1h, T= 0 20 °C Reddy, Sabbasani Rajasekhara; Chadha, Anju; RSC Advances; vol. 3; nb. 35; (2013); p. 14929 - 14933 View in Reaxys

89 %

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

88 %

2 With Jone's reagent Patent; UNIVERSITY OF VIRGINIA PATENT FOUNDATION; WO2006/23757; (2006); (A2) English View in Reaxys

88 %

With oxygen, acetic acid, carbonic acid dimethyl ester, 2,3-dicyano-5,6-dichloro-p-benzoquinone, sodium nitrite, Time= 10h, T= 18 °C , Irradiation, Sealed tube Walsh, Katie; Sneddon, Helen F.; Moody, Christopher J.; Organic Letters; vol. 16; nb. 19; (2014); p. 5224 - 5227 View in Reaxys

86 %

With Iron(III) nitrate nonahydrate, 9-azabicyclo[3.3.1]nonane-N-oxyl in acetonitrile, Time= 12h, T= 20 °C Wang, Lianyue; Shang, SenSen; Li, Guosong; Ren, Lanhui; Lv, Ying; Gao, Shuang; Journal of Organic Chemistry; vol. 81; nb. 5; (2016); p. 2189 - 2193 View in Reaxys

85 %

With chromium(VI) oxide, sulfuric acid in water, acetone, Time= 7h, T= 4 °C , Oxidation Caliendo, Giuseppe; Fiorino, Ferdinando; Grieco, Paolo; Perissutti, Elisa; Santagada, Vincenzo; Albrizio, Stefania; Spadola, Loredana; Bruni, Giancarlo; Romeo, Maria Rosaria; European Journal of Medicinal Chemistry; vol. 34; nb. 9; (1999); p. 719 - 727 View in Reaxys

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Caliendo, Giuseppe; Fiorino, Ferdinando; Grieco, Paolo; Perissutti, Elisa; Santagada, Vincenzo; Meli, Rosaria; Raso, Giuseppina Mattace; Zanesco, Angelina; De Nucci, Gilberto; European Journal of Medicinal Chemistry; vol. 34; nb. 12; (1999); p. 1043 - 1051 View in Reaxys 85 %

With oxygen, calcium phosphate-vanadate apatite in various solvent(s), Time= 20h, T= 100 °C , p= 760Torr , Product distribution, Further Variations: Catalysts, Solvents, Temperatures, reaction times Maeda, Yasunari; Washitake, Yosuke; Nishimura, Takahiro; Iwai, Keisuke; Yamauchi, Takayoshi; Uemura, Sakae; Tetrahedron; vol. 60; nb. 41; (2004); p. 9031 - 9036 View in Reaxys

85 %

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

84 %

With oxygen, 2,3-dicyano-5,6-dichloro-p-benzoquinone, sodium nitrite in dichloromethane, acetic acid, Time= 30h, T= 20 °C Wang, Lianyue; Li, Jun; Yang, Hua; Lv, Ying; Gao, Shuang; Journal of Organic Chemistry; vol. 77; nb. 1; (2012); p. 790 - 794 View in Reaxys

84 %

1-Phenylprop-2-yn-1-one (12b) In a similar way as described previously [2], a solution of o-iodoxybenzoic acid (IBX) (6.6 g, 24 mmol) in DMSO (350 mL) was stirred for 15 min at room temperature until homogeneous. A solution of 1-phenylprop-2-yn-1-ol (2.4 g, 18 mmol) in DMSO (10 mL) was added and the mixture was stirred for 16 h. H2O(35 mL) was added and the mixture was stirred at room temperature for 10 min, cooled in ice and partitioned between H2O (290 mL) and Et2O (210 mL). The mixture was filtered through Celite and the aqueous layer was further extracted with Et2O (170 mL). The organic extracts were combined, washed sequentially with H2O (3 x 170 mL), saturated aqueous NaHCO3 (230 mL) and brine (230 mL), dried (MgSO4) and evaporated in vacuo to give the title compound (2.0 g, 84percent) as a pale yellow solid, mp 48–50 °C (MeOH) (lit.[2] mp 49–50 °C) (Found: M•+, 130.0411. C9H6O [M] requires 130.0413); Rf 0.44 (CH2Cl2); IR (nujol)/cm−1 1647, 1591, 1583, 1452, 1314, 1269, 1170, 1004, 696; 1H NMR (400 MHz; CDCl3) 8.09 (2H, m, o-PhH), 7.56 (1H, m, p-PhH), 7.40(2H, m, m-PhH), 3.37 (1H, s, CH); 13C NMR (100 MHz; CDCl3) 177.5 (C), 136.1 (C),134.6 (CH), 129.7 (CH), 128.7 (CH), 80.9 (C), 80.3 (CH); m/z (EI) 130 (M•+, 156percent), 102(21), 77 (32), 53 (100), 51 (40). With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide, Time= 16h Bagley, Mark C.; Fusillo, Vincenzo; Jenkins, Robert L.; Lubinu, M. Caterina; Mason, Christopher; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1957 - 1968 View in Reaxys

83 %

With cyclic iodinane oxide in dichloromethane, Time= 0.5h, Ambient temperature Stickley, Sharon H.; Martin, J. C.; Tetrahedron Letters; vol. 36; nb. 50; (1995); p. 9117 - 9120 View in Reaxys

83 %

With tert.-butylhydroperoxide, [copper(II)(salqu)] in decane, acetonitrile, Time= 1h, T= 70 °C , Time, Concentration, Solvent Weerasiri, Kushan C.; Gorden, Anne E. V.; European Journal of Organic Chemistry; nb. 8; (2013); p. 1546 - 1550 View in Reaxys

80 %

With lt;MoO(O2)2(C5H4N(O)COO)gt;-Bu4N+ (MoO5PICO) in dichloromethane, Time= 0.5h, T= 50 °C Campestrini, Sandro; Furia, Fulvio Di; Modena, Giorgio; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3658 - 3660 View in Reaxys

77 %

With 2-iodoxybenzoic acid in dimethyl sulfoxide, Time= 5h

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Bagley, Mark C.; Glover, Christian; Molecules; vol. 15; nb. 5; (2010); p. 3211 - 3227 View in Reaxys 75 %

3 : 1-phenyl-2-propyn-1-ol oxidation The 13.2g (100mmol) 1-phenyl-2-propyn-1-ol, 2.72g (9.8mmol) DDQ, is added to 30 ml of methylene chloride in a solvent of, ice-water bath cooling, slowly dripping 1.15g (18mmol) nitric acid, into the 0.2 MPa oxygen, 25 °C reaction under 18h, slow depressurization, neutralized by adding NaOH aqueous solution, dichloromethane extraction, water washing, drying, distilling solvent. The resulting mixture is separated to obtain 9.8g (yield: 75percent) 1-phenyl-2-propyn-1-one. The yellow solid With oxygen, nitric acid, 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane, Time= 18h, T= 25 °C , p= 1500.15Torr , Cooling with ice Patent; Dalian Institute of Chemical Physics, Chinese Academy of Sciences.; GAO, SHUANG; LI, JUN; WANG, LIANYUE; (8 pag.); CN103880617; (2016); (B) Chinese View in Reaxys

67 %

With chromium(VI) oxide, sulfuric acid in water, acetone, Time= 5.33333h, T= 0 °C Chisholm, David R.; Valentine, Roy; Pohl, Ehmke; Whiting, Andrew; Journal of Organic Chemistry; vol. 81; nb. 17; (2016); p. 7557 - 7565 View in Reaxys

38 %

Catalytic Oxidation of 1-phenyl-2-propyn-1-ol.Complex 8 (2.9 mg, 0.0070 mmol), NEt3 (4.8 μL, 0.035 mmol), 1-phenyl-2-propyn-1-ol (46 mg, 0.35 mmol), and a 1,3,5-tri-tert-butylbenzene internal standard (14 mg, 0.056 mmol) were dissolved in 1,2-dichloroethane-d4. An initial 1H NMR spectrum was recorded, and then the reaction mixture heated at 60° C. for 24 h with stirring in a 50 mL roundbottom flask equipped with an air condenser. The mixture was cooled to room temperature and transferred to an NMR tube. 1H and 13C NMR spectra revealed complete consumption of the starting material and the formation of 1-phenyl-2-propyn-1-one in 38percent yield. 1H NMR (400 MHz, 1,2-dichloroethane-d4) δ 8.39 (s, 1H), 7.87 (d, 2H, J=7.6 Hz), 7.64 (t, 1H, J=7.6 Hz), 7.54 (t, 2H, J=7.6). 13C{1H} NMR (100 MHz, 1,2-dichloroethane-d4): δ 194.6, 138.3, 136.8, 134.1, 133.3, 130.2, 128.8. With triethylamine, (8-oxyquinolinate)2VV(O)(OiPr), Time= 24h, T= 60 °C Patent; LOS ALAMOS NATIONAL SECURITY, LLC; US2012/232279; (2012); (A1) English View in Reaxys With chromium(VI) oxide, sulfuric acid, acetone, T= 5 °C Bowden; Jones; Journal of the Chemical Society; (1946); p. 52 View in Reaxys With manganese(IV) oxide Iwai; Okajima; Yakugaku Zasshi; vol. 78; (1958); p. 1252,1254; ; (1959); p. 5191 View in Reaxys Iwai et al.; Yakugaku Zasshi; vol. 78; (1958); p. 505,508; ; (1958); p. 17200 View in Reaxys With sodium dichromate, sulfuric acid in DME, water, Time= 2h, Heating Heasley, Victor L.; Shellhamer, Dale F.; Chappell, Alfred E.; Cox, Jason M.; Hill, David J.; McGovern, Shanna L.; Eden, Cyndi C.; Kissel, Charles L.; Journal of Organic Chemistry; vol. 63; nb. 13; (1998); p. 4433 - 4437 View in Reaxys

100 % Chromat.

With 3 A molecular sieve, oxygen, bis(acetylacetonate)oxovanadium in acetonitrile, Time= 3h, T= 80 °C , p= 760Torr , Product distribution, Further Variations: Solvents, Temperatures, catalyst mol percent; time Maeda, Yasunari; Kakiuchi, Nobuyuki; Matsumura, Satoshi; Nishimura, Takahiro; Uemura, Sakae; Tetrahedron Letters; vol. 42; nb. 50; (2001); p. 8877 - 8879 View in Reaxys With manganese(IV) oxide in hexane, Time= 0.0583333h, microwave irradiation

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Lai, Tapan K.; Banerji, Julie; Chatterjee, Asima; Basak, Bidyut; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 44; nb. 6; (2005); p. 1309 - 1311 View in Reaxys 100 % Chromat.

With 3 A molecular sieve, oxygen, bis(acetylacetonate)oxovanadium in acetonitrile, Time= 3h, T= 80 °C , p= 760.051Torr Maeda, Yasunari; Kakiuchi, Nobuyuki; Matsumura, Satoshi; Nishimura, Takahiro; Kawamura, Takashi; Uemura, Sakae; Journal of Organic Chemistry; vol. 67; nb. 19; (2002); p. 6718 - 6724 View in Reaxys With manganese(IV) oxide in dichloromethane, T= 20 °C Scansetti, Myriam; Hu, Xiangping; McDermott, Benjamin P.; Lam, Hon Wai; Organic Letters; vol. 9; nb. 11; (2007); p. 2159 - 2162 View in Reaxys With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in ethyl acetate, T= 80 °C Kueny-Stotz, Marie; Isorez, Geraldine; Chassaing, Stefan; Brouillard, Raymond; Synlett; nb. 8; (2007); p. 1223 - 1226 View in Reaxys With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran, ethyl acetate, T= 80 °C Kueny-Stotz, Marie; Isorez, Geraldine; Chassaing, Stefan; Brouillard, Raymond; Synlett; nb. 7; (2007); p. 1067 - 1070 View in Reaxys 1 :In a 1 L flask fitted with magnetic stirrer and 250 mL methylene chloride was added 12.25 g (56.8 mmol) pyridinium dichloride. The mixture was cooled to 00C and 5 g (37.9 mmol) phenyl alkynyl methanol was added dropwise via syringe. The reaction was allowed to stir for 2 hours and then purified directly through a thick plug (200 mL) of silica on a fritted funnel using methylene chloride as solvent. The solutions were concentrated with no heating to yield 3.6 g (27.7 mmol) phenyl-alkynyl ketone that was immediately place in a 00C freezer. With pyridine; hydrochloride in dichloromethane, Time= 2h, T= 0 °C Patent; CYTOKINETICS, INC.; WO2007/59113; (2007); (A2) English View in Reaxys With Jone's reagent in acetone, T= 0 - 20 °C , Jones oxidation Gao, Ge; Brown, Neil; Minatoya, Machiko; Buszek, Keith R.; Tetrahedron Letters; vol. 49; nb. 46; (2008); p. 6491 - 6494 View in Reaxys

1.2 g

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide, Time= 12h, T= 35 °C , Inert atmosphere Aulakh, Virender S.; Ciufolini, Marco A.; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5750 - 5753 View in Reaxys 7.7B :7B.1-Phenyl-propynone: To a solution of I -phenylprop-2-yn- I -ol (0.5 g, 3.8 mmol) in CH2C12 (10 mL) was added Dess-Martin Periodinane (1.6 g, 3.8 mmol). The reaction was stirred at rt for 5 min. The reaction was diluted with CH2C12 (10 mL) and washed with a 1: 1 mixture of 10percent aqueous Na2S203 and saturated aqueous NaHC03 (200 mL), water and brine. The organic layer was dried over MgSO4, filtered and evaporated in vacuo to provide 1.12 g of a light tan solid. The crude product was purified by silca gel chromatography to produce 600 mg of a white solid which was used without further purification in the next step. 1H NMR (500 MHz, d-CHC13) 8 3.45 (s, 1H) 7.51 (t, J = 7.97 Hz, 2H) 7.64 (t, J = 7.42 Hz, 1H) 8.17 (d, J = 7.15 Hz, 2H). With Dess-Martin periodane in dichloromethane, Time= 0.0833333h, T= 20 °C Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2005/123680; (2005); (A1) English View in Reaxys With ruthenium trichloride, potassium hydrogen persulfate, 4-iodobenzenesulfonic acid in water, acetonitrile, Time= 1h, T= 20 °C

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Yusubov, Mekhman S.; Zagulyaeva, Aleksandra A.; Zhdankin, Viktor V.; Chemistry - A European Journal; vol. 15; nb. 42; (2009); p. 11091 - 11094 View in Reaxys With manganese(IV) oxide in dichloromethane, Time= 1h, T= 20 °C Ismaili, Hossein; Alizadeh, Abdoihamid; Snell, Kristen E.; Workentin, Mark S.; Canadian Journal of Chemistry; vol. 87; nb. 12; (2009); p. 1708 - 1715 View in Reaxys With manganese(IV) oxide in dichloromethane, Time= 2h, T= 20 °C De Haro, Teresa; Nevado, Cristina; Journal of the American Chemical Society; vol. 132; nb. 5; (2010); p. 1512 1513 View in Reaxys 90 %Chromat.

With ruthenium trichloride, iodobenzene, OXONE in water, acetonitrile, Time= 1h, T= 20 °C , Inert atmosphere Yusubov, Mekhman S.; Nemykin, Victor N.; Zhdankin, Viktor V.; Tetrahedron; vol. 66; nb. 31; (2010); p. 5745 5752 View in Reaxys

96 %Chromat.

With dihydrogen peroxide in water, acetone, Time= 2h, T= 56 °C Kikukawa, Yuji; Yamaguchi, Kazuya; Mizuno, Noritaka; Inorganic Chemistry; vol. 49; nb. 18; (2010); p. 8194 8196 View in Reaxys With manganese(IV) oxide, potassium permanganate Tanaka, Makoto; Nakamura, Kazuya; Iwado, Tatsuya; Sato, Toshiyuki; Okada, Masaki; Sue, Kiwamu; Iwamura, Hiizu; Hiaki, Toshihiko; Chemistry - A European Journal; vol. 17; nb. 2; (2011); p. 606 - 612 View in Reaxys

38 %Spectr.

With (8-oxyquinolinate)2VV(O)(OiPr), triethylamine in 1,2-dichloroethane-d4, Time= 24h, T= 60 °C Hanson, Susan K.; Wu, Ruilian; Silks, L. A. Pete; Organic Letters; vol. 13; nb. 8; (2011); p. 1908 - 1911 View in Reaxys With chromium(VI) oxide, sulfuric acid in water, acetone, Time= 8h, T= 0 - 22 °C Fan, Yi Chiao; Kwon, Ohyun; Molecules; vol. 16; nb. 5; (2011); p. 3802 - 3825 View in Reaxys With manganese(IV) oxide in dichloromethane, T= 0 - 20 °C Shi, Feng; Luo, Shi-Wei; Tao, Zhong-Lin; He, Long; Yu, Jie; Tu, Shu-Jiang; Gong, Liu-Zhu; Organic Letters; vol. 13; nb. 17; (2011); p. 4680 - 4683 View in Reaxys General Procedure for the synthesis of propynones 1 General procedure: A solution of o-iodoxybenzoic acid (IBX) (1.83 g, 6.5 mmol) in DMSO (55 mL)was stirred for 15 min at room temperature until homogeneous. A solution of propargylic alcohol 5 (10.0 mmol) in DMSO (5 mL) was added and the mixture was stirred for 5 h. H2O (15 mL) was added and the mixture was stirred at room temperature for 10 min, cooled in ice and partitioned between H2O (60 mL) and ether (45 mL). The mixture was filtered through Celite and the aqueous layer was further extracted with ether (25 mL). The organic extracts were combined, washed sequentially with H2O (3 x 15 mL), saturated aqueous NaHCO3 solution (35 mL) and brine (35 mL), dried (Na2SO4) and evaporated in vacuo. The residue was subject to flash chromatography on silica gel (petroleum ether/ethyl acetate, 10:1) to afford pure propynone 1. With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide, Time= 5h Shen, Yang; Cai, Shuying; He, Chi; Lin, Xufeng; Lu, Ping; Wang, Yanguang; Tetrahedron; vol. 67; nb. 43; (2011); p. 8338 - 8342 View in Reaxys With H4N(1+)*Zn2Sb2, dihydrogen peroxide in water, Time= 7h, T= 85 °C

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Ni, Lubin; Patzke, Greta R.; Patscheider, Joerg; Baldridge, Kim K.; Chemistry--A European Journal; vol. 18; nb. 42; (2012); p. 13293 - 13298,6 View in Reaxys Ni, Lubin; Patscheider, Joerg; Baldridge, Kim K.; Patzke, Greta R.; Chemistry - A European Journal; vol. 18; nb. 42; (2012); p. 13293 - 13298 View in Reaxys With Dess-Martin periodane in dichloromethane, T= 0 - 20 °C , Inert atmosphere Ge, Guang-Cun; Mo, Dong-Liang; Ding, Chang-Hua; Dai, Li-Xin; Hou, Xue-Long; Organic Letters; vol. 14; nb. 22; (2012); p. 5756 - 5759 View in Reaxys With 2O34W9Zn(12-)*24H2O*10H4N(1+)*4Zn(2+)*2Sb(3+), dihydrogen peroxide in water, Time= 7h, T= 85 °C , Reagent/ catalyst Ni, Lubin; Patscheider, Joerg; Baldridge, Kim K.; Patzke, Greta R.; Chemistry - A European Journal; vol. 18; nb. 42; (2012); p. 13293 - 13298 View in Reaxys With oxygen in N,N-dimethyl acetamide, Time= 3h, T= 120 °C , p= 760.051Torr Gao, Qingsheng; Giordano, Cristina; Antonietti, Markus; Angewandte Chemie - International Edition; vol. 51; nb. 47; (2012); p. 11740 - 11744; Angew. Chem.; vol. 124; nb. 47; (2012); p. 11910 - 11914,5 View in Reaxys With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide, Time= 6h, T= 35 °C Wang, Zheng; Shi, Ying; Luo, Xiaoyan; Han, De-Man; Deng, Wei-Ping; New Journal of Chemistry; vol. 37; nb. 6; (2013); p. 1742 - 1745 View in Reaxys With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in ethyl acetate, Time= 2h, Reflux, Inert atmosphere Kommagalla, Yadagiri; Cornea, Sinziana; Riehle, Robert; Torchilin, Vladimir; Degterev, Alexei; Ramana, Chepuri V.; MedChemComm; vol. 5; nb. 9; (2014); p. 1359 - 1363 View in Reaxys With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in ethyl acetate, Time= 2h, Reflux Patent; TUFTS UNIVERSITY; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; DEGTEREV, Alexei; RAMANA, Chepuri, Venkata; LEE, Jinbo; KOMMAGALLA, Yadagiri; WO2014/153337; (2014); (A2) English View in Reaxys in N,N-dimethyl-formamide, Time= 12h, 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 With manganese(IV) oxide in dichloromethane, Time= 2h, T= 20 °C , Inert atmosphere, Schlenk technique Zheng, Min; Wu, Feng; Chen, Kai; Zhu, Shifa; Organic Letters; vol. 18; nb. 15; (2016); p. 3554 - 3557 View in Reaxys O

Rx-ID: 1143162 View in Reaxys 4/43 Yield

Conditions & References With borax Walton; Waugh; Journal of Organometallic Chemistry; vol. 37; nb. 1; (1972); p. 45 - 56 View in Reaxys

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With borax in methanol Bromidge; Entwistle; Goldstein; Orlek; Synthetic Communications; vol. 23; nb. 4; (1993); p. 487 - 494 View in Reaxys O

H E

Rx-ID: 2064089 View in Reaxys 5/43 Yield

Conditions & References

84 %, 80 %

With oxygen, 5,15,10,20-tetraphenylporphyrin in chloroform, Time= 75h, Irradiation Lee-Ruff, Edward; Maleki, Mehran; Duperrouzel, Paul; Lien, Min H.; Hopkinson, Alan C.; Journal of the Chemical Society, Chemical Communications; nb. 7; (1983); p. 346 - 347 View in Reaxys

80 %, 84 %

Rx-ID: 2770233 View in Reaxys 6/43 Yield

Conditions & References With water, ortho-hydrogen phosphate in tetrahydrofuran, T= 25 °C , Rate constant Kresge, A. Jerry; Pruszynski, Przemyslaw; Stang, Peter J.; Williamson, Bobby L.; Journal of Organic Chemistry; vol. 56; nb. 15; (1991); p. 4808 - 4811 View in Reaxys O O

B N

Rx-ID: 4961307 View in Reaxys 7/43 Yield

Conditions & References With hydrogenchloride in tetrahydrofuran, hexane, Ambient temperature, Yield given Blanchard, Christiane; Vaultier, Michel; Mortier, Jacques; Tetrahedron Letters; vol. 38; nb. 51; (1997); p. 8863 8866 View in Reaxys O

Rx-ID: 5931113 View in Reaxys 8/43 Yield

Conditions & References Goldwhite,H. et al.; Tetrahedron; vol. 20; (1964); p. 1649 - 1656 View in Reaxys Barrelle,M.; Glenat,R.; Bulletin de la Societe Chimique de France; (1967); p. 453 - 458 View in Reaxys Degrand,C. et al.; Bulletin de la Societe Chimique de France; (1973); p. 281 - 288

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View in Reaxys Smith,P.A.S.; Wirth,J.G.; Journal of Organic Chemistry; vol. 33; nb. 3; (1968); p. 1145 - 1155 View in Reaxys Patent; Squibb; FR2356650; (1978); US4112096; ; vol. 92; nb. 146801 View in Reaxys Grosjean; Compagnon; Bulletin de la Societe Chimique de France; (1975); p. 775 View in Reaxys Gavrilov et al.; Zhurnal Organicheskoi Khimii; vol. 10; (1974); p. 2064,2081 View in Reaxys Naito et al.; Journal of Antibiotics, Series A; vol. 20; (1967); p. 77,83 View in Reaxys Patent; Bristol-Banyu Res.Inst.; US3360527; (1966); ; vol. 69; nb. 36117g; (1968) View in Reaxys Appleton; Tyrrell; Journal of Physical Chemistry; vol. 81; (1977); p. 1201,1202, 1204 View in Reaxys Appleton; Tyrrell; Journal of Physical Chemistry; vol. 82; (1978); p. 325 View in Reaxys Karpf; Dreiding; Helvetica Chimica Acta; vol. 62; (1979); p. 852,862, 865 View in Reaxys Cavalchi et al.; Journal of the Chemical Society [Section] C: Organic; (1969); p. 1204,1207,1208 View in Reaxys O OH

O Se

Rx-ID: 7061790 View in Reaxys 9/43 Yield

Conditions & References Iwai; Okajima; Yakugaku Zasshi; vol. 78; (1958); p. 1252,1254; ; (1959); p. 5191 View in Reaxys

O NH N N

Rx-ID: 8840162 View in Reaxys 10/43 Yield 53 %

Conditions & References With lead(IV) acetate in 1,4-dioxane, Time= 0.5h, T= 0 °C Fetter; Nagy; Giang; Kajtar-Peredy; Rockenbauer; Korecz; Czira; Journal of the Chemical Society. Perkin Transactions 1; nb. 9; (2001); p. 1131 - 1139 View in Reaxys O

Fmoc-L-tert-leucine on Wang resin O

Rx-ID: 11332887 View in Reaxys 11/43 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran / 0 - 20 °C 2: IBX / ethyl acetate; tetrahydrofuran / 80 °C With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran, ethyl acetate Kueny-Stotz, Marie; Isorez, Geraldine; Chassaing, Stefan; Brouillard, Raymond; Synlett; nb. 7; (2007); p. 1067 - 1070 View in Reaxys

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Reaction Steps: 2 1: tetrahydrofuran / 0 - 20 °C 2: IBX / ethyl acetate / 80 °C With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran, ethyl acetate Kueny-Stotz, Marie; Isorez, Geraldine; Chassaing, Stefan; Brouillard, Raymond; Synlett; nb. 8; (2007); p. 1223 - 1226 View in Reaxys O

(E)-n-C6H13CH=CHZrCp2Cl

Rx-ID: 11645783 View in Reaxys 12/43 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether / 0 °C 2: MnO2 / CH2Cl2 / 20 °C With manganese(IV) oxide in diethyl ether, dichloromethane Scansetti, Myriam; Hu, Xiangping; McDermott, Benjamin P.; Lam, Hon Wai; Organic Letters; vol. 9; nb. 11; (2007); p. 2159 - 2162 View in Reaxys O O

α-methoxy-phenylacetic acid O

Rx-ID: 15292947 View in Reaxys 13/43 Yield

Conditions & References Reaction Steps: 3 1: 72 percent / NaH / tetrahydrofuran / Heating 2: 86 percent / NaN3; AlCl3 / tetrahydrofuran / 5 h / Heating 3: 53 percent / Pb(OAc)4 / dioxane / 0.5 h / 0 °C With lead(IV) acetate, aluminium trichloride, sodium azide, sodium hydride in tetrahydrofuran, 1,4-dioxane Fetter; Nagy; Giang; Kajtar-Peredy; Rockenbauer; Korecz; Czira; Journal of the Chemical Society. Perkin Transactions 1; nb. 9; (2001); p. 1131 - 1139 View in Reaxys O

O N

Rx-ID: 15303475 View in Reaxys 14/43 Yield

Conditions & References Reaction Steps: 2 1: 86 percent / NaN3; AlCl3 / tetrahydrofuran / 5 h / Heating 2: 53 percent / Pb(OAc)4 / dioxane / 0.5 h / 0 °C With lead(IV) acetate, aluminium trichloride, sodium azide in tetrahydrofuran, 1,4-dioxane Fetter; Nagy; Giang; Kajtar-Peredy; Rockenbauer; Korecz; Czira; Journal of the Chemical Society. Perkin Transactions 1; nb. 9; (2001); p. 1131 - 1139 View in Reaxys

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(+-)-<4-isopropyl-benzylamino>-phenyl-acetonitrile Cl

Rx-ID: 16836195 View in Reaxys 15/43 Yield

Conditions & References Reaction Steps: 2 1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C 2: 3N HCl / tetrahydrofuran; hexane / Ambient temperature With hydrogenchloride, n-butyllithium in tetrahydrofuran, hexane Blanchard, Christiane; Vaultier, Michel; Mortier, Jacques; Tetrahedron Letters; vol. 38; nb. 51; (1997); p. 8863 8866 View in Reaxys O

Cl Cl Cl Cl

Rx-ID: 18819279 View in Reaxys 16/43 Yield

Conditions & References Reaction Steps: 2 1: 22 percent / EtONa / 18 h / Heating 2: 18 percent / EtONa / ethanol / 18 h / 80 °C With sodium ethanolate in ethanol Akiyama, Takeo; Yoshida, Yasuki; Hanawa, Tokiko; Sugimori, Akira; Bulletin of the Chemical Society of Japan; vol. 56; nb. 6; (1983); p. 1795 - 1798 View in Reaxys O O

ammonium carbonate

Rx-ID: 19634055 View in Reaxys 17/43 Yield

Conditions & References Reaction Steps: 2 2: borax / methanol With borax in methanol Bromidge; Entwistle; Goldstein; Orlek; Synthetic Communications; vol. 23; nb. 4; (1993); p. 487 - 494 View in Reaxys O

ammonium carbonate

lead sulfide Cl

Rx-ID: 19643462 View in Reaxys 18/43 Yield

Conditions & References Reaction Steps: 3 1: pyridine 3: borax / methanol With pyridine, borax in methanol Bromidge; Entwistle; Goldstein; Orlek; Synthetic Communications; vol. 23; nb. 4; (1993); p. 487 - 494 View in Reaxys

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(+-)-2.3-dibromo-propylamine hydrobromide Cl

Rx-ID: 22449369 View in Reaxys 19/43 Yield

Conditions & References Reaction Steps: 2 1: (i) AlCl3, (ii) /BRN= 906870/ 2: Na2B4O7 With borax Walton; Waugh; Journal of Organometallic Chemistry; vol. 37; nb. 1; (1972); p. 45 - 56 View in Reaxys O

H O

Rx-ID: 30911625 View in Reaxys 20/43 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran / 4 h / 0 - 22 °C 2: chromium(VI) oxide; sulfuric acid / water; acetone / 8 h / 0 - 22 °C With chromium(VI) oxide, sulfuric acid in tetrahydrofuran, water, acetone Fan, Yi Chiao; Kwon, Ohyun; Molecules; vol. 16; nb. 5; (2011); p. 3802 - 3825 View in Reaxys Reaction Steps: 3 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 - 20 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 2 h / 20 °C 3.1: manganese(IV) oxide / dichloromethane / 0 - 20 °C With manganese(IV) oxide, n-butyllithium, potassium carbonate in tetrahydrofuran, methanol, hexane, dichloromethane Shi, Feng; Luo, Shi-Wei; Tao, Zhong-Lin; He, Long; Yu, Jie; Tu, Shu-Jiang; Gong, Liu-Zhu; Organic Letters; vol. 13; nb. 17; (2011); p. 4680 - 4683 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran / 0 - 20 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran, dimethyl sulfoxide Shen, Yang; Cai, Shuying; He, Chi; Lin, Xufeng; Lu, Ping; Wang, Yanguang; Tetrahedron; vol. 67; nb. 43; (2011); p. 8338 - 8342 View in Reaxys Reaction Steps: 3 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / |Inert atmosphere 1.2: 1 h / -78 - 20 °C / |Inert atmosphere 2.1: potassium carbonate / methanol / 2 h / 20 °C / |Inert atmosphere 3.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / |Inert atmosphere With n-butyllithium, potassium carbonate, Dess-Martin periodane in tetrahydrofuran, methanol, hexane, dichloromethane Ge, Guang-Cun; Mo, Dong-Liang; Ding, Chang-Hua; Dai, Li-Xin; Hou, Xue-Long; Organic Letters; vol. 14; nb. 22; (2012); p. 5756 - 5759 View in Reaxys Reaction Steps: 2

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1: tetrahydrofuran / 2 h / 0 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 6 h / 35 °C With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran, dimethyl sulfoxide Wang, Zheng; Shi, Ying; Luo, Xiaoyan; Han, De-Man; Deng, Wei-Ping; New Journal of Chemistry; vol. 37; nb. 6; (2013); p. 1742 - 1745 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran / 20 °C / |Inert atmosphere 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 2 h / |Reflux; |Inert atmosphere With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran, ethyl acetate Kommagalla, Yadagiri; Cornea, Sinziana; Riehle, Robert; Torchilin, Vladimir; Degterev, Alexei; Ramana, Chepuri V.; MedChemComm; vol. 5; nb. 9; (2014); p. 1359 - 1363 View in Reaxys Reaction Steps: 2 1: n-Butyl chloride; magnesium; iodine / tetrahydrofuran 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 2 h / |Reflux With n-Butyl chloride, iodine, magnesium, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran, ethyl acetate Patent; TUFTS UNIVERSITY; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; DEGTEREV, Alexei; RAMANA, Chepuri, Venkata; LEE, Jinbo; KOMMAGALLA, Yadagiri; WO2014/153337; (2014); (A2) English View in Reaxys Reaction Steps: 2 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / 0 °C / |Inert atmosphere; |Schlenk technique 1.2: 1 h / 0 - 20 °C / |Inert atmosphere; |Schlenk technique 1.3: 2 h / 20 °C / |Inert atmosphere; |Schlenk technique 2.1: manganese(IV) oxide / dichloromethane / 2 h / 20 °C / |Inert atmosphere; |Schlenk technique With manganese(IV) oxide, n-butyllithium in tetrahydrofuran, hexane, dichloromethane Zheng, Min; Wu, Feng; Chen, Kai; Zhu, Shifa; Organic Letters; vol. 18; nb. 15; (2016); p. 3554 - 3557 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran / 2.5 h / -78 - 20 °C / |Inert atmosphere 2: chromium(VI) oxide; sulfuric acid / acetone; water / 5.33 h / 0 °C With chromium(VI) oxide, sulfuric acid in tetrahydrofuran, water, acetone Chisholm, David R.; Valentine, Roy; Pohl, Ehmke; Whiting, Andrew; Journal of Organic Chemistry; vol. 81; nb. 17; (2016); p. 7557 - 7565 View in Reaxys OH

Rx-ID: 31769440 View in Reaxys 21/43 Yield

Conditions & References Reaction Steps: 2 1: potassium carbonate / methanol / 2 h / 20 °C 2: manganese(IV) oxide / dichloromethane / 0 - 20 °C With manganese(IV) oxide, potassium carbonate in methanol, dichloromethane Shi, Feng; Luo, Shi-Wei; Tao, Zhong-Lin; He, Long; Yu, Jie; Tu, Shu-Jiang; Gong, Liu-Zhu; Organic Letters; vol. 13; nb. 17; (2011); p. 4680 - 4683 View in Reaxys Reaction Steps: 2 1: potassium carbonate / methanol / 2 h / 20 °C / |Inert atmosphere 2: Dess-Martin periodane / dichloromethane / 0 - 20 °C / |Inert atmosphere

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With potassium carbonate, Dess-Martin periodane in methanol, dichloromethane Ge, Guang-Cun; Mo, Dong-Liang; Ding, Chang-Hua; Dai, Li-Xin; Hou, Xue-Long; Organic Letters; vol. 14; nb. 22; (2012); p. 5756 - 5759 View in Reaxys O

H Br Mg

Rx-ID: 33653647 View in Reaxys 22/43 Yield

Conditions & References Stage 1:Inert atmosphere Stage 2: With Jone's reagent, Inert atmosphere Fan, Yi Chiao; Kwon, Ohyun; Organic Letters; vol. 14; nb. 13; (2012); p. 3264 - 3267 View in Reaxys

O O

H 13C N

NH13 C N

Rx-ID: 8905928 View in Reaxys 23/43 Yield

Conditions & References

65 %

With lead(IV) acetate Bertha, Ferenc; Fetter, Jozsef; Lempert, Karoly; Kajtar-Peredy, Maria; Czira, Gabor; Koltai, Erno; Tetrahedron; vol. 57; nb. 42; (2001); p. 8889 - 8895 View in Reaxys O

O H 13C

N 13C

Rx-ID: 15274875 View in Reaxys 24/43 Yield

Conditions & References Reaction Steps: 2 1: AlCl3; NaN3 / tetrahydrofuran 2: 65 percent / lead tetraacetate With lead(IV) acetate, aluminium trichloride, sodium azide in tetrahydrofuran Bertha, Ferenc; Fetter, Jozsef; Lempert, Karoly; Kajtar-Peredy, Maria; Czira, Gabor; Koltai, Erno; Tetrahedron; vol. 57; nb. 42; (2001); p. 8889 - 8895 View in Reaxys O

Rx-ID: 3399477 View in Reaxys 25/43 Yield 91 %

Conditions & References With copper diacetate, Time= 72h, Ambient temperature Demuth, Martin; Amrein, Walter; Bender, Christopher O.; Braslavsky, Silvia E.; Burger, Ulrich; George, Manapurathu V.; Lemmer, Dieter; Schaffner, Kurt; Tetrahedron; vol. 37; nb. 19; (1981); p. 3245 - 3261 View in Reaxys

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Rx-ID: 3399476 View in Reaxys 26/43 Yield

Conditions & References With superheavy water, N,N,N',N'-Tetramethyl-N'-lt;2,6-dimethyl-phenylgt;-guanidin in 1,4-dioxane, Time= 24h, Ambient temperature Kresge, A. Jerry; Pruszynski, Przemyslaw; Stang, Peter J.; Williamson, Bobby L.; Journal of Organic Chemistry; vol. 56; nb. 15; (1991); p. 4808 - 4811 View in Reaxys 2H

2H 2H

Rx-ID: 7599081 View in Reaxys 27/43 Yield

Conditions & References Pentadeuterobenzaldehyd, 1. Na-Acetylid, (-> Carbinol), 2. CrO3, Oxidation Prilezhaeva et al.; Journal of Organic Chemistry USSR (English Translation); vol. 8; (1972); p. 1534,1536; Zhurnal Organicheskoi Khimii; vol. 8; (1972); p. 1505 View in Reaxys O

O O

Rx-ID: 2132851 View in Reaxys 28/43 Yield 85 %, 83 %

Conditions & References With oxygen, 5,15,10,20-tetraphenylporphyrin in chloroform, Irradiation Lee-Ruff, Edward; Maleki, Mehran; Duperrouzel, Paul; Lien, Min H.; Hopkinson, Alan C.; Journal of the Chemical Society, Chemical Communications; nb. 7; (1983); p. 346 - 347 View in Reaxys

83 %, 85 %

With oxygen, 5,15,10,20-tetraphenylporphyrin in chloroform, Irradiation Lee-Ruff, Edward; Maleki, Mehran; Duperrouzel, Paul; Lien, Min H.; Hopkinson, Alan C.; Journal of the Chemical Society, Chemical Communications; nb. 7; (1983); p. 346 - 347 View in Reaxys O

C–

(v4)

Na + (v3)

Rx-ID: 26572955 View in Reaxys 29/43 Yield

Conditions & References in ammonia vol. C: MVol.C4; 6.1.3, page 123 - 125 View in Reaxys Patent; Ginsburg, D.; Hescheles, J.; Technion Research and Development Foundation; IL10518; (1958); C. A.; (1958); p. 14683 ; (from Gmelin) View in Reaxys

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Rx-ID: 5301470 View in Reaxys 30/43 Yield

Conditions & References With water, pyridinium p-toluenesulfonate, Hydrolysis Obrecht, Daniel; Zumbrunn, Cornelia; Mueller, Klaus; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6891 - 6895 View in Reaxys O

H Si Si

Rx-ID: 41723027 View in Reaxys 31/43 Yield

Conditions & References

40 %, 10 %

Stage 1: With indium tribromide, triethylamine in diethyl ether, Time= 1h, T= 20 °C , Inert atmosphere, Sealed tube Stage 2: in diethyl ether, Time= 24h, T= 40 °C , Inert atmosphere, Sealed tube Ogiwara, Yohei; Kubota, Masahito; Kurogi, Kotaro; Konakahara, Takeo; Sakai, Norio; Chemistry - A European Journal; vol. 21; nb. 51; (2015); p. 18598 - 18600 View in Reaxys Cl Cl

Cl Cl

Rx-ID: 1870714 View in Reaxys 32/43 Yield

Conditions & References

14 %, 33 %, 5 %, 2 %

With potassium hydroxide, Time= 18h, Heating, Further byproducts given Akiyama, Takeo; Yoshida, Yasuki; Hanawa, Tokiko; Sugimori, Akira; Bulletin of the Chemical Society of Japan; vol. 56; nb. 6; (1983); p. 1795 - 1798 View in Reaxys Cl Cl

Cl Cl

O O

Rx-ID: 1870716 View in Reaxys 33/43 Yield 14 %, 33 %, 5 %, 8 %

Conditions & References With potassium hydroxide, Time= 18h, Heating, Further byproducts given Akiyama, Takeo; Yoshida, Yasuki; Hanawa, Tokiko; Sugimori, Akira; Bulletin of the Chemical Society of Japan; vol. 56; nb. 6; (1983); p. 1795 - 1798

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View in Reaxys

Cl O

Rx-ID: 1870718 View in Reaxys 34/43 Yield

Conditions & References

14 %, 33 %, 5 %, 2 %

Cl Cl

O O

Rx-ID: 1870715 View in Reaxys 35/43 Yield

Conditions & References

14 %, 33 %, 5 %, 2 %

Cl Cl

Cl O

Rx-ID: 1870717 View in Reaxys 36/43 Yield

Conditions & References

59 %, 2 %, With sodium ethanolate, Time= 18h, Heating, Further byproducts given 2 %, 22 % Akiyama, Takeo; Yoshida, Yasuki; Hanawa, Tokiko; Sugimori, Akira; Bulletin of the Chemical Society of Japan; vol. 56; nb. 6; (1983); p. 1795 - 1798 View in Reaxys –C

Ag2O

Ag+

Rx-ID: 35606479 View in Reaxys 37/43 Yield

Conditions & References With sodium acetate in N,N-dimethyl-formamide, T= 20 °C , Schlenk technique, regioselective reaction Li, Feng; Nie, Jing; Sun, Long; Zheng, Yan; Ma, Jun-An; Angewandte Chemie - International Edition; vol. 52; nb. 24; (2013); p. 6255 - 6258 View in Reaxys

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E O

Rx-ID: 1870719 View in Reaxys 38/43 Yield

Conditions & References

14 %, 5 %, With potassium hydroxide, Time= 18h, Heating, Further byproducts given 3 %, 33 % Akiyama, Takeo; Yoshida, Yasuki; Hanawa, Tokiko; Sugimori, Akira; Bulletin of the Chemical Society of Japan; vol. 56; nb. 6; (1983); p. 1795 - 1798 View in Reaxys 14 %, 33 %, 5 %, 3 %

E O

Rx-ID: 1990806 View in Reaxys 39/43 Yield

Conditions & References

33 %, 5 %, With potassium hydroxide in ethanol, Time= 18h, Heating, Further byproducts given 3 %, 14 % Akiyama, Takeo; Yoshida, Yasuki; Hanawa, Tokiko; Sugimori, Akira; Bulletin of the Chemical Society of Japan; vol. 56; nb. 6; (1983); p. 1795 - 1798 View in Reaxys 14 %, 33 %, 3 %, 5 %

With potassium hydroxide in ethanol, Time= 18h, Heating, Further byproducts given Akiyama, Takeo; Yoshida, Yasuki; Hanawa, Tokiko; Sugimori, Akira; Bulletin of the Chemical Society of Japan; vol. 56; nb. 6; (1983); p. 1795 - 1798 View in Reaxys

Cl Cl

E O

Rx-ID: 2150418 View in Reaxys 40/43 Yield

Conditions & References

72 %, 9 %, With sodium ethanolate in ethanol, Time= 18h, T= 80 °C 18 % Akiyama, Takeo; Yoshida, Yasuki; Hanawa, Tokiko; Sugimori, Akira; Bulletin of the Chemical Society of Japan; vol. 56; nb. 6; (1983); p. 1795 - 1798 View in Reaxys 18 %, 9 %, With sodium ethanolate in ethanol, Time= 18h, T= 80 °C 72 % Akiyama, Takeo; Yoshida, Yasuki; Hanawa, Tokiko; Sugimori, Akira; Bulletin of the Chemical Society of Japan; vol. 56; nb. 6; (1983); p. 1795 - 1798 View in Reaxys 18 %, 72 %, 9 %

With sodium ethanolate in ethanol, Time= 18h, T= 80 °C Akiyama, Takeo; Yoshida, Yasuki; Hanawa, Tokiko; Sugimori, Akira; Bulletin of the Chemical Society of Japan; vol. 56; nb. 6; (1983); p. 1795 - 1798

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View in Reaxys

Cl O

O 2H

Rx-ID: 1905358 View in Reaxys 41/43 Yield

Conditions & References With sodium ethanolate, Time= 8h, Heating, Mechanism Akiyama, Takeo; Yoshida, Yasuki; Hanawa, Tokiko; Sugimori, Akira; Bulletin of the Chemical Society of Japan; vol. 56; nb. 6; (1983); p. 1795 - 1798 View in Reaxys

OH Se Cl

Rx-ID: 3760330 View in Reaxys 42/43 Yield 74 %, 12 %

Conditions & References With sulfuric acid, N(Et)4ClO4 in water, acetonitrile, Time= 14h, T= 65 °C , electrochemical oxidation Uneyama, Kenji; Takano, Kunikaju; Torii, Sigeru; Tetrahedron Letters; vol. 23; nb. 11; (1982); p. 1161 - 1164 View in Reaxys

12 %, 74 %

With sulfuric acid, N(Et)4ClO4 in water, acetonitrile, Time= 14h, T= 65 °C , electrochemical oxidation Uneyama, Kenji; Takano, Kunikaju; Torii, Sigeru; Tetrahedron Letters; vol. 23; nb. 11; (1982); p. 1161 - 1164 View in Reaxys

OH H

O O

Rx-ID: 3760357 View in Reaxys 43/43 Yield 28 %, 4 %

Conditions & References T= 5 °C , electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: 0.1M KOH/t-butanol - water (1:1) Kaulen, Johannes; Schaefer, Hans-J.; Tetrahedron; vol. 38; nb. 22; (1982); p. 3299 - 3308 View in Reaxys

4 %, 28 %

T= 5 °C , electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: KOH/t-butanol - water (1:1) Kaulen, Johannes; Schaefer, Hans-J.; Tetrahedron; vol. 38; nb. 22; (1982); p. 3299 - 3308 View in Reaxys

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