1-Phenyl-2-propanol (P2Pol) [C9H12O] by Asch

Query 1. Query

Query

Results

Date

RX.PXRN=1858667

162 reactions in Reaxys

2018-05-22 18h:20m:33s (UTC)

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Rx-ID: 780109 View in Reaxys 1/162 Yield

Conditions & References With diethoxymethylane, cesium fluoride, Time= 5h, T= 25 °C Corriu, R. J. P.; Perz, R.; Reye, C.; Tetrahedron; vol. 39; nb. 6; (1983); p. 999 - 1010 View in Reaxys With diethoxymethylane, ethyl laurate, cesium fluoride, Time= 5h, T= 25 °C Boyer, J.; Corriu, R. J. P.; Perz, R.; Reye, C.; Tetrahedron; vol. 37; (1981); p. 2165 - 2172 View in Reaxys With C28H18Co(1-)*K(1+)*2C4H10O2, hydrogen in toluene, Time= 24h, T= 60 °C , p= 8025.8Torr , chemoselective reaction Gaertner, Dominik; Welther, Alice; Rad, Babak Rezaei; Wolf, Robert; Von Wangelin, Axel Jacobi; Angewandte Chemie International Edition; vol. 53; nb. 14; (2014); p. 3722 - 3726; Angew. Chem.; vol. 126; nb. 14; (2014); p. 3796 - 3800,5 View in Reaxys With polymeric 2,4-ionene borohydride in isopropyl alcohol, Time= 1.5h, Heating Lakouraj, Moslem M.; Tajbakhsh, Mahmood; Mahalli, Majid S.; Monatshefte fur Chemie; vol. 139; nb. 2; (2008); p. 117 123 View in Reaxys With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate in tetrahydrofuran, Time= 1.4h, Heating Firouzabadi, Habib; Zeynizadeh, Behzad; Bulletin of the Chemical Society of Japan; vol. 70; nb. 1; (1997); p. 156 - 168 View in Reaxys With hydrogenchloride, samarium in tetrahydrofuran, T= 20 °C Talukdar; Fang; Journal of Organic Chemistry; vol. 66; nb. 1; (2001); p. 330 - 333 View in Reaxys With sodium tetrahydroborate in ethanol, Time= 0.5h, Ambient temperature Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro; Journal of Organic Chemistry; vol. 60; nb. 8; (1995); p. 2430 2435 View in Reaxys With sodium tetrahydroborate, poly[N-(2-aminoethyl)acrylamido]trimethyl ammonium chloride in tetrahydrofuran, water, Time= 0.5h, T= 20 °C Tamami, Bahman; Mahdavi, Hossein; Tetrahedron; vol. 59; nb. 6; (2003); p. 821 - 826 View in Reaxys 172 : Synthesis of Compound 172.2. Into a 100-mL 3-necked round-bottom flask, maintained with an inert atmosphere of nitrogen, was placed 1-phenylpropan-2-one (3 g, 22.36 mmol, 1.00 equiv) and ethanol (50 mL). This was followed by the addition of NaBH4 (1.7 g, 44.94 mmol, 2.01 equiv) at 5° C. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 10 mL of ammonium chloride (sat.). The resulting solution was extracted with 2*50 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:2). This resulted in 2.8 g (92percent) of 1-phenylpropan-2-ol as a colorless oil. With sodium tetrahydroborate in ethanol, Petroleum ether, T= 5 - 20 °C , Inert atmosphere Patent; Nimbus Apollo, Inc.; Harriman, Geraldine C.; Masse, Craig E.; Harwood, James; Bhat, Sathesh; Greenwood, Jeremy Robert; US2013/123231; (2013); (A1) English

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View in Reaxys With sodium tetrahydroborate in ethanol Valenta, Vladimir; Holubek, Jiri; Svatek, Emil; Protiva, Miroslav; Collection of Czechoslovak Chemical Communications; vol. 52; nb. 12; (1987); p. 3013 - 3023 View in Reaxys With C46H60Fe2N4SSi, hydrogen in toluene, Time= 20h, T= 50 °C , p= 37503.8Torr , Autoclave, Catalytic behavior Luecke, Marcel-Philip; Porwal, Digvijay; Kostenko, Arseni; Zhou, Yu-Peng; Yao, Shenglai; Keck, Matthias; Limberg, Christian; Oestreich, Martin; Driess, Matthias; Dalton Transactions; vol. 46; nb. 47; (2017); p. 16412 - 16418 View in Reaxys With alumina-supported potassium hydroxide, isopropyl alcohol, Time= 0.25h, microwave irradiation, Meerwein-Ponndorf-Verley reduction Kazemi; Kiasat; Synthetic Communications; vol. 32; nb. 14; (2002); p. 2255 - 2260 View in Reaxys 1 : Preparation of 1-phenyl-2-propanol STEP (1) Preparation of 1-phenyl-2-propanol In a 4 liter three-necked flask fitted with a mechanical stirrer and a reflux condenser, were placed 1500 ml of water, 150 g of sodium hydroxide (pellets), 190 ml of ethanol and 180 g of phenylacetone. The mixture was stirred and heated to 80° C., and 150 g of Raney alloy was added very cautiously by small amounts over about 1 hour. During the addition, heating was discontinued and the temperature was maintained at 85°-87° C. After the addition was complete, the mixture was heated for 30 minutes at 85° C. The mixture was cooled, filtered, the alcohol solvent evaporated in a rotary evaporator under reduced pressure, and the remaining aqueous phase was extracted three times with 400 ml of ether. The ether extracts were dried over anhydrous sodium sulfate, evaporated and distilled. 155 g of a colorless liquid were obtained. Boiling point (9 mm Hg)=92° C. nD 23 =1.5198. Yield=85percent With sodium hydroxide in ethanol, water Patent; Eastman Kodak Company; US4605697; (1986); (A) English View in Reaxys With sodium tetrahydroborate, ammonium carbonate in ethanol, Time= 0.05h, T= 20 °C Mohanazadeh, Farajollah; Hosini, Mostafa; Tajbakhsh, Mahmoud; Monatshefte fur Chemie; vol. 136; nb. 12; (2005); p. 2041 - 2043 View in Reaxys Stage 1: With iron(II) acetate, tricyclohexylphosphine in tetrahydrofuran, T= 65 °C , Inert atmosphere Stage 2: in tetrahydrofuran, T= 65 °C , Inert atmosphere Stage 3: With water, sodium hydroxide in tetrahydrofuran, methanol, T= 0 - 20 °C , Inert atmosphere Addis, Daniele; Shaikh, Nadim; Zhou, Shaolin; Das, Shoubhik; Junge, Kathrin; Beller, Matthius; Chemistry - An Asian Journal; vol. 5; nb. 7; (2010); p. 1687 - 1691 View in Reaxys With MnN(salen-3,5-tBu2), phenylsilane in [D3]acetonitrile, Time= 1.5h, T= 80 °C , Sealed tube Chidara, Vamshi K.; Du, Guodong; Organometallics; vol. 32; nb. 18; (2013); p. 5034 - 5037 View in Reaxys With lithium aluminium tetrahydride, ethanol, (-)-(S)-10,10'-dihydroxy-9,9'-biphenanthryl in tetrahydrofuran, Time= 1h, T= -5 °C Yamamoto, Koji; Fukushima, Hitoshi; Nakazaki, Masao; Journal of the Chemical Society, Chemical Communications; nb. 22; (1984); p. 1490 - 1491 View in Reaxys With hydrogen, sodium methylate, nickel in methanol, hydrogen generated in situ electrochemically on Raney nickel electrode

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Chiba; Okimoto; Nagai; Takata; Bulletin of the Chemical Society of Japan; vol. 56; nb. 3; (1983); p. 719 - 723 View in Reaxys With hydrogen, lt;Rh(NBD)(PEt3)2gt;(1+)*ClO4 (1-) in diethylene glycol dimethyl ether, water, Time= 5h, T= 30 °C , p= 735.5Torr , influence of the structure of ketones on their reactivities in catalytic hydrogenation and influence of the phosphorus ligands in cationic rhodium complexes on its catalytic activity, Kinetics, Product distribution Fujitsu, Hiroshi; Matsumura, Eiichi; Takeshita, Kenjiro; Mochida, Isao; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2650 - 2655 View in Reaxys With PEG-400, sodium tetrahydroborate in water, benzene, Time= 5h, Heating, other reagents (phase-transfer catalysts), other temperatures, also in the presence of NaOH, Product distribution Zupancic, Boris G.; Kokalj, Martina; Synthetic Communications; vol. 12; nb. 11; (1982); p. 881 - 886 View in Reaxys With potassium hydroxide, phosphinerhodium, isopropyl alcohol, Time= 41h, T= 82 °C , hydrogen transfer reduction using various chiral catalysts, various optical yields, Product distribution Spogliarich, R.; Kaspar, J.; Graziani, M.; Morandini, F.; Journal of Organometallic Chemistry; vol. 306; (1986); p. 407 - 412 View in Reaxys With sodium amalgam, ethanol Errera; Gazzetta Chimica Italiana; vol. 16; (1886); p. 322 View in Reaxys Tiffeneau; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 359; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 134; (1902); p. 1506 View in Reaxys With sodium tetrahydroborate in ethanol Deniau, Jean; Van Duong, Kiem Nguyen; Merienne, Claude; Gaudemer, Alain; Bulletin de la Societe Chimique de France; vol. 2; nb. 5-6; (1983); p. 180 - 184 View in Reaxys With hydrogenchloride, lithium aluminium tetrahydride, (S)-2-(2,6-xylidinomethyl)pyrrolidine in diethyl ether, Time= 3h, T= -100 °C , Yield given Mukaiyama, Teruaki; Tetrahedron; vol. 37; nb. 23; (1981); p. 4111 - 4119 View in Reaxys With hydrogen, lt;Rh(NBD)(PEt3)2gt;(1+)*ClO4 (1-) in diethylene glycol dimethyl ether, water, Time= 5h, T= 30 °C , p= 735.5Torr , cationic rhodium complexes with other phosphorus ligands as catalysts Fujitsu, Hiroshi; Matsumura, Eiichi; Takeshita, Kenjiro; Mochida, Isao; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2650 - 2655 View in Reaxys With lithium aluminium tetrahydride Pritzkow, Wilhelm; Thomas, Gerda; Willecke, Lothar; Journal fuer Praktische Chemie (Leipzig); vol. 327; nb. 5; (1985); p. 847 - 851 View in Reaxys With lithium aluminium tetrahydride in tetrahydrofuran Guerin, Philippe; Battioni, Jean Paul; Leclerq, Martine; Dumas, Philippe; Phosphorus and Sulfur and the Related Elements; vol. 15; (1983); p. 351 - 358 View in Reaxys With diethoxymethylane, ethyl laurate, cesium fluoride, Time= 5h, T= 25 °C , Yield given Boyer, Jacqueline; Corriu, Robert J. P.; Perz, Robert; Reye, Catherine; Journal of the Chemical Society, Chemical Communications; nb. 3; (1981); p. 121 - 122

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View in Reaxys With sodium hydroxide, 1,1,3,3-Tetramethyldisiloxane, chloro(1,5-cyclooctadiene)rhodium(I) dimer, 1.) benzene, 50 deg C, 145 h, Yield given. Multistep reaction Brunner, Henri; Fisch,Heinrich; Monatshefte fuer Chemie; vol. 119; (1988); p. 525 - 532 View in Reaxys With polymethylhydrosiloxane, (MeO)2BuSnlt;CH2gt;5Si(OMe)2O-silica in methanol, Heating Matlin, Stephen A.; Gandham, Permjit S.; Journal of the Chemical Society, Chemical Communications; nb. 12; (1984); p. 798 - 799 View in Reaxys With diethylaluminium chloride, 1,9-dimethyl-1,4-dihydrolt;9Hgt;pyridolt;2,3-bgt;indole-3-carboxamide in acetonitrile, Time= 18h, Ambient temperature Berkous, Rabia; Dupas, Georges; Bourguignon, Jean; Queguiner, Guy; Bulletin de la Societe Chimique de France; vol. 131; nb. 6; (1994); p. 632 - 635 View in Reaxys With samarium diiodide, N,N,N,N,-tetramethylethylenediamine, water in tetrahydrofuran, T= 20 °C Dahlen, Anders; Hilmersson, Goeran; Tetrahedron Letters; vol. 43; nb. 40; (2002); p. 7197 - 7200 View in Reaxys With iso-butanol, Sn-beta (2 wt percent SnO2) zeolite, Time= 20h, T= 100 °C , Meerwein-Ponndorf-Verley reduction Corma, Avelino; Domine, Marcelo E.; Valencia, Susana; Journal of Catalysis; vol. 215; nb. 2; (2003); p. 294 - 304 View in Reaxys With Zr-100 Al-free Zr-zeolite beta, isopropyl alcohol, Time= 24h, Meerwein-Ponndorf-Verley reduction Zhu, Yongzhong; Chuah, Gaikhuan; Jaenicke, Stephan; Journal of Catalysis; vol. 227; nb. 1; (2004); p. 1 - 10 View in Reaxys With lithium aluminium tetrahydride Hatzakis, Nikos S.; Smonou, Ioulia; Bioorganic Chemistry; vol. 33; nb. 4; (2005); p. 325 - 337 View in Reaxys With lithium aluminium tetrahydride, diethyl ether House; Gannon; Journal of Organic Chemistry; vol. 23; (1958); p. 879,882 View in Reaxys Bailey; King; Journal of Organic Chemistry; vol. 21; (1956); p. 858,860 View in Reaxys Price; Berti; Journal of the American Chemical Society; vol. 76; (1954); p. 1207,1208 View in Reaxys DeTar; Weis; Journal of the American Chemical Society; vol. 79; (1957); p. 3045,3048 View in Reaxys With methanol, sodium tetrahydroborate Eliel; Lukach; Journal of the American Chemical Society; vol. 79; (1957); p. 5986,5990 View in Reaxys van der Zanden; Rix; Recueil des Travaux Chimiques des Pays-Bas; vol. 76; (1957); p. 75,77 View in Reaxys With nickel, Hydrogenation Elpern et al.; Journal of the American Chemical Society; vol. 79; (1957); p. 1951,1954 View in Reaxys With aluminum tri-sec-butoxide, iso-butanol Ferrier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 220; (1945); p. 460

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View in Reaxys With aluminum isopropoxide, isopropyl alcohol Kuriaki; Yakugaku Zasshi; vol. 64; (1944); p. 128; ; (1951); p. 2898 View in Reaxys With sodium hydroxide, ethanol, platinized Raney nickel, Hydrogenation Delepine; Horeau; Bulletin de la Societe Chimique de France; vol. <5> 4; (1937); p. 31,41 View in Reaxys With ethanol, sodium Pickard; Kenyon; Journal of the Chemical Society; vol. 105; (1914); p. 1124 View in Reaxys With samarium diiodide, N,N,N,N,-tetramethylethylenediamine, water in tetrahydrofuran, T= 20 °C Dahlen, Anders; Hilmersson, Goeran; Chemistry - A European Journal; vol. 9; nb. 5; (2003); p. 1123 - 1128 View in Reaxys With sodium tetrahydroborate in ethanol, T= 0 °C Armellin, Silvia; Brenna, Elisabetta; Frigoli, Samuele; Fronza, Giovanni; Fuganti, Claudio; Mussida, Daniele; Analytical Chemistry; vol. 78; nb. 9; (2006); p. 3113 - 3117 View in Reaxys 1 : 1. 1. 1-Phenylpropan-2-ol Sodium borohydride (10.0 g) was added portionwise to an ice cold stirred solution of 1-phenylpropan-2-one (30.0 g) in methanol (500 ml). The mixture was stirred for 4 hours, evaporated and partitioned between water (100 ml) and chloroform (200 ml). The organic phase was dried (MgSO4) and evaporated to give the product as a colourless oil (26.4 g). τ(CDCl3): 8.95 (3H, d, J=6 Hz), 7.4 (2H, d, J=6 Hz), 7.15 (1H, d, disappears with D2 O), 5.9-6.4 (1H, m), 2.7-3.1 (5H, m). With sodium borohydrid in methanol Patent; Beecham Group Limited; US4396627; (1983); (A) English View in Reaxys With sodium tetrahydroborate in methanol, T= 20 °C , Inert atmosphere, Reflux Lu, Yi; Wang, Dong-Hui; Engle, Keary M.; Yu, Jin-Quan; Journal of the American Chemical Society; vol. 132; nb. 16; (2010); p. 5916 - 5921 View in Reaxys General remarks General procedure: All reactions were carried out using Schlenk techniques. Proline derived ligands 3a-3c and 3e-k were prepared from Boc-L-proline and the corresponding commercially available amines, as described in the literature[i]. [RuCl2 (p-cymene)]2 and (1R,2S)-(+)-cis-1-amino-indanol 3d were purchased. Racemic alcohols 2a-m were prepared by LiAlH4 reductions of the corresponding ketone. Other reagents are commercially available. Products were purified by preparative thin layer chromatography using plates prepared from silica gel. Bruker AM 250 spectrometer, operating at 250 MHz for 1H, and at 62.5 MHz for 13C, was used for the NMR spectra which are referenced to the solvent as internal standard. Infrared spectra were recorded in CHCl3 solution using CaF2 cells on a Perkin-Elmer 1000 FT-IR spectrometer. HRMS were measured with a Thermo-FinniganMat 95 spectrometer. Optical rotations were determined using a Perkin-Elmer 241 Polarimeter at room temperature using a cell of 1 dm length and l = 589 nm. Data are reported as follows: [a]D 20 (concentration in g/100 mL, solvent). Reactions were monitored by gas chromatography analysis on apparatus Fisons 8000 equipped with column τ-P1. Enantiomeric excesses of alcohols were determined by gas chromatograph analysis on Fisons 9000 apparatus equipped with Chiraldex τ-PM column. For the separation of the enantiomers of the mixture of alcohols 2a-g, the program was as follows: oven temperature was maintained at 50°C during 30 min, then heated to 100°C (5°C/min) maintained at 100°C during 65 min, then heated to 120°C (5°C/min) and maintained at 120°C during 100 min.

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With lithium aluminium tetrahydride, Inert atmosphere Boukachabia, Mourad; Zeror, Saoussen; Collin, Jacqueline; Fiaud, Jean-Claude; Zouioueche, Louisa Aribi; Tetrahedron Letters; vol. 52; nb. 13; (2011); p. 1485 - 1489 View in Reaxys With sodium tetrahydroborate in ethanol Vitale, Paola; Perna, Filippo Maria; Perrone, Maria Grazia; Scilimati, Antonio; Tetrahedron Asymmetry; vol. 22; nb. 23; (2011); p. 1985 - 1993 View in Reaxys 25 :Examples 24-48; Catalytic hydrogenation of ketones or aldehydes using various invention's ruthenium complexes; The hydrogenation substrate (20 mmol), the base (as in Table 2), τ-propanol (10 ml), and the catalyst precursor RuCl2(L4) (0.01 mmol) were placed into a pressure reactor and stirred under 3/4 (50 bar) at the given temperature for the given amount of time as indicated in Table 2. With hydrogen, potassium hydoxide, C36H54Cl2N2RuS2 in isopropyl alcohol, Time= 2.5h, T= 60 °C , p= 37503.8Torr , autoclave, Product distribution / selectivity Patent; FIRMENICH SA; SANTORO, Francesco; SAUDAN, Lionel; SAUDAN, Michel, Alfred, Joseph; SAUDAN, Sylvia, Joyeuse, Adelaide; WO2012/84810; (2012); (A1) English View in Reaxys With sodium tetrahydroborate in ethanol, Time= 2h, T= 0 - 20 °C Li, Gang; Leow, Dasheng; Wan, Li; Yu, Jin-Quan; Angewandte Chemie - International Edition; vol. 52; nb. 4; (2013); p. 1245 - 1247; Angew. Chem.; vol. 125; nb. 4; (2013); p. 1283 - 1285,3 View in Reaxys 2.3. Catalytic testing For a typical reduction, 2 mmol of the aldehyde substrate,0.504 g (6 mmol) potassium formate, 0.54 mL (30 mmol) water and5 mL (65 mmol) dimethylformamide (DMF) were added to a 25 mLround-bottom flask. After heating the reaction mixture to 100Cunder a flow of nitrogen, 100 mg of 1 wt.percent Ru/AlO(OH) (0.5 mol percentof Ru) was added. Samples were taken at regular intervals and ana-lyzed by gas chromatography (GC) and gas chromatography massspectrometry (GC–MS). For comparison, the direct hydrogenationof benzaldehyde using molecular H2at 0.5 MPa was carried out in a Parr autoclave at 100C. Due to their lower reactivity, the catalytictransfer hydrogenation of ketones was carried out using 200 mg of2 wt.percent Ru/AlO(OH). For recycling tests, the used catalyst was recov-ered by centrifugation, washed with water followed by ethanol anddried at room temperature before use With potassium formate in water, N,N-dimethyl-formamide, Time= 24h, T= 100 °C , Inert atmosphere, Green chemistry, Catalytic behavior Gao, Yanxiu; Jaenicke, Stephan; Chuah, Gaik-Khuan; Applied Catalysis A: General; vol. 484; (2014); p. 51 - 58 View in Reaxys With formic acid in water, Time= 2h, T= 40 °C , pH= 3.64, Schlenk technique, Inert atmosphere, enantioselective reaction Xie, Yinzheng; Wang, Mengpan; Wu, Xiaohui; Chen, Chen; Ma, Wenbo; Dong, Qifeng; Yuan, Mingming; Hou, Zhenshan; ChemPlusChem; vol. 81; nb. 6; (2016); p. 541 - 549 View in Reaxys With sodium tetrahydroborate in ethanol, Time= 16h, T= 0 - 20 °C Vitale, Paola; Abbinante, Vincenzo Mirco; Perna, Filippo Maria; Salomone, Antonio; Cardellicchio, Cosimo; Capriati, Vito; Advanced Synthesis and Catalysis; vol. 359; nb. 6; (2017); p. 1049 - 1057 View in Reaxys With [K(dme)2][Co(τ4-anthracene)2], hydrogen in toluene, Time= 24h, T= 60 °C , p= 7500.75Torr , Schlenk technique, Glovebox, Mechanism, Catalytic behavior, Solvent Büschelberger, Philipp; Gärtner, Dominik; Reyes-Rodriguez, Efrain; Kreyenschmidt, Friedrich; Koszinowski, Konrad; Jacobi von Wangelin, Axel; Wolf, Robert; Chemistry - A European Journal; vol. 23; nb. 13; (2017); p. 3139 - 3151 View in Reaxys With methanol, sodium tetrahydroborate, Time= 1h, T= 0 °C

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Alsafadi, Diya; Alsalman, Safaa; Paradisi, Francesca; Organic and Biomolecular Chemistry; vol. 15; nb. 43; (2017); p. 9169 - 9175 View in Reaxys Cl HO

Si Si

Rx-ID: 33851963 View in Reaxys 2/162 Yield

Conditions & References

19 %Chromat.

Time= 1h, UV-irradiation, Inert atmosphere Protti, Stefano; Ravelli, Davide; Mannucci, Barbara; Albini, Angelo; Fagnoni, Maurizio; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8577 - 8580 View in Reaxys

35 %Chromat.

in water, Time= 15h, Irradiation Pedroli, Chiara; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Journal of Organic Chemistry; vol. 82; nb. 13; (2017); p. 6592 - 6603 View in Reaxys

Rx-ID: 33851968 View in Reaxys 3/162 Yield 10 %Chromat.

Conditions & References With water, Time= 1h, UV-irradiation, Inert atmosphere Protti, Stefano; Ravelli, Davide; Mannucci, Barbara; Albini, Angelo; Fagnoni, Maurizio; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8577 - 8580 View in Reaxys

29 %Chromat.

Rx-ID: 39283902 View in Reaxys 4/162 Yield 58 %Chromat.

Conditions & References With (x)C4H8O*(x)C18H15P*Ru, hydrogen in tetrahydrofuran, Time= 2.5h, T= 30 °C , p= 15001.5Torr , Autoclave, Glovebox, Reagent/catalyst Castelbou, Jessica Llop; Bres-Femenia, Emma; Blondeau, Pascal; Chaudret, Bruno; Castilln, Sergio; Claver, Carmen; Godard, Cyril; ChemCatChem; vol. 6; nb. 11; (2014); p. 3160 - 3168 View in Reaxys

30 %Chromat.

With (x)C4H8O*(x)C28H28P2*Ru, hydrogen in tetrahydrofuran, Time= 5h, T= 30 °C , p= 15001.5Torr , Autoclave, Glovebox Castelbou, Jessica Llop; Bres-Femenia, Emma; Blondeau, Pascal; Chaudret, Bruno; Castilln, Sergio; Claver, Carmen; Godard, Cyril; ChemCatChem; vol. 6; nb. 11; (2014); p. 3160 - 3168 View in Reaxys

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53 %Chromat.

3.3 General procedure for the catalytic hydrogenation reactions General procedure: Autoclave Par 477 equipped with PID control temperature and reservoir for kinetic measurements and HEL 24 Cat reactor for substrate scope were used as reactors for the hydrogenation reactions. In a typical experiment, the autoclave was charged in the glove-box with the desired Rh NPs (1.25 or 0.625molpercent; the catalyst concentration was calculated based on the total number of metallic Rh atoms in the surface of the NPs) and the substrate (0.124M) in THF. Molecular hydrogen was then introduced until the desired pressure was reached and the reaction was stirred for the desired reaction time at the selected temperature. At the end of the reaction, the autoclave was depressurised and the solution was filtered through silica for subsequent analysis by GC. The conversion and selectivities for each reaction product were determined by GC-FID on an Agilent Technologies 7890A spectrometer, with a HP-5 column (30m×0.25mm×0.25μm) using undecane as internal standard. TOF was defined as moles of products per mol Rh at the surface of the NPs per hour. With hydrogen in tetrahydrofuran, Time= 5h, T= 30 °C , p= 15001.5Torr , Autoclave, Glovebox Martinez-Espinar, Francisco; Blondeau, Pascal; Nolis, Pau; Chaudret, Bruno; Claver, Carmen; Castillón, Sergio; Godard, Cyril; Journal of Catalysis; vol. 354; (2017); p. 113 - 127 View in Reaxys

50 %Chromat.

HO HO

Rx-ID: 44473289 View in Reaxys 5/162 Yield

Conditions & References Stage 1: With bis(cyclopentadienyl)titanium dichloride, magnesium in diethyl ether, Time= 14h, Schlenk technique, Inert atmosphere Stage 2: With dihydrogen peroxide, T= 0 °C , Inert atmosphere, Alkaline conditions, Schlenk technique Khusainova, Liliya I.; Khafizova, Leila O.; Tyumkina, Tatyana V.; Ryazanov, Kirill S.; Dzhemilev, Usein M.; Journal of Organometallic Chemistry; vol. 832; (2017); p. 12 - 17 View in Reaxys

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Rx-ID: 45900080 View in Reaxys 6/162 Yield 25 %Chromat., 14 %Chromat., 5 %Chromat., 18 %Chromat.

Conditions & References in water, Time= 15h, Irradiation Pedroli, Chiara; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Journal of Organic Chemistry; vol. 82; nb. 13; (2017); p. 6592 - 6603 View in Reaxys

Rx-ID: 46404229 View in Reaxys 7/162 Yield

Conditions & References 4.5. General procedure for methyl xanthate cleavage (Tables 1 and3) General procedure: To a 0.5e2.0 mL microwave vial with a magnetic stirring bar,were added methyl xanthate ester (0.3e0.6 mmol) and dieth-ylenetriamine (0.5 mL, 4.6 mmol) under air and the vial was sealedwith a microwave vial cap with septum. The reaction mixture washeated to 160C for 30 min by microwave heating. Aq. HCl (1 M,15 ml) was added and the aqueous phase was extracted with CH2Cl2(3 15 mL). The combined organic phases were washed with satd.aq. NaHCO3 (20 mL) and brine (20 mL) before being dried andreduced in vacuo to yield the alcohols, which all are eithercommercially available (hexane-1,6-diol, 2a, 2b, 2c, 2d, and 2e) orknown (2f,382g,382h,395a,405b,415c,415d,425e,415f41). Summa-rized details of individual cleavage reactions are found as sup-porting information (Table S3). With 3-azapentane-1,5-diamine, Time= 0.5h, T= 160 °C , Sealed tube, Microwave irradiation, Reagent/catalyst Thorsheim, Karin; Manner, Sophie; Ellervik, Ulf; Tetrahedron; vol. 73; nb. 44; (2017); p. 6329 - 6333 View in Reaxys

H HO

Rx-ID: 46594807 View in Reaxys 8/162 Yield

Conditions & References With ferredoxin reductase, ferredoxin, P450 monooxygenase CYP101B1 from a Novosphingobium bacterium, H85F mutant, NADH, bovine liver catalase in aq. buffer, T= 30 °C , pH= 7.4, Enzymatic reaction, Kinetics, Reagent/catalyst, enantioselective reaction Sarkar, Md. Raihan; Lee, Joel H. Z.; Bell, Stephen G.; ChemBioChem; vol. 18; nb. 21; (2017); p. 2119 - 2128 View in Reaxys

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Rx-ID: 46701501 View in Reaxys 9/162 Yield

Conditions & References With water, diphenyldisulfane, 9-(2-mesityl)-10-methylacridinium perchlorate in acetonitrile, Time= 24h, T= 20 °C , Irradiation, Inert atmosphere, regioselective reaction Hu, Xia; Zhang, Guoting; Bu, Faxiang; Lei, Aiwen; ACS Catalysis; vol. 7; nb. 2; (2017); p. 1432 - 1437 View in Reaxys

Rx-ID: 41526501 View in Reaxys 10/162 Yield

Conditions & References 4 : Enzyme-Catalysed Kinetic Resolution of Chiral Esters General procedure: Preparative enzymatic conversions of racemic chiral esters were performed on a 10 ml scale with 0.25-0.3 mmol substrate and 1-2 ml enzyme preparation (50 U/ml based on p-nitrophenyl butyrate assay) in 50 mM phosphate-buffer pH 7.5. The reaction was stirred in a water bath at 37° C. up to a conversion of 50percent. After addition of the same volume A. dest educts and/or products were extracted as follows: ethylesters were acidified with HCl (aq. 10percent, 10 ml) and afterwards extracted with 4×20 ml diethylether. Methylesters were extracted first using a neutral to slight alkaline pH, afterwards the reaction was acidified to extract the reaction products. Acetylated substrates were extracted with 4×20 ml methylen chloride. In each case the organic phases were pooled, dried with Na2SO4 and afterwards evaporated. Reaction educts and products were separated by chromatography and analysed by NMR, polarimetric and GC-analysis to determine the grade of purity, the degree and sense of optical rotation and the enantiomeric excess. With MTTSTQNISELPLLPGRLGDPSRVLKTDPRADPRLVAACAPFALDVAPPPVPVTANSPLADKLAYAAANESGMEAVFAAVFADLSPITNVKRRTEVIKGVDENDISLYIHTPQNMSGPLPCVYHAHGGGMVLLTAAGPTYVRWRDELAALGMVVVGVEFRNGAGKLGNHPFPAGLNDCMSGLQWVFDHKAALGISKIITSGESGGGNLALAVCLKAKKDNRLAQIAGVYALCPYIYGAWAQKSKELPSLVENNCYLIDVRSMEVLASIYDPENKNATNPLCWPYWATREDLQGLPPHVISVNELDPLRDEGLKYYQKLMAAGVRVYSRTVNGTCHAADVLFRKALPEVYAATLRDIKGFADSL in aq. phosphate buffer, T= 37 °C , pH= 7.5, Enzymatic reaction, Reagent/catalyst, enantioselective reaction Patent; B.R.A.I.N. AG; Liebeton, Klaus; Eck, Jürgen; Bornscheuer, Uwe; Böttcher, Dominique; Langer, Peter; Bellur, Esen; US9193961; (2015); (B2) English View in Reaxys With Sulfolobus tokodaii esterase ST0071, G274W mutant in aq. buffer, Time= 1.5h, T= 50 °C , pH= 8, Enzymatic reaction, Reagent/catalyst, Temperature, Time Ozaki, Masanaru; Kawakami, Norifumi; Ohta, Hiromichi; Miyamoto, Kenji; Biocatalysis and Biotransformation; vol. 34; nb. 5; (2016); p. 249 - 252 View in Reaxys H2 Si

Rx-ID: 42698773 View in Reaxys 11/162 Yield

Conditions & References Stage 1: With tetrafluoroboric acid diethyl ether in dichloromethane, Time= 2h, T= 0 - 25 °C , Schlenk technique, Inert atmosphere Stage 2: With potassium fluoride, dihydrogen peroxide, potassium hydrogencarbonate in tetrahydrofuran, methanol, dichloromethane, water, Time= 18h, Inert atmosphere, Schlenk technique, Reflux

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Du, Xiaoyong; Zhang, Yanlu; Peng, Dongjie; Huang, Zheng; Angewandte Chemie - International Edition; vol. 55; nb. 23; (2016); p. 6671 - 6675; Angew. Chem.; vol. 128; (2016); p. 6783 - 6787,5 View in Reaxys

Rx-ID: 42698814 View in Reaxys 12/162 Yield

Conditions & References Reaction Steps: 2 1.1: C22H31Cl2CoN2P / tetrahydrofuran / 0.17 h / Inert atmosphere; Glovebox 1.2: 24 h / 60 °C / Inert atmosphere; Sealed tube 2.1: tetrafluoroboric acid diethyl ether / dichloromethane / 2 h / 0 - 25 °C / Schlenk technique; Inert atmosphere 2.2: 18 h / Inert atmosphere; Schlenk technique; Reflux With tetrafluoroboric acid diethyl ether, C22H31Cl2CoN2P in tetrahydrofuran, dichloromethane Du, Xiaoyong; Zhang, Yanlu; Peng, Dongjie; Huang, Zheng; Angewandte Chemie - International Edition; vol. 55; nb. 23; (2016); p. 6671 - 6675; Angew. Chem.; vol. 128; (2016); p. 6783 - 6787,5 View in Reaxys

Rx-ID: 29422789 View in Reaxys 13/162 Yield

Conditions & References With aluminum oxide, sodium tetrahydroborate, palladium dichloride in hexane, water, Time= 1h, T= 30 °C Yakabe, Shigetaka; Synthetic Communications; vol. 40; nb. 9; (2010); p. 1339 - 1344 View in Reaxys in isopropyl alcohol, Time= 6h, T= 29.84 °C , p= 760.051Torr , Inert atmosphere, UV-irradiation, Sealed tube Hirakawa, Hiroaki; Shiraishi, Yasuhiro; Sakamoto, Hirokatsu; Ichikawa, Satoshi; Tanaka, Shunsuke; Hirai, Takayuki; Chemical Communications; vol. 51; nb. 12; (2015); p. 2294 - 2297 View in Reaxys

B Cl

(v4)

S (v3)

Rx-ID: 41596773 View in Reaxys 14/162 Yield

Conditions & References With dihydrogen peroxide, Alkaline conditions Khusainova; Khafizova; Tyumkina; Dzhemilev; Russian Journal of Organic Chemistry; vol. 51; nb. 11; (2015); p. 1517 1523; Zh. Org. Khim.; vol. 51; nb. 11; (2015); p. 1551 - 1557,7 View in Reaxys

HO O

Rx-ID: 8965110 View in Reaxys 15/162

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Yield

Conditions & References With pyridine, 1,3 -dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, 4,4'-bipyridine, NiI2*3.9H2O, triethylamine hydrochloride, sodium iodide, zinc, Time= 12h, T= 20 °C Zhao, Yang; Weix, Daniel J.; Journal of the American Chemical Society; vol. 136; nb. 1; (2014); p. 48 - 51 View in Reaxys Stage 1: With n-butyllithium in tetrahydrofuran, hexane, T= -70 °C Stage 2: in tetrahydrofuran, hexane, T= -50 - 20 °C Erdelyi, Balazs; Szabo, Antal; Seres, Gabor; Birincsik, Laszlo; Ivanics, Jozsef; Szatzker, Gabor; Poppe, Laszlo; Tetrahedron Asymmetry; vol. 17; nb. 2; (2006); p. 268 - 274 View in Reaxys Stage 1: With n-butyllithium in tetrahydrofuran, Time= 0.5h, T= -30 °C Stage 2: in tetrahydrofuran, Time= 1h, T= 20 °C , Further stages. Allan; Carnell; Journal of Organic Chemistry; vol. 66; nb. 19; (2001); p. 6495 - 6497 View in Reaxys

HO O

Rx-ID: 37023073 View in Reaxys 16/162 Yield

Conditions & References With 1,3 -dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, 4,4'-bipyridine, bis(cyclopentadienyl)titanium dichloride, manganese, NiCl2*0.97C2H6O, triethylamine hydrochloride, Time= 12h, T= 20 °C , Inert atmosphere, Glovebox, Overall yield = 70 percent; Overall yield = 48 mg Zhao, Yang; Weix, Daniel J.; Journal of the American Chemical Society; vol. 136; nb. 1; (2014); p. 48 - 51 View in Reaxys

HO O

Rx-ID: 37023075 View in Reaxys 17/162 Yield 16 %, 54 %

Conditions & References With 1,3 -dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, 4,4'-bipyridine, bis(cyclopentadienyl)titanium dichloride, manganese, NiCl2*0.97C2H6O, triethylamine hydrochloride, Time= 12h, T= 20 °C , Inert atmosphere, Glovebox Zhao, Yang; Weix, Daniel J.; Journal of the American Chemical Society; vol. 136; nb. 1; (2014); p. 48 - 51 View in Reaxys

HO Br

Rx-ID: 37023110 View in Reaxys 18/162 Yield

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Rx-ID: 36978607 View in Reaxys 19/162 Yield 69 %Spectr., 6.6 %Chromat.

Conditions & References With acetylacetonatodicarbonylrhodium(l), 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II), carbon monoxide, C70H72O2P2, hydrogen in 1,4-dioxane, Time= 36h, T= 120 °C , p= 3750.38Torr , Inert atmosphere, Autoclave Yuki, Yamato; Takahashi, Kohei; Tanaka, Yoshiyuki; Nozaki, Kyoko; Journal of the American Chemical Society; vol. 135; nb. 46; (2013); p. 17393 - 17400 View in Reaxys

Rx-ID: 3821325 View in Reaxys 20/162 Yield

Conditions & References With palladium 10 on activated carbon, hydrogen in methanol, Time= 2h, T= 20 °C , p= 760.051Torr , regioselective reaction Blasio, Nadia Di; Lopardo, Maria Teresa; Lupattelli, Paolo; European Journal of Organic Chemistry; nb. 6; (2009); p. 938 944 View in Reaxys With ammonium formate in ethyl acetate, Time= 12h, T= 25 °C , Inert atmosphere Erathodiyil, Nandanan; Ooi, Samuel; Seayad, Abdul M.; Han, Yu; Lee, Su Seong; Ying, Jackie Y.; Chemistry - A European Journal; vol. 14; nb. 10; (2008); p. 3118 - 3125 View in Reaxys With alkaline hydrogen peroxide, lithium triethylborohydride in tetrahydrofuran, Time= 1h Brown, Herbert C.; Narasimhan, S.; Somayaji, Vishwanatha; Journal of Organic Chemistry; vol. 48; nb. 18; (1983); p. 3091 - 3096 View in Reaxys With Al-trifluoromethanesulfonyldiisobutylalane in diethyl ether, Time= 0.5h, T= 25 °C , Inert atmosphere, Meerwein-Ponndorf-Verley reduction, regioselective reaction Cha, Jin Soon; Park, Seung Jin; Bulletin of the Korean Chemical Society; vol. 31; nb. 8; (2010); p. 2135 - 2136 View in Reaxys Reaction Steps: 2 1: dimethyltitanocene / tetrahydrofuran / 18 h / Inert atmosphere; Reflux 2: water; potassium carbonate / tetrahydrofuran; acetone / 16 h / Inert atmosphere With dimethyltitanocene, water, potassium carbonate in tetrahydrofuran, acetone Gansaeuer, Andreas; Klatte, Max; Braendle, Gerhard M.; Friedrich, Joachim; Angewandte Chemie - International Edition; vol. 51; nb. 35; (2012); p. 8891 - 8894 View in Reaxys

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Rx-ID: 9060430 View in Reaxys 21/162 Yield

Conditions & References

12 %

With dichloro bis(acetonitrile) palladium(II), 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μhydrotetracarbonyldiruthenium(II), water, isopropyl alcohol, p-benzoquinone, copper dichloride, tert-butyl alcohol, T= 85 °C Dong, Guangbin; Teo, Peili; Wickens, Zachary K.; Grubbs, Robert H.; Science; vol. 333; nb. 6049; (2011); p. 1609 - 1612 View in Reaxys

12 %

2 :The substrate scope was examined on a preparative scale (0.4 mmol, Scheme 6). The primary alcohol products were isolated, purified using silica-gel flash column chromatography and characterized via NMR spectroscopy and High Resolution Mass Spectrometry (HRMS), or identified by comparison of the NMR and Gas chromatography-mass spectrometric (GC-MS) data with the authentic samples. In general, aryl substituted terminal olefins provide good yields of primary alcohols with excellent anti-Markovnikov selectivity (20:1). A number of functional groups are tolerated under these reaction conditions, such as alkyl, naphthyl, trifluormethyl and nitro groups as well as various halides. Aliphatic olefins also provided hydration products, despite the challenging nature of these substrates (entries 11 and 12). Although obtaining high regioselectivity for aliphatic substrates is more difficult, these results are promising because under previous (Spencer's) conditions only Markovnikov product was observed for aliphatic substrates. One key merit of this method is that the major stoichiometric byproduct, 1,4-hydroquinone (HBQ) can be easily recovered and converted to BQ in an excellent yield via a facile aerobic oxidation. With isopropyl alcohol, p-benzoquinone, copper dichloride, dichloro bis(acetonitrile) palladium(II), 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) in tert-butyl alcohol, T= 85 °C , Inert atmosphere Patent; Dong, Guangbin; Grubbs, Robert H.; Teo, Peili; Wickens, Zach K.; US2012/172634; (2012); (A1) English View in Reaxys Stage 1: With boron trifluoride-tetrahydrofuran complex in tetrahydrofuran, Time= 2h, T= 24 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in tetrahydrofuran, water, T= 24 °C , Further stages. Morrill, Terence C.; D'Souza, Christopher A.; Yang, Lu; Sampognaro, Anthony J.; Journal of Organic Chemistry; vol. 67; nb. 8; (2002); p. 2481 - 2484 View in Reaxys

Li O

Rx-ID: 10128577 View in Reaxys 22/162 Yield

Conditions & References in tetrahydrofuran, diethyl ether, Time= 3.88333h, T= 0 - 20 °C Blakemore, Paul R.; Marsden, Stephen P.; Vater, Huw D.; Organic Letters; vol. 8; nb. 4; (2006); p. 773 - 776 View in Reaxys in tetrahydrofuran, T= 0 °C , Inert atmosphere Fernandez-Mateos, Emilio; MacIa, Beatriz; Yus, Miguel; European Journal of Organic Chemistry; nb. 20; (2012); p. 3732 3736 View in Reaxys Cl HO

Si Si

Rx-ID: 33851964 View in Reaxys 23/162

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Yield

Conditions & References

69 %Chromat., 9 %Chromat.

Rx-ID: 33851965 View in Reaxys 24/162 Yield

Conditions & References

69 %Chromat.

Rx-ID: 33851966 View in Reaxys 25/162 Yield

Conditions & References

22 %Chromat., 12 %Chromat., 21 %Chromat.

HO Si

Rx-ID: 33851967 View in Reaxys 26/162 Yield 14 %Chromat., 11 %Chromat., 6 %Chromat.

Conditions & References Time= 1h, UV-irradiation, Inert atmosphere Protti, Stefano; Ravelli, Davide; Mannucci, Barbara; Albini, Angelo; Fagnoni, Maurizio; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8577 - 8580 View in Reaxys

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Rx-ID: 33919382 View in Reaxys 27/162 Yield

Conditions & References With 2-hydroperoxypropane in acetonitrile, Time= 36h, T= 70 °C Biradar, Ankush V.; Asefa, Tewodros; Applied Catalysis A: General; vol. 435-436; (2012); p. 19 - 26 View in Reaxys

O SiH

Rx-ID: 33931399 View in Reaxys 28/162 Yield

Conditions & References With water, potassium carbonate in tetrahydrofuran, acetone, Time= 16h, Inert atmosphere Gansaeuer, Andreas; Klatte, Max; Braendle, Gerhard M.; Friedrich, Joachim; Angewandte Chemie - International Edition; vol. 51; nb. 35; (2012); p. 8891 - 8894 View in Reaxys

Rx-ID: 33951186 View in Reaxys 29/162 Yield

Conditions & References

4 %, 56 %

Stage 1: With (1,3-dimethylimidazol-2-ylidene)borane, bis(trifluoromethanesulfonyl)amide in 1,2-dichloro-ethane, Time= 3h, T= 25 °C , Inert atmosphere Stage 2: With dihydrogen peroxide, sodium hydroxide in methanol, water, 1,2-dichloro-ethane, Time= 16h, T= 25 °C Prokofjevs, Aleksandrs; Boussonniere, Anne; Li, Linfeng; Bonin, Helene; Lacote, Emmanuel; Curran, Dennis P.; Vedejs, Edwin; Journal of the American Chemical Society; vol. 134; nb. 29; (2012); p. 12281 - 12288 View in Reaxys

O Si

Rx-ID: 34466052 View in Reaxys 30/162 Yield

Conditions & References With SO3H silica gel, Time= 0.5h, T= 25 °C Fujii, Hideaki; Yamada, Takaaki; Hayashida, Kohei; Kuwada, Miki; Hamasaki, Atom; Nobuhara, Kazunori; Ozeki, Sumio; Nagase, Hiroshi; Heterocycles; vol. 85; nb. 11; (2012); p. 2685 - 2691 View in Reaxys

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Rx-ID: 31782517 View in Reaxys 31/162 Yield

Conditions & References Stage 1: With Al-trifluoromethanesulfonyldiisobutylalane in diethyl ether, Time= 0.5h, T= 25 °C , Inert atmosphere, MeerweinPonndorf-Verley reduction Stage 2: With hydrogenchloride, water in diethyl ether, regioselective reaction Cha, Jin Soon; Bulletin of the Korean Chemical Society; vol. 32; nb. 1; (2011); p. 219 - 224 View in Reaxys

Rx-ID: 7019863 View in Reaxys 32/162 Yield

Conditions & References 2 Patent; Agency for Science ,Technology and Research; US2010/113832; (2010); (A1) English View in Reaxys Kharasch,M.S. et al.; Journal of the American Chemical Society; vol. 83; (1961); p. 3229 - 3232 View in Reaxys Nordlander,J.E.; Deadman,W.G.; Journal of the American Chemical Society; vol. 90; (1968); p. 1590 - 1598 View in Reaxys Schadt,F.L. et al.; Journal of the American Chemical Society; vol. 100; (1978); p. 228 - 246 View in Reaxys Schulz; Jassmann; Bekker; Die Pharmazie; vol. 26; nb. 8; (1971); p. 477 - 481 View in Reaxys Newman,H.; Angier,R.B.; Tetrahedron; vol. 26; (1970); p. 825 - 836 View in Reaxys McKillop; Ford; Tetrahedron; vol. 30; nb. 15; (1974); p. 2467 - 2475 View in Reaxys Traynelis,V.J. et al.; Journal of Organic Chemistry; vol. 29; (1964); p. 123 - 129 View in Reaxys DePuy,C.H. et al.; Journal of Organic Chemistry; vol. 35; (1970); p. 2746 - 2750 View in Reaxys Schaap,A.; Arense,J.F.; Recueil des Travaux Chimiques des Pays-Bas; vol. 87; (1968); p. 1249 - 1263 View in Reaxys Meyers,A.I.; Kendall,P.M.; Tetrahedron Letters; nb. 14; (1974); p. 1337 - 1340 View in Reaxys Huynh,C. et al.; Tetrahedron Letters; (1979); p. 1503 - 1506 View in Reaxys Boireau,G.; Abenhaim,D.; Journal of Organometallic Chemistry; vol. 92; (1975); p. 131 - 138 View in Reaxys Brown; Zweifel; Journal of the American Chemical Society; vol. 82; (1960); p. 4708,4709 View in Reaxys Asami et al.; Bulletin of the Chemical Society of Japan; vol. 51; (1978); p. 1869 View in Reaxys Asami; Mukaiyama; Heterocycles; vol. 12; (1979); p. 499,501 View in Reaxys Eberson; Persson; Journal of Medicinal and Pharmaceutical Chemistry; vol. 5; (1962); p. 738,746 View in Reaxys Lansbury; Peterson; Journal of the American Chemical Society; vol. 85; (1963); p. 2236,2242 View in Reaxys Eliel; Rerick; Journal of the American Chemical Society; vol. 82; (1960); p. 1362,1365 View in Reaxys

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Namy et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 269; (1969); p. 1222 View in Reaxys Deniau et al.; Bulletin de la Societe Chimique de France; (1969); p. 4414 View in Reaxys Kursanov et al.; Synthesis; (1974); p. 633,647 View in Reaxys Nakagawa; Minami; Tetrahedron Letters; (1972); p. 343,345 View in Reaxys Sacharkin; Gawrilenko; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); (1960); p. 2081; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1960); p. 2245 View in Reaxys Thakar; Rao; Journal of Scientific and Industrial Research, Section B: Physical Sciences; vol. 21; (1962); p. 583,586 View in Reaxys Vigneron; Jacquet; Tetrahedron; vol. 32; (1976); p. 939,944 View in Reaxys Beckwith; Thomas; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1973); p. 861,869 View in Reaxys Alberola; Tetrahedron Letters; (1970); p. 3471 View in Reaxys Bernardon; Bourdais; Tetrahedron Letters; (1970); p. 4711 View in Reaxys Merchant et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 17; (1979); p. 267 View in Reaxys Solodar; Chemical Technology (Washington, DC, United States); vol. 5; (1975); p. 421; ; vol. 83; nb. 113607k View in Reaxys Suga et al.; Kogyo Kagaku Zasshi; vol. 70; (1967); p. 487,489 View in Reaxys Rossi; Bunnett; Journal of the American Chemical Society; vol. 94; (1972); p. 683 View in Reaxys Brown; Yoon; Chemical Communications (London); (1968); p. 1549 View in Reaxys Cristol; Greenwald; Tetrahedron Letters; (1976); p. 2105,2106 View in Reaxys Rao et al.; Journal of Organometallic Chemistry; vol. 166; (1979); p. 9,10, 12, 15 View in Reaxys Mason; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1975); p. 1664 View in Reaxys Bernardon; Tetrahedron Letters; (1979); p. 1581,1582, 1583 View in Reaxys Sacharkin et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); (1965); p. 1159; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1965); p. 1194 View in Reaxys Thibault; Annales de Chimie (Cachan, France); vol. 6; nb. 14; (1971); p. 263,264,265,269 View in Reaxys Lundeen; Oehlschlager; Journal of Organometallic Chemistry; vol. 25; (1970); p. 337,343 View in Reaxys Gossauer; Perez Ossorio; Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica; vol. 59; (1963); p. 185,188 View in Reaxys Pines; Schappell; Journal of Organic Chemistry; vol. 29; (1964); p. 1503,1507 View in Reaxys Christol et al.; Bulletin de la Societe Chimique de France; (1961); p. 2317 View in Reaxys Gelli et al.; Annali di Chimica (Rome, Italy); vol. 54; (1964); p. 1143,1146 View in Reaxys Ehrhart; Angewandte Chemie; vol. 75; (1963); p. 855 View in Reaxys Sano et al.; Nippon Kagaku Kaishi; (1972); p. 1699,1700,1701 View in Reaxys

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Larson; Fuentes; Synthetic Communications; vol. 9; (1979); p. 841,843 View in Reaxys Laurent et al.; Bulletin de la Societe Chimique de France; (1967); p. 1995 View in Reaxys Deniau et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 264; (1967); p. 1560 View in Reaxys Horner; Singer; Chemische Berichte; vol. 101; (1968); p. 3329 View in Reaxys Namy et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 268; (1969); p. 287 View in Reaxys Herstellung von (+-)-<18 O>-1-Phenyl-propan-2-ol Denney; Goldstein; Journal of the American Chemical Society; vol. 79; (1957); p. 4948,4951 View in Reaxys B : rac-3-Phenyl-propan-2-ol STR107 rac-3-Phenyl-propan-2-ol STR107 66 mg (83percent) of the title compound were obtained analogously as a colorless liquid from 171 mg (0.59 mmol) of the carbamate from Example 8 of the formula I'. Example 7 of the formula I: Patent; Bayer Aktiengesellschaft; US5223633; (1993); (A) English View in Reaxys 2 : 1-Phenyl-2-propanol Substrate (1b) Example 2 1-Phenyl-2-propanol Substrate (1b) 1-Phenyl-2-propanol (1b) (3.5 mL; 25 mmol) was dissolved in DCM (25 mL). Triethylamine (5.21 mL; 37.5 mmol; 1.5 equiv.) was added followed by DMAP (153 mg; 1.25 mmol; 0.05 equiv.). The reaction mixture was cooled to 0° and acetic anhydride (2.83 mL; 30 mmol; 1.2 equiv.) was added. The reaction mixture was allowed to warm slowly to room temperature overnight to completely consume 1b (tlc analysis). The reaction mixture was diluted with 50 mL of 1:1 ether:hexanes and washed with water (25 mL), 1N HCl (2*25 mL), and saturated NaHCO3 (25 mL). The organic layer was dried (MgSO4) and concentrated to afford 4.67 g (99percent) of crude 2b which was used as is. 1 H nmr (300 MHz, CDCl3): 7.35-7.15 (5H, m); 5.12 (1H, m(6), J=6.5 Hz); 2.927 (1H, dd, J=6.68, 13.56 Hz); 2.748 (1H, dd, J=6.53, 13.64 Hz); 1.996 (3H, s); 1.215 (3H, d, J=6.25 Hz). IR (neat film, cm-1): 3000 (b); 1790 (s). Patent; Eastman Kodak Company; US5312950; (1994); (A) English View in Reaxys

OH H HO

Rx-ID: 8613715 View in Reaxys 33/162 Yield

Conditions & References Stage 1: With trimethylsilyl trifluoromethanesulfonate, benzo[1,3,2]dioxaborole, acethylacetonato(1,5-cyclooctadiene)rhodium(I), (R)-1-(2-phenylquinazolin-4-yl)-2-(Ph2P)-naphthalene in tetrahydrofuran, Time= 2h, T= 25 °C , Addition, Hydroboration Stage 2: With sodium hydroxide, dihydrogen peroxide in tetrahydrofuran, Time= 1h, T= 20 °C , Oxidation, Hydrolysis, Further stages. Title compound not separated from byproducts. McCarthy, Mary; Hooper, Mark W.; Guiry, Patrick J.; Chemical Communications; nb. 14; (2000); p. 1333 - 1334 View in Reaxys Stage 1: With CF3O3S(1-)*C45H36F3N2PRh(1+), benzo[1,3,2]dioxaborole in tetrahydrofuran, T= 0 °C , Inert atmosphere

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Stage 2: With dihydrogen peroxide, sodium hydroxide in ethanol, water, T= 0 - 20 °C , optical yield given as percent ee, enantioselective reaction Maxwell, Aoife C.; Flanagan, Susan P.; Goddard, Richard; Guiry, Patrick J.; Tetrahedron Asymmetry; vol. 21; nb. 11-12; (2010); p. 1458 - 1473 View in Reaxys Stage 1: With CF3O3S(1-)*C41H38ClN2PRh(1+), benzo[1,3,2]dioxaborole in tetrahydrofuran, Time= 2h, T= 20 °C , Inert atmosphere Stage 2: With dihydrogen peroxide, sodium hydroxide in tetrahydrofuran, ethanol, water, Time= 1h, T= 0 - 20 °C , Inert atmosphere, optical yield given as percent ee, enantioselective reaction Fleming, William J.; Mueller-Bunz, Helge; Guiry, Patrick J.; European Journal of Organic Chemistry; nb. 31; (2010); p. 5996 - 6004 View in Reaxys

HO O

Rx-ID: 9507685 View in Reaxys 34/162 Yield

Conditions & References With hydrogen, Pd0-EnCatTM in methanol, Time= 19h, T= 23 °C , p= 30002.4Torr

15 %

Ley, Steven V.; Mitchell, Claire; Pears, David; Ramarao, Chandrashekar; Yu, Jin-Quan; Zhou, Wuzong; Organic Letters; vol. 5; nb. 24; (2003); p. 4665 - 4668 View in Reaxys 33 %

With aluminum oxide, sodium tetrahydroborate, palladium dichloride in hexane, water, Time= 3h, T= 60 °C Yakabe, Shigetaka; Synthetic Communications; vol. 40; nb. 9; (2010); p. 1339 - 1344 View in Reaxys

15 % Chromat.

With hydrogen, Pd/magnetite in ethyl acetate, Time= 4h, T= 23 °C , p= 760.051Torr Kwon, Min Serk; Park, In Soo; Jang, Jum Suk; Lee, Jae Sung; Park, Jaiwook; Organic Letters; vol. 9; nb. 17; (2007); p. 3417 - 3419 View in Reaxys

H S

–

K+

O O

Rx-ID: 29321325 View in Reaxys 35/162 Yield 63 %

Conditions & References Time= 3h, T= 95 °C , optical yield given as percent ee Shi, Xiao-Xin; Shen, Chun-Li; Yao, Jian-Zhong; Nie, Liang-Deng; Quan, Na; Tetrahedron Asymmetry; vol. 21; nb. 3; (2010); p. 277 - 284 View in Reaxys

21/58

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H S

–O

Cs +

Rx-ID: 29321327 View in Reaxys 36/162 Yield

Conditions & References

60 %

Time= 3h, T= 95 °C , optical yield given as percent ee Shi, Xiao-Xin; Shen, Chun-Li; Yao, Jian-Zhong; Nie, Liang-Deng; Quan, Na; Tetrahedron Asymmetry; vol. 21; nb. 3; (2010); p. 277 - 284 View in Reaxys

H S

–O

Na +

O O

Rx-ID: 29321329 View in Reaxys 37/162 Yield 62 %

Rx-ID: 29790625 View in Reaxys 38/162 Yield

Conditions & References Stage 1: With CF3O3S(1-)*C45H39N2OPRh(1+), benzo[1,3,2]dioxaborole in tetrahydrofuran, T= 20 °C , Inert atmosphere Stage 2: With dihydrogen peroxide, sodium hydroxide in ethanol, water, T= 0 - 20 °C , optical yield given as percent ee, enantioselective reaction Maxwell, Aoife C.; Flanagan, Susan P.; Goddard, Richard; Guiry, Patrick J.; Tetrahedron Asymmetry; vol. 21; nb. 11-12; (2010); p. 1458 - 1473 View in Reaxys Stage 1: With CF3O3S(1-)*C45H39N2OPRh(1+), benzo[1,3,2]dioxaborole in tetrahydrofuran, T= 0 °C , Inert atmosphere

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Rx-ID: 29790631 View in Reaxys 39/162 Yield

Conditions & References Stage 1: With CF3O3S(1-)*C45H36F3N2PRh(1+), benzo[1,3,2]dioxaborole in tetrahydrofuran, T= 0 °C , Inert atmosphere Stage 2: With dihydrogen peroxide, sodium hydroxide in ethanol, water, T= 0 - 20 °C Maxwell, Aoife C.; Flanagan, Susan P.; Goddard, Richard; Guiry, Patrick J.; Tetrahedron Asymmetry; vol. 21; nb. 11-12; (2010); p. 1458 - 1473 View in Reaxys

OH H HO

Rx-ID: 29790632 View in Reaxys 40/162 Yield

Conditions & References Stage 1: With CF3O3S(1-)*C45H39N2OPRh(1+), benzo[1,3,2]dioxaborole in tetrahydrofuran, T= 0 °C , Inert atmosphere Stage 2: With dihydrogen peroxide, sodium hydroxide in ethanol, water, T= 0 - 20 °C , optical yield given as percent ee, enantioselective reaction Maxwell, Aoife C.; Flanagan, Susan P.; Goddard, Richard; Guiry, Patrick J.; Tetrahedron Asymmetry; vol. 21; nb. 11-12; (2010); p. 1458 - 1473 View in Reaxys

Rx-ID: 29790633 View in Reaxys 41/162 Yield

23/58

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Rx-ID: 28522362 View in Reaxys 42/162 Yield

Conditions & References With [ruthenium(II)(τ6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2, water, bis[2-(diphenylphosphino)phenyl] ether in 5,5-dimethyl-1,3-cyclohexadiene, Time= 24.1667h, T= 20 - 150 °C , Inert atmosphere Hamid, M. Haniti S. A.; Allen, C. Liana; Lamb, Gareth W.; Maxwell, Aoife C.; Maytum, Hannah C.; et al.; Journal of the American Chemical Society; vol. 131; (2009); p. 1766 - 1774 View in Reaxys

H N

H 2N

N H

H 2N

Rx-ID: 29189896 View in Reaxys 43/162 Yield

Conditions & References

69 %

With aluminum amalgam, sodium hydroxide in methanol, Time= 1.5h, T= -10 - 60 °C Kunalan, Vanitha; Daeid, Niamh Nic; Kerr, William J.; Buchanan, Hilary A. S.; McPherson, Allan R.; Analytical Chemistry; vol. 81; nb. 17; (2009); p. 7342 - 7348 View in Reaxys

Rx-ID: 29608009 View in Reaxys 44/162 Yield

Conditions & References Stage 1: With silica gel, Time= 0.0166667h, T= 20 °C Stage 2: With silica gel, Time= 0.05h, T= 110 °C Ghorbani-Vaghei, Ramin; Veisi, Hojat; Amiri, Mostafa; Chegini, Mohammad; Karimi, Mehdi; Dadamahaleh, Somayeh Akbari; Sedrpoushan, Alireza; South African Journal of Chemistry; vol. 62; (2009); p. 39 - 43

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View in Reaxys

Rx-ID: 1839908 View in Reaxys 45/162 Yield

Conditions & References With sodium hydroxide, diphenylamine borane, dihydrogen peroxide, 1.) THF, 0 deg C, 1 h; 20 deg C, 1 h, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Camacho, Carlos; Uribe, Guillermo; Contreras, Rosalinda; Synthesis; nb. 12; (1982); p. 1027 - 1030 View in Reaxys Stage 1: With C6H14BN, iodine in dichloromethane, T= 20 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in methanol, water Scheideman, Matthew; Wang, Guoqiang; Vedejs, Edwin; Journal of the American Chemical Society; vol. 130; nb. 27; (2008); p. 8669 - 8676 View in Reaxys

Rx-ID: 26019900 View in Reaxys 46/162 Yield 60 %

Conditions & References With Furukawa reagent in dichloromethane, Time= 2h, T= 20 °C Li, Lezhen; Cai, Peijie; Guo, Qingxiang; Xue, Song; Journal of Organic Chemistry; vol. 73; nb. 9; (2008); p. 3516 - 3522 View in Reaxys

OH HO

Rx-ID: 26049093 View in Reaxys 47/162 Yield 65 % Chromat.

Conditions & References With NADPH in dimethyl sulfoxide, T= 30 °C , pH= 7.4, Product distribution Whitehouse, Christopher J. C.; Bell, Stephen G.; Tufton, Henry G.; Kenny, Richard J. P.; Ogilvie, Lydia C. I.; Wong, Luet-Lok; Chemical Communications; nb. 8; (2008); p. 966 - 968 View in Reaxys OH HO

Rx-ID: 26049094 View in Reaxys 48/162

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Yield

Conditions & References

30 % Chromat., 68 % Chromat.

7.8 %Chromat., 77.2 %Chromat.

With NADPH in dimethyl sulfoxide, T= 30 °C , pH= 7.4, Product distribution, Further Variations: Reagents Whitehouse, Christopher J. C.; Bell, Stephen G.; Tufton, Henry G.; Kenny, Richard J. P.; Ogilvie, Lydia C. I.; Wong, Luet-Lok; Chemical Communications; nb. 8; (2008); p. 966 - 968 View in Reaxys With cytochrome P450BM3 CYP102A1 variant GVQ (A74G/F87V/L188Q) monooxygenase, NADPH, bovine liver catalase in dimethyl sulfoxide, T= 30 °C , pH= 7.4, aq. buffer, Enzymatic reaction Whitehouse, Christopher J.C.; Bell, Stephen G.; Wong, Luet-Lok; Chemistry - A European Journal; vol. 14; nb. 35; (2008); p. 10905 - 10908 View in Reaxys

Rx-ID: 26049095 View in Reaxys 49/162 Yield

Conditions & References

46 % Chromat.

53.1 %Chromat.

With cytochrome P450BM3 CYP102A1 variant KSK19 (F87A/H171L/Q307H/N319Y) monooxygenase, NADPH, bovine liver catalase in dimethyl sulfoxide, T= 30 °C , pH= 7.4, aq. buffer, Enzymatic reaction Whitehouse, Christopher J.C.; Bell, Stephen G.; Wong, Luet-Lok; Chemistry - A European Journal; vol. 14; nb. 35; (2008); p. 10905 - 10908 View in Reaxys

20.3 %Chromat.

With cytochrome P450BM3 CYP102A1 variant KT5 (F87A/A330P/E377A/D425N) monooxygenase, NADPH, bovine liver catalase in dimethyl sulfoxide, T= 30 °C , pH= 7.4, aq. buffer, Enzymatic reaction Whitehouse, Christopher J.C.; Bell, Stephen G.; Wong, Luet-Lok; Chemistry - A European Journal; vol. 14; nb. 35; (2008); p. 10905 - 10908 View in Reaxys

H 2N

Rx-ID: 28157771 View in Reaxys 50/162 Yield

Conditions & References Stage 1: in dichloromethane Stage 2: With iodine in dichloromethane, Time= 5h, T= 20 °C Stage 3: With sodium hydroxide, dihydrogen peroxide in methanol, water Scheideman, Matthew; Wang, Guoqiang; Vedejs, Edwin; Journal of the American Chemical Society; vol. 130; nb. 27; (2008); p. 8669 - 8676 View in Reaxys

Rx-ID: 5096072 View in Reaxys 51/162

26/58

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Yield

Conditions & References With potassium hydroxide, (.eta.5-indenyl)ruthenium(bis(triphenylphosphine))chloride in dichloromethane, Time= 3.5h, T= 25 °C Koh, Jeong Hwan; Jeong, Hyun Min; Park, Jaiwook; Tetrahedron Letters; vol. 39; nb. 31; (1998); p. 5545 - 5548 View in Reaxys With potassium tert-butylate, chlorodicarbonyl(1,2,3,4,5-pentaphenylcyclopentadienyl)ruthenium(II) in isopropyl alcohol, toluene, Time= 0.75h, T= 20 °C Csjernyik, Gabor; Bogar, Krisztian; Baeckvall, Jan-E.; Tetrahedron Letters; vol. 45; nb. 36; (2004); p. 6799 - 6802 View in Reaxys With silver(l) oxide, (τ5-Ph5C5)Ru(CO)(PPh3)Br in toluene, Time= 2.5h, T= 25 °C Ko, Soo-Byung; Baburaj, Baskar; Kim, Mahn-Joo; Park, Jaiwook; Journal of Organic Chemistry; vol. 72; nb. 18; (2007); p. 6860 - 6864 View in Reaxys

Rx-ID: 9941118 View in Reaxys 52/162 Yield

Conditions & References Stage 1: With iodine, borane pyridine complex in dichloromethane, Time= 2h, T= 20 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in methanol, dichloromethane, T= 0 - 20 °C , Title compound not separated from byproducts Clay, Julia M.; Vedejs, Edwin; Journal of the American Chemical Society; vol. 127; nb. 16; (2005); p. 5766 - 5767 View in Reaxys With benzo[1,3,2]dioxaborole, 1,3-dibutyl-4,5-dichloro-imidazole-1,3-divinylsiloxane Pt(0) in tetrahydrofuran, Time= 3h, T= 25 °C Lillo, Vanesa; Mata, Jose A.; Segarra, Anna M.; Peris, Eduardo; Fernandez, Elena; Chemical Communications; nb. 21; (2007); p. 2184 - 2186 View in Reaxys With benzo[1,3,2]dioxaborole, 1,3-dibutyl-triazole-1,3-divinylsiloxane Pt(0) in tetrahydrofuran, Time= 3h, T= 25 °C Lillo, Vanesa; Mata, Jose A.; Segarra, Anna M.; Peris, Eduardo; Fernandez, Elena; Chemical Communications; nb. 21; (2007); p. 2184 - 2186 View in Reaxys

Rx-ID: 11106836 View in Reaxys 53/162 Yield

Conditions & References With silica triflate in methanol, Time= 0.166667h, Heating Shirini; Marjani; Nahzomi, H. Taherpour; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 182; nb. 9; (2007); p. 2235 - 2240

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View in Reaxys

Rx-ID: 10118992 View in Reaxys 54/162 Yield

Conditions & References With trinitratocerium(IV) bromate, Time= 0.0833333h, T= 20 °C Shirini, Farhad; Esm-Hosseini, Majid; Hejazi, Zoha; Synthetic Communications; vol. 35; nb. 22; (2005); p. 2913 - 2919 View in Reaxys With tris[trinitratocerium(IV)] paraperiodate, Time= 0.0166667h, T= 20 °C Shirini; Esm-Hosseini; Hejazi; Mohammadpoor-Baltork; Journal of Chemical Research; nb. 1; (2006); p. 29 - 31 View in Reaxys F F F

F F

F N

F F

F F F F F

F F F F

F F

F N

F F

Rx-ID: 10267424 View in Reaxys 55/162 Yield

Conditions & References With 3-chloro-benzenecarboperoxoic acid in dichloromethane, Time= 1h, T= -78 °C Kojima, Masaru; Nakamura, Yutaka; Ishikawa, Takuma; Takeuchi, Seiji; Tetrahedron Letters; vol. 47; nb. 35; (2006); p. 6309 - 6314 View in Reaxys

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F F F F F

F F F

F F F F

F F

F N

F F

F S

F F F F F

F F F

F F F F

F F

N F

F F

Rx-ID: 10268866 View in Reaxys 56/162 Yield

29/58

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F F F F F

F F F

F F F F

F F

F N

F F

F S

F F F F F

F F F

F F

F F F F

F F

N F

F F

Rx-ID: 10269670 View in Reaxys 57/162 Yield

30/58

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F F F F F

F F F

F F F F

F F

N F

F F

F S

F F F F F

F F F

F F F F

F F

N F

F F

Rx-ID: 10270036 View in Reaxys 58/162 Yield

HO O

Rx-ID: 11054504 View in Reaxys 59/162 Yield

Conditions & References Stage 1: With aluminium trichloride, Time= 4h, T= 6 - 7 °C Stage 2: With water, Further stages. Mamedov; Russian Journal of Applied Chemistry; vol. 79; nb. 3; (2006); p. 408 - 410 View in Reaxys

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Rx-ID: 9794241 View in Reaxys 60/162 Yield

Conditions & References Stage 1: With magnesium in diethyl ether Stage 2: in diethyl ether, Time= 2h, T= 20 °C , Grignard reaction Choukchou-Braham; Mostefa-Kara; Cheikh; Didi; Villemin; Synthetic Communications; vol. 35; nb. 2; (2005); p. 169 - 178 View in Reaxys O

Rx-ID: 10070514 View in Reaxys 61/162 Yield

Conditions & References

79 %, 3 %, 7%

With samarium diiodide, water in tetrahydrofuran, Time= 0.166667h, T= 20 °C , Further byproducts given Kamochi, Yasuko; Kudo, Tadahiro; Masuda, Toshinobu; Takadate, Akira; Chemical and Pharmaceutical Bulletin; vol. 53; nb. 8; (2005); p. 1017 - 1020 View in Reaxys

H HO

S O

Rx-ID: 9654329 View in Reaxys 62/162 Yield

Conditions & References With cesium hydroxide in water, Time= 2h, T= 250 °C , p= 37503Torr Yamasaki, Yuki; Hirayama, Takaharu; Oshima, Koichiro; Matsubara, Seijiro; Chemistry Letters; vol. 33; nb. 7; (2004); p. 864 - 865 View in Reaxys With sodium hydroxide in water, Time= 2h, T= 250 °C , p= 37503Torr Yamasaki, Yuki; Hirayama, Takaharu; Oshima, Koichiro; Matsubara, Seijiro; Chemistry Letters; vol. 33; nb. 7; (2004); p. 864 - 865 View in Reaxys

O S O

Rx-ID: 9668774 View in Reaxys 63/162

32/58

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Yield

Conditions & References

30 %

With sodium hydroxide in water, Time= 2h, T= 250 °C , p= 37503Torr Yamasaki, Yuki; Hirayama, Takaharu; Oshima, Koichiro; Matsubara, Seijiro; Chemistry Letters; vol. 33; nb. 7; (2004); p. 864 - 865 View in Reaxys

35 %

With cesium hydroxide in water, Time= 2h, T= 250 °C , p= 37503Torr Yamasaki, Yuki; Hirayama, Takaharu; Oshima, Koichiro; Matsubara, Seijiro; Chemistry Letters; vol. 33; nb. 7; (2004); p. 864 - 865 View in Reaxys

Rx-ID: 9729923 View in Reaxys 64/162 Yield

Conditions & References With lithium aluminium tetrahydride in diethyl ether Ranu, Brindaban C.; Banerjee, Subhash; Das, Arijit; Tetrahedron Letters; vol. 45; nb. 46; (2004); p. 8579 - 8581 View in Reaxys

Rx-ID: 1564467 View in Reaxys 65/162 Yield

Conditions & References With sodium tetrahydroborate, alpha cyclodextrin in water, Time= 24h, Ambient temperature, presence of τ-, and τ-cyclodextrin; kinetic resolution; further epoxides, Product distribution Hu, Ying; Uno, Mitsunari; Harada, Akira; Takahashi, Shigetoshi; Bulletin of the Chemical Society of Japan; vol. 64; nb. 6; (1991); p. 1884 - 1888 View in Reaxys Stage 1: With sodium tetrahydroborate, diselenide resin in ethanol Stage 2: With 2,2'-azobis(isobutyronitrile), tris-(trimethylsilyl)silane Berlin, Stefan; Ericsson, Cecilia; Engman, Lars; Journal of Organic Chemistry; vol. 68; nb. 22; (2003); p. 8386 - 8396 View in Reaxys With sodium tetrahydroborate, alpha cyclodextrin in water, Time= 5h, Ambient temperature, Yield given Hu, Ying; Uno, Mitsunari; Harada, Akira; Takahashi, Shigetoshi; Bulletin of the Chemical Society of Japan; vol. 64; nb. 6; (1991); p. 1884 - 1888 View in Reaxys

Rx-ID: 9316923 View in Reaxys 66/162 Yield

Conditions & References Stage 1: With isocyanate de chlorosulfonyle, sodium carbonate in dichloromethane, Time= 20h, Heating Stage 2: With sodium hydroxide in methanol, Time= 1h, T= 20 °C

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Kim, Ji Duck; Han, Gyoonhee; Zee, Ok Pyo; Jung, Young Hoon; Tetrahedron Letters; vol. 44; nb. 4; (2003); p. 733 - 735 View in Reaxys O HO

N O

Rx-ID: 9446186 View in Reaxys 67/162 Yield

Conditions & References With [RuH2{(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl}2], hydrogen in toluene, Time= 24h, T= 125 °C Li, Yanjun; Izumi, Taeko; Journal of Chemical Research - Part S; nb. 3; (2003); p. 128 - 129 View in Reaxys

Rx-ID: 9547981 View in Reaxys 68/162 Yield

Conditions & References With formic acid, triethylamine, Pd0-EnCatTM in ethyl acetate, Time= 3h, T= 23 °C Ley, Steven V.; Mitchell, Claire; Pears, David; Ramarao, Chandrashekar; Yu, Jin-Quan; Zhou, Wuzong; Organic Letters; vol. 5; nb. 24; (2003); p. 4665 - 4668 View in Reaxys

Rx-ID: 13818102 View in Reaxys 69/162 Yield

Conditions & References Reaction Steps: 2 1: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 14 h / 20 °C 2: 87 percent / formic acid; triethylamine / Pd0-EnCatTM / ethyl acetate / 3 h / 23 °C With formic acid, triethylamine, 3-chloro-benzenecarboperoxoic acid, Pd0-EnCatTM in dichloromethane, ethyl acetate Ley, Steven V.; Mitchell, Claire; Pears, David; Ramarao, Chandrashekar; Yu, Jin-Quan; Zhou, Wuzong; Organic Letters; vol. 5; nb. 24; (2003); p. 4665 - 4668 View in Reaxys

methylacetylene metal salt O

Rx-ID: 13911829 View in Reaxys 70/162 Yield

Conditions & References Reaction Steps: 2 1: 63 percent / ammonium acetate / 5 h / Heating 2: 48 percent / [RuH2{(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl}2]; H2 / toluene / 24 h / 125 °C With ammonium acetate, [RuH2{(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl}2], hydrogen in toluene Li, Yanjun; Izumi, Taeko; Journal of Chemical Research - Part S; nb. 3; (2003); p. 128 - 129 View in Reaxys Reaction Steps: 2

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1: 63 percent / NH4OAc / 5 h / Heating 2: RuCl2(PPh3)3; H2 / toluene / 24 h / 125 - 150 °C / 14710.2 Torr With tris(triphenylphosphine)ruthenium(II) chloride, ammonium acetate, hydrogen in toluene Li, Yanjun; Izumi, Taeko; Journal of the Chinese Chemical Society (Taipei, Taiwan); vol. 49; nb. 4; (2002); p. 505 - 508 View in Reaxys

Rx-ID: 9060431 View in Reaxys 71/162 Yield

Conditions & References

9.9 %

Stage 1: With rhodium(III) chloride, boron trifluoride-tetrahydrofuran complex in tetrahydrofuran, Time= 2h, T= 20 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in water Morrill, Terence C.; D'Souza, Christopher A.; Yang, Lu; Sampognaro, Anthony J.; Journal of Organic Chemistry; vol. 67; nb. 8; (2002); p. 2481 - 2484 View in Reaxys

9.9 %

Stage 1: With rhodium(III) chloride, boron trifluoride-tetrahydrofuran complex in tetrahydrofuran, Time= 2h, T= 24 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in tetrahydrofuran, water, T= 24 °C Morrill, Terence C.; D'Souza, Christopher A.; Yang, Lu; Sampognaro, Anthony J.; Journal of Organic Chemistry; vol. 67; nb. 8; (2002); p. 2481 - 2484 View in Reaxys

H 2N

N O

Rx-ID: 9178684 View in Reaxys 72/162 Yield

Conditions & References With tris(triphenylphosphine)ruthenium(II) chloride, hydrogen in toluene, Time= 24h, T= 125 - 150 °C , p= 14710.2Torr Li, Yanjun; Izumi, Taeko; Journal of the Chinese Chemical Society (Taipei, Taiwan); vol. 49; nb. 4; (2002); p. 505 - 508 View in Reaxys

Rx-ID: 8897874 View in Reaxys 73/162 Yield

Conditions & References With scandium tris(trifluoromethanesulfonate), trimethyleneglycol in acetonitrile, Time= 2h, Heating Oriyama; Watahiki; Kobayashi; Hirano; Suzuki; Synthetic Communications; vol. 31; nb. 15; (2001); p. 2305 - 2311 View in Reaxys

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Al O HO

Rx-ID: 8930653 View in Reaxys 74/162 Yield

Conditions & References With triphenylphosphine in toluene, Time= 3h, T= 0 °C Schneider, Christoph; Brauner, Joerg; European Journal of Organic Chemistry; nb. 23; (2001); p. 4445 - 4450 View in Reaxys

O O

Rx-ID: 8556274 View in Reaxys 75/162 Yield

Conditions & References With Novozym 435, 2,6-dimethyl-4-heptanol, (Ph4C4CO)2H(μ-H)(CO)4Ru2 in toluene, Time= 110h, T= 70 °C , Enzymatic reaction, Reduction, Title compound not separated from byproducts. Jung, Hyun M.; Koh, Jeong H.; Kim, Mahn-Joo; Park, Jaiwook; Organic Letters; vol. 2; nb. 3; (2000); p. 409 - 411 View in Reaxys

O O

Rx-ID: 8556937 View in Reaxys 76/162 Yield

O O

Rx-ID: 8579540 View in Reaxys 77/162

36/58

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Yield

Conditions & References With Novozym 435, 2,6-dimethyl-4-heptanol, Ru(II)-carbonyl in toluene, Time= 44h, T= 70 °C , Enzymatic reaction, Reduction, acetylation, Product distribution Jung, Hyun M.; Koh, Jeong H.; Kim, Mahn-Joo; Park, Jaiwook; Organic Letters; vol. 2; nb. 3; (2000); p. 409 - 411 View in Reaxys With Novozym 435, 2,6-dimethyl-4-heptanol, Ru(II)-carbonyl in toluene, Time= 44h, T= 70 °C , Enzymatic reaction, Reduction, acetylation, Title compound not separated from byproducts Jung, Hyun M.; Koh, Jeong H.; Kim, Mahn-Joo; Park, Jaiwook; Organic Letters; vol. 2; nb. 3; (2000); p. 409 - 411 View in Reaxys With Novozym 435, 2,6-dimethyl-4-heptanol, (Ph4C4CO)2H(μ-H)(CO)4Ru2 in toluene, Time= 44h, T= 70 °C , Enzymatic reaction, Reduction, acetylation, Product distribution Jung, Hyun M.; Koh, Jeong H.; Kim, Mahn-Joo; Park, Jaiwook; Organic Letters; vol. 2; nb. 3; (2000); p. 409 - 411 View in Reaxys With Novozym 435, 2,6-dimethyl-4-heptanol, (Ph4C4CO)2H(μ-H)(CO)4Ru2 in toluene, Time= 44h, T= 70 °C , Enzymatic reaction, Reduction, acetylation, Title compound not separated from byproducts Jung, Hyun M.; Koh, Jeong H.; Kim, Mahn-Joo; Park, Jaiwook; Organic Letters; vol. 2; nb. 3; (2000); p. 409 - 411 View in Reaxys

OH H HO

Rx-ID: 8618423 View in Reaxys 78/162 Yield

F O

F F

Rx-ID: 5085905 View in Reaxys 79/162 Yield 2 %, 1 %, 32 %

Conditions & References With titanium tetrachloride, ethyl trifluoroacetaldehyde hemiacetal in dichloromethane, Time= 24h, Ambient temperature Sakumo, Kunihiro; Kuki, Noriko; Kuno, Terumi; Takagi, Toshiyuki; Koyama, Mayumi; Ando, Akira; Kumadaki, Itsumaro; Journal of Fluorine Chemistry; vol. 93; nb. 2; (1999); p. 165 - 170

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View in Reaxys F

O F OH

F O

F F

Rx-ID: 5132129 View in Reaxys 80/162 Yield 2 %, 1 %, 32 %

Conditions & References With titanium tetrachloride in dichloromethane, Time= 24h, Ambient temperature Sakumo, Kunihiro; Kuki, Noriko; Kuno, Terumi; Takagi, Toshiyuki; Koyama, Mayumi; Ando, Akira; Kumadaki, Itsumaro; Journal of Fluorine Chemistry; vol. 93; nb. 2; (1999); p. 165 - 170 View in Reaxys

18 %, 15 %, With tin(IV) chloride in dichloromethane, Time= 24h, Ambient temperature 24 % Sakumo, Kunihiro; Kuki, Noriko; Kuno, Terumi; Takagi, Toshiyuki; Koyama, Mayumi; Ando, Akira; Kumadaki, Itsumaro; Journal of Fluorine Chemistry; vol. 93; nb. 2; (1999); p. 165 - 170 View in Reaxys 6.9 %, 13.5 %, 23.4 %

With aluminium trichloride in dichloromethane, Time= 2.5h, Ambient temperature, other Lewis acids, other time, Product distribution Sakumo, Kunihiro; Kuki, Noriko; Kuno, Terumi; Takagi, Toshiyuki; Koyama, Mayumi; Ando, Akira; Kumadaki, Itsumaro; Journal of Fluorine Chemistry; vol. 93; nb. 2; (1999); p. 165 - 170 View in Reaxys

5.9 %, 19.7 %, 2.8 %

With boron trifluoride diethyl etherate in dichloromethane, Time= 24h, Ambient temperature Sakumo, Kunihiro; Kuki, Noriko; Kuno, Terumi; Takagi, Toshiyuki; Koyama, Mayumi; Ando, Akira; Kumadaki, Itsumaro; Journal of Fluorine Chemistry; vol. 93; nb. 2; (1999); p. 165 - 170 View in Reaxys

F Sn F F

Rx-ID: 5234768 View in Reaxys 81/162 Yield

Conditions & References With dihydrogen peroxide, potassium hydrogencarbonate in tetrahydrofuran, methanol, water, Time= 14h, T= 20 °C , Oxidation Falck; Lai, Jing-Yu; Venkata Ramana; Lee, Sang-Gyeong; Tetrahedron Letters; vol. 40; nb. 14; (1999); p. 2715 - 2718 View in Reaxys

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F F

F F F F

F F

F F F F O

Si O

Rx-ID: 5242796 View in Reaxys 82/162 Yield

Conditions & References With tetrabutyl ammonium fluoride in tetrahydrofuran, Time= 3h, T= 20 °C , deprotection Roever, Stephan; Wipf, Peter; Tetrahedron Letters; vol. 40; nb. 31; (1999); p. 5667 - 5670 View in Reaxys

N O

Rx-ID: 4676679 View in Reaxys 83/162 Yield

Conditions & References

12 %

With ethylbenzene, tri-n-butyl-tin hydride in benzene-d6, Time= 2h, T= 40 °C , Irradiation Easton, Christopher J.; Ivory, Andrew J.; Smith, Craig A.; Journal of the Chemical Society. Perkin Transactions 2; nb. 3; (1997); p. 503 - 507 View in Reaxys

HO O

Rx-ID: 4712998 View in Reaxys 84/162 Yield 70 % Chromat.

Conditions & References With tin(IV) chloride in dichloromethane, Time= 5h, T= 0 °C Park, Byeong-Deog; Lee, Hyeong-Ik; Ryoo, Sun-Jong; Lee, Yoon-Sik; Tetrahedron Letters; vol. 38; nb. 4; (1997); p. 591 594 View in Reaxys

Rx-ID: 1548715 View in Reaxys 85/162 Yield

Conditions & References With zinc borohydride, silica gel in N,N-dimethyl-formamide, Time= 1.5h, Ambient temperature, Yield given. Yields of byproduct given Ranu, Brindaban C.; Sarkar, Arunkanti; Saha, Manika; Chakraborty, Rupak; Tetrahedron; vol. 50; nb. 22; (1994); p. 6579 - 6584 View in Reaxys

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O O

Rx-ID: 1849347 View in Reaxys 86/162 Yield 57 %, 9 %

Conditions & References With bromethyl methyl ether, tin(II) bromide in 1,2-dichloro-ethane, Time= 24h, Ambient temperature Oriyama, Takeshi; Kimura, Mikio; Koga, Gen; Bulletin of the Chemical Society of Japan; vol. 67; nb. 3; (1994); p. 885 - 887 View in Reaxys Li

HO B

Rx-ID: 3385426 View in Reaxys 87/162 Yield

Conditions & References With sodium hydroxide, dihydrogen peroxide, 1.) THF, hexane, 0 deg C, 0.5 h, 2.) THF, hexane, methanol, 25 deg C, 15 h (or 68 deg C, 1 h), Yield given. Multistep reaction Pelter; Warren; Wilson; Tetrahedron; vol. 49; nb. 14; (1993); p. 2988 - 3006 View in Reaxys

HO Mg

Rx-ID: 1569282 View in Reaxys 88/162 Yield

Conditions & References With titanium(IV) isopropylate in diethyl ether, Time= 6h, Ambient temperature, other Grignard reagents, var. time, Product distribution Sosnovskii, G. M.; Astapovich, I. V.; Journal of Organic Chemistry USSR (English Translation); vol. 28; nb. 7.1; (1992); p. 1082 - 1084; Zhurnal Organicheskoi Khimii; vol. 28; nb. 7; (1992); p. 1377 - 1379 View in Reaxys With titanium(IV) isopropylate in diethyl ether, Time= 6h, Ambient temperature Sosnovskii, G. M.; Astapovich, I. V.; Journal of Organic Chemistry USSR (English Translation); vol. 28; nb. 7.1; (1992); p. 1082 - 1084; Zhurnal Organicheskoi Khimii; vol. 28; nb. 7; (1992); p. 1377 - 1379 View in Reaxys

HO Mg

O HO

Rx-ID: 1569283 View in Reaxys 89/162 Yield

Conditions & References With water, 1) Et2O, -78 deg C to 20 deg C, 18 h, Yield given. Multistep reaction. Yields of byproduct given

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Kauffmann, Thomas; Neiteler, Christel; Robbe, Sonja; Chemische Berichte; vol. 125; nb. 11; (1992); p. 2409 - 2418 View in Reaxys

Rx-ID: 2480000 View in Reaxys 90/162 Yield

Conditions & References

20 % Chromat., 15 % Chromat.

With sodium periodate, acetic acid, Time= 24h, T= 25 °C Hirai, Yasuyuki; Ohe, Kouichi; Toshimitsu, Akio; Uemura, Sakae; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 67; nb. 1-4; (1992); p. 173 - 176 View in Reaxys

S O

O O

Rx-ID: 2777439 View in Reaxys 91/162 Yield

Conditions & References With lithium aluminium tetrahydride in diethyl ether, T= 0 °C Chong, J. Michael; Tetrahedron Letters; vol. 33; nb. 1; (1992); p. 33 - 36 View in Reaxys

Rx-ID: 2881553 View in Reaxys 92/162 Yield 20 % Chromat., 15 % Chromat.

Conditions & References With sodium periodate in water, Time= 24h, T= 25 °C Hirai, Yasuyuki; Ohe, Kouichi; Toshimitsu, Akio; Uemura, Sakae; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 67; nb. 1-4; (1992); p. 173 - 176 View in Reaxys

Rx-ID: 3343071 View in Reaxys 93/162 Yield 27 % Chromat.

Conditions & References With 3-chloro-benzenecarboperoxoic acid, Time= 2h, T= 80 °C

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Hirai, Yasuyuki; Ohe, Kouichi; Toshimitsu, Akio; Uemura, Sakae; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 67; nb. 1-4; (1992); p. 173 - 176 View in Reaxys

Rx-ID: 3343720 View in Reaxys 94/162 Yield

Conditions & References

33 % Chromat.

With 3-chloro-benzenecarboperoxoic acid, Time= 2h, T= 80 °C Hirai, Yasuyuki; Ohe, Kouichi; Toshimitsu, Akio; Uemura, Sakae; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 67; nb. 1-4; (1992); p. 173 - 176 View in Reaxys

Mg Br

Rx-ID: 1825181 View in Reaxys 95/162 Yield 80 %

Conditions & References With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride, Time= 14h, Ambient temperature Menicagli, Rita; Malanga, Corrado; Finato, Barbara; Lardicci, Luciano; Gazzetta Chimica Italiana; vol. 119; nb. 1; (1989); p. 69 - 70 View in Reaxys

Rx-ID: 2007647 View in Reaxys 96/162 Yield

Conditions & References With lithium aluminium tetrahydride, oxygen, dibenzoyl peroxide, 1.) 150 deg C, 2.) ether, reflux, 30 min, Yield given. Multistep reaction. Yields of byproduct given Batke, Birgit; Lauterbach, Gerlinde; Pritzkow, Wilhelm; Voerckel, Volkmar; Belyakov, Vladimir A.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 3; (1989); p. 424 - 430 View in Reaxys

49 % Chromat.

With lithium aluminium tetrahydride, oxygen, dibenzoyl peroxide, chain termination and propagation constants, oxidabilities; multistep reaction, Product distribution Batke, Birgit; Lauterbach, Gerlinde; Pritzkow, Wilhelm; Voerckel, Volkmar; Belyakov, Vladimir A.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 3; (1989); p. 424 - 430 View in Reaxys O– C O

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Rx-ID: 3134032 View in Reaxys 97/162 Yield

Conditions & References in ethanol, isopropyl alcohol, T= 22 °C , Irradiation, rate of decomposition to form alkyl radical and carboxylate anion; other solvent, also in the presence of oxygen, Rate constant Masnovi; Journal of the American Chemical Society; vol. 111; nb. 25; (1989); p. 9081 - 9089 View in Reaxys

O HO

S O

Rx-ID: 3130128 View in Reaxys 98/162 Yield

Conditions & References With diisobutylaluminium hydride in hexane Eisch, John J.; Galle, James E.; Journal of Organometallic Chemistry; vol. 341; (1988); p. 293 - 314 View in Reaxys

Rx-ID: 3821290 View in Reaxys 99/162 Yield

Conditions & References With sodium tetrahydroborate in isopropyl alcohol, Time= 7h, Heating, Yields of byproduct given Ookawa, Atsuhiro; Kitade, Masaya; Soai, Kenso; Heterocycles; vol. 27; nb. 1; (1988); p. 213 - 216 View in Reaxys With sodium tetrahydroborate in methanol, tert-butyl alcohol, Time= 4h, Yield given. Yields of byproduct given Ookawa, Atsuhiro; Hiratsuka, Hiroshi; Soai, Kenso; Bulletin of the Chemical Society of Japan; vol. 60; (1987); p. 1813 1818 View in Reaxys With sodium tetrahydroborate in methanol, tert-butyl alcohol, Time= 4h, Yield given Ookawa, Atsuhiro; Hiratsuka, Hiroshi; Soai, Kenso; Bulletin of the Chemical Society of Japan; vol. 60; (1987); p. 1813 1818 View in Reaxys

S O

Rx-ID: 18312585 View in Reaxys 100/162

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Yield

Conditions & References Reaction Steps: 2 1: 1.) n-butyllithium / 1.) THF, ethyl ether, hexane, -95 deg C, 60 min; 2.) thf, hexane, ethyl ether, -95 deg C, 15 min 2: i-Bu2AlH / hexane With n-butyllithium, diisobutylaluminium hydride in hexane Eisch, John J.; Galle, James E.; Journal of Organometallic Chemistry; vol. 341; (1988); p. 293 - 314 View in Reaxys

Si Si SiSi (v4)

(v4)

In (v3) HO OH Si (v3) OH (v4) Si (v5) (v5) O In (v5) O In Si HO Si InH OH Si (v3) (v3) (v3) Si Si Si

In Si

Si (v5)

(v3)

H Si

(v4) H

(v2)

Rx-ID: 26961073 View in Reaxys 101/162 Yield

Conditions & References in tetrahydrofuran, A soln. of PhCH2COMe in THF was added to a suspn. of complex in THF at -78°C; 1 h;; evapd., chromy. on silica; eluent - ethyl acetate-light petroleum; Atwood, Jerry L.; Bott, Simon G.; Hitchcock, Peter B.; Eaborn, Colin; Shariffudin, Rio S.; et al.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1987); p. 747 - 756 ; (from Gmelin) View in Reaxys

Rx-ID: 2007959 View in Reaxys 102/162 Yield

Conditions & References With lithium aluminium tetrahydride, Perbenzoic acid, 2.) ether, 30 min, reflux; study of the regioselectivity of autoxidation by reduction of the corresponding oxidation-mixture, Mechanism, Product distribution Pritzkow, Wilhelm; Thomas, Gerda; Willecke, Lothar; Journal fuer Praktische Chemie (Leipzig); vol. 327; nb. 5; (1985); p. 847 - 851 View in Reaxys

O HO

Ti (v4)

Rx-ID: 2393327 View in Reaxys 103/162 Yield

Conditions & References in diethyl ether, Time= 2h, -40 deg C to 0 deg C Reetz, Manfred T.; Westermann, Juergen; Steinbach, Rainer; Wenderoth, Bernd; Peter, Roland; et al.; Chemische Berichte; vol. 118; nb. 4; (1985); p. 1421 - 1440 View in Reaxys

Rx-ID: 3821326 View in Reaxys 104/162

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Yield

Conditions & References With alkaline hydrogen peroxide, lithium triethylborohydride in tetrahydrofuran, Time= 1h, T= 0 °C , var. time, var. reducing agent, isotope effect, Rate constant, Product distribution, Mechanism Brown, Herbert C.; Narasimhan, S.; Somayaji, Vishwanatha; Journal of Organic Chemistry; vol. 48; nb. 18; (1983); p. 3091 - 3096 View in Reaxys With sodium tert-pentoxide, sodium hydride, nickel dichloride in 1,2-dimethoxyethane, Time= 18h, T= 65 °C , Yield given. Yields of byproduct given Fort, Yves; Vanderesse, Regis; Caubere, Paul; Tetrahedron Letters; vol. 26; nb. 26; (1985); p. 3111 - 3114 View in Reaxys

Rx-ID: 1548763 View in Reaxys 105/162 Yield 1.1 % Turnov., 5 % Turnov., 29.9 % Turnov., 5.9 % Turnov., 56.7 % Turnov.

Conditions & References With lithium aluminium tetrahydride, oxygen, Time= 61h, T= 80 °C , p= 759.8Torr , autoxidation, Product distribution Dao, Le Thi Anh; Blau, Karla; Pritzkow, Wilhelm; Schmidt-Renner, Wolfgang; Voerckel, Volkmar; Willecke, Lothar; Journal fuer Praktische Chemie (Leipzig); vol. 326; nb. 1; (1984); p. 73 - 80 View in Reaxys

Rx-ID: 1569178 View in Reaxys 106/162 Yield

Conditions & References With sodium carbonate, Irradiation, Yield given. Yields of byproduct given Sonawane, H. R.; Sethi, S. C.; Merchant, S. N.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 23; nb. 10; (1984); p. 940 - 943 View in Reaxys

Rx-ID: 3923371 View in Reaxys 107/162 Yield

Conditions & References With lithium triethylborohydride, other reagents, rel. rates, Product distribution Brown, Herbert C.; Kim, Suk-Choong; Journal of Organic Chemistry; vol. 49; nb. 6; (1984); p. 1064 - 1071 View in Reaxys

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Rx-ID: 2130817 View in Reaxys 108/162 Yield

Conditions & References

55 % Chromat., 2 % Chromat.

With lithium triethylborohydride in tetrahydrofuran, T= 65 °C , Product distribution Brandaenge, Svante; Dahlman, Olof; Oelund, Jonas; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 37; nb. 2; (1983); p. 141 - 146 View in Reaxys

Rx-ID: 2203071 View in Reaxys 109/162 Yield

Conditions & References With tert-butyl alcohol in chloroform, T= 26 °C , Equilibrium constant Doyle, Michael P.; Terpstra, Jan W.; Pickering, Ruth A.; LePoire, Diane M.; Journal of Organic Chemistry; vol. 48; nb. 20; (1983); p. 3379 - 3382 View in Reaxys

Rx-ID: 2397944 View in Reaxys 110/162 Yield

Conditions & References With samarium diiodide in tetrahydrofuran, Time= 0.025h, Ambient temperature Souppe, J.; Namy, J. L.; Kagan, H. B.; Tetrahedron Letters; vol. 23; nb. 34; (1982); p. 3497 - 3500 View in Reaxys Souppe, J.; Danon, L.; Namy, J.L.; Kagan, H.B.; Journal of Organometallic Chemistry; vol. 250; nb. 1; (1983); p. 227 - 236 View in Reaxys

B HO

Rx-ID: 3385350 View in Reaxys 111/162 Yield

Conditions & References Yield given. Multistep reaction Pelter, Andrew; Williams, Lorraine; Wilson, John W.; Tetrahedron Letters; vol. 24; nb. 6; (1983); p. 627 - 630 View in Reaxys

Rx-ID: 3536849 View in Reaxys 112/162

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Yield

Conditions & References in acetone, Time= 24h, Ambient temperature, Irradiation, Yield given Pasternak, Mordechai; Morduchowitz, Abraham; Tetrahedron Letters; vol. 24; nb. 33; (1983); p. 3439 - 3442 View in Reaxys

Rx-ID: 3821343 View in Reaxys 113/162 Yield

Rx-ID: 1571220 View in Reaxys 114/162 Yield

Conditions & References in solid matrix, T= -110 °C , Irradiation, temperature dependence of product distributions, Product distribution Tomioka, Hideo; Suzuki, Shinji; Izawa, Yasuji; Journal of the American Chemical Society; vol. 104; nb. 11; (1982); p. 3156 3162 View in Reaxys

N N Mg

H N

Mg Cl

Rx-ID: 2731198 View in Reaxys 115/162 Yield

Conditions & References 1.) tetrahydrofuran, 0 deg C, few minutes 2) reflux, 3 h, THF, 65 deg C, Yield given. Multistep reaction Comins, Daniel L.; Dernell, William; Tetrahedron Letters; vol. 22; (1981); p. 1085 - 1088 View in Reaxys

H 2N

Rx-ID: 2950953 View in Reaxys 116/162 Yield

Conditions & References With monoamineoxidase from rat liver mitochondria, phosphate-buffer in water, Time= 1h, T= 37 °C , biotransformation studies, metabolism, the enzyme activity; other enzymes: ketoreductase; aerobic and anaerobic incubations; various cosubstrates

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Blume; Arzneimittel-Forschung/Drug Research; vol. 31; nb. 6; (1981); p. 994 - 997 View in Reaxys

Rx-ID: 3756737 View in Reaxys 117/162 Yield

Conditions & References With potassium hydroxide, Ru(CF3CO2)CO(PPh3)2, Time= 35h, T= 140 °C , Equilibrium constant Graser, Barbara; Strohmeier, Walter; Marcec, Radovan; Steigerwald, Hannelore; Berichte der Bunsen-Gesellschaft; vol. 85; nb. 7; (1981); p. 671 - 677 View in Reaxys O

Rx-ID: 3756834 View in Reaxys 118/162 Yield

Conditions & References With potassium hydroxide, Ru(CF3CO2)CO(PPh3)2, Time= 7h, T= 140 °C , Equilibrium constant Graser, Barbara; Strohmeier, Walter; Marcec, Radovan; Steigerwald, Hannelore; Berichte der Bunsen-Gesellschaft; vol. 85; nb. 7; (1981); p. 671 - 677 View in Reaxys With potassium hydroxide, carbonylbis(trifluoroacetato)bis(triphenylphosphine)ruthenium, T= 140 °C , ΔG (gas), further temp., Equilibrium constant, Thermodynamic data Strohmeier, Walter; Graser, Barbara; Zeitschrift fuer Physikalische Chemie (Muenchen, Germany); vol. 121; (1980); p. 121 130 View in Reaxys

Rx-ID: 3756882 View in Reaxys 119/162 Yield

Conditions & References With τ-D-glucose 6-phosphate, glucose-6-phosphat-degydrogenase, rat liver mitochondria enzyme, NADP, magnesium chloride in water, Time= 1h, T= 37 °C , relative activity, Kinetics Blume; Arzneimittel-Forschung/Drug Research; vol. 31; nb. 5; (1981); p. 805 - 809 View in Reaxys

Rx-ID: 1564448 View in Reaxys 120/162

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Yield

Conditions & References With nickel dichloride, Time= 2h, T= 35 °C , Yield given. Yields of byproduct given Boireau, G.; Abenhaim, D.; Henry-Basch, E.; Tetrahedron; vol. 36; (1980); p. 3061 - 3070 View in Reaxys

HO Al

Rx-ID: 1564450 View in Reaxys 121/162 Yield

Conditions & References in hexane, Time= 2h, T= 35 °C , Yield given Boireau, G.; Abenhaim, D.; Henry-Basch, E.; Tetrahedron; vol. 36; (1980); p. 3061 - 3070 View in Reaxys

Na +

Al–

Cl OH

Rx-ID: 1564455 View in Reaxys 122/162 Yield

Conditions & References With nickel dichloride in hexane, Time= 2h, T= 35 °C , other Al compounds, catalyst, solvents, further epoxides, Product distribution Boireau, G.; Abenhaim, D.; Henry-Basch, E.; Tetrahedron; vol. 36; (1980); p. 3061 - 3070 View in Reaxys

Rx-ID: 1564470 View in Reaxys 123/162 Yield 82 % Chromat.

Conditions & References With samarium diiodide, tert-butyl alcohol in tetrahydrofuran, Time= 24h, Ambient temperature, Title compound not separated from byproducts Girard, P.; Namy, J. L.; Kagan, H. B.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2693 - 2698 View in Reaxys

O– K+

Rx-ID: 1710103 View in Reaxys 124/162 Yield 12 % Chromat., 29 % Chromat.

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O– K+

Rx-ID: 1710685 View in Reaxys 125/162 Yield 78 % Chromat., 6 % Chromat.

O– K+

Rx-ID: 1769111 View in Reaxys 126/162 Yield 7 % Chromat., 41 % Chromat.

O– K+

Rx-ID: 1793324 View in Reaxys 127/162 Yield 65 % Chromat., 4 % Chromat.

65 % Chromat., 4 % Chromat.

Conditions & References With ammonia, T= -33 °C Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys With ammonia, T= -33 °C , various aryl halides; reactions of acetone enolate ion with halobenzenes, leaving group effect, Product distribution Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

Br OH

+Mg

Cl –

Rx-ID: 1904128 View in Reaxys 128/162 Yield

Conditions & References in tetrahydrofuran, Time= 4h, T= -40 - 20 °C , Yield given. Yields of byproduct given Bourgain-Commercon, Monique; Normant, Jean F.; Bulletin de la Societe Chimique de France; vol. 2; nb. 5-6; (1980); p. 289 - 294 View in Reaxys

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O– K+

Rx-ID: 2017552 View in Reaxys 129/162 Yield

Conditions & References

30 % Chromat., 17 % Chromat.

With ammonia, T= -33 °C Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

O– K+

Rx-ID: 2063722 View in Reaxys 130/162 Yield

Conditions & References

21 % Chromat., 25 % Chromat.

With ammonia in tetrahydrofuran, T= -33 °C Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys With ammonia, T= -33 °C Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

O– K+

N+

I–

Rx-ID: 2303947 View in Reaxys 131/162 Yield

Conditions & References

54 % Chromat., 12 % Chromat.

With ammonia, T= -33 °C Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

Rx-ID: 2694719 View in Reaxys 132/162 Yield

Conditions & References

25 % Chro- Irradiation mat., 14 % Chromat., 5 Appleton, David C.; Brocklehurst, Brian; Kenna, James Mc; Kenna, Jean M. Mc; Thackeray, Stephen; Walley, Andrew % Chromat. R.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 87 - 90 View in Reaxys

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O– K+

Rx-ID: 3377385 View in Reaxys 133/162 Yield

Conditions & References

20 % Chromat., 18 % Chromat.

With ammonia, T= -33 °C Bard, Raymond R.; Bunnett, J. F.; Creary, Xavier; Tremelling, Michael, J.; Journal of the American Chemical Society; vol. 102; nb. 8; (1980); p. 2852 - 2854 View in Reaxys

Na +

Al–

Rx-ID: 3756792 View in Reaxys 134/162 Yield

Conditions & References

82 %

With nickel dichloride in pentane, Time= 2h, T= 35 °C Boireau, G.; Abenhaim, D.; Henry-Basch, E.; Tetrahedron; vol. 36; (1980); p. 3061 - 3070 View in Reaxys

OH O

O Sn

H H HO

Rx-ID: 26388811 View in Reaxys 135/162 Yield

Conditions & References With di-tert-butyl peroxide in neat (no solvent), addn. of peroxide to equimolar mixt. of (CH2CHCH2)4Sn and PhCHOCH2, 24h, 130°C, acidolysis by addn. of malonic acid in ether, reflux, 48h, ether removed, pptn. of malonate by addn. of pentane, under Ar; alcohol detected by chromy., total yield: 34percent Daude, Gerard; Pereyre, Michel; Journal of Organometallic Chemistry; vol. 190; nb. 1; (1980); p. 43 - 52 ; (from Gmelin) View in Reaxys

OH O

O Sn

H HO HO

Rx-ID: 26482839 View in Reaxys 136/162 Yield 2 %, 2 %

Conditions & References With di-tert-butyl peroxide in neat (no solvent), addn. of peroxide to equimolar mixt. of (CH2CHCH2)4Sn and PhCHOCH2, 24h, 130°C, acidolysis by addn. of malonic acid in ether, reflux, 48h, ether removed, pptn. of malonate by addn. of pentane, under Ar; alcohol detected by chromy., total yield: 30percent Daude, Gerard; Pereyre, Michel; Journal of Organometallic Chemistry; vol. 190; nb. 1; (1980); p. 43 - 52 ; (from Gmelin)

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View in Reaxys

Rx-ID: 25260662 View in Reaxys 137/162 Yield

Conditions & References 8 : EXAMPLE 8 EXAMPLE 8 Into a 3 ounce glass pressure bottle are placed 49 milligrams of [Rh(1,5-cyclooctadiene) (o-anisylcyclohexylmethylphosphine)2 ]BF4 (phosphine optical purity ~95percent), 10.2 grams phenylacetone and 10 ml iso-butyric acid. The bottle is flushed by filling 4 times for at least 30 seconds with at least 30 psig hydrogen, followed by venting the gas and a final filling with hydrogen to 70 psig. The bottle is warmed to 80°C and stirred for 24 hours. The reaction mass is dissolved in 50 ml chloroform, washed three times with 50 ml 5percent aqueous sodium hydroxide solution, once with 20 ml water and then dried over anhydrous magnesium sulfate. Distillation affords a mixture of 1-phenyl-2-propanol and phenylacetone. The 1-phenyl-2-propanol has [τ]D 25 = -5.31°, optical purity = 19.9percent. With hydrogen in chloroform Patent; Monsanto Company; US3968147; (1976); (A) English View in Reaxys

(+) -2,3-O-isopropylidene-1,4-bis-(diphenylphosphino)-butane O

[Rh(norbornadiene)Cl]

Rx-ID: 25260663 View in Reaxys 138/162 Yield

Conditions & References 13 : EXAMPLE 13 EXAMPLE 13 To a 3 oz. glass pressure reactor are charged 10.0 milliliters of phenylacetone, 88 milligrams of [Rh(norbornadiene)Cl] 2, 190 milligrams of (+) -2,3-O-isopropylidene-1,4-bis-(diphenylphosphino)-butane and 10 milliliters of isobutyric acid. The contents are sparged with nitrogen for 20 minutes and the bottle is flushed by filling with hydrogen 5 times at 135 psig for 2 minutes. Finally, the bottle is filled with 135 psig hydrogen and heated to 70°C while the contents are stirred for 18 hours. The reaction mass is distilled to afford a mixture of phenylacetone and 1-phenyl-2-propanol which has [τ]D RT = - 0.703° (neat); optical purity = 2.5percent. With hydrogen Patent; Monsanto Company; US3968147; (1976); (A) English View in Reaxys

HO O

Rx-ID: 802782 View in Reaxys 139/162 Yield

Conditions & References With aluminium trichloride, benzene Lichterow; Etlis; Zhurnal Obshchei Khimii; vol. 27; (1957); p. 2867; engl. Ausg. S. 2903

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View in Reaxys With diethyl ether, phenyllithium Cristol et al.; Journal of the American Chemical Society; vol. 73; (1951); p. 816 View in Reaxys

Rx-ID: 5487462 View in Reaxys 140/162 Yield

Conditions & References Lichterow; Etlis; Zhurnal Obshchei Khimii; vol. 27; (1957); p. 2867; engl. Ausg. S. 2903 View in Reaxys Smith; Natelson; Journal of the American Chemical Society; vol. 53; (1931); p. 3476,3479 View in Reaxys

HO Mg Cl

Rx-ID: 818409 View in Reaxys 141/162 Yield

Conditions & References With diethyl ether, acetaldehyde Siegel et al.; Journal of the American Chemical Society; vol. 73; (1951); p. 3237,3238 View in Reaxys With diethyl ether, paracetaldehyde Malinowskii; Eremizkaja; Zhurnal Obshchei Khimii; vol. 25; (1955); p. 293,294; engl. Ausg. S. 277, 278 View in Reaxys

HO Mg

O Cl

Rx-ID: 637244 View in Reaxys 142/162 Yield

Conditions & References With diethyl ether Siegel et al.; Journal of the American Chemical Society; vol. 73; (1951); p. 3237,3238 View in Reaxys

HO O

Br–

+Mg

Rx-ID: 802553 View in Reaxys 143/162 Yield

Conditions & References With diethyl ether Huston; Bostwick; Journal of Organic Chemistry; vol. 13; (1948); p. 334 View in Reaxys Newman; Journal of the American Chemical Society; vol. 62; (1940); p. 2295,2298

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View in Reaxys

I I

Rx-ID: 93944 View in Reaxys 144/162 Yield

Conditions & References With diethyl ether, benzene Golumbic; Cottle; Journal of the American Chemical Society; vol. 61; (1939); p. 996,999 View in Reaxys

I HO

Rx-ID: 94442 View in Reaxys 145/162 Yield

Conditions & References With diethyl ether, benzene Golumbic; Cottle; Journal of the American Chemical Society; vol. 61; (1939); p. 996,999 View in Reaxys

HO O

Rx-ID: 802640 View in Reaxys 146/162 Yield

Conditions & References With aluminium trichloride Calcott; Tinker; Weinmayr; Journal of the American Chemical Society; vol. 61; (1939); p. 1010,1014 View in Reaxys Smith; Natelson; Journal of the American Chemical Society; vol. 53; (1931); p. 3476,3479 View in Reaxys

etheric (+-)-1-methyl-2-phenyl-ethyl magnesium chloride

Rx-ID: 8094924 View in Reaxys 147/162 Yield

Conditions & References With oxygen, anschliessendes Behandeln mit Wasser Truffault; Bulletin de la Societe Chimique de France; vol. <5> 6; (1939); p. 726,733 View in Reaxys

Rx-ID: 22114620 View in Reaxys 148/162 Yield

Conditions & References Reaction Steps: 3 1: diethyl ether; iodine; mercury (II)-oxide / behandeln der Reaktionsloesung mit Kaliumhydroxid

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2: magnesium iodide; diethyl ether; benzene / 0 °C / anschliessende Behandlung mit wss. NH4Cl-Loesung 3: diethyl ether; benzene With diethyl ether, iodine, mercury(II) oxide, magnesium iodide, benzene Golumbic; Cottle; Journal of the American Chemical Society; vol. 61; (1939); p. 996,999 View in Reaxys

Rx-ID: 22114874 View in Reaxys 149/162 Yield

Conditions & References Reaction Steps: 2 1: magnesium iodide; diethyl ether; benzene / 0 °C / anschliessende Behandlung mit wss. NH4Cl-Loesung 2: diethyl ether; benzene With diethyl ether, magnesium iodide, benzene Golumbic; Cottle; Journal of the American Chemical Society; vol. 61; (1939); p. 996,999 View in Reaxys

sodium

Rx-ID: 5806230 View in Reaxys 150/162 Yield

Conditions & References unter Entfernung des entstehenden Acetons Verley; Bulletin de la Societe Chimique de France; vol. <4>37; (1925); p. 872,873 View in Reaxys

HO Mg

Rx-ID: 572991 View in Reaxys 151/162 Yield

Conditions & References Austerweil; Cochin; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 150; (1910); p. 1694 View in Reaxys With diethyl ether v. Auwers; Jordan; Biochemische Zeitschrift; vol. 144; (1924); p. 35,41 View in Reaxys

H 2N

Rx-ID: 317448 View in Reaxys 152/162 Yield

Conditions & References With sodium amalgam Emde; Runne; Archiv der Pharmazie (Weinheim, Germany); vol. 249; (1911); p. 379 View in Reaxys

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Cl –

sodium amalgam

N+

Rx-ID: 8261830 View in Reaxys 153/162 Yield

Conditions & References Emde; Runne; Archiv der Pharmazie (Weinheim, Germany); vol. 249; (1911); p. 379 View in Reaxys OH

Cl – H

N+

sodium amalgam

H O

Rx-ID: 8264618 View in Reaxys 154/162 Yield

Conditions & References Emde; Runne; Archiv der Pharmazie (Weinheim, Germany); vol. 249; (1911); p. 379 View in Reaxys Eberhard; Chem. Zentralbl.; vol. 81; nb. II; (1910); p. 1477 View in Reaxys

H 2N

Rx-ID: 41161 View in Reaxys 155/162 Yield

Conditions & References With sodium amalgam Emde; Chem. Zentralbl.; vol. 81; nb. II; (1910); p. 1477 View in Reaxys

Rx-ID: 573168 View in Reaxys 156/162 Yield

Conditions & References v. Braun; Chemische Berichte; vol. 43; (1910); p. 1351 View in Reaxys

styrene oxide

Rx-ID: 7019864 View in Reaxys 157/162

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Yield

Conditions & References With methylmagnesium bromide Tiffeneau; Fourneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 146; (1908); p. 699 View in Reaxys

Br–

+Mg

phenylethylene oxide

Rx-ID: 7980159 View in Reaxys 158/162 Yield

Conditions & References Tiffeneau; Fourneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 146; (1908); p. 699 View in Reaxys O

Cl –

Mg+

Rx-ID: 804717 View in Reaxys 159/162 Yield

Conditions & References Tiffeneau; Delange; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 137; (1903); p. 574 View in Reaxys O

HO Mg O

Rx-ID: 804784 View in Reaxys 160/162 Yield

Conditions & References Tiffeneau; Delange; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 137; (1903); p. 575 View in Reaxys

K+

–O

S O

N N

Rx-ID: 193608 View in Reaxys 161/162 Yield

Conditions & References Paal; Lowitsch; Chemische Berichte; vol. 30; (1897); p. 879 View in Reaxys

sodium amalgam

Rx-ID: 5806229 View in Reaxys 162/162 Yield

Conditions & References Errera; Gazzetta Chimica Italiana; vol. 16; (1886); p. 322 View in Reaxys

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