Phenylacetic acid (2-phenylacetic acid, PAA) [CAS 103-82-2; InChIKey WLJVXDMOQOGPHL-UHFFFAOYS by Asch

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2016-04-10 14h:10m:17s (EST)

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HO C

Rx-ID: 2694880 View in Reaxys 1/834 Yield 95 %

Conditions & References With sodium hydroxide, NaCo(CO)4, Kastel A101 in methanol, Time= 3h, T= 55 °C Foa, M.; Francalanci, F.; Gardano, A.; Cainelli, G.; Umani-Ronchi, A.; Journal of Organometallic Chemistry; vol. 248; nb. 2; (1983); p. 225 - 232 View in Reaxys

90.4 %

Stage 1: With Co(MBTC)2(DMF)2, tetrabutylammomium bromide, sodium hydroxide in water, toluene, Time= 2h, T= 20 °C , p= 750.075Torr , Autoclave Stage 2: in water, toluene, Time= 18h, T= 80 °C , p= 750.075Torr , Autoclave Zhang, Bin; Li, Jianli; Chen, Wei; Wang, Yunxia; Shi, Zhen; Chinese Journal of Chemistry; vol. 28; nb. 1; (2010); p. 111 - 114 View in Reaxys

89 %

With sodium hydroxide, cerium(III) chloride, N-hexadecyl-N,N,N-trimethylammonium bromide, nickel cyanide in toluene, Time= 4.5h, T= 85 - 95 °C , p= 760Torr Amer, Ibrahim; Alper, Howard; Journal of the American Chemical Society; vol. 111; nb. 3; (1989); p. 927 - 930 View in Reaxys

87 %

With sodium hydroxide, NaCo(CO)4, Amberlyst A26 in methanol, Time= 6h, T= 55 °C , var. supports, bases, temp. times; other organic halides, Product distribution Foa, M.; Francalanci, F.; Gardano, A.; Cainelli, G.; Umani-Ronchi, A.; Journal of Organometallic Chemistry; vol. 248; nb. 2; (1983); p. 225 - 232 View in Reaxys

84 %

4.4 Synthesis of 2a–u General procedure: A 100 mL reactor equipped with Teflon-coated magnetic stir bars was charged with n-Butyl alcohol (20 mL) and the catalyst (0.5 mmol). The reactor was then taken out of the glove box and pressured with carbon monoxide (1 atm). The mixture was stirred 2 h at 60 °C, cooled to ambient temperature and slowly vented. After benzyl chloride (10 mmol), NaOH (15 mL, 15percent), and TBAI (0.25 mmol) were added, the reactor was sealed and the reaction mixtures were stirred for 22 h at 60 °C under carbon monoxide (1 atm). After the reaction, the water phase was detached and washing the organic phase three times with H2O (3×5 mL), the combined water layer was washed with Et2O, then the resulting solution was cooled to 0 °C and adjusted to pH=1–2 with HCl (6 mol/L). The product was filtered, dried in RT, and then recrystallized. Stage 1: With C28H22CoN4O6 in butan-1-ol, Time= 2h, T= 60 °C , p= 760.051Torr , Glovebox, High pressure, Green chemistry Stage 2: With tetra-(n-butyl)ammonium iodide, sodium hydroxide in butan-1-ol, Time= 22h, T= 60 °C , p= 760.051Torr , Glovebox, High pressure, Green chemistry, Reagent/catalyst, Solvent, Temperature, regioselective reaction She, Meng-Yao; Xiao, Da-Wei; Yin, Bing; Yang, Zheng; Liu, Ping; Li, Jian-Li; Shi, Zhen; Tetrahedron; vol. 69; nb. 35; (2013); p. 7264 - 7268 View in Reaxys

80 %

With [RhCl(η2:η2-cycloocta-1,5-diene)]2, potassium iodide in formic acid, Time= 18h, T= 85 °C , p= 760Torr , Carbonylation Giroux; Nadeau; Han; Tetrahedron Letters; vol. 41; nb. 40; (2000); p. 7601 - 7604 View in Reaxys

70 %

With sodium hydroxide, sodium tetrahydroborate in tetrahydrofuran, Time= 3h, T= 55 °C Satyanarayana, N.; Periasamy, M.; Tetrahedron Letters; vol. 28; nb. 23; (1987); p. 2633 - 2636 View in Reaxys

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15 %

With N-benzyl-N,N,N-triethylammonium chloride, pentacarbonyliron(0) in sodium hydroxide, Time= 48h, p= 760Torr , Ambient temperature, other temperature, other reaction times, Product distribution Tustin, Gerald C.; Hembre, Robert T.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1761 - 1764 View in Reaxys

12 %

With N-benzyl-N,N,N-triethylammonium chloride, Fe2(CO)9 in sodium hydroxide, Time= 72h, p= 760Torr , Ambient temperature, or Fe3(CO)12, Product distribution Tustin, Gerald C.; Hembre, Robert T.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1761 - 1764 View in Reaxys With sodium hydroxide, PdCl2lt;PPh(m-C6H4SO3Na)gt;2, 1-heptanesulfonic acid,sodium salt in n-heptane, water, Time= 6h, T= 30 °C , other reagent, other solvent, var. time, Product distribution Okano, Tamon; Hayashi, Tetsuji; Kiji, Jitsuo; Bulletin of the Chemical Society of Japan; vol. 67; nb. 8; (1994); p. 2339 - 2341 View in Reaxys With sodium hydroxide, water, PdCl2(dpm)2 in n-heptane, T= 56 °C , p= 760Torr , various solvents, catalysts, stirring speed; also in the presence of surfactant or phase transfer agent, Rate constant Lapidus; Petrovskii; Beletskaya; Russian Journal of Organic Chemistry; vol. 33; nb. 8; (1997); p. 1083 - 1092 View in Reaxys With sodium hydroxide, PdCl2lt;PPh(m-C6H4SO3Na)gt;2, 1-heptanesulfonic acid,sodium salt in n-heptane, water, Time= 6h, T= 30 °C Okano, Tamon; Hayashi, Tetsuji; Kiji, Jitsuo; Bulletin of the Chemical Society of Japan; vol. 67; nb. 8; (1994); p. 2339 - 2341 View in Reaxys

96.6 With water, palladium diacetate, Time= 2h, T= 110 °C , p= 37503.8Torr , Ionic liquid %Chromat. Lapidus, Albert L.; Eliseev, Oleg L.; Bondarenko, Tatyana N.; Chau, Nguen H.; Kazantsev, Ruslan V.; Mendeleev Communications; vol. 19; nb. 5; (2009); p. 256 - 257 View in Reaxys

Rx-ID: 4614628 View in Reaxys 2/834 Yield 94 %

Conditions & References 4 : Preparation of Phenylacetic Acid from Toluene and Isopropanol Toluene (1.38 g), isopropanol (60 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol percent) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 75 mg isopropyl phenylacetate was obtained by column chromatography, in a yield of 84percent. 1HNMR (400 MHz, CDCl3) δ 1.21 (s, 3H), 1.23 (s, 3H), 3.58 (s, 2H), 4.96-5.06 (m, 1H), 7.23-7.34 (m, 5H); 13CNMR (100 MHz, CDCl3) δ 21.8, 41.7, 68.2, 126.9, 128.5, 129.2, 134.4, 171.1; HRMS (ESI) calcd. for C11H14NaO2 [M+Na]: 201.0886. found: 201.0886. The isopropyl phenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 54 mg product phenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 94percent. With water, sodium hydroxide in 1,4-dioxane, Time= 2h, T= 60 °C , pH= 10 - 14 Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); (A1) English View in Reaxys

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84 %

With trimethyltin hydroxide in toluene, Time= 6h, T= 100 °C Furlan, Ricardo L. E.; Mata, Ernesto G.; Mascaretti, Oreste A.; Tetrahedron Letters; vol. 37; nb. 30; (1996); p. 5229 - 5232 View in Reaxys

HO O

Rx-ID: 10033679 View in Reaxys 3/834 Yield

Conditions & References

96 %

7 : Preparation of Phenylacetic Acid from Toluene and Tert-Butanol Toluene (1.38 g), tert-butanol (74 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol percent) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 53 mg tert-butyl phenylacetate was obtained by column chromatography, in a yield of 58percent. 1HNMR (400 MHz, CDCl3) δ 1.43 (s, 9H), 3.51 (s, 2H), 7.21-7.31 (m, 5H); 13CNMR (100 MHz, CDCl3) δ 28.1, 42.7, 80.8, 126.9, 128.6, 129.2, 134.8, 170.9; HRMS (ESI) calcd. for C12H16NaO2 [M+Na]: 215.1043. found: 215.1045. The tert-butyl phenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 36 mg product phenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 96percent. With water, sodium hydroxide in 1,4-dioxane, Time= 2h, T= 60 °C , pH= 10 - 14 Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); (A1) English View in Reaxys

80 %

With toluene-4-sulfonic acid, Time= 0.0666667h, microwave irradiation Lee, Jong Chan; Yoo, Eun Sang; Lee, Jin Seo; Synthetic Communications; vol. 34; nb. 16; (2004); p. 3017 - 3020 View in Reaxys

HO O

Rx-ID: 36643241 View in Reaxys 4/834 Yield 94 %

Conditions & References 3 : Preparation of Phenylacetic Acid from Toluene and n-Propanol Toluene (1.38 g), n-propanol (60 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol percent) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 78 mg n-propyl phenylacetate was obtained by column chromatography, in a yield of 88percent. 1HNMR (400 MHz, CDCl3) δ 0.88 (t, J=7.6 Hz, 3H), 1.59-1.67 (m, 2H), 3.61 (s, 2H), 4.12 (t, J=6.8 Hz, 2H), 7.23-7.33 (m, 5H); 13CNMR (100 MHz, CDCl3) δ 10.3, 21.9, 41.5, 66.4, 127.0, 129.3, 134.3, 171.7; HRMS (ESI) calcd. for C11H14NaO2 [M+Na]: 201.0886. found: 201.0886. The n-propyl phenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 56 mg product phenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 94percent. With water, sodium hydroxide in 1,4-dioxane, Time= 2h, T= 60 °C , pH= 10 - 14 Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); (A1) English View in Reaxys

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HO O

Rx-ID: 36643243 View in Reaxys 5/834 Yield

Conditions & References

94 %

5 : Preparation of Phenylacetic Acid from Toluene and n-Butanol Toluene (1.38 g), n-butanol (74 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol percent) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 65 mg n-butyl phenylacetate was obtained by column chromatography, in a yield of 68percent. 1HNMR (400 MHz, CDCl3) δ 0.88 (t, J=7.6 Hz, 3H), 1.29-1.38 (m, 2H), 1.55-1.62 (m, 2H), 3.60 (s, 2H), 4.06 (t, J=6.8 Hz, 2H), 7.23-7.33 (m, 5H); 13CNMR (100 MHz, CDCl3) δ 13.7, 19.1, 30.6, 41.5, 64.7, 127.0, 128.5, 129.3, 134.3, 171.7; HRMS (ESI) calcd. for C12H16NaO2 [M+Na]: 215.1043. found: 215.1042. The n-butyl phenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 43 mg product phenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 94percent. With water, sodium hydroxide in 1,4-dioxane, Time= 2h, T= 60 °C , pH= 10 - 14 Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); (A1) English View in Reaxys

Rx-ID: 36643244 View in Reaxys 6/834 Yield

Conditions & References

93 %

6 : Preparation of Phenylacetic Acid from Toluene and Isobutanol Toluene (1.38 g), isobutanol (74 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol percent) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 69 mg isobutyl phenylacetate was obtained by column chromatography, in a yield of 72percent. 1HNMR (400 MHz, CDCl3) δ 0.88 (s, 3H), 0.89 (s, 3H), 1.85-1.96 (m, 1H), 3.62 (s, 2H), 3.86 (d, J=6.8 Hz, 1H), 7.23-7.34 (m, 5H); 13CNMR (100 MHz, CDCl3) δ 19.0, 27.7, 41.5, 70.9, 127.0, 128.5, 129.3, 134.3, 171.6; HRMS (ESI) calcd. for C12H16NaO2 [M+Na]: 215.1043. found: 215.1037. The isobutyl phenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 53 mg product phenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 93percent. With water, sodium hydroxide in 1,4-dioxane, Time= 2h, T= 60 °C , pH= 10 - 14 Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); (A1) English View in Reaxys

O O

Rx-ID: 40460121 View in Reaxys 7/834 Yield 94 %

Conditions & References Hydrolysis of coupling product 2a providing 3 A solution of 2a (204 mg, 0.99 mmol) in 5 mL of 1 M hydrochloric acid was stirred at rt for 12 h. After addition of water (10 mL) and Et2O (10 mL), the ethereal solution was separated and theresulting aqueous solution was extrac-

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ted with Et2O (10 mL). The combined ethereal solutionwas washed with water (20 mL2) and then dried over MgSO4. Evaporation of the solvent gave 126 mg (0.93 mmol, 94percent) of phenylacetic acid 3. With hydrogenchloride in water, Time= 12h, T= 20 °C Senboku, Hisanori; Nagakura, Kotaro; Fukuhara, Tsuyoshi; Hara, Shoji; Tetrahedron; vol. 71; nb. 23; (2015); p. 3850 - 3856 View in Reaxys O HO

HO O

Rx-ID: 309576 View in Reaxys 8/834 Yield 96 %

Conditions & References With copper(I) oxide in acetonitrile, Time= 1h, T= 65 °C Toussaint, Olivier; Capdevielle, Patrice; Maumy, Michel; Synthesis; nb. 12; (1986); p. 1029 - 1031 View in Reaxys

> 95 %

Activity measurement of purified enzyme General procedure: PurifiedAMDase protein (100 μL) was added to the reactionsolution of 1 M Tris-HCl (pH 7.0, 100 μL) and 25 mMsubstrate solution (1a-d, 800 μL) and incubated at37 °C. The reaction was quenched by the addition ofan equal volume of 2 M HCl, and then, the solutionwas analyzed with reverse-phase high-performance liquidchromatography (HPLC) using a Cosmosil 5C18-AR-II analytical column (Nacalai Tesque). Initial reactionrates were plotted against 1a concentrations of0.25–20 mM, and the kinetic parameters, kcat and Km,were determined by Lineweaver-Burk plot analysis. With tris(hydroxymethyl)methylamine hydrochloride in water, Time= 24h, T= 37 °C , pH= 7.0, Enzymatic reaction, Reagent/catalyst Yoshida, Shosuke; Enoki, Junichi; Kourist, Robert; Miyamoto, Kenji; Bioscience, Biotechnology and Biochemistry; vol. 79; nb. 12; (2015); p. 1965 - 1971 View in Reaxys

90 %

in water, Time= 0.25h, microwave irradiation, Decarboxylation Zara, Cynthia Lynn; Jin, Thomas; Giguere, Raymond J.; Synthetic Communications; vol. 30; nb. 12; (2000); p. 2099 - 2104 View in Reaxys beim Schmelzen Wislicenus,W.; Chemische Berichte; vol. 27; (1894); p. 1094 View in Reaxys With bis(tricyclohexylphosphane)copper(I) hydrogenphenylmalonate in tetrahydrofuran, T= 55 °C , also in the presence of various additives, various temp., time, Rate constant Brunner; Mueller; Spitzer; Monatshefte fur Chemie; vol. 127; nb. 8-9; (1996); p. 845 - 858 View in Reaxys With AMDase, buffer solution, T= 15 - 35 °C , ΔS(excit.), ΔH(excit.), ΔG(excit.), Kinetics Kawasaki, Takayasu; Horimai, Emiko; Ohta, Hiromichi; Bulletin of the Chemical Society of Japan; vol. 69; nb. 12; (1996); p. 3591 - 3594 View in Reaxys With AMDase, buffer solution, T= 15 °C , Rate constant Kawasaki, Takayasu; Horimai, Emiko; Ohta, Hiromichi; Bulletin of the Chemical Society of Japan; vol. 69; nb. 12; (1996); p. 3591 - 3594 View in Reaxys With AMDase, buffer solution, T= 25 °C , Rate constant

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Kawasaki, Takayasu; Horimai, Emiko; Ohta, Hiromichi; Bulletin of the Chemical Society of Japan; vol. 69; nb. 12; (1996); p. 3591 - 3594 View in Reaxys With AMDase, buffer solution, T= 35 °C , Rate constant Kawasaki, Takayasu; Horimai, Emiko; Ohta, Hiromichi; Bulletin of the Chemical Society of Japan; vol. 69; nb. 12; (1996); p. 3591 - 3594 View in Reaxys With arylmalonate decarboxylase, trifluoromethyl phosphonic acid in water, Time= 0.0833333h, T= 35 °C , add. of Tris buffer: pH 8; determination of inhibition effect of the 3-fluorophenylmethanephosphoric acid, Mechanism Kawasaki, Takayasu; Saito, Koji; Ohta, Hiromichi; Chemistry Letters; nb. 4; (1997); p. 351 - 352 View in Reaxys With Tris-HCl buffer, arylmalonate decarboxylase in water, T= 35 °C , pH= 8.5, Decarboxylation, Enzyme kinetics, Further Variations: Catalysts Miyazaki, Mamoru; Kakidani, Hitoshi; Hanzawa, Satoshi; Ohta, Hiromichi; Bulletin of the Chemical Society of Japan; vol. 70; nb. 11; (1997); p. 2765 - 2769 View in Reaxys T= 160 °C Shabanov; Seidov; Gasanova; Kakhramanova; Russian Journal of Organic Chemistry; vol. 45; nb. 1; (2009); p. 26 - 29 View in Reaxys With MQQASTPTIGMIVPPAAGLVPADGARLYPDLPFIASGLGLGSVTPEGYDAVIESVVDHARRLQKQGAAVVSLMGTSLSFYRGAAFNAALTVAMREATGLPCTTMSTAVLNGLRALGVRRVALATAYIDDVNERLAAFLAEESLVPTGCRSLGITGVEAMARVDTATLVDLCVRAFEAAPDSDGILLSCGGLLTLDAIPEVERRLGVPVVSSSPAGFWDAVRLAGGGAKARPGYGRLFDESLEHHHHHH, Time= 8h, T= 30 °C , pH= 8, aq. buffer, Enzymatic reaction, Kinetics, Reagent/catalyst, enantioselective reaction Okrasa, Krzysztof; Levy, Colin; Hauer, Bernhard; Baudendistel, Nina; Leys, David; Micklefield, Jason; Chemistry - A European Journal; vol. 14; nb. 22; (2008); p. 6609 - 6613 View in Reaxys With recombinant Bordetella bronchiseptica arylmalonate decarboxylase mutant M159V from E. coli BL21 (DE3), Time= 24h, T= 30 °C , pH= 8, aq. buffer, Enzymatic reaction, Kinetics, Mechanism, Reagent/catalyst, Time Okrasa, Krzysztof; Wilding, Matthew; Goodall, Mark; Micklefield, Jason; Levy, Colin; Leys, David; Baudendistel, Nina; Hauer, Bernhard; Angewandte Chemie, International Edition; vol. 48; nb. 41; (2009); p. 7691 - 7694 View in Reaxys With glutamate racemase from Aquifex pyrofilus in water, pH= 7.2, MOPS buffer, Enzymatic reaction, Kinetics, Reagent/catalyst Wong, Lu Shin; Okrasa, Krzysztof; MicKlefield, Jason; Organic and Biomolecular Chemistry; vol. 8; nb. 4; (2010); p. 782 - 787 View in Reaxys With arylmalonate decarboxylase (wild-type) in Tris-HCl buffer, pH= 8.5 - 8.6 Obata, Rika; Nakasako, Masayoshi; Biochemistry; vol. 49; nb. 9; (2010); p. 1963 - 1969 View in Reaxys Heating Malki, Fatiha; Touati, Abdelkader; Rahal, Said; Moulay, Saad; Asian Journal of Chemistry; vol. 23; nb. 3; (2011); p. 961 - 967 View in Reaxys

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HO O

Rx-ID: 605545 View in Reaxys 9/834 Yield 92.5%

Conditions & References 3 : Carbonylation of Benzyl Chloride EXAMPLE 3 Carbonylation of Benzyl Chloride 2.53 g (20 mmol) of benzyl chloride and 45 mg (0.2 mmol) of Pd(OAc)2 are dissolved in 30 ml of toluene and admixed with 8 ml of an aqueous solution of BINAS (100 mmol/kg of solution). A further 30 ml of water are subsequently added. The two-phase mixture is stirred for a period of 20 hours in a 200 ml Hastelloy autoclave at a temperature of 70° C. and a CO pressure of 20 bar. At the end of the reaction time, the autoclave is cooled, vented and the reaction mixture is placed in a separating funnel. The supernatant organic phase is separated off and evaporated to dryness. This gives 2.52 g of phenylacetic acid as a white powder (92.5percent of theory). Elemental Analysis: Calc.: C 70.58, H 5.92, O 23.50. Found: C 70.30, H 5.80, O 23.90 (1st determination). Found: C 70.60, H 6.00, O 23.40 (2nd determination). With palladium diacetate in CO, water, toluene Patent; Hoechst Aktiengesellschaft; US5631393; (1997); (A1) English View in Reaxys

89.9%

4 : Recycling of the Catalyst EXAMPLE 4 Recycling of the Catalyst The aqueous catalyst solution separated off in Example 1 is adjusted to a pH of 7 prior to the commencement of the reaction and is stirred together with 2.53 g (20 mmol) of benzyl chloride, dissolved in 30 ml of toluene, in a 200 ml Hastelloy autoclave for 20 hours at 70° C. under a CO pressure of 20 bar. At the end of the reaction, the organic phase is separated off and evaporated to dryness on a rotary evaporator. This gives 2.45 g of phenylacetic acid as a white powder (89.9percent of theory). in toluene Patent; Hoechst Aktiengesellschaft; US5631393; (1997); (A1) English View in Reaxys

87%

Example 1 Preparation of Phenylacetic Acid Example 1 11.6 g of a solution of 50percent by weight of water [321 mmol] in N-methylpyrrolidone are added over a period of 1 hour to a solution of 36.9 g of benzyl chloride [291.5 mmol] and 26 mg of palladium chloride [0.145 mmol] in 76 g of N-methylpyrrolidone at a pressure of 30 bar of carbon monoxide with a temperature of 150° C. in a 300 ml HC4 autoclave. The pressure is kept constant during the addition at 30 bar. After approximately 10 hours of post-stirring, the carbon monoxide uptake is ended. After cooling, a GC yield of 87percent phenylacetic acid is obtained. With carbon monoxide, palladium(II) chloride in 1-methyl-pyrrolidin-2-one, water Patent; Clariant GmbH; US2002/62041; (2002); (A1) English View in Reaxys

84.7%

1 : EXAMPLE 1 EXAMPLE 1 Into a 250-cc flask, equipped with a stirrer, a thermometer, a water-cooler and a dropping funnel, there were introduced, under a CO head: Keeping a temperature of 55°-56° C, 16.5 g of benzyl chloride were dropped thereinto in 1 hour.

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The reaction mixture was stirred for further 2 hours, until conclusion of the CO absorption. The raw reaction mixture was diluted with water an HCl and extracted with ethyl ether. A sample was esterified with diazomethane and subjected to gas-chromatographic analysis. Such analysis revealed that the phenylacetic acid yield was equal to 84.7percent calculated on the benzyl chloride introduced. Patent; Montedison S.p.A.; US4128572; (1978); (A1) English View in Reaxys 74.6%

3 : EXAMPLE 3 EXAMPLE 3 Into the apparatus described in example 1 and following the same modalities, there were introduced: Following the modalities of example 1, 16.5 g of benzyl chloride were introduced. It was then operated conforming to example 1, and the gas-chromatographic analysis revealed a phenylacetic acid yield of 74.6percent calculated on the fed benzyl chloride. Patent; Montedison S.p.A.; US4128572; (1978); (A1) English View in Reaxys

74%

4 : EXAMPLE 4 EXAMPLE 4 Into the apparatus described in example 1 and following the same modalities, there were introduced: Following the modalities of example 1, 16.5 g of benzyl chloride were introduced. It was then operated as in example 1, and the gas-chromatographic analysis revealed a phenylacetic acid yield of 74percent calculated on the fed benzyl chloride. Patent; Montedison S.p.A.; US4128572; (1978); (A1) English View in Reaxys effect of the concentration, solvent and current density to the yield Sock, Oumar; Troupel, Michel; Perichon, Jacques; Tetrahedron Letters; vol. 26; nb. 12; (1985); p. 1509 - 1512 View in Reaxys With sodium hydroxide, tetracarbonylcobaltate(1-) ion in methanol, Time= 4h, T= 55 °C , other benzyl chloride derivatives as educts, other reaction temps., Product distribution Rao, B. Nageswara; Adapa, Srinivas R.; Pardhasaradhi, M.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 27; nb. 1-12; (1988); p. 84 - 85 View in Reaxys With diethyl ether, magnesium, Einleiten von CO2 und Zerlegen des Produkts mit verd. Schwefelsaeure Houben; Kesselkaul; Chemische Berichte; vol. 35; (1902); p. 2521 View in Reaxys

O O

Rx-ID: 3843204 View in Reaxys 10/834 Yield 100 %

Conditions & References With bis(tri-n-butyltin)oxide in toluene, Time= 0.333333h, Irradiation, var. carboxylic ester, organotin oxide and hydroxide, solvent, time of temp. or microwave irrad., Product distribution Furlan, Ricardo L. E.; Mata, Ernesto G.; Mascaretti, Oreste A.; Tetrahedron Letters; vol. 37; nb. 30; (1996); p. 5229 - 5232 View in Reaxys

100 %

With bis(tri-n-butyltin)oxide in neat (no solvent), Time= 0.5h, T= 200 °C Furlan, Ricardo L. E.; Mata, Ernesto G.; Mascaretti, Oreste A.; Tetrahedron Letters; vol. 37; nb. 30; (1996); p. 5229 - 5232 View in Reaxys

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100 %

With aluminium trichloride, dodecyl-methyl-sulphide, Time= 2h, T= 0 - 20 °C Node, Manabu; Kajimoto, Tetsuya; Heteroatom Chemistry; vol. 18; nb. 5; (2007); p. 572 - 583 View in Reaxys

99 %

With Candida antarctica lipase, phosphate buffer in methanol, hexane, Time= 24h, T= 37 °C Barbayianni, Efrosini; Fotakopoulou, Irene; Schmidt, Marlen; Constantinou-Kokotou, Violetta; Bornscheuer, Uwe T.; Kokotos, George; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 8730 - 8733 View in Reaxys

99 %

With phosphate buffer, Bacillus subtilis esterase in methanol, hexane, Time= 24h, T= 37 °C Barbayianni, Efrosini; Fotakopoulou, Irene; Schmidt, Marlen; Constantinou-Kokotou, Violetta; Bornscheuer, Uwe T.; Kokotos, George; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 8730 - 8733 View in Reaxys

96 %

2-Phenylacetic acid (I-6) A solution of methyl 2-phenylacetate (10 g, 64 mmol) in methanol (60 mL) was treated with solution of sodium hydroxide (5.1 g, 127 mmol) in water (40 mL) at 70°C for 3 hrs. The resulting mixture was concentrated under vacuum to remove the methanol. The residue was diluted with water (40 mL) and washed with diethyl ether (40 mL). The separated water layer was acidified to pH 2 using a mixture of water and HC1 (1 : 1) and extracted with DCM (3 X 80 mL). Combined organic extracts were washed with brine, 80 mL, separated, dried over sodium sulfate and concentrated to give 2-phenylacetic acid (1-6) as a white solid (9 g, 96percent) used without further characterization. NMR (400 MHz, CDC13) δ 3.64 (2H, s), 7.27- 7.35 (5H, m), 1 1.5 (lH, bs). With methanol, sodium hydroxide in water, Time= 3h, T= 70 °C Patent; VIDA THERAPEUTICS, INC.; CAMERON, Dale R.; WO2014/153667; (2014); (A1) English View in Reaxys

95 %

With 2,2'-azo-bisisobutyronitrile, bis(tri-n-butyltin)oxide in benzene, Time= 13h, T= 80 °C Mata; Mascaretti; Tetrahedron Letters; vol. 29; nb. 52; (1988); p. 6893 - 6896 View in Reaxys

95 %

With potassium carbonate, thiophenol in 1-methyl-pyrrolidin-2-one, Time= 0.166667h, T= 190 °C , Substitution Sharma, Lalima; Nayak, Mrinal K.; Chakraborti, Asit K.; Tetrahedron; vol. 55; nb. 31; (1999); p. 9595 - 9600 View in Reaxys

95 %

1; 26-38; 43-50 : Preparation of Phenylacetic Acid from Toluene and Methanol Toluene (1.38 g), methanol (32 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol percent) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 67 mg methyl phenylacetate was obtained by column chromatography, in a yield of 89percent. 1HNMR (400 MHz, CDCl3) δ 3.60 (s, 2H), 3.65 (s, 3H), 7.22-7.32 (m, 5H); 13CNMR (100 MHz, CDCl3) δ 41.2, 52.0, 127.1, 128.6, 129.3, 134.1, 172.0; HRMS (ESI) calcd. for C9H10NaO2 [M+Na]: 173.0568. found: 173.0573. The methyl phenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 58 mg product phenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 95percent. With water, sodium hydroxide in 1,4-dioxane, Time= 2h, T= 60 °C , pH= 10 - 14 Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); (A1) English View in Reaxys

92 %

With sodium hydroxide, Time= 2h, Heating Myrboh, B.; Ila, H.; Junjappa, H.; Synthesis; nb. 2; (1981); p. 126 - 127 View in Reaxys

92 %

With water, InI3, silica gel, Time= 0.416667h, Irradiation, Hydrolysis

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Ranu; Dutta; Sarkar; Synthetic Communications; vol. 30; nb. 22; (2000); p. 4167 - 4171 View in Reaxys 90 %

Stage 1: With Corey's ylide, Time= 0.333333h, T= 0 °C , Inert atmosphere Stage 2: With hydrogenchloride, water in ethyl acetate, pH= 2 Leggio, Antonella; De Marco, Rosaria; Perri, Francesca; Spinella, Mariagiovanna; Liguori, Angelo; European Journal of Organic Chemistry; nb. 1; (2012); p. 114 - 118 View in Reaxys

87 %

With potassium hydroxide in methanol, Time= 0.333333h, T= 35 °C Khurana, Jitender M.; Chauhan, Sushma; Bansal, Geeti; Monatshefte fur Chemie; vol. 135; nb. 1; (2004); p. 83 87 View in Reaxys

85 %

With potassium fluoride, thiophenol in various solvent(s), Time= 0.166667h, T= 190 °C Nayak, Mrinal K.; Chakraborti, Asit K.; Chemistry Letters; nb. 4; (1998); p. 297 - 298 View in Reaxys

85 %

With potassium fluoride, thiophenol in 1-methyl-pyrrolidin-2-one, Time= 0.166667h, Heating Chakraborti, Asit K.; Sharma, Lalima; Nayak, Mrinal K.; Journal of Organic Chemistry; vol. 67; nb. 8; (2002); p. 2541 - 2547 View in Reaxys

52 %

With potassium hydroxide in methanol, Time= 4h, Ambient temperature Prakash; Goyal; Moriatry; Khosrowshahi; Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry; vol. 29; nb. 4; (1990); p. 304 - 309 View in Reaxys

52 %

With water, Time= 36h Moriarty, Robert M.; Khosrowshahi, Jaffar S.; Prakash, Om; Tetrahedron Letters; vol. 26; nb. 25; (1985); p. 2961 - 2964 View in Reaxys

47 %

With hydrogenchloride, water in methanol, Time= 2h, Inert atmosphere, Reflux Tsubo, Tatsuyuki; Chen, Hsiu-Hui; Yokomori, Minako; Fukui, Kosuke; Kikuchi, Satoshi; Yamada, Tohru; Chemistry Letters; vol. 41; nb. 8; (2012); p. 780 - 782 View in Reaxys With sodium hydroxide in methanol, Time= 4h, Heating, Yield given Castaldi, Graziano; Belli, Aldo; Uggeri, Fulvio; Giordano, Claudio; Journal of Organic Chemistry; vol. 48; nb. 24; (1983); p. 4658 - 4661 View in Reaxys With water, hydroxide, Yield given Giordano, Claudio; Castaldi, Graziano; Casagrande, Francesco; Abis, Luigi; Tetrahedron Letters; vol. 23; nb. 13; (1982); p. 1385 - 1386 View in Reaxys With selenium, sodium tetrahydroborate, 1.) DMF, 80-90 deg C, 4 h, 2.) acidification, Yield given. Multistep reaction Kong, Fangming; Chen, Jian; Zhou, Xunjun; Synthetic Communications; vol. 18; nb. 8; (1988); p. 801 - 804 View in Reaxys With sodium hydroxide in methanol, Time= 4h, Ambient temperature, Yield given Giordano, Claudio; Castaldi, Graziano; Casagrande, Francesco; Belli, Aldo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 11; (1982); p. 2575 - 2582 View in Reaxys

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16.1 :Step 1: Methyl phenylacetate (5.03 g, 33.5 mmol) was treated with 1N aqueous NaOH (22 mL, 22 mmol) in THF (40 mL) and MeOH (4 mL), and stirred overnight at room temperature. Additional 1N aqueous NaOH (22 mL, 22 mmol) was added, and the reaction was stirred for 6 hours at room temperature. The mixture was acidified with 1N aqueous HCl to pH 3-4 and extracted with EtOAc three times. The combined organic layers were dried and concentrated to give phenyl-acetic acid. Stage 1: With water, sodium hydroxide in tetrahydrofuran, methanol, Time= 6h, T= 20 °C Stage 2: With hydrogenchloride in tetrahydrofuran, methanol, water, pH= 3 - 4 Patent; AMIRA PHARMACEUTICALS, INC.; US2010/81673; (2010); (A1) English View in Reaxys 3.8. Hydrolysis of Methyl Phenylacetate Enzyme activity was determined by using methyl phenylacetate; 200 mg of the immobilized preparations were added to 0.6 mL of 5 mM substrate in 50 mM buffer containing 50percent CH3CN.The buffer was sodium acetate at pH 5, sodium phosphate at pH 7 and sodium carbonate at pH 8.5. All experiments were carried out at 25 °C under continuous stirring. The conversion degree was analyzed by RP-HPLC (Spectra Physics SP 100 coupled with a Spectra Physics SP 8450 UV detector) using a Kromasil C18 (15 cm × 0.46 cm) column. Samples (20 μL) were injected and eluted at a flowrate of 1.0 mL/min using acetonitrile, 10 mM ammonium acetate aqueous solution (35:65, v/v) and pH 2.8, as mobile phase and UV detection was performed at 230 nm. Phenylacetic acid has a retention volume of 4.2 mL while the ester has a retention volume of 12.5 mL. One unit of enzyme activity was defined as the amount of enzyme necessary to produce 1 nmol of phenylacetic acid per minute under theconditions described above. Activity was determined by triplicate with a maximum conversionof 20percent–30percent, and data are given as average values. With Rhizomucor miehei lipase immobilized in anion-exchange resin Lipozyme® in acetonitrile, T= 25 °C , pH= 8.5, Enzymatic reaction, Reagent/catalyst, pH-value, Solvent Garcia-Galan, Cristina; Barbosa, Oveimar; Hernandez, Karel; Dos Santos, Jose C. S.; Rodrigues, Rafael C.; Fernandez-Lafuente, Roberto; Molecules; vol. 19; nb. 6; (2014); p. 7629 - 7645 View in Reaxys With sodium acetate, sodium hydrogencarbonate, sodium salt of phosphorous acid in aq. phosphate buffer, T= 25 °C , pH= 7, Enzymatic reaction, Reagent/catalyst, pH-value Dos Santos, Jose C. S.; Rueda, Nazzoly; Sanchez, Alfredo; Villalonga, Reynaldo; Gonalves, Luciana R. B.; Fernandez-Lafuente, Roberto; RSC Advances; vol. 5; nb. 45; (2015); p. 35801 - 35810 View in Reaxys

Rx-ID: 2393557 View in Reaxys 11/834 Yield 95 %

Conditions & References With oxygen in n-heptane, T= 25 °C , p= 3750.38Torr , Flow reactor, Autoclave Vanoye, Laurent; Pablos, Mertxe; Smith, Neil; De Bellefon, Claude; Favre-Rguillon, Alain; RSC Advances; vol. 4; nb. 100; (2014); p. 57159 - 57163 View in Reaxys

88 %

With Fe(III)PFP(Cl), 3-chloro-benzenecarboperoxoic acid in dichloromethane, Time= 0.333333h, T= -78 °C Watanabe, Yoshihito; Ishimura, Yuzuru; Journal of the American Chemical Society; vol. 111; nb. 20; (1989); p. 8047 - 8049 View in Reaxys

86 %

With potassium hydroxide, sodium tetrahydroborate, air, palladium on activated charcoal in methanol, Time= 17h, T= 20 °C Lim, Minkyung; Yoon, Cheol Min; An, Gwangil; Rhee, Hakjune; Tetrahedron Letters; vol. 48; nb. 22; (2007); p. 3835 - 3839

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View in Reaxys 84 %

General Procedure. General procedure: To a solution of 30percent hydrogen peroxide(5.0 mmol) was added aldehyde (1.0 mmol), PTSA(1.0 mmol) and β-cyclodextrin (0.1 mmol). The reactionmixture was stirred for 15 h at 50 oC. After cooling to roomtemperature, the reaction mixture was dissolved in the solutionof 10percent aqueous sodium bicarbonate, extracted intodiethyl ether (2 × 25 mL), and washed with water. The aqueouslayer was acidified to pH 3 with 2 M hydrochloric acid.The product was extracted with dichloromethane (2 × 25mL) and dried over magnesium sulfate. Evaporation of organiclayer under reduced pressure gave the desired carboxylicacid. With dihydrogen peroxide, toluene-4-sulfonic acid, β-cyclodextrin in water, Time= 15h, T= 50 °C Jeong, Se Young; Kim, Nagyeong; Lee, Jong Chan; Bulletin of the Korean Chemical Society; vol. 35; nb. 11; (2014); p. 3366 - 3368 View in Reaxys

80 %

With oxygen, Time= 5h, T= 120 °C , Neat (no solvent) Choudhary, Vasant R.; Dumbre, Deepa K.; Catalysis Communications; vol. 13; nb. 1; (2011); p. 82 - 86 View in Reaxys

75 %

With barium permanganate in acetonitrile, Time= 4h, Heating Firouzabadi; Seddighi; Mottaghineiad; Bolourchian; Tetrahedron; vol. 46; nb. 19; (1990); p. 6869 - 6878 View in Reaxys

75 %

With oxygen, 3,3-dimethyldioxirane, T= 20 °C Bravo, Anna; Fontana, Francesca; Fronza, Giovanni; Minisci, Francesco; Serri, Anna; Tetrahedron Letters; vol. 36; nb. 38; (1995); p. 6945 - 6948 View in Reaxys

63 %

With Oxonereg;, ethylenediaminetetraacetic acid, sodium hydrogencarbonate in water, acetone, Time= 15h, T= 0 - 2 °C , Oxidation Webb, Kevin S.; Ruszkay, Stephen J.; Tetrahedron; vol. 54; nb. 3-4; (1998); p. 401 - 410 View in Reaxys

55 %

With dihydrogen peroxide, 7-(trifluoromethyl)-1,10-ethyleneisoalloxazinium chloride in water, acetonitrile, Time= 18h, T= 85 °C Murray, Alexander T.; Matton, Pascal; Fairhurst, Nathan W. G.; John, Matthew P.; Carbery, David R.; Organic Letters; vol. 14; nb. 14; (2012); p. 3656 - 3659 View in Reaxys

48 %

With formic acid, dihydrogen peroxide, Time= 12h, T= 0 - 4 °C Dodd; Le Hyaric; Synthesis; nb. 3; (1993); p. 295 - 297 View in Reaxys With phosphate buffer, permanganate(VII) ion in water, T= 25 °C , Rate constant Freeman, Fillmore; Lin, Doris K.; Moore, Gregory R.; Journal of Organic Chemistry; vol. 47; nb. 1; (1982); p. 56 59 View in Reaxys With oxygen, 3,3-dimethyldioxirane in acetone, Time= 6h, T= 20 °C , Product distribution, Mechanism Bravo, Anna; Fontana, Francesca; Fronza, Giovanni; Minisci, Francesco; Zhao, Lihua; Journal of Organic Chemistry; vol. 63; nb. 2; (1998); p. 254 - 263 View in Reaxys With rat hepatic microsomal aldehyde dehydrogenase, nicotinamide adenine dinucleotide in phosphate buffer, N,Ndimethyl-formamide, T= 37 °C , pH= 7.4, Dehydrogenation, Enzyme kinetics Martini, Robert; Murray, Michael; Chemical Research in Toxicology; vol. 9; nb. 1; (1996); p. 268 - 276 View in Reaxys

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With [3,2-c]pyrazole, female BDF-1 mouse liver class I aldehyde dehydrogenase, nicotinamide adenine dinucleotide in phosphate buffer, T= 36.5 °C , pH= 7.4, Enzyme kinetics, Further Variations: Reagents Russo, James; Chung, Song; Contreras, Kristi; Lian, Brian; Lorenz, Jon; Stevens, David; Trousdell, Wendy; Biochemical Pharmacology; vol. 50; nb. 3; (1995); p. 399 - 406 View in Reaxys 62.6 g

With hydrogenchloride, sodium chlorite in ethyl acetate, Time= 3h, T= 20 °C , pH= 5.0 Zanka, Atsuhiko; Chemical and Pharmaceutical Bulletin; vol. 51; nb. 7; (2003); p. 888 - 889 View in Reaxys With oxygen-covered Au(111), T= 156.84 °C , p= 2E-10Torr , UHV chamber Quiller, Ryan G.; Liu, Xiaoying; Friend, Cynthia M.; Chemistry - An Asian Journal; vol. 5; nb. 1; (2010); p. 78 - 86 View in Reaxys With Deinococcus geothermalis DSM 11300 aldehyde dehydrogenase, nicotinamide adenine dinucleotide, T= 30 °C , pH= 9, aq. buffer, Enzymatic reaction, Kinetics, Reagent/catalyst Wulf; Perzborn; Sievers; Scholz; Bornscheuer; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 144 - 150 View in Reaxys With potassium permanganate in water, acetonitrile Pratihar, Sanjay; Organic and Biomolecular Chemistry; vol. 12; nb. 30; (2014); p. 5781 - 5788 View in Reaxys

HO C

Rx-ID: 4713455 View in Reaxys 12/834 Yield

Conditions & References

90 %, 3 %, With hydrogen iodide, tetrakis(triphenylphosphine) palladium(0) in acetone, Time= 44h, T= 90 °C , p= 68400Torr , 6% Carbonylation, reduction Lin, Yong-Shou; Yamamoto, Akio; Bulletin of the Chemical Society of Japan; vol. 71; nb. 3; (1998); p. 723 - 734 View in Reaxys 3% Spectr., 6 % Spectr., 90 % Spectr.

With tetrakis(triphenylphosphine) palladium(0), hydrogen iodide in acetone, Time= 44h, T= 90 °C , p= 68400Torr

24 % Spectr., 7 % Spectr., 58 % Spectr.

With tetrakis(triphenylphosphine) palladium(0), hydrogen iodide in acetone, Time= 44h, T= 90 °C , p= 68400Torr

Lin, Yong-Shou; Yamamoto, Akio; Tetrahedron Letters; vol. 38; nb. 21; (1997); p. 3747 - 3750 View in Reaxys

O Cl O

Rx-ID: 2506525 View in Reaxys 13/834 Yield 91 %

Conditions & References With sodium tetrahydroborate, selenium in N,N-dimethyl-formamide, Time= 1h, T= 40 - 50 °C Huang, Zhi-Zhen; Zhou, Xun-Jun; Synthesis; nb. 9; (1989); p. 693 - 694

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View in Reaxys 80 %

With indium, ND4Cl, deuterated ammonium chloride in THF-d8 (tetrahydrofuran-d8), water-d2, Time= 40h, T= 20 °C , Reflux, chemoselective reaction Mineno, Tomoko; Hirayama, Haruyasu; Nakahara, Kazuhide; Yamashita, Mitsuaki; Kansui, Hisao; Moriwaki, Hiroshi; Tetrahedron Letters; vol. 51; nb. 46; (2010); p. 6045 - 6048 View in Reaxys

71 %

With bis(cyclopentadienyl)titanium dichloride, 4-chloro-2,6-dimethylpyridine hydrochloride, zinc in tetrahydrofuran, Time= 2.5h, T= 20 °C Gansaeuer, Andreas; Dahmen, Tobias; Chimia; vol. 66; nb. 6; (2012); p. 433 - 434 View in Reaxys

HO O

Rx-ID: 2964212 View in Reaxys 14/834 Yield 96 %

Conditions & References 2; 41 : Preparation of Phenylacetic Acid from Toluene and Ethanol Toluene (1.38 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg), iridium trichloride (1 mg, 1 mol percent), and Xantphos (2.9 mg, 1 mol percent) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 24 h. After the reaction was completed, carbon monoxide was discharged, and 43 mg ethyl phenylacetate was obtained by column chromatography, in a yield of 53percent. The ethyl phenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 34 mg product phenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 96percent. With water, sodium hydroxide in 1,4-dioxane, Time= 2h, T= 60 °C , pH= 10 - 14 Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); (A1) English View in Reaxys

70 %

Stage 1: With titanium tetrachloride in tetrachloroethane, 1,1,2,2-, Time= 24h, T= 115 °C , Inert atmosphere Stage 2: With hydrogenchloride, water in tetrachloroethane, 1,1,2,2-, Inert atmosphere Lian, Xiaoyan; Fu, Shaomin; Ma, Tongmei; Li, Shunbin; Zeng, Wei; Applied Organometallic Chemistry; vol. 25; nb. 6; (2011); p. 443 - 447 View in Reaxys With alkaline H2O in dimethyl sulfoxide, T= 30 °C , other solvent (EtOH); variation of water concentrations, Rate constant Venkoba Rao, G.; Balakrishnan, M.; Venkatasubramanian, N.; Subramanian, P. V.; Subramanian, V.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. <B> 20; nb. 9; (1981); p. 793 - 795 View in Reaxys Reaction Steps: 4 1: sodium ethanolate 2: 12 h / 170 - 180 °C 3: water; potassium hydroxide / 51 - 73 °C 4: Heating With water, sodium ethanolate, potassium hydroxide, 1: Claisen condensation Malki, Fatiha; Touati, Abdelkader; Rahal, Said; Moulay, Saad; Asian Journal of Chemistry; vol. 23; nb. 3; (2011); p. 961 - 967 View in Reaxys

15/258

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O S

O O

Rx-ID: 38878311 View in Reaxys 15/834 Yield

Conditions & References

56 %, 34 %

A representative synthetic procedure of skeletons 3 and 5 is as follows General procedure: Ce(NH4)2(NO3)6 (CAN, 274 mg, 0.5 mmol) was added to a solution of β-ketosulfones 2 (0.5 mmol) in MeCN (10 mL) at rt. The reaction mixture was stirred at 50 oC for 4 h, cooled to rt, and the solvent was concentrated. The residue was diluted with water (10 mL) and the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product. Products 3 and 5 were isolated and recrystalised from EtOAc and THF. With ammonium cerium (IV) nitrate, oxygen in acetonitrile, Time= 4h, T= 20 - 50 °C Chang, Meng-Yang; Tsai, Chung-Yu; Tetrahedron Letters; vol. 55; nb. 40; (2014); p. 5548 - 5550 View in Reaxys

HO C

O O

Rx-ID: 5053516 View in Reaxys 16/834 Yield

Conditions & References

98 %, 17 %

With hydrogen iodide, tetrakis(triphenylphosphine) palladium(0) in acetone, Time= 42h, T= 100 °C , p= 76000Torr , Carbonylation, reduction Lin, Yong-Shou; Yamamoto, Akio; Bulletin of the Chemical Society of Japan; vol. 71; nb. 3; (1998); p. 723 - 734 View in Reaxys

tetracarbonyl(phenylacetyl)cobalt

O–

N+

Rx-ID: 25926402 View in Reaxys 17/834 Yield

Conditions & References

73 %, 40 mg, 190 mg

Stage 1: in 1,4-dioxane, hexane, Time= 6h, T= 50 °C , p= 41372.9Torr Stage 2: With hydrogenchloride, Time= 24h, Heating, Further stages. Sun, Huailin; Zhang, Jian; Liu, Qiuhua; Yu, Lei; Zhao, Jiangyu; Angewandte Chemie - International Edition; vol. 46; nb. 32; (2007); p. 6068 - 6072 View in Reaxys

O O

Rx-ID: 38878312 View in Reaxys 18/834 Yield 52 %, 35 %

Conditions & References A representative synthetic procedure of skeletons 3 and 5 is as follows General procedure: Ce(NH4)2(NO3)6 (CAN, 274 mg, 0.5 mmol) was added to a solution of β-ketosulfones 2 (0.5 mmol) in MeCN (10 mL) at rt. The reaction mixture was stirred at 50 oC for 4 h, cooled to rt, and the solvent was

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concentrated. The residue was diluted with water (10 mL) and the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product. Products 3 and 5 were isolated and recrystalised from EtOAc and THF. With ammonium cerium (IV) nitrate, oxygen in acetonitrile, Time= 4h, T= 20 - 50 °C Chang, Meng-Yang; Tsai, Chung-Yu; Tetrahedron Letters; vol. 55; nb. 40; (2014); p. 5548 - 5550 View in Reaxys

O O

Rx-ID: 41637493 View in Reaxys 19/834 Yield

Conditions & References

97 %

General procedure General procedure: A solution of the silyl ester (1 mmol) in DMF–H2O (20:1) (5 mL) was heated to 70 °C, and stirred for 1–2 h (or until all starting material has been consumed). The reaction was cooled to rt, diluted with ether (20 mL), washed successively with sat. aq. NH4Cl and brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography With anhydrous lithium acetate, water, DMFA, Time= 0.5h, T= 25 °C , Reagent/catalyst, Temperature, Solvent, chemoselective reaction Chen, Bo; Sun, Hui-Xia; Qin, Jian-Feng; Wang, Bing; Tetrahedron Letters; vol. 57; nb. 3; (2016); p. 253 - 255 View in Reaxys

Rx-ID: 41637496 View in Reaxys 20/834 Yield 96 %

Conditions & References General procedure General procedure: A solution of the silyl ester (1 mmol) in DMF–H2O (20:1) (5 mL) was heated to 70 °C, and stirred for 1–2 h (or until all starting material has been consumed). The reaction was cooled to rt, diluted with ether (20 mL), washed successively with sat. aq. NH4Cl and brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography With anhydrous lithium acetate, water, DMFA, Time= 0.25h, T= 25 °C , Reagent/catalyst, Temperature, chemoselective reaction Chen, Bo; Sun, Hui-Xia; Qin, Jian-Feng; Wang, Bing; Tetrahedron Letters; vol. 57; nb. 3; (2016); p. 253 - 255 View in Reaxys

HO O

Rx-ID: 1546476 View in Reaxys 21/834 Yield 88 %

Conditions & References With Oxonereg;, iodine in DME, water, Time= 6h, T= 20 °C , regioselective reaction Kodumuri, Srujana; Peraka, Swamy; Mameda, Naresh; Chevella, Durgaiah; Banothu, Rammurthy; Nama, Narender; RSC Advances; vol. 6; nb. 8; (2016); p. 6719 - 6723 View in Reaxys With chromium(VI) oxide, sodium tetrahydroborate, sulfuric acid, water, acetic acid, tert-butanol, 1.) THF, a.) r.t., 2 h, a.) 50 deg C, 2 h, 2.) acetone, r.t., 10 h, Yield given. Multistep reaction

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Periasamy, M.; Narayana, C.; Anitha, N.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 844 - 846 View in Reaxys With potassium hydroxide, sodium tetrahydroborate, potassium permanganate, boron trifluoride diethyl etherate, 1.) THF, 0-10 deg C, 1 h, 2.) H2O, 20 deg C, 8 h, Yield given. Multistep reaction Hao, Nguen Kong; Mavrov, M. V.; Serebryakov, E. P.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 35; nb. 1; (1986); p. 235; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1986); p. 251 - 252 View in Reaxys With oxygen-covered Au(111), T= 146.84 °C , p= 2E-10Torr , UHV chamber Quiller, Ryan G.; Liu, Xiaoying; Friend, Cynthia M.; Chemistry - An Asian Journal; vol. 5; nb. 1; (2010); p. 78 - 86 View in Reaxys OH HO

Cl SH

Rx-ID: 25114426 View in Reaxys 22/834 Yield

Conditions & References

90%

29 : EXAMPLE 29 EXAMPLE 29 A solution of methyl mercaptan (1.8 g, 37.5 mmoles) and 1-phenyl-2,2,2-trichloroethanol (1.13 g, 5 mmoles) in dimethyl sulfoxide (10ml) was added to a 50percent aqueous solution of dimethyl sulfoxide (40 ml) under ice-water cooling with stirring. Then, potassium hydroxide (1.7 g, 26 mmoles) was dissolved in a 50percent aqueous soluton of dimethyl sulfoxide (20 ml) and the solution was added dropwise to the above mixture. The mixture was stirred at room temperature for 2 hours and then heated at 70° C. for 2 hours. After allowing the mixture to cool to room temperature, water and diethyl ether were added to the mixture and the ether-soluble material was removed. The aqueous layer was rendered acidic with dilute hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography to afford 0.61 g. of phenylacetic acid. Yield 90percent. m.p.: 75°-76° C. (Lit. 76.5° C.) NMR (CDCl3, TMS): δ 3.62 (s, 2H), 7.23 (s, 5H), 10.4 (bs, 1H). With potassium hydroxide in diethyl ether, water, dimethyl sulfoxide Patent; Sagami Chemical Research Center; US4268442; (1981); (A1) English View in Reaxys

P(C6 H5)3

PdCl2.(C6 H5 CN)2

Rx-ID: 25331055 View in Reaxys 23/834 Yield 83%

Conditions & References 14 : EXAMPLE 14 EXAMPLE 14 Into the same autoclave as in Example 13, there were introduced 200 cc of water, 80 g of NaOH, 50 cc of p.xylene, 0.1 g of PdCl2.(C6 H5 CN)2, 0.2 g of P(C6 H5)3, and 0.6 g of tetrabutylammonium iodide. Thereupon the autoclave was brought up to a temperature of 95° C. and a CO pressure of 5-6 atmospheres and over a period of about 4 hours about 50 g of benzyl chloride and 0.2 g of P(C6 H5)3 were fed in. A pressure of 5-6 atmospheres CO was maintained for a total of about 6 hours. The reaction mass was processed as in Example 13, thereby yielding 45 g of phenylacetic acid. The yield amounted to 83percent based on the benzyl chloride introduced.

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With sodium hydroxide, tetra-(n-butyl)ammonium iodide in water Patent; Montedison Fibre S.p.A.; US4034004; (1977); (A1) English View in Reaxys

O O

H 2N

H HN

Rx-ID: 32222871 View in Reaxys 24/834 Yield

Conditions & References

47 %, 46 %

4.3. Enzymatic hydrolysis Compound 2 (5 g) was suspended in water (20 mL) and dissolved by the dropwise addition of 5percent aqueous ammonia solution. The pH was adjusted to 7.5 after which immobilized penicillin G acylase (5 g, wet) was added. The reaction mixture was shaken in a conical flask at 80 rpm (25 °C) on an orbital shaker and the reaction was followed by reverse phase HPLC analysis. The reaction virtually stopped at 50percent hydrolysis (1 h). The enzyme was filtered, after which the aqueous filtrate was acidified to pH 2 with 1 M HCl and extracted with cyclohexane to remove the phenylacetic acid. The aqueous extract was freeze dried and the dry powder was extracted with acetone to recover the unreacted (S)-N-phenylacetyl derivative. The residue after acetone extraction consisted of the hydrolyzed (R)-homoserine. The products were stirred separately with methanolic HCl (1 M, 20 mL) overnight at room temperature. Evaporation of methanol gave the cyclic lactone hydrochlorides 1 and 2. Stage 1: With ammonia, water, Time= 1h, T= 25 °C , pH= 7.5, Enzymatic reaction Stage 2: With hydrogenchloride in water, pH= 2, enantioselective reaction Venkataiah, Mallam; Reddipalli, Gowrisankar; Jasti, Lakshmi Swarnalatha; Fadnavis, Nitin W.; Tetrahedron Asymmetry; vol. 22; nb. 20-22; (2011); p. 1855 - 1860 View in Reaxys

Rx-ID: 438069 View in Reaxys 25/834 Yield 90.5 %

Conditions & References With orthophosphorus acid, methanesulfonic acid, sodium iodide in water, T= 95 °C , Inert atmosphere Milne, Jacqueline E.; Storz, Thomas; Colyer, John T.; Thiel, Oliver R.; Dilmeghani Seran, Mina; Larsen, Robert D.; Murry, Jerry A.; Journal of Organic Chemistry; vol. 76; nb. 22; (2011); p. 9519 - 9524 View in Reaxys With platinum on activated charcoal, ethanol, palladium dichloride, Hydrogenation Zelinsky; Packendorff; Leder-Packendorff; Chemische Berichte; vol. 67; (1934); p. 300 View in Reaxys With palladium, acetic acid, Hydrogenation Hahn; Stiehl; Schulz; Chemische Berichte; vol. 72; (1939); p. 1291,1296 View in Reaxys With phosphoric acid, potassium iodide Miescher; Billeter; Helvetica Chimica Acta; vol. 22; (1939); p. 601,609 View in Reaxys With phosphoric acid, iodine Miescher; Billeter; Helvetica Chimica Acta; vol. 22; (1939); p. 601,609 View in Reaxys

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With phosphorus, iodine Miescher; Billeter; Helvetica Chimica Acta; vol. 22; (1939); p. 601,609 View in Reaxys With phosphorus, potassium iodide Miescher; Billeter; Helvetica Chimica Acta; vol. 22; (1939); p. 601,609 View in Reaxys With phosphorus, hydrogen iodide Crum Brown; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1865); p. 340; ; (1865); p. 443 View in Reaxys Reaction Steps: 2 Glaser; Radziszewski; ; (1868); p. 142 View in Reaxys Reaction Steps: 2 1: 120 - 130 °C / im geschlossenen Rohr Glaser; Radziszewski; ; (1868); p. 142 View in Reaxys Reaction Steps: 2 1: 120 - 130 °C / im geschlossenen Rohr 2: sodium amalgam; ethanol With sodium amalgam, ethanol Glaser; Radziszewski; ; (1868); p. 142 View in Reaxys Reaction Steps: 2 2: sodium amalgam; ethanol With sodium amalgam, ethanol Glaser; Radziszewski; ; (1868); p. 142 View in Reaxys

Rx-ID: 578117 View in Reaxys 26/834 Yield 99 %

Conditions & References With 1,2-benzenedicarboxylic acid, Time= 0.5h, T= 250 °C , p= 7600Torr , microwave irradiation Chemat, Farid; Tetrahedron Letters; vol. 43; nb. 32; (2002); p. 5555 - 5557 View in Reaxys

97 %

With enzyme from Synechocystis sp. PCC 6803 in phosphate buffer, Time= 12h, T= 30 °C , pH= 7.2 Mukherjee, Chandrani; Zhu, Dunming; Biehl, Edward R.; Hua, Ling; European Journal of Organic Chemistry; nb. 23; (2006); p. 5238 - 5242 View in Reaxys

95 %

With sodium perborate, Time= 1h, T= 240 °C , p= 4500.4Torr , also copper salts as hydrolysis agents, other nitriles, var. pressure, var. ratio of reagents, Mechanism, Product distribution Chemat, Farid; Poux, Martine; Berlan, Jacques; Journal of the Chemical Society. Perkin Transactions 2; vol. 8; (1996); p. 1781 - 1784 View in Reaxys

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95 %

With 1,2-benzenedicarboxylic acid, Time= 0.833333h, microwave-irradiation Bratulescu, George; Revue Roumaine de Chimie; vol. 46; nb. 3; (2001); p. 207 - 209 View in Reaxys

94.3 %

With CuCl2*2H2O, Time= 1h, T= 240 °C Chemat, Farid; Poux, Martine; Berlan, Jacques; Journal of the Chemical Society. Perkin Transactions 2; vol. 8; (1996); p. 1781 - 1784 View in Reaxys

94 %

General procedure for the synthesis of carboxylic acids from nitriles General procedure: Aromatic or aliphatic nitriles (2 mmol) were dissolved in 5 ml of [bmim]HSO4 and the reaction mixture was heated at 60-65 °C for 1-3 h. The progress of reaction was monitored by TLC. After completion of reaction, as checked by TLC, the reaction mixture was poured into water containing crushed ice. The product was precipitated out, filtered and dried. The yield of the final product was high (>90percent) in all cases. All final products obtained were found sufficiently pure so it didn’t need further purification.The filtrate was concentrated under vacuum, washed with diethylether twice and concentrated under high vacuum. After proper drying under reduced pressure, approximately 95percent ionic liquid was recovered from the reaction and compared with the original ionic liquid to check its authenticity. The efficiency of recovered ionic liquid in conversion of nitriles to acids was found unchanged in comparison to the original one and we reused it up to 5-6 cycles without any significant loss of its activity. With [BMIm][HSO4], water, Time= 1.4h, T= 60 - 65 °C , Green chemistry Kumar, Satyanand; Dixit, Sandeep Kumar; Awasthi, Satish Kumar; Tetrahedron Letters; vol. 55; nb. 28; (2014); p. 3802 - 3804 View in Reaxys

91.3 %

With potassium phosphate buffer, Time= 17h, T= 30 °C , Rhodococcus sp. AJ270 cells Meth-Cohn, Otto; Wang, Mei-Xiang; Journal of the Chemical Society - Perkin Transactions 1; nb. 8; (1997); p. 1099 - 1104 View in Reaxys

82 %

With sodium hydroxide in water, Time= 5h, T= 115 - 120 °C , Inert atmosphere Tao, Renjie; Zhao, Jianzhang; Zhong, Fangfang; Zhang, Caishun; Yang, Wenbo; Xu, Kejing; Chemical Communications; vol. 51; nb. 62; (2015); p. 12403 - 12406 View in Reaxys

71 %

With water, nitrile hydratase SP361, Time= 23h, T= 30 °C , in potassium phosphate buffer (pH = 7) Cohen, Mark A.; Sawden, Janette; Turner, Nicholas J.; Tetrahedron Letters; vol. 31; nb. 49; (1990); p. 7223 7226 View in Reaxys

With Dowex-50 in water, Time= 12h, Heating Basu, Manas K.; Sarkar, Dipak C.; Ranu, Brindaban C.; Synthetic Communications; vol. 19; nb. 3and4; (1989); p. 627 - 632 View in Reaxys With potassium permanganate, tetrabutylammomium bromide in water, benzene, Time= 0.25h, Ambient temperature, other catalysts, Product distribution Hanumantha Rao; Bhagawanth Rao; Journal of the Indian Chemical Society; vol. 68; nb. 3; (1991); p. 132 - 134 View in Reaxys With hydrogenchloride Wenner; Organic Syntheses; vol. Coll. Vol. IV; (1963); p. 760 View in Reaxys With bis-(2-hydroxy-ethyl)-amine Rauscher; Goldstein; Breslau; Journal of the American Chemical Society; vol. 71; (1949); p. 359

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View in Reaxys With steam, thorium(IV) dioxide, T= 420 °C Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 171; (1920); p. 247; Bulletin de la Societe Chimique de France; vol. <4>27; (1920); p. 756 View in Reaxys Hydrolysis Schwyzer,J.; View in Reaxys With sulfuric acid Patent; Nordmark-Werke; DE802818; (1950); View in Reaxys With sulfuric acid, water Staedel; Chemische Berichte; vol. 19; (1886); p. 1948 View in Reaxys View in Reaxys With 0.8 equ. Cu(NO3)2*3 H2O on montmorillonite K10 clay, dihydrogen peroxide, under microwave irradiation Varma, Rajender S.; Dahiya, Rajender; Tetrahedron Letters; vol. 39; nb. 11; (1998); p. 1307 - 1308 View in Reaxys With phosphate buffer, Rhodococcus rhodochrous IFO 15564 in water, Time= 4h, T= 30 °C , pH= 6.0 Kimura, Mayumi; Kuboki, Atsuhito; Sugai, Takeshi; Tetrahedron Asymmetry; vol. 13; nb. 10; (2002); p. 1059 1068 View in Reaxys With sulfuric acid, acetic acid Nabil Aboul-Enein; El-Azzounya; Maklad; Attia; Wiese; Scientia Pharmaceutica; vol. 69; nb. 4; (2001); p. 329 350 View in Reaxys With dipotassium hydrogenphosphate, phosphoric acid, water, nitrile aminohydrolase E.C. 3.5.5.1, T= 25 °C , pH= 7.43, Thermodynamic data Tewari, Yadu B.; Goldberg, Robert N.; Journal of Chemical Thermodynamics; vol. 37; nb. 7; (2005); p. 720 - 728 View in Reaxys Reaction Steps: 5 1: sulfuric acid; water 2: sodium ethanolate 3: 12 h / 170 - 180 °C 4: water; potassium hydroxide / 51 - 73 °C 5: Heating With sulfuric acid, water, sodium ethanolate, potassium hydroxide, 2: Claisen condensation Malki, Fatiha; Touati, Abdelkader; Rahal, Said; Moulay, Saad; Asian Journal of Chemistry; vol. 23; nb. 3; (2011); p. 961 - 967 View in Reaxys With hydrogenchloride, water, Time= 24h, Reflux Yousefi; Mohammadi; Habibi; Cheraghi; Biocatalysis and Biotransformation; vol. 29; nb. 2-3; (2011); p. 54 - 59 View in Reaxys PfNLase

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To a 1.5mL Eppendorf tube containing 20mM citrate buffer pH 5.5 (0.98mL), NLase solution (10μL, 100×prediluted; 0.003mg protein), 1,2-dimethoxybenzene (IS) and 2-phenylacetonitrile (10mM) were added. Samples were taken and analysed by HPLC (procedure B). One unit (U) of PfNLase will hydrolyse 1μmol of 2-phenylacetonitrile per min. With non-selective nitrilase from Pseudomonas fluorescens EBC 191, water in di-isopropyl ether, T= 25 °C , pH= 5.5, Enzymatic reaction, Catalytic behavior, Concentration, Reagent/catalyst Chmura, Andrzej; Rustler, Sven; Paravidino, Monica; Van Rantwijk, Fred; Stolz, Andreas; Sheldon, Roger A.; Tetrahedron Asymmetry; vol. 24; nb. 19; (2013); p. 1225 - 1232 View in Reaxys With bradyrhizobium species BTAi1 (A5EKU8), water, Enzymatic reaction, Reagent/catalyst Black, Gary W.; Brown, Nicola L.; Perry, Justin J. B.; Randall, P. David; Turnbull, Graeme; Zhang, Meng; Chemical Communications; vol. 51; nb. 13; (2015); p. 2660 - 2662 View in Reaxys With nitrilase from Gordonia terrae in aq. phosphate buffer, Time= 1h, T= 35 °C , pH= 8, Enzymatic reaction Kumar, Vijay; Seth, Amit; Kumari, Vijaya; Kumar, Virender; Bhalla, Tek C.; Protein and Peptide Letters; vol. 22; nb. 1; (2015); p. 52 - 62 View in Reaxys

NH 2

Rx-ID: 2951124 View in Reaxys 27/834 Yield 97 %

Conditions & References With 1,2-benzenedicarboxylic acid, Time= 0.333333h, T= 250 °C , p= 7600Torr , microwave irradiation Chemat, Farid; Tetrahedron Letters; vol. 43; nb. 32; (2002); p. 5555 - 5557 View in Reaxys

95 %

With phthalic anhydride, Time= 0.75h, T= 240 - 250 °C , p= 3040Torr , Hydrolysis Chemat, Farid; Tetrahedron Letters; vol. 41; nb. 20; (2000); p. 3855 - 3857 View in Reaxys

91 %

With titanium tetrachloride in 1,4-dioxane, water, Time= 17h, Heating Fisher; Caroon; Stabler; Lundberg; Zaidi; Sorensen; Sparacino; Muchowski; Canadian Journal of Chemistry; vol. 72; nb. 1; (1994); p. 142 - 145 View in Reaxys 2.9 Substrate specificity and stereoselectivity General procedure: The substrate specificity of recombinant KamH was tested using various aliphatic and aromatic amides. Cell-free extract of E. coli BL21(DE3)/pET-Ami2 was mixed with various concentrations of substrate under standard reaction conditions; 10percent (v/v) methanol was added as cosolvent to solubilize the substrate. The enzyme activity toward the various amides was determined by monitoring the formation of either carboxylic acid or ammonia [36]. Several racemic amides were used to study the stereoselectivity of the recombinant enzyme, including 2phenylacetamide, mandelamide, 2,2-dimethylcyclopropanecarboxamide, and 2-(4-chlorophenyl)-3-methylbutyramide. Enantiomeric excess values were obtained by HPLC analysis using an AY-RH column. The enantiomeric excess and enantiomeric ratio of the product were determined according to Chen et al. [37]. With cell-free extract of amidase gene cloned from Klebsiella oxytoca KCTC 1686 and functionally expressed in Escherichia coli BL21(DE3) in methanol, Enzymatic reaction Guo, Fa-Mou; Wu, Jian-Ping; Yang, Li-Rong; Xu, Gang; Process Biochemistry; vol. 50; nb. 8; (2015); p. 1264 1271 View in Reaxys

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HO O

Rx-ID: 3959262 View in Reaxys 28/834 Yield

Conditions & References

100 %

With diethylamine, Pd(0) (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) in water, acetonitrile, Time= 0.0833333h, 2 molpercent catlyst Lemaire-Audoire; Lemaire-Audoire, Sandrine; Savignac; Savignac, Monique; Blart; Blart, Errol; Pourcelot; Pourcelot, Guy; Genet; Genet, Jean Pierre; Bernard; Bernard, Jean-Marie; Tetrahedron Letters; vol. 35; nb. 47; (1994); p. 8783 - 8786 View in Reaxys

91 %

Stage 1: With sodium tetrahydroborate in dimethyl sulfoxide, T= 20 °C Stage 2: With hydrogenchloride, water in dimethyl sulfoxide, Time= 0.5h, chemoselective reaction Pawar, Bharati V.; Lokhande, Pradeep D.; Synthetic Communications; vol. 39; nb. 14; (2009); p. 2445 - 2453 View in Reaxys

85 %

With iodine, dimethyl sulfoxide, Time= 0.5h, Heating Taksande, Kiran N.; Sakate, Sachin S.; Lokhande, Pradeep D.; Tetrahedron Letters; vol. 47; nb. 5; (2006); p. 643 - 646 View in Reaxys

72 %

With toluene-4-sulfonic acid, Time= 0.0666667h, microwave irradiation Lee, Jong Chan; Yoo, Eun Sang; Lee, Jin Seo; Synthetic Communications; vol. 34; nb. 16; (2004); p. 3017 - 3020 View in Reaxys

O N

Rx-ID: 4724861 View in Reaxys 29/834 Yield

Conditions & References

95 %

With acetic acid, sodium nitrite in dimethyl sulfoxide, Time= 6h, T= 35 °C Matt, Christophe; Wagner, Alain; Mioskowski, Charles; Journal of Organic Chemistry; vol. 62; nb. 2; (1997); p. 234 - 235 View in Reaxys

75 %

With acetic acid, sodium nitrite in water, dimethyl sulfoxide, T= 65 °C Gissot, Arnaud; N'Gouela, Silvere; Matt, Christophe; Wagner, Alain; Mioskowski, Charles; Journal of Organic Chemistry; vol. 69; nb. 26; (2004); p. 8997 - 9001 View in Reaxys With (S)-1-Phenylethylamine, sodium nitrite, isoamyl nitrite in DMFA, Time= 48h Schwieter, Kenneth E.; Johnston, Jeffrey N.; Chemical Communications; vol. 52; nb. 1; (2016); p. 152 - 155 View in Reaxys

OH N

HO O

Rx-ID: 24194950 View in Reaxys 30/834 Yield 78.6%

Conditions & References 165 : Synthesis of Phenylacetic Acid (72) Synthesis of Phenylacetic Acid (72)

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A mixture of 26.7 g (F.W. 243.10, 110 mmol) of carboxylic acid (75), 18.7 g (F.W. 170.23, 110 mmol) of 3,4-dimethoxythiophenol (76), 3.50 g (F.W. 63.55, 55.0 mmol) of copper (powder), 10.5 g (F.W. 190.45, 55.0 mmol) of copper (I) iodide, 18.2 g (F.W. 138.21, 132 mmol) of potassium carbonate and 140 mL of N-methyl-2-pyrrolidone was stirred at 140° C. for 3.5 hours. To the reaction solution was added ice and the resulting solution was made pH 6 to 7 with concentrated hydrochloric acid under cooling with ice. Toluene and water were added thereto to dissolve the product, and insolubles were separated by filtration. To the filtrate was added a 20percent sodium hydroxide aqueous solution to effect partition. The organic layer was separated and further extracted with a 2percent sodium hydroxide aqueous solution and then, combined with the aqueous layer and made pH 2 to 3 with concentrated hydrochloric acid under cooling with ice. The obtained solution was extracted with ethyl acetate and the organic layer was washed with water, and dried with anhydrous sodium sulfate and then, the solvent was removed under reduced pressure to obtain 35.1 g of a crude product. This product was washed with a small amount of diisopropyl ether and then, dried to obtain 28.7 g (yield 78.6percent) of phenylacetic acid (72). With sodium hydroxide, potassium carbonate in water, toluene Patent; Nippon Suisan Kaisha, Ltd.; US6602898; (2003); (B1) English View in Reaxys

HO O

Rx-ID: 705491 View in Reaxys 31/834 Yield 85 %

Conditions & References With lt;meso-tetrakis(2,6-dichlorophenyl)porphyrinatogt;manganese(III) chloride, sodium hydrogencarbonate in water, acetonitrile Wei, Wei; Hu, Xiao-Yu; Yan, Xiao-Wei; Zhang, Qiang; Cheng, Ming; Ji, Jian-Xin; Chemical Communications; vol. 48; nb. 2; (2012); p. 305 - 307 View in Reaxys

84 %

Stage 1: With 1-methyl-pyrrolidin-2-one, C17H11ClF6N2Ru(1+) in water, Time= 24h, T= 25 °C , Inert atmosphere Stage 2: With [bis(acetoxy)iodo]benzene, Time= 1h, T= 25 °C , Reagent/catalyst Zeng, Mingshuo; Herzon, Seth B.; Journal of Organic Chemistry; vol. 80; nb. 17; (2015); p. 8604 - 8618 View in Reaxys With cyclohexane, water, Nitrous oxide, T= 300 °C , p= 367754Torr Buckley; Levy; Journal of the Chemical Society; (1951); p. 3016 View in Reaxys With benzoyl peroxide, diethyl ether Prileshajew; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 42; (1910); p. 1409; Chem. Zentralbl.; vol. 82; nb. I; (1911); p. 1280 View in Reaxys Reaction Steps: 2 1: <hydroxy(tosyloxy)iodo>benzene, NaHCO3 / methanol / 72 h / Heating 2: 2N NaOH With sodium hydroxide, hydroxy(tosyloxy)iodobenzene, sodium hydrogencarbonate in methanol Moriarty, Robert M.; Vaid, Radhe K.; Duncan, Michael P.; Vaid, Beena K.; Tetrahedron Letters; vol. 28; nb. 25; (1987); p. 2845 - 2848 View in Reaxys Reaction Steps: 3 1: absolute ether solution; sulfuryl chloride 2: sodium ethylate 3: alcoholic alkali

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With sulfuryl dichloride, diethyl ether, sodium ethanolate Nef; Justus Liebigs Annalen der Chemie; vol. 308; (1899); p. 325 View in Reaxys

HO O

Rx-ID: 3536993 View in Reaxys 32/834 Yield 96 - 98 %

Conditions & References 1 :One representative carboxylation of benzyl sodium process according to the inventive principles is shown in the process diagram of FIG. 3. To 11.45 g (0.1 mol) of toluene/benzene solution of benzyl-sodium, prepared from 11.25 g (0.1 mol) of chlorobenzene, 9.4 g (0.2 mol) of sodium and 60 ml of toluene as described above and shown at Block 31 in FIG. 3, is added 1.1 g of [(C4H9)4N]X(XCl, Br) in toluene (12 ml) under nitrogen at 25-27° C. (Block 32). The mixture is stirred 15 min and is added slowly to crushed dry ice (Block 33). The mixture is kept until removal of dry the ice (in CO2 form), and then the residue is treated with HCl (hydrochloric) acid (10percent, pH=1) (Block 34) and the sediment of phenylacetic acid is separated and crystallized from water (Block 35). Yield of pure phenylacetic acid is 13.32 g (98percent). Melting point of prepared product is 77° C. The toluene/benzene solution containing the phase-transfer catalyst may be recycled many times in the carboxylation process with no loss in catalytic activity. Phenylacetic acid is thus obtained to the extent of more than 800 moles per mole of [(C4H9)4N]Br taken. Another important advantage of this system is the possibility of achieving selective carboxylation of benzyl-sodium yield of phenylacetic acid, and a carboxylation yield to 96-98percent. An important practical aspect of this process is the continuous separation of the product from the catalyst, which in effect heterogenizes the homogenous catalyst. This point accounts for the high catalyst turnover, the selectivity encountered in the carboxylation of benzyl-sodium and the high activity of the catalyst. Table 2 summarizes experimental results demonstrating carboxylation processes using the phase-transfer catalysis techniques of the present inventive principles. TABLE 2 Mass-balance of laboratory pilot plant experiment on preparation of phenylacetic acid Amount of Amount Compound formed and Compounds of taken prepared and returned taken to to reaction returned other compounds, No reaction compounds, g No reaction, g g 1 Chlorobenzene 56.3 1 Phenylacetic 66.7 acid 2 Sodium 27.0 2 Returned 123.62 toluene 3 Toluene 187.5 3 Formed 35.9 benzene 4 Dry ice 440 4 Lost toluene 14.58 5 Hydrogen 214 5 Lost benzene 3.1 chloride acid 10percent 6 Catalyst 0.27 6 Returned dry 418 ice in from of CO2 7 7 Catalyst 0.27 8 8 Water 192.6 9 9 Minor products 2.3 10 10 NaCl 68 Sum 925.07 Sum 925.07 * Theoretical yield of phenylacetic acid on chlorobenzene is 98percent Stage 1: With sodium, chlorobenzene in benzene, Time= 0.25h, T= 25 - 27 °C Stage 2: in toluene, benzene Stage 3: With hydrogenchloride, water in toluene, benzene, pH= 1, Product distribution / selectivity Patent; Property Development Coporation International Ltd.; US2007/10686; (2007); (A1) English View in Reaxys

55 %

With n-butyllithium, (cyclopentadienyl)potassium in diethyl ether, Ambient temperature Scott, Frederick; Hamese, Augustine M.; Raubenheimer, Helgard G.; Journal of Organometallic Chemistry; vol. 393; nb. 3; (1990); p. C40 - C42 View in Reaxys

16.2 - 92 %

1 :4.7 g. of sodium, 30 ml of absolute toluene and 6 mg of catalyst are put into a stainless-steel preliminary reactor that has a mixer capable of mixing at 10,000 revolutions per minute, a heater, a backflow condenser, a viewing window, and a cooling jacket. All processes are carried out in a dry-nitrogen atmosphere. The reactor is heated up to the toluene boiling point. Then the high-speed mixer is switched on for 1-1.5 minutes for sodium crushing. The suspension is then cooled down to 25-30° C. and placed in a phenylsodium-conversion reactor. 5-8ml of a chlorobenzene and toluene solution, made by mixing the 2 reagents in equal proportion with catalyst, is added to toluene-sodium suspension while mixing and cooling the reactor to 27-40° C. The reaction begins immediately and black sediments of phenylsodium are generated in the reactor. The temperature of reaction mixture is kept at 27-40° C. The chlorobenzene metallizing reaction takes approximately 1 hour. The suspension of phenylsodium is taken from the phenylsodium-conversion reactor to a reserve tank, where reaction is completed in a nitrogen atmosphere. In order to transform phenylsodium into benzylsodium, the contents of the reserve tank are placed into a benzylsodium-conversion reactor, where the suspension boils for 1-1.5 hours. While boiling, the solution's color gets brick-red and then black again. Upon completion of the reaction, the hot solution is removed from the benzylsodium-conversion reactor and placed into a cooling tank. Then as soon as possible, the cooled reaction mass is poured into crushed dry ice in a carbonation reactor and mixed. When vaporization of the CO2 is completed, 20 ml of water is added to the residue

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during cooling and mixing. The water layer is then separated and acidulated with hydrochloric acid to a pH around pH 2. The generated sediment phenylacetic acid is separated by filtration in a vacuum-filter. 12.5 g. of phenylacetic acid (92percent) with melting point 77° C. is produced. The results of other experiments are given in the Table 1. TABLE 1 Experimental results of PhAA production in the absence and presence of catalyst respectively PhAA production PhAA yields in the absence in the presence of catalyst, percent of catalyst, percent Rate of addition of Rate of addition toluene solution of of toluene solution Time of chlorobenzene and of chlorobenzene and boiling of toluene suspension of toluene suspension phenylsodium sodium, 4.3 mole/hr. of sodium, 4.3 mole/hr. in toluene, hr. 2.5 3.5 4.3 5 2.5 3.5 4.3 5 0.5 16.2 18.9 27 33 66 74 75 70 1 34.6 40.5 48 54 83.5 90 94.5 89 2 42.8 44.8 52 58 83.4 89.8 93.7 86.7 3 52.5 60.4 62.5 69 80.8 90.6 90.3 85.9 4 49.6 58.4 66.5 - 76 87 88 80.8 Table 1 shows that including a catalyst greatly increases phenylacetic-acid yield . The highest yield of the product is observed when the time of boiling in toluene equals 1 hour time. Further increase in boiling time causes a decrease in desired product field. Also, the application of a catalyst improves the stability of the results. It was also observed that the increase in catalyst amount to 0.001percent leads to a raise in yield of the desired product. Further increases in catalyst amount do not generally give an increase of the desired product. Stage 1: With sodium, chlorobenzene, Time= 1.51667 - 5.025h, T= 25 - 40 °C , Heating / reflux Stage 2: in toluene Stage 3: With hydrogenchloride, water, Product distribution / selectivity, more than 3 stages Patent; Property Development Coporation International Ltd.; US2007/10686; (2007); (A1) English View in Reaxys

O O

Rx-ID: 5053401 View in Reaxys 33/834 Yield

Conditions & References

68 %, 3 %, With hydrogen iodide, tetrakis(triphenylphosphine) palladium(0) in acetone, Time= 42h, T= 100 °C , p= 76000Torr , 20 % Carbonylation, reduction Lin, Yong-Shou; Yamamoto, Akio; Bulletin of the Chemical Society of Japan; vol. 71; nb. 3; (1998); p. 723 - 734 View in Reaxys

HO O

O O

Rx-ID: 5266176 View in Reaxys 34/834 Yield 100 %

Conditions & References With scandium(III) tris(trifluoromethylsulfonyl)methide, methoxybenzene, Time= 0.5h, T= 100 °C , debenzylation Ishihara, Kazuaki; Hiraiwa, Yukihiro; Yamamoto, Hisashi; Synlett; nb. 1; (2000); p. 80 - 82 View in Reaxys

90 %

Stage 1: With sodium methylate, Corey's ylide in tetrahydrofuran, Time= 0.666667h, T= 20 °C Stage 2: With hydrogenchloride, water in ethyl acetate Leggio, Antonella; De Marco, Rosaria; Perri, Francesca; Spinella, Mariagiovanna; Liguori, Angelo; European Journal of Organic Chemistry; nb. 1; (2012); p. 114 - 118 View in Reaxys

83 %

With methanol, sodium tetrahydroborate, NiII chloride hexahydrate, Time= 0.166667h, T= 20 °C , chemoselective reaction Khurana, Jitender M.; Arora, Reema; Synthesis; nb. 7; (2009); p. 1127 - 1130; Art.No: Z23308SS View in Reaxys

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O S

NH O

Rx-ID: 10404902 View in Reaxys 35/834 Yield

Conditions & References

60 %

With sodium hydroxide in methanol, T= 90 °C Cassidy, Michael P.; Raushel, Jessica; Fokin, Valery V.; Angewandte Chemie - International Edition; vol. 45; nb. 19; (2006); p. 3154 - 3157 View in Reaxys

Rx-ID: 728430 View in Reaxys 36/834 Yield

Conditions & References

99%

With chlorobenzene in methanol, Time= 5h, T= 40 °C , Sealed tube, Green chemistry, chemoselective reaction Volkov, Alexey; Gustafson, Karl P. J.; Tai, Cheuk-Wai; Verho, Oscar; Bäckvall, Jan-E.; Adolfsson, Hans; Angewandte Chemie - International Edition; vol. 54; nb. 17; (2015); p. 5122 - 5126; Angew. Chem.; vol. 54; nb. 17; (2015); p. 5211 - 5215,5 View in Reaxys

94.3 %

With orthophosphorus acid, methanesulfonic acid, sodium iodide in water, Time= 48h, T= 95 °C , Inert atmosphere Milne, Jacqueline E.; Storz, Thomas; Colyer, John T.; Thiel, Oliver R.; Dilmeghani Seran, Mina; Larsen, Robert D.; Murry, Jerry A.; Journal of Organic Chemistry; vol. 76; nb. 22; (2011); p. 9519 - 9524 View in Reaxys With hydrazine hydrate, anschliessend Erhitzen mit KOH Lock; ; vol. 51; (1950); p. 77 View in Reaxys With phosphorus, hydrogen iodide, T= 160 °C Claisen; Chemische Berichte; vol. 10; (1877); p. 847 View in Reaxys

O O

Rx-ID: 1659239 View in Reaxys 37/834 Yield 86 %, 91 %

Conditions & References With oxygen, zinc(II) chloride, CoCl2 in ethylene glycol dimethyl ether, Time= 28h, T= 90 °C Li, Pei; Alper, Howard; Canadian Journal of Chemistry; vol. 71; nb. 1; (1993); p. 84 - 89 View in Reaxys

91 %, 86 %

With oxygen, zinc(II) chloride, CoCl2 in ethylene glycol dimethyl ether, Time= 28h, T= 90 °C Li, Pei; Alper, Howard; Canadian Journal of Chemistry; vol. 71; nb. 1; (1993); p. 84 - 89 View in Reaxys

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Rx-ID: 3975967 View in Reaxys 38/834 Yield

Conditions & References

100 %

With diethylamine, Pd(0) (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) in water, acetonitrile, Time= 0.333333h, 2 molpercent catalyst Lemaire-Audoire; Lemaire-Audoire, Sandrine; Savignac; Savignac, Monique; Blart; Blart, Errol; Pourcelot; Pourcelot, Guy; Genet; Genet, Jean Pierre; Bernard; Bernard, Jean-Marie; Tetrahedron Letters; vol. 35; nb. 47; (1994); p. 8783 - 8786 View in Reaxys

85 %

With Montmorillonite K-10 clay, methoxybenzene, Time= 0.333333h, Microwave irradiation, Dealkylation Gajare, Anil S.; Shaikh, Nadim S.; Bonde, Bhushan K.; Deshpande, Vishnu H.; Journal of the Chemical Society, Perkin Transactions 1; nb. 5; (2000); p. 639 - 640 View in Reaxys

80 %

With sulphated SnO2, methoxybenzene in toluene, Time= 12h, Heating Chavan, Subhash P.; Zubaidha; Dantale, Shubhada W.; Keshavaraja; Ramaswamy; Ravindranathan; Tetrahedron Letters; vol. 37; nb. 2; (1996); p. 237 - 240 View in Reaxys

HO O

O O

Rx-ID: 5054009 View in Reaxys 39/834 Yield

Conditions & References

70 %, 6 %, With hydrogen iodide, tetrakis(triphenylphosphine) palladium(0) in acetone, Time= 42h, T= 100 °C , p= 76000Torr , 18 % Carbonylation, reduction Lin, Yong-Shou; Yamamoto, Akio; Bulletin of the Chemical Society of Japan; vol. 71; nb. 3; (1998); p. 723 - 734 View in Reaxys

S S

Rx-ID: 8585996 View in Reaxys 40/834 Yield 87.4 %

Conditions & References With lithium perchlorate in acetonitrile, T= 20 °C , Electrochemical reaction, Oxidation Barnhurst, Loren A.; Wan, Yongqin; Kutateladze, Andrei G.; Organic Letters; vol. 2; nb. 6; (2000); p. 799 - 801 View in Reaxys

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OH HO

Cl Cl

Rx-ID: 28456087 View in Reaxys 41/834 Yield

Conditions & References

92 %

Stage 1: With sodium hydroxide in tert-butyl alcohol, Time= 0.166667h, T= 30 °C Stage 2: With sodium tetrahydroborate in tert-butyl alcohol Cafiero, Lauren R.; Snowden, Timothy S.; Organic Letters; vol. 10; nb. 17; (2008); p. 3853 - 3856 View in Reaxys

HO C O

Rx-ID: 37758553 View in Reaxys 42/834 Yield 11 %

Conditions & References 2-Phenyl-3-(1,1,3,3-tetramethyl-2-ylidene)propenoic acid (S16) The solid dichloroalkene 6 (153 mg, 0.60 mmol) was added to an ice-cooled, red solution of PhCH2K (S11, max. 3.0 mmol) [S11] in anhydrous THF (2.0 mL) under argon gas cover. The instantaneously blackened mixture was stirred at rt for 30 min, then poured onto solid CO2, warmed up, and dissolved in aqueous NaOH and Et2O. The aqueous layer waswashed with Et2O, acidified with conc. hydrochloric acid, and extracted with Et2O which afforded the crude acid S16 together with phenylacetic acid. Crystallizationfrom CCl4 yielded colorless S16 (11percent) Stage 1: With n-butyllithium, potassium tert-butylate Stage 2: in tetrahydrofuran, Time= 0.5h, T= 20 °C , Inert atmosphere Stage 3: in tetrahydrofuran, Heating Knorr, Rudolf; Menke, Thomas; Freudenreich, Johannes; Pires, Claudio; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 307 - 315 View in Reaxys

O O

Rx-ID: 11282031 View in Reaxys 43/834 Yield 82 %, 8 %

Conditions & References 4.3. General procedure for the oxidation of the long chainalcohol 3a-3h General procedure: Under Oxygen atmosphere, alcohol (2 mmol), precatalyst(SIMesHCl or SIPrHCl, 0.06 mmol), NaOtBu (960.5 mg, 10 mmol),and 1 g 3 A molecular sieve were added to dichloromethane(20 mL). This solution was allowed to stir for 30 h. After filtratingthrough a pad of Celite, the cake was added to hydrochloric acid(2N, 50 mL) and extracted with ethyl acetate (50 mL3). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. With oxygen, sodium t-butanolate, (1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1Himidazol-2-ylidene)·HCl in dichloromethane, Time= 30h, T= 20 °C , Molecular sieve, Reagent/catalyst Yu, Dong-Fang; Xing, Ping; Jiang, Biao; Tetrahedron; vol. 71; nb. 25; (2015); p. 4269 - 4273 View in Reaxys

34 % Spectr., 19 % Spectr.

With sodium hydroxide, T= 50 °C , Electrochemical reaction, Product distribution, Further Variations: Temperatures Lyalin; Petrosyan; Russian Chemical Bulletin; vol. 56; nb. 3; (2007); p. 499 - 503 View in Reaxys

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HO Se

Rx-ID: 28346102 View in Reaxys 44/834 Yield

Conditions & References

88 %

Stage 1: With AlCl3, aluminium chloride, zinc in acetonitrile, Time= 1.25h, T= 70 °C , p= 760.051Torr , Neutral Stage 2: in acetonitrile, Time= 12h, T= 70 °C , p= 760.051Torr , Neutral Nazari, Mohammad; Movassagh, Barahman; Tetrahedron Letters; vol. 50; nb. 4; (2009); p. 438 - 441 View in Reaxys

Se Se

Rx-ID: 28346107 View in Reaxys 45/834 Yield

Conditions & References

92 %

Stage 1: With AlCl3, aluminium chloride, zinc in acetonitrile, Time= 1.25h, T= 70 °C , p= 760.051Torr , Neutral Stage 2: in acetonitrile, Time= 5.5h, T= 70 °C , p= 760.051Torr , Neutral Nazari, Mohammad; Movassagh, Barahman; Tetrahedron Letters; vol. 50; nb. 4; (2009); p. 438 - 441 View in Reaxys

HO O

N Cl

O O

Rx-ID: 40460126 View in Reaxys 46/834 Yield

Conditions & References

69 %, 4 %

Three-component coupling reaction of benzylic halides 1 or allylic bromides 5, carbon dioxide and DMF: general procedure General procedure: A solution of halide 1 or 5 (1 mmol) in anhyd DMF (16 mL) containing Bu4NBF4 (0.1M) was electrolyzed at 0°C with a constant current (20 mA / cm2, 10 mA / cm2 for 1b-1d) under atmospheric pressure of bubbling carbon dioxide. A test tube-like (ca. 26 mmΦ) undivided cell equipped with a Pt plate cathode (2x2 cm2) and a Pt wire anode (1.0 mmΦ, ca. 20 mm) was used for the electrolysis. After an appropriate amount of electricity had been passed (shown in the tables and schemes), the electrolyzed solution was poured into 30 mL of Et2O and then 50 mL of satd brine was added. The organic layer was separated and the resulting aqueous solutionwas extracted with Et2O (30 mLx2). The combined ethereal solution was washed with satd NaHCO3 (30 mL) and dried over MgSO4. Evaporation of the solvent gave a crude product, which was purified by column chromatography on silica gel (hexane / ethyl acetate1 / 1, hexane / ethyl acetate 2 / 3 for 2d) to give coupling products 2, 6, and 7. With tetra-n-butylammonium tetrafluoroborate, N-ethyl-N,N-diisopropylamine, T= 0 °C , Electrolysis, Electrochemical reaction, Reagent/catalyst Senboku, Hisanori; Nagakura, Kotaro; Fukuhara, Tsuyoshi; Hara, Shoji; Tetrahedron; vol. 71; nb. 23; (2015); p. 3850 - 3856 View in Reaxys

N+

HO O

I–

N+

Rx-ID: 40681515 View in Reaxys 47/834

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Yield

Conditions & References

92.6 %

With sodium sulfate, ascorbic acid powder in chloroform-d1, water-d2, acetonitrile, Time= 1h, T= 20 °C , UV-irradiation, Concentration, Reagent/catalyst Kunsberg, David J.; Kipping, Allison H.; Falvey, Daniel E.; Organic Letters; vol. 17; nb. 14; (2015); p. 3454 3457 View in Reaxys

HO C

Rx-ID: 2394491 View in Reaxys 48/834 Yield

Conditions & References

93 %

With [RhCl(η2:η2-cycloocta-1,5-diene)]2, potassium iodide in formic acid, Time= 18h, T= 60 °C , p= 760Torr , Carbonylation Giroux; Nadeau; Han; Tetrahedron Letters; vol. 41; nb. 40; (2000); p. 7601 - 7604 View in Reaxys

89 %

With NaCo(CO)4, phenylmethyltriethylammonium bromide, Time= 2h, T= 50 °C Satyanarayana, Nistala; Periasamy, Mariappan; Journal of Organometallic Chemistry; vol. 333; (1987); p. C33 C36 View in Reaxys

88 %

With [Co(triphenylphosphane)2Cl2], tetrabutylammomium bromide in benzene, Time= 8h, other benzyl halides, var. phase transfer catalysts, var. temp., Mechanism Hu; Wang; Cui; Synthetic Communications; vol. 24; nb. 12; (1994); p. 1743 - 1748 View in Reaxys

88 %

With sodium hydroxide, sodium tetrahydroborate in tetrahydrofuran, Time= 3h, T= 55 °C Satyanarayana, N.; Periasamy, M.; Tetrahedron Letters; vol. 28; nb. 23; (1987); p. 2633 - 2636 View in Reaxys

80 %

With pentacarbonyliron(0), water, tetra(n-butyl)ammonium hydrogensulfate in dichloromethane, p= 30400Torr Laurent, Pascale; Tanguy, Guy; Abbayes, Herve des; Journal of the Chemical Society, Chemical Communications; nb. 24; (1986); p. 1754 - 1756 View in Reaxys With sodium hydroxide, tetracarbonylcobaltate(1-) ion, N-hexadecyl-N,N,N-trimethylammonium bromide in water, toluene, p= 760Torr , Ambient temperature Arzoumanian, Henri; Petrignani, Jean-Francois; Tetrahedron Letters; vol. 27; nb. 49; (1986); p. 5979 - 5980 View in Reaxys

69 %Chromat.

With water, palladium diacetate, Time= 4h, T= 110 °C , p= 37503.8Torr , Ionic liquid Lapidus, Albert L.; Eliseev, Oleg L.; Bondarenko, Tatyana N.; Chau, Nguen H.; Kazantsev, Ruslan V.; Mendeleev Communications; vol. 19; nb. 5; (2009); p. 256 - 257 View in Reaxys

N O

Rx-ID: 2590250 View in Reaxys 49/834

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Yield

Conditions & References

91 %

With lithium hydroxide in tetrahydrofuran, Time= 1h, T= 25 °C Flynn, Daniel L.; Zelle, Robert E.; Grieco, Paul A.; Journal of Organic Chemistry; vol. 48; nb. 14; (1983); p. 2424 2426 View in Reaxys

HO O

H 2N

Rx-ID: 2947633 View in Reaxys 50/834 Yield

Conditions & References

87 % Turn- With air, Na5PV2Mo10O40 on activated carbon in toluene, Time= 7h, T= 100 °C , p= 760Torr ov. Neumann, Ronny; Levin, Michal; Journal of Organic Chemistry; vol. 56; nb. 19; (1991); p. 5707 - 5710 View in Reaxys

HO O

Rx-ID: 4733809 View in Reaxys 51/834 Yield

Conditions & References

85 %

With acetic acid, sodium nitrite in dimethyl sulfoxide, T= 35 °C Matt, Christophe; Wagner, Alain; Mioskowski, Charles; Journal of Organic Chemistry; vol. 62; nb. 2; (1997); p. 234 - 235 View in Reaxys I HO

Rx-ID: 4870982 View in Reaxys 52/834 Yield

Conditions & References

87 %

With 2,2'-azo-bisisobutyronitrile, triphenylstannane, sodium hydrogencarbonate in water, Time= 6h, T= 90 °C Sarma, Koushik Das; Maitra, Uday; Tetrahedron; vol. 54; nb. 19; (1998); p. 4965 - 4976 View in Reaxys Stage 1: With potassium tert-butylate, adamantan-1-yl-ethan-1-one in ammonia, Time= 1h, Inert atmosphere, Cooling, Irradiation, liquid NH3 Stage 2: With nitric acid in water, pH= Ca. 1 Guastavino, Javier F.; Buden, Maria E.; Garcia, Carolina S.; Rossi, Roberto A.; Arkivoc; vol. 2011; nb. 7; (2011); p. 389 - 405 View in Reaxys

O N

N + CH –

HO O

Rx-ID: 164636 View in Reaxys 53/834 Yield 78 %

Conditions & References With water, Time= 24h, T= 27 °C , Irradiation, Wolff Rearrangement Bernardim, Barbara; Hardman-Baldwin, Andrea M.; Burtoloso, Antonio C. B.; RSC Advances; vol. 5; nb. 18; (2015); p. 13311 - 13314 View in Reaxys

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With 1,4-dioxane, Irradiation.UV-Licht Patent; Farbw. Hoechst; DE915214; (1951) View in Reaxys With sodium thiosulfate, silver(l) oxide, T= 50 - 60 °C Wolff; Justus Liebigs Annalen der Chemie; vol. 394; (1912); p. 44 View in Reaxys With silver(l) oxide in 1,4-dioxane, Rearrangement Young, Jonathan R.; Huang, Song X.; Chen, Irene; Walsh, Thomas F.; DeVita, Robert J.; Wyvratt Jr., Matthew J.; Goulet, Mark T.; Ren, Ning; Lo, Jane; Yang, Yi Tien; Yudkovitz, Joel B.; Cheng, Kang; Smith, Roy G.; Bioorganic and Medicinal Chemistry Letters; vol. 10; nb. 15; (2000); p. 1723 - 1727 View in Reaxys

HO O

Rx-ID: 750314 View in Reaxys 54/834 Yield

Conditions & References With phenyl-sodium, Petroleum ether, anschliessendes Behandeln mit festem Kohlendioxid Gilman; Pacevitz; Baine; Journal of the American Chemical Society; vol. 62; (1940); p. 1514,1519 View in Reaxys Gilman; Pacevitz; Journal of the American Chemical Society; vol. 62; (1940); p. 673 View in Reaxys With sodium, (nC5H11)2Hg, Schuetteln des Reaktionsgemisches mit Kohlendioxid Morton; Hechenbleikner; Journal of the American Chemical Society; vol. 58; (1936); p. 1024,2599,2604 View in Reaxys With pentyl sodium, Petroleum ether, T= 40 - 45 °C , anschliessendes Behandeln mit festem Kohlendioxid Morton; Hechenbleikner; Journal of the American Chemical Society; vol. 58; (1936); p. 2599,2604 View in Reaxys Morton; Little; Strong; Journal of the American Chemical Society; vol. 65; (1943); p. 1339,1345 View in Reaxys With phenyl-sodium, anschliessend Behandeln mit CO2 Nobis; Moormeier; Industrial and Engineering Chemistry; vol. 46; (1954); p. 539,543 View in Reaxys With caesium, anschliessend Behandeln mit CO2 de Postis; View in Reaxys With Na2O, potassium, T= 90 °C , anschliessend Behandeln mit CO2 Claff; Morton; Journal of Organic Chemistry; vol. 20; (1955); p. 981,984 View in Reaxys With sodium-potassium alloy, ethyl-lithium, anschliessend Behandeln mit CO2 Bryce-Smith; Journal of the Chemical Society; (1954); p. 1079,1080, 1084 View in Reaxys With octane, pentyl sodium, T= 30 - 35 °C , anschliessendes Behandeln mit festem Kohlendioxid Morton; Hechenbleikner; Journal of the American Chemical Society; vol. 58; (1936); p. 2599,2604 View in Reaxys

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Morton; Little; Strong; Journal of the American Chemical Society; vol. 65; (1943); p. 1339,1345 View in Reaxys With carbon dioxide, sodium, diethyl mercure Schorigin; Chemische Berichte; vol. 41; (1908); p. 2717,2723; Chemische Berichte; vol. 43; (1910); p. 1931 View in Reaxys Reaction Steps: 2 1: Pd(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)Cl2; di-tert-butyl peroxide / 16 h / 120 °C / 7600.51 Torr 2: water; sodium hydroxide / 1,4-dioxane / 2 h / 60 °C / pH 10 - 14 With di-tert-butyl peroxide, Pd(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)Cl2, water, sodium hydroxide in 1,4-dioxane Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); (A1) English View in Reaxys Reaction Steps: 2 1: Pd(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)Cl2; di-tert-butyl peroxide / 16 h / 120 °C / 7600.51 Torr 2: water; sodium hydroxide / 1,4-dioxane / 2 h / 60 °C / pH 10 - 14 With di-tert-butyl peroxide, Pd(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)Cl2, water, sodium hydroxide in 1,4-dioxane Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); (A1) English View in Reaxys Reaction Steps: 2 1: Pd(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)Cl2; di-tert-butyl peroxide / 16 h / 120 °C / 7600.51 Torr 2: water; sodium hydroxide / 1,4-dioxane / 2 h / 60 °C / pH 10 - 14 With di-tert-butyl peroxide, Pd(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)Cl2, water, sodium hydroxide in 1,4-dioxane Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); (A1) English View in Reaxys Reaction Steps: 2 1: Pd(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)Cl2; di-tert-butyl peroxide / 16 h / 120 °C / 7600.51 Torr 2: water; sodium hydroxide / 1,4-dioxane / 2 h / 60 °C / pH 10 - 14 With di-tert-butyl peroxide, Pd(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)Cl2, water, sodium hydroxide in 1,4-dioxane Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); (A1) English View in Reaxys Reaction Steps: 2 1: Pd(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)Cl2; di-tert-butyl peroxide / 16 h / 120 °C / 7600.51 Torr 2: water; sodium hydroxide / 1,4-dioxane / 2 h / 60 °C / pH 10 - 14 With di-tert-butyl peroxide, Pd(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)Cl2, water, sodium hydroxide in 1,4-dioxane Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); (A1) English View in Reaxys Reaction Steps: 2 1: Pd(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)Cl2; di-tert-butyl peroxide / 16 h / 120 °C / 7600.51 Torr 2: water; sodium hydroxide / 1,4-dioxane / 2 h / 60 °C / pH 10 - 14 With di-tert-butyl peroxide, Pd(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)Cl2, water, sodium hydroxide in 1,4-dioxane

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Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); (A1) English View in Reaxys Reaction Steps: 2 1: Pd(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)Cl2; di-tert-butyl peroxide / toluene / 16 h / 120 °C / 7600.51 Torr 2: water; sodium hydroxide / 1,4-dioxane / 2 h / 60 °C / pH 10 - 14 With di-tert-butyl peroxide, Pd(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)Cl2, water, sodium hydroxide in 1,4-dioxane, toluene Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); (A1) English View in Reaxys

N+

Cl –

Rx-ID: 2002577 View in Reaxys 55/834 Yield

Conditions & References

85 %

With sodium hydroxide, dicobalt octacarbonyl, T= 65 °C , Irradiation Brunet, Jean-Jaques; Sidot, Christian; Caubere, Paul; Journal of Organic Chemistry; vol. 48; nb. 11; (1983); p. 1919 - 1921 View in Reaxys

Br–

N+

Rx-ID: 2002673 View in Reaxys 56/834 Yield 85 %

Conditions & References With sodium hydroxide, dicobalt octacarbonyl, T= 65 °C , Irradiation Brunet, Jean-Jaques; Sidot, Christian; Caubere, Paul; Journal of Organic Chemistry; vol. 48; nb. 11; (1983); p. 1919 - 1921 View in Reaxys

Rx-ID: 2013369 View in Reaxys 57/834 Yield 100 %

Conditions & References With 2,2,6,6-tetramethyl-piperidine-N-oxyl, sodium hypochlorite, sodium chlorite in acetonitrile, T= 35 °C , pH 6.7 Zhao; Li; Mano; Song; Tschaen; Grabowski; Reider; Journal of Organic Chemistry; vol. 64; nb. 7; (1999); p. 2564 - 2566 View in Reaxys

98 %

With hydrochlorid acid, 2,2,6,6-tetramethyl-piperidine-N-oxyl, Amberlite IRA 900 chlorite in dichloromethane, Time= 4h, T= 20 °C Kloth, Katrin; Bruenjes, Marco; Kunst, Eike; Joege, Thomas; Gallier, Florian; Adibekian, Alexander; Kirschning, Andreas; Advanced Synthesis and Catalysis; vol. 347; nb. 10; (2005); p. 1423 - 1434 View in Reaxys

96 %

With chromium(VI) oxide, periodic acid in water, acetonitrile, T= 0 °C Zhao, Mangzhu; Li, Jing; Song, Zhiguo; Desmond, Richard; Tschaen, David M.; Grabowski, Edward J. J.; Reider, Paul J.; Tetrahedron Letters; vol. 39; nb. 30; (1998); p. 5323 - 5326

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View in Reaxys 96 %

With chromium(VI) oxide, periodic acid in water, acetonitrile, T= 0 °C , oxidation of various alcohols, Product distribution Zhao, Mangzhu; Li, Jing; Song, Zhiguo; Desmond, Richard; Tschaen, David M.; Grabowski, Edward J. J.; Reider, Paul J.; Tetrahedron Letters; vol. 39; nb. 30; (1998); p. 5323 - 5326 View in Reaxys

93 %

With ruthenium trichloride, sodium periodate in ethyl acetate, acetonitrile, Time= 2h, T= 20 °C , Oxidation Prashad, Mahavir; Lu, Yansong; Kim, Hong-Yong; Hu, Bin; Repic, Oljan; Blacklock, Thomas J.; Synthetic Communications; vol. 29; nb. 17; (1999); p. 2937 - 2942 View in Reaxys

91 %

With sodium tetrahydroborate, 1 Pd/C, water, potassium hydroxide in methanol, Time= 17h, T= 20 °C , In air An, Gwangil; Ahn, Hyunseok; De Castro, Kathlia A.; Rhee, Hakjune; Synthesis; nb. 3; (2010); p. 477 - 485; Art.No: F19009SS View in Reaxys

90 %

Stage 1: With C29H44Cl2N2Ru, sodium hydroxide in water, Time= 24h, Reflux Stage 2: With hydrochlorid acid in water Malineni, Jagadeesh; Keul, Helmut; Möller, Martin; Dalton Transactions; vol. 44; nb. 39; (2015); p. 17409 - 17414 View in Reaxys

78 %

Stage 1: With C20H28ClN2OPRu, water, sodium hydroxide, Time= 18h, Inert atmosphere, Reflux Stage 2:Acidic conditions Balaraman, Ekambaram; Khaskin, Eugene; Leitus, Gregory; Milstein, David; Nature Chemistry; vol. 5; nb. 2; (2013); p. 122 - 125 View in Reaxys

40 %

With Sodium bromate, hydrogen bromide, tert-butanol in tetrachloromethane, water, Time= 2h, Ambient temperature Veeraiah, T.; Periasamy, M.; Synthetic Communications; vol. 19; nb. 11-12; (1989); p. 2151 - 2158 View in Reaxys With acetobacter sp. ALEG in water, Time= 3h Gandolfi, Raffaella; Ferrara, Nicola; Molinari, Francesco; Tetrahedron Letters; vol. 42; nb. 3; (2001); p. 513 - 514 View in Reaxys

33 % Chromat.

With N -hydroxyphthalimide, oxygen, benzaldehyde, CoNiCr in acetic acid, Time= 7h, T= 22 °C , p= 750.06Torr De Vondervoort, Lizette Schmieder-van; Bouttemy, Sabine; Heu, Ferdinand; Weissenboeck, Kurt; Alsters, Paul L.; European Journal of Organic Chemistry; nb. 3; (2003); p. 578 - 586 View in Reaxys With ruthenium trichloride, (NH4)2Ce(NO3)2, nitric acid in acetonitrile, T= 24.85 °C , Kinetics Rao, N. Vijaya Bhaskar; Rao, M. Anand; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 44; nb. 1; (2005); p. 80 - 84 View in Reaxys

86 % Chromat.

With NADH oxidase, nicotinamide adenine dinucleotide, 2-phenylethanol dehydrogenase, phenylacetaldehyde dehydrogenase, Time= 12h, T= 25 °C , p= 760.051Torr , pH= 9.0 Hirano, Jun-ichiro; Miyamoto, Kenji; Ohta, Hiromichi; Tetrahedron Letters; vol. 49; nb. 7; (2008); p. 1217 - 1219 View in Reaxys With Oxonereg; in water, Time= 21h, T= 70 °C , chemoselective reaction Wu, Shang; Ma, Hengchang; Lei, Ziqiang; Synlett; nb. 18; (2010); p. 2818 - 2822 View in Reaxys Reaction Steps: 2

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1: oxygen / 5 h / 120 °C / Neat (no solvent) 2: oxygen / 5 h / 120 °C / Neat (no solvent) With oxygen Choudhary, Vasant R.; Dumbre, Deepa K.; Catalysis Communications; vol. 13; nb. 1; (2011); p. 82 - 86 View in Reaxys With Acetobacter sp. MIM 2000/61 in water, Time= 1h, T= 28 °C , pH= 7.5, phosphate buffer, Enzymatic reaction Zambelli, Paolo; Pinto, Andrea; Romano, Diego; Crotti, Elena; Conti, Paola; Tamborini, Lucia; Villa, Raffaella; Molinari, Francesco; Green Chemistry; vol. 14; nb. 8; (2012); p. 2158 - 2161 View in Reaxys With (n-Bu4N)4W10O32, hydrogen peroxide in water, 1,2-DICHLOROETHANE, Time= 0.25h, T= 80 °C , Microwave irradiation, Catalytic behavior, Time Galica, Mateusz; Kasprzyk, Wiktor; Bednarz, Szczepan; Bogdal, Dariusz; Chemical Papers; vol. 67; nb. 9; (2013); p. 1240 - 1244 View in Reaxys With oxygen in toluene, Time= 24h, T= 100 °C , p= 7500.75Torr Wang, Min; Wang, Feng; Ma, Jiping; Chen, Chen; Shi, Song; Xu, Jie; Chemical Communications; vol. 49; nb. 59; (2013); p. 6623 - 6625 View in Reaxys With Ir(III) chloride, cerium(IV) sulphate, sulfuric acid, acetic acid, T= 35 °C , Kinetics, Concentration Tandon, Praveen K.; Dwivedi, Priv B.; Singh, Santosh B.; Yadav, Suresh C.; Journal of the Indian Chemical Society; vol. 90; nb. 12; (2013); p. 2237 - 2245 View in Reaxys With E. coli perisplasmic aldehyde oxidase, F. graminearum galactose oxidase, catalase in aq. phosphate buffer, acetonitrile, Time= 10h, T= 37 °C , pH= 7, Enzymatic reaction McKenna, Shane M.; Leimkühler, Silke; Herter, Susanne; Turner, Nicholas J.; Carnell, Andrew J.; Green Chemistry; vol. 17; nb. 6; (2015); p. 3271 - 3275 View in Reaxys

O N

Rx-ID: 5092765 View in Reaxys 58/834 Yield

Conditions & References

96 %, 60 %

With nitric acid in dichloromethane, Time= 2h, T= 0 °C Strazzolini, Paolo; Dali'Arche, Maria Grazia; Giumanini, Angelo G.; Tetrahedron Letters; vol. 39; nb. 50; (1998); p. 9255 - 9258 View in Reaxys

92 %

With sulfuric acid, potassium nitrate in dichloromethane, Time= 2h, T= 0 °C Strazzolini, Paolo; Giumanini, Angelo G.; Runcio, Antonio; Tetrahedron Letters; vol. 42; nb. 7; (2001); p. 1387 1389 View in Reaxys

HO C

O O HO

Rx-ID: 8628185 View in Reaxys 59/834

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Yield

Conditions & References

40.2 %, 11.0 %

With CaO, cobalt pyridine-2-carboxylate tetrahydrate in methanol, water, Time= 10h, T= 59.85 °C , p= 22501.8Torr , Carbonylation Guang-Xing; Han-Min; Fu-Ming; Synthetic Communications; vol. 30; nb. 19; (2000); p. 3585 - 3588 View in Reaxys

H O

H+

Rx-ID: 9006702 View in Reaxys 60/834 Yield

Conditions & References

75 %, 25 %

With 9,10-anthracenedicarbonitrile, oxygen, trifluoroacetic acid, scandium tris(trifluoromethanesulfonate) in acetonitrile-D3, Time= 1h, T= 24.85 °C , Irradiation Fukuzumi, Shunichi; Fujita, Shunsuke; Suenobu, Tomoyoshi; Imahori, Hiroshi; Araki, Yasuyuki; Ito, Osamu; Journal of Physical Chemistry A; vol. 106; nb. 7; (2002); p. 1465 - 1472 View in Reaxys

(1-{benzyl[4-(N'-phenylacetyl-hydrazinomethyl)-benzyl]-amino}ethyl)-terminated poly(acrylamide-co-ethylene glycol)+ HO

{1-[benzyl-(4-hydrazinomethyl-benzyl)-amino]-ethyl}-terminated poly(acrylamide-co-ethylene glycol)+

Rx-ID: 9950716 View in Reaxys 61/834 Yield

Conditions & References

60 %

With penicillin G amidase in phosphate buffer, Time= 24h, T= 30 °C , pH= 8.0 Basso, Alessandra; Ebert, Cynthia; Gardossi, Lucia; Linda, Paolo; Phuong, Thao Tran; Zhu, Mingzhao; Wessjohann, Ludger; Advanced Synthesis and Catalysis; vol. 347; nb. 7-8; (2005); p. 963 - 966 View in Reaxys 2

K+

HO C

O Cl

O O–

O–

Rx-ID: 11217626 View in Reaxys 62/834 Yield

Conditions & References

95 %

With potassium hydroxide, dicobalt octacarbonyl, benzyl chloride in methanol, T= 55 - 62 °C , p= 760.051 1140.08Torr Zhesko; Boyarskii; Nikitina; Russian Journal of Applied Chemistry; vol. 80; nb. 6; (2007); p. 945 - 950 View in Reaxys

HO C

Ca 2+

O O– O

Rx-ID: 11217627 View in Reaxys 63/834 Yield 85 %

Conditions & References With calcium hydroxide powder, dicobalt octacarbonyl in isopropyl alcohol, T= 35 - 40 °C , p= 760.051 - 3800.26Torr Zhesko; Boyarskii; Nikitina; Russian Journal of Applied Chemistry; vol. 80; nb. 6; (2007); p. 945 - 950

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View in Reaxys

NH 2

Rx-ID: 23068976 View in Reaxys 64/834 Yield

Conditions & References 7 : EXAMPLE 7; Selective hydrolysis catalyzed by penicillin acylase in different buffers Three sets of reactions were prepared generally as follows. For reactions in buffered media, APN-phenylacetamide was transferred to a 2.5 mL glass vial and to this vial, penicillin acylase (PGA-450) was added followed by the addition of buffer. For reactions in buffer-solvent mixtures, APN-phenylacetamide was dissolved in a solvent/water mixture and a calculated amount of this solution was transferred to the vial following the addition of the enzyme, penicillin acylase (PGA-450) to make up the volume to 1.0 mL, and the contents were stirred continuously with a magnetic stirrer. [0061] The progress of the hydrolysis reaction was followed by determining the concentrations OF 3-AMINOPENTANENITRILE phenylacetamide and phenylacetic acid formed at different time intervals with an HPLC. The reaction mixture after diluting with acetonitrile was injected on to a PHENOMENEX C18 column (PHENOMENEX is a trademark of Phenomenex, Torrence, CA) and eluting with acetonitrile: water mixture (40: 60) both containing (0.1percent perchloric acid) following the elution profile with a UV detector at 254 nm. [0062] A study (TABLE 7A) indicates that APN-phenylacetamide can be hydrolyzed by penicillin acylase in the presence of a polar solvent, such as acetonitrile. The results show that penicillin acylase is more active towards hydrolysis of S-APN-phenylacetamide, producing enantiomeric excess of S-APN, leaving R-APN-phenylacetamide unreacted. In this particular study, 0.1 M APN-phenylacetamide was used. The pH was adjusted with 0.5 M of phosphate or bicarbonate buffer. The analysis was carried out after 18 hours. With water, penicillin acylase PGA-450, Time= 18h, pH= 6.0 - 9.0, Aqueous phosphate buffer, Aqueous bicarbonate buffer, Reactivity Patent; PCBU SERVICES, INC.; WO2004/58701; (2004); (A2) English View in Reaxys 7 : EXAMPLE 7; Selective hydrolysis catalyzed by penicillin acylase in different buffers Three sets of reactions were prepared generally as follows. For reactions in buffered media, APN-phenylacetamide was transferred to a 2.5 mL glass vial and to this vial, penicillin acylase (PGA-450) was added followed by the addition of buffer. For reactions in buffer-solvent mixtures, APN-phenylacetamide was dissolved in a solvent/water mixture and a calculated amount of this solution was transferred to the vial following the addition of the enzyme, penicillin acylase (PGA-450) to make up the volume to 1.0 mL, and the contents were stirred continuously with a magnetic stirrer. [0061] The progress of the hydrolysis reaction was followed by determining the concentrations OF 3-AMINOPENTANENITRILE phenylacetamide and phenylacetic acid formed at different time intervals with an HPLC. The reaction mixture after diluting with acetonitrile was injected on to a PHENOMENEX C18 column (PHENOMENEX is a trademark of Phenomenex, Torrence, CA) and eluting with acetonitrile: water mixture (40: 60) both containing (0.1percent perchloric acid) following the elution profile with a UV detector at 254 nm. [0062] A study (TABLE 7A) indicates that APN-phenylacetamide can be hydrolyzed by penicillin acylase in the presence of a polar solvent, such as acetonitrile. The results show that penicillin acylase is more active towards hydrolysis of S-APN-phenylacetamide, producing enantiomeric excess of S-APN, leaving R-APN-phenylacetamide unreacted. In this particular study, 0.1 M APN-phenylacetamide was used. The pH was adjusted with 0.5 M of phosphate or bicarbonate buffer. The analysis was carried out after 18 hours. With water, penicillin acylase PGA-450 in acetonitrile, Time= 18h, pH= 6.0 - 9.0, Aqueous phosphate buffer, Aqueous bicarbonate buffer, Reactivity Patent; PCBU SERVICES, INC.; WO2004/58701; (2004); (A2) English View in Reaxys 7 :The study in TABLE 7C indicates that selective hydrolysis of APN- phenylacetamide may be performed in a twophase solvent system at relatively low pH (4.7- 6.0). In this study, the reactions were buffered by phosphate (pH=6.0), acetate (pH=4.7), citrate (pH=5.5) and formate (pH=5. 5X). 10 mg PGA-450,0. 02 mL buffer solution (0.5 M), and 65 LLMOLES OF APN-PHENYLACETAMIDE were present in each vial. A two phase solvent system containing 1: 1 ratio of MTBE to aqueous phase was used. The product from aqueous phase was analyzed (percent EES-APN WAS determined).

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With water, penicillin acylase PGA-450 in tert-butyl methyl ether, Time= 18h, T= 10 - 40 °C , pH= 4.7, Aqueous acetate buffer, Reactivity Patent; PCBU SERVICES, INC.; WO2004/58701; (2004); (A2) English View in Reaxys 7 :The study in TABLE 7C indicates that selective hydrolysis of APN- phenylacetamide may be performed in a twophase solvent system at relatively low pH (4.7- 6.0). In this study, the reactions were buffered by phosphate (pH=6.0), acetate (pH=4.7), citrate (pH=5.5) and formate (pH=5. 5X). 10 mg PGA-450,0. 02 mL buffer solution (0.5 M), and 65 LLMOLES OF APN-PHENYLACETAMIDE were present in each vial. A two phase solvent system containing 1: 1 ratio of MTBE to aqueous phase was used. The product from aqueous phase was analyzed (percent EES-APN WAS determined). With water, penicillin acylase PGA-450 in tert-butyl methyl ether, Time= 18h, T= 10 - 40 °C , pH= 5.5, Aqueous citrate buffer, Reactivity Patent; PCBU SERVICES, INC.; WO2004/58701; (2004); (A2) English View in Reaxys 7 :The study in TABLE 7C indicates that selective hydrolysis of APN- phenylacetamide may be performed in a twophase solvent system at relatively low pH (4.7- 6.0). In this study, the reactions were buffered by phosphate (pH=6.0), acetate (pH=4.7), citrate (pH=5.5) and formate (pH=5. 5X). 10 mg PGA-450,0. 02 mL buffer solution (0.5 M), and 65 LLMOLES OF APN-PHENYLACETAMIDE were present in each vial. A two phase solvent system containing 1: 1 ratio of MTBE to aqueous phase was used. The product from aqueous phase was analyzed (percent EES-APN WAS determined). With water, penicillin acylase PGA-450 in tert-butyl methyl ether, Time= 18h, T= 10 - 40 °C , pH= 5.5, Aqueous formate buffer, Reactivity Patent; PCBU SERVICES, INC.; WO2004/58701; (2004); (A2) English View in Reaxys 7 :The study in TABLE 7C indicates that selective hydrolysis of APN- phenylacetamide may be performed in a twophase solvent system at relatively low pH (4.7- 6.0). In this study, the reactions were buffered by phosphate (pH=6.0), acetate (pH=4.7), citrate (pH=5.5) and formate (pH=5. 5X). 10 mg PGA-450,0. 02 mL buffer solution (0.5 M), and 65 LLMOLES OF APN-PHENYLACETAMIDE were present in each vial. A two phase solvent system containing 1: 1 ratio of MTBE to aqueous phase was used. The product from aqueous phase was analyzed (percent EES-APN WAS determined). With water, penicillin acylase PGA-450 in tert-butyl methyl ether, Time= 18h, T= 10 - 40 °C , pH= 6, Aqueous phosphate buffer, Reactivity Patent; PCBU SERVICES, INC.; WO2004/58701; (2004); (A2) English View in Reaxys 7 :The study (TABLE 7B) indicates that the selective hydrolysis of APN- phenylacetamide may also be performed using a solvent including MTBE. The pH of the reaction may also varied from about 6 to about 9. In this particular experiment, 65 moles APN-phenylacetamide was used with 10 mg of the enzyme, PGA-450. The reactions were buffered with 0.025 mL of 0.5 M solution of phosphate and bicarbonate. For percent ee determination, the solvent of the reaction mixture was dried under a stream of nitrogen, water was added to make up the volume to 1.0 mL, and analyzed by HPLC. With water, penicillin acylase PGA-450 in tert-butyl methyl ether, Time= 18h, T= 25 - 45 °C , pH= 6.0 - 9.0, Aqueous phosphate buffer, Aqueous bicarbonate buffer, Reactivity Patent; PCBU SERVICES, INC.; WO2004/58701; (2004); (A2) English View in Reaxys H HO

borane-THF

Rx-ID: 23987641 View in Reaxys 65/834

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Yield

Conditions & References 2 : Example 2 Example 2 A (4.2 g, 11.3 mmol) was placed in a 100 mL round-bottomed flask and dissolved in NEt3 (50 mL). To this solution was added Pd(PPh3)2Cl2 (0.16 g, 0.23 mmol), CuI (21 mg, 0.12 mmol), and trimethylsilylacetylene (1.38 g, 13.5 mmol). This mixture was stirred at room temp for 14 hr. The reaction mixture was quenched by the addition of 1 N HCl (100 mL). The solution was then extracted 3* with EtOAc, dried over MgSO4, and then concentrated in vacuo to afford a yellow oil. This oil was chromatographed with 15percent EtOAc:hexanes to afford 3.8 g 2 as a colorless viscous oil. A solution of dicyclohexylborane was generated by the addition of borane-THF (12.0 mL, 12 mmol), at 0° C. to a solution of cyclohexene (2.3 mL) in 6 mL of anhydrous THF. This solution was stirred for an additional 1 hr at 0° C. The acetylene (2) (2.0 g, 5.84 mmol) was then added dropwise over 15 min at 0° C. and then allowed to warm to room temp over 1 hr. The reaction mixture was then diluted with MeOH (20 mL) and then recooled to 0° C. A solution of 2 N NaOH (6 mL) and 30percent H2O2 (3.5 mL) was then added dropwise. The reaction mixture was then stirred at 0° C. for 1 hr and then warmed to 40° C. for 2.5 hr. The mixture was then cooled to room temp and an additional 6 mL of 2 N NaOH was added. The organics were removed in vacuo and the remaining aqueous solution was extracted 3* Et2O and the organics were discarded. The aqueous extracts were then acidified with 1 N HCl and extracted with EtOAc dried over MgSO4, and then concentrated in vacuo to afford 1.7 g of the phenylacetic acid as a tan crystalline solid. The acid (1.7 g, 5.6 mmol) was then deprotected by the addition of a 25percent TFA/CH2Cl2 solution and stirred for 2 hr at room temp. With hydrogenchloride, sodium hydroxide, CuI, dihydrogen peroxide, Pd(PPh3)2Cl2 in tetrahydrofuran, triethylamine, cyclohexene Patent; Daiichi Pharmaceutical Co., LTD.; US2003/78249; (2003); (A1) English View in Reaxys Cl

HO O

Rx-ID: 24124768 View in Reaxys 66/834 Yield 96.8%

Conditions & References C.1 : Comparative Example 1 Comparative Example 1 30 g of 2-methyl phenylacetic acid, 60 g of monochlorobenzene and 2,2'-azobisisobutyronitrile as a radical initiator were charged to a 200 ml flask equipped with a reflux condenser, a stirrer and a thermometer, and the reaction temperature was controlled to 70° C. and 29.7 g of sulfuryl chloride was added dropwise thereto for 5 hours. When the reaction solution after the completion of the reaction was analyzed on gas chromatography, each of the compounds was present at the ratio shown in Table 1. The selectivity to 2-chloromethylphenylacetic acid was 75.4percent. After the completion of the reaction, the reaction solution was cooled to 20° C., and precipitates were filtered and separated to obtain 23.0 g of 2-chloromehtyl phenylacetic acid (purity: 96.8percent, yield: 62percent). With sulfuryl dichloride Patent; Ihara Chemical Industry Co., Ltd.; US6414186; (2002); (B1) English View in Reaxys

HO O

Rx-ID: 31153108 View in Reaxys 67/834

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Yield

Conditions & References 2.4. Catalytic tests General procedure: Olefin oxidations were carried out in a 40-ml glass reactor with a magnetic stirrer. Typically, substrate, solvent, and catalyst were mixed in the reactor, then the mixture was stirred (900 rpm). After increasing the temperature (the temperature was measured with a thermometer in an oil bath), pure O2 was introduced and sealed in the reaction system at atmosphere pressure by a U tube made by ourselves. After reaction, the products were analyzed by gas chromatography (GC-14C and GC-17A, Shimadzu, FID) with a flexible quartz capillary column (OV-17 or OV-1). The recyclability of the catalyst was tested by separating it from the reaction system by centrifugation, washing with large quantity of methanol, and drying at 373 K for 6 h, then the catalyst was reused in the next reaction. With tert.-butylhydroperoxide, oxygen in acetonitrile, Time= 8h, p= 760.051Torr , Heating Wang, Liang; Wang, Hong; Hapala, Prokop; Zhu, Longfeng; Ren, Limin; Meng, Xiangju; Lewis, James P.; Xiao, Feng-Shou; Journal of Catalysis; vol. 281; nb. 1; (2011); p. 30 - 39 View in Reaxys

HO O

Rx-ID: 41287114 View in Reaxys 68/834 Yield

Conditions & References

37 %, 20 %, 43 %Spectr.

With 3,4-benzo-1,1,2,2-tetraethyl-1,2-disilacyclobut-3-ene, cesium fluoride in DMFA, Time= 2h, T= 0 - 20 °C , p= 760.051Torr Mita, Tsuyoshi; Suga, Kenta; Sato, Kaori; Sato, Yoshihiro; Organic Letters; vol. 17; nb. 21; (2015); p. 5276 5279 View in Reaxys

HO O

Rx-ID: 2203477 View in Reaxys 69/834 Yield

Conditions & References

92 %

With sodium tetrahydroborate, selenium in ethanol, N,N-dimethyl-formamide, 1) 5 deg C, 0.5h, 2) RT, 1h; also with Te as cat. Huang, Zhi-Zhen; Zhou, Xun-Jun; Synthesis; nb. 7; (1990); p. 633 - 634 View in Reaxys

HO O

O O

Rx-ID: 2395353 View in Reaxys 70/834 Yield

Conditions & References

69 %, 7 %, With pentacarbonyliron(0), tetra-n-butyl-ammonium sulfate in sodium hydroxide, dichloromethane, Time= 20h, T= 20 3 %, 20 % °C , p= 760Torr Tanguy, Guy; Weinberger, Berndt; Abbayes, Herve des; Tetrahedron Letters; vol. 24; nb. 37; (1983); p. 4005 4008 View in Reaxys

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66 %, 11 %, 4 %, 8 %

With pentacarbonyliron(0), tetra-n-butyl-ammonium sulfate in sodium hydroxide, dichloromethane, Time= 27h, T= 25 °C , p= 45600Torr Tanguy, Guy; Weinberger, Berndt; Abbayes, Herve des; Tetrahedron Letters; vol. 24; nb. 37; (1983); p. 4005 4008 View in Reaxys

Rx-ID: 2670605 View in Reaxys 71/834 Yield

Conditions & References

95 %

With ammonium cerium(IV) nitrate in water, acetonitrile, Time= 4h, T= 0 °C , pH=2.0 Kim, C. U.; Misco, P. F.; Tetrahedron Letters; vol. 26; nb. 17; (1985); p. 2027 - 2030 View in Reaxys

HO O

O O

Rx-ID: 2695398 View in Reaxys 72/834 Yield

Conditions & References

61 %, 2 %, With pentacarbonyliron(0), tetra-n-butyl-ammonium sulfate in sodium hydroxide, toluene, Time= 29h, T= 50 °C , p= 4 %, 7 % 45600Torr Tanguy, Guy; Weinberger, Berndt; Abbayes, Herve des; Tetrahedron Letters; vol. 24; nb. 37; (1983); p. 4005 4008 View in Reaxys 61 %, 2 %, With pentacarbonyliron(0), tetra-n-butyl-ammonium sulfate in sodium hydroxide, toluene, Time= 29h, T= 50 °C , p= 7 %, 4 % 45600Torr Tanguy, Guy; Weinberger, Berndt; Abbayes, Herve des; Tetrahedron Letters; vol. 24; nb. 37; (1983); p. 4005 4008 View in Reaxys 61 %, 4 %, With pentacarbonyliron(0), tetra-n-butyl-ammonium sulfate in sodium hydroxide, toluene, Time= 29h, T= 50 °C , p= 7 %, 2 % 45600Torr Tanguy, Guy; Weinberger, Berndt; Abbayes, Herve des; Tetrahedron Letters; vol. 24; nb. 37; (1983); p. 4005 4008 View in Reaxys

HO O

Rx-ID: 4469480 View in Reaxys 73/834 Yield 70 %

Conditions & References With sulfuric acid, mercuric sulphate in acetic acid, Time= 24h, T= 80 °C Schmitz, Carole; Rouanet-Dreyfuss, Anne-Claire; Tueni, Marie; Biellmann, Jean-Francois; Journal of Organic Chemistry; vol. 61; nb. 5; (1996); p. 1817 - 1821

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View in Reaxys

HO O

Rx-ID: 8952474 View in Reaxys 74/834 Yield

Conditions & References

88 %

With sodium hydride in N,N-dimethyl-formamide, T= 20 °C Serrano-Wu, Michael H; Regueiro-Ren, Alicia; St. Laurent, Denis R; Carroll, Tina M; Balasubramanian, Balu N; Tetrahedron Letters; vol. 42; nb. 49; (2001); p. 8593 - 8595 View in Reaxys

H O

O O

Rx-ID: 31153107 View in Reaxys 75/834 Yield

Conditions & References 2.4. Catalytic tests General procedure: Olefin oxidations were carried out in a 40-ml glass reactor with a magnetic stirrer. Typically, substrate, solvent, and catalyst were mixed in the reactor, then the mixture was stirred (900 rpm). After increasing the temperature (the temperature was measured with a thermometer in an oil bath), pure O2 was introduced and sealed in the reaction system at atmosphere pressure by a U tube made by ourselves. After reaction, the products were analyzed by gas chromatography (GC-14C and GC-17A, Shimadzu, FID) with a flexible quartz capillary column (OV-17 or OV-1). The recyclability of the catalyst was tested by separating it from the reaction system by centrifugation, washing with large quantity of methanol, and drying at 373 K for 6 h, then the catalyst was reused in the next reaction. With tert.-butylhydroperoxide, oxygen in toluene, Time= 8h, p= 760.051Torr , Heating Wang, Liang; Wang, Hong; Hapala, Prokop; Zhu, Longfeng; Ren, Limin; Meng, Xiangju; Lewis, James P.; Xiao, Feng-Shou; Journal of Catalysis; vol. 281; nb. 1; (2011); p. 30 - 39 View in Reaxys

O O

HO NH 2

NH 2

O HN

OH H

Rx-ID: 31677136 View in Reaxys 76/834 Yield

Conditions & References General procedure of enzymatic reaction General procedure: A typical acylation was carried out in a thermostatted cell of a pH-stat at pH 10, 35°C in an aqueous medium (total volume 30 ml) with 0.1 M DL-phenylalanine (3a) and 0.25 M phenylacetamide (2a). The reaction was started by adding 0.1 g of immobilized A. faecalis PGA to the reaction mixture and the pH was kept constant by automatic titration of 2 M KOH solution. The course of reaction was monitored with HPLC. After full conversion of the L-phenylalanine to N-phenylacetyl-L- phenylalanine the enzyme was filtered off. The aqueous phase was acidified to pH 1 using 32 wt.percent aqueous HCl solution, which resulted in precipitation of N-phenylacetyl-L- phenylalanine, phenylacetamide and phenylacetic acid. The precipitates were isolated by filtration. The aqueous phase was evaporated under reduced pressure and the residue was recrystallized from water/ethanol to afford D-phenylalanine. The precipitates were washed by cyclohexane (3.x.20 ml) and recrystallized from ethanol to afford N-phenylacetyl-L-phenylalanine. Stage 1: With recombinant Alcaligenes faecalis penicillin G acylase immobilized on oxirane acrylic carrier, potassium hydroxide in water, Time= 3.66667h, T= 35 °C , pH= 10, Enzymatic reaction Stage 2: With hydrogenchloride in water, pH= 1, optical yield given as percent ee, enantioselective reaction

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Gong, Xiangyu; Su, Erzheng; Wang, Pixiang; Wei, Dongzhi; Tetrahedron Letters; vol. 52; nb. 41; (2011); p. 5398 - 5402 View in Reaxys

O O O

N O

HO O

NH 2

N H

H 2N

Rx-ID: 31677139 View in Reaxys 77/834 Yield

Conditions & References General procedure of enzymatic reaction General procedure: A typical acylation was carried out in a thermostatted cell of a pH-stat at pH 10, 35°C in an aqueous medium (total volume 30 ml) with 0.1 M DL-phenylalanine (3a) and 0.25 M phenylacetamide (2a). The reaction was started by adding 0.1 g of immobilized A. faecalis PGA to the reaction mixture and the pH was kept constant by automatic titration of 2 M KOH solution. The course of reaction was monitored with HPLC. After full conversion of the L-phenylalanine to N-phenylacetyl-L- phenylalanine the enzyme was filtered off. The aqueous phase was acidified to pH 1 using 32 wt.percent aqueous HCl solution, which resulted in precipitation of N-phenylacetyl-L- phenylalanine, phenylacetamide and phenylacetic acid. The precipitates were isolated by filtration. The aqueous phase was evaporated under reduced pressure and the residue was recrystallized from water/ethanol to afford D-phenylalanine. The precipitates were washed by cyclohexane (3.x.20 ml) and recrystallized from ethanol to afford N-phenylacetyl-L-phenylalanine. Stage 1: With recombinant Alcaligenes faecalis penicillin G acylase immobilized on oxirane acrylic carrier, potassium hydroxide in water, Time= 5.66667h, T= 35 °C , pH= 10, Enzymatic reaction Stage 2: With hydrogenchloride in water, pH= 1, optical yield given as percent ee, enantioselective reaction Gong, Xiangyu; Su, Erzheng; Wang, Pixiang; Wei, Dongzhi; Tetrahedron Letters; vol. 52; nb. 41; (2011); p. 5398 - 5402 View in Reaxys

O NH 2

NH 2

N H

H 2N

Rx-ID: 31677140 View in Reaxys 78/834 Yield

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NH 2

Cl O O

Cl O

NH 2 HO

NH 2

N H

OH O

Rx-ID: 31677141 View in Reaxys 79/834 Yield

F O

F NH 2

OH NH 2

NH 2

N H

OH O

Rx-ID: 31677142 View in Reaxys 80/834 Yield

Conditions & References General procedure of enzymatic reaction General procedure: A typical acylation was carried out in a thermostatted cell of a pH-stat at pH 10, 35°C in an aqueous medium (total volume 30 ml) with 0.1 M DL-phenylalanine (3a) and 0.25 M phenylacetamide (2a). The reaction was started by adding 0.1 g of immobilized A. faecalis PGA to the reaction mixture and the pH was kept constant by automatic titration of 2 M KOH solution. The course of reaction was monitored with HPLC. After full conversion of the L-phenylalanine to N-phenylacetyl-L- phenylalanine the enzyme was filtered off. The aqueous phase was acidified to pH 1 using 32 wt.percent aqueous HCl solution, which resulted in precipitation of N-phenylacetyl-L- phenylalanine, phenylacetamide and phenylacetic acid. The precipitates were isolated by filtration. The aqueous phase was evaporated under reduced pressure and the residue was recrystallized from water/ethanol to afford D-phenylalanine. The precipitates were washed by cyclohexane (3.x.20 ml) and recrystallized from ethanol to afford N-phenylacetyl-L-phenylalanine. Stage 1: With recombinant Alcaligenes faecalis penicillin G acylase immobilized on oxirane acrylic carrier, potassium hydroxide in water, Time= 3h, T= 35 °C , pH= 10, Enzymatic reaction Stage 2: With hydrogenchloride in water, pH= 1, optical yield given as percent ee, enantioselective reaction Gong, Xiangyu; Su, Erzheng; Wang, Pixiang; Wei, Dongzhi; Tetrahedron Letters; vol. 52; nb. 41; (2011); p. 5398 - 5402 View in Reaxys

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O O O

O O

O H N

O O

O HN

F F

O O

O H 2N

O O O

O O

O H N

O O

F F

HN S

NH O

Rx-ID: 33576059 View in Reaxys 81/834 Yield

Conditions & References 4.2. Enzyme activity release PGA (penicillin-G-amidase, 1 U/μL) was purchased from Zhejiang Shunfeng Haider Co. Ltd. Compound 1 was dissolved in DMSO (not more than 10percent, V/V) and further diluted with 0.1 M PBS (pH 7.4) to give the final stock solution, followed by treating with PGA. The incubation was kept at 37 °C and the fluorescence spectra were measured every 30 min by RF-5301PC spectroscopy. With Escherichia coli penicillin-G-amidase, water in dimethyl sulfoxide, Time= 4h, T= 37 °C , pH= 7.4, aq. phosphate buffer, Enzymatic reaction Jin, Hui-Juan; Lu, Jing; Wu, Xue; Bioorganic and Medicinal Chemistry; vol. 20; nb. 11; (2012); p. 3465 - 3469 View in Reaxys

HO O

(v5)

P Ni (v4) Cl

Rx-ID: 34834416 View in Reaxys 82/834 Yield 71 %

Conditions & References With magnesium chloride, zinc, tricyclopentyl-phosphine in N,N-dimethyl-formamide, T= 20 °C , p= 760.051Torr , Schlenk technique Leon, Thierry; Correa, Arkaitz; Martin, Ruben; Journal of the American Chemical Society; vol. 135; nb. 4; (2013); p. 1221 - 1224 View in Reaxys

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Br C

Rx-ID: 2002284 View in Reaxys 83/834 Yield

Conditions & References

93 %

With potassium hydroxide, dicobalt octacarbonyl, N-benzyl-N,N,N-triethylammonium chloride in benzene, Time= 8h, p= 760Torr , Ambient temperature Shim, Sang Chul; Doh, Chil Hoon; Park, Woo Hyun; Kwon, Young Gil; Lee, Hyung Soo; Journal of Organometallic Chemistry; vol. 382; nb. 3; (1990); p. 419 - 421 View in Reaxys

HO O

Rx-ID: 9724348 View in Reaxys 84/834 Yield 71 %

Conditions & References With dihydrogen peroxide in tetrahydrofuran, water, Time= 1h, T= 20 °C Tiecco, Marcello; Testaferri, Lorenzo; Temperini, Andrea; Bagnoli, Luana; Marini, Francesca; Santi, Claudio; Terlizzi, Raffaella; European Journal of Organic Chemistry; nb. 16; (2004); p. 3447 - 3458 View in Reaxys

aqueous LiOH

N O

Rx-ID: 23925662 View in Reaxys 85/834 Yield

Conditions & References 5 : EXAMPLE 5 EXAMPLE 5 To a 0° C. solution of methyl 4-hydroxyphenylacetate (2.66 g; 1.6 mmol), 5-phenyl 2-methyl oxazole-3-ethanol (3.25 g; 1.6 mmol) and Ph3P (5.0 g; 1.9 mmol) in anhydrous THF (30 mL) was added DEAD (3.5 g; 2.0 mmol) dropwise. The reaction mixture was stirred at 0° C. for 30 min and then was allowed to warm to RT and stirred at RT overnight. Volatiles were removed in vacuo and the residue was chromatographed (SiO2; stepwise gradient; hexane:EtOAc 5:1 to 5:2) to give Part A compound (3.5 g; 62percent) as a white solid. A solution of Part A compound (2.85 g; 0.812 mmol) and aqueous LiOH (2.0 mL of a 1 M solution; 2.0 mmol) in THF (2 mL) was stirred at RT for 3 h. At this point, HPLC/MS indicated that all starting material had been consumed. Volatiles were removed in vacuo and the reaction was acidified with aqueous 1 N HCl. The aqueous phase was extracted with EtOAc (2*250 mL); the combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give the crude phenylacetic acid. With triphenylphosphine, diethylazodicarboxylate in tetrahydrofuran, ethyl acetate Patent; Cheng, Peter T.; Zhang, Hao; Hariharan, Narayanan; US2003/92736; (2003); (A1) English View in Reaxys Patent; Cheng, Peter T.; Zhang, Hao; Hariharan, Narayanan; US2003/158232; (2003); (A1) English View in Reaxys Patent; Bristol-Myers Squibb Company; US6967212; (2005); (B2) English View in Reaxys

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OH O

O O

H 2N

N E N

HO O

Rx-ID: 23996499 View in Reaxys 86/834 Yield

Conditions & References 5 : Compound 77 of Table 1 (Method C): Benzeneacetic acid, 2-[2-[3,4-dihydro-3-oxo-4-(5-oxohexyl)-2H-1,4benzoxazin-2-yl]ethoxy]-, methyl ester EXAMPLE 5 Compound 77 of Table 1 (Method C): Benzeneacetic acid, 2-[2-[3,4-dihydro-3-oxo-4-(5-oxohexyl)-2H-1,4-benzoxazin-2-yl]ethoxy]-, methyl ester A solution of Intermediate 4 (8.75 g, 0.029 mol), methyl (2-hydroxyphenyl)acetate (7.48 g, 0.045 mol), and tributylphosphine (11.2 mL, 0.045 mol) in 500 mL anhydrous benzene, under N2, was cooled to 4° C. 1,1'-(Azodicarbonyl)dipiperidine (11.34 g, 0.045 mol) was added in one portion, and the solution was stirred, with an overhead stirrer, at room temperature overnight. The organic phase was washed with 4*50 mL 2 N NaOH, 50 mL water and 50 mL brine. The organics were dried (Na2SO4) filtered, and solvent was removed in vacua. The product was purified by silica gel chromatography with hexane/ethyl acetate. Compound 77 was obtained as a colorless oil (8.58 g, 0.02 mol). 1H (CDCl ) 7.28-6.89 (m, 8H), 4.76 (dd, 1H, J=9.5, 4.0), 4.19 (m, 2H), 3.93 (br t, 2H), 3.61 and 3.60 (two singlets, 3 5H), 2.51 (m, 3H), 2.13 (m and s, 4H), 1.66 (m, 4H) With tributylphosphine in benzene Patent; Burris, Thomas P.; Combs, Donald W.; Rybczynski, Philip J.; US2002/165228; (2002); (A1) English View in Reaxys 5 : Compound 77 of Table 1 (Method C): Benzeneacetic acid, 2-[2-[3,4-dihydro-3-oxo-4-(5-oxohexyl)-2H-1,4benzoxazin-2-yl]ethoxy]-, methyl ester EXAMPLE 5 Compound 77 of Table 1 (Method C): Benzeneacetic acid, 2-[2-[3,4-dihydro-3-oxo-4-(5-oxohexyl)-2H-1,4-benzoxazin-2-yl]ethoxy]-, methyl ester A solution of Intermediate 4 (8.75 g, 0.029 mol), methyl (2-hydroxyphenyl)acetate (7.48 g, 0.045 mol), and tributylphosphine (11.2 mL, 0.045 mol) in 500 mL anhydrous benzene, under N2, was cooled to 4° C. 1,1'-(Azodicarbonyl)dipiperidine (11.34 g, 0.045 mol) was added in one portion, and the solution was stirred, with an overhead stirrer, at room temperature overnight. The organic phase was washed with 4*50 mL 2 N NaOH, 50 mL water and 50 mL brine. The organics were dried (Na2SO4), filtered, and solvent was removed in vacuo. The product was purified by silica gel chromatography with hexane/ethyl acetate. Compound 77 was obtained as a colorless oil (8.58 g, 0.02 mol). 1H (CDCl ): 7.28-6.89 (m, 8H), 4.76 (dd, 1H, J=9.5, 4.0), 4.19 (m, 2H), 3.93 (br t, 2H), 3.61 and 3.60 (two singlets, 3 5H), 2.51 (m, 3H), 2.13 (m and s, 4H), 1.66 (m, 4H). With tributylphosphine in benzene Patent; Burris, Thomas P.; Combs, Donald W.; Rybczynski, Philip J.; Dudash JR., Joseph; US2003/83329; (2003); (A1) English View in Reaxys Patent; Ortho-McNeil Pharmaceutical, Inc.; US6908908; (2005); (B2) English View in Reaxys

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HO O O

H N

Rx-ID: 30828215 View in Reaxys 87/834 Yield

Conditions & References 6.4. Photogeneration of carboxylic acids and its quantum yield measurement General procedure: Carboxylates (3a-h and 6a-c) (0.05 mmol) was dissolved in MeOH/H2O (9:1), and it was irradiated using 125 W medium pressure Hg lamp using quartz filter. In each case the photolysis was stopped when conversion reached at least 95percent (as indicated by HPLC). After the completion of the photolysis, the solvent was removed under vacuum and the photoproducts (carboxylic acids and carboxyanilide) were separated by column chromatography using ethyl acetate/hexane as eluant.The quantum yield of photogeneration of carboxylic acids was analyzed by employing valerophenone as an actinometer. The progress of the photolysis was monitored by taking 5 μl of aliquot at regular interval of time and analyzed by HPLC, using eluant hexane/isopropanol (9:1), at a flow rate of 1 ml/min (detection: UV 254 nm). The percent of carboxylic acid generated was determined by calculating the gradual increase in the peak area of the carboxylic acid. With water in methanol, Time= 0.833333h, UV-irradiation Ikbal, Mohammed; Jana, Avijit; Singh, N.D. Pradeep; Banerjee, Rakesh; Dhara, Dibakar; Tetrahedron; vol. 67; nb. 20; (2011); p. 3733 - 3742 View in Reaxys

H O

O O

Rx-ID: 31153106 View in Reaxys 88/834 Yield

Conditions & References 2.4. Catalytic tests General procedure: Olefin oxidations were carried out in a 40-ml glass reactor with a magnetic stirrer. Typically, substrate, solvent, and catalyst were mixed in the reactor, then the mixture was stirred (900 rpm). After increasing the temperature (the temperature was measured with a thermometer in an oil bath), pure O2 was introduced and sealed in the reaction system at atmosphere pressure by a U tube made by ourselves. After reaction, the products were analyzed by gas chromatography (GC-14C and GC-17A, Shimadzu, FID) with a flexible quartz capillary column (OV-17 or OV-1). The recyclability of the catalyst was tested by separating it from the reaction system by centrifugation, washing with large quantity of methanol, and drying at 373 K for 6 h, then the catalyst was reused in the next reaction. With tert.-butylhydroperoxide, oxygen in para-xylene, Time= 8h, p= 760.051Torr , Heating Wang, Liang; Wang, Hong; Hapala, Prokop; Zhu, Longfeng; Ren, Limin; Meng, Xiangju; Lewis, James P.; Xiao, Feng-Shou; Journal of Catalysis; vol. 281; nb. 1; (2011); p. 30 - 39 View in Reaxys

O O

HO O

NH 2

O HN

H 2N

OH H

Rx-ID: 31677138 View in Reaxys 89/834 Yield

Conditions & References General procedure of enzymatic reaction

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General procedure: A typical acylation was carried out in a thermostatted cell of a pH-stat at pH 10, 35°C in an aqueous medium (total volume 30 ml) with 0.1 M DL-phenylalanine (3a) and 0.25 M phenylacetamide (2a). The reaction was started by adding 0.1 g of immobilized A. faecalis PGA to the reaction mixture and the pH was kept constant by automatic titration of 2 M KOH solution. The course of reaction was monitored with HPLC. After full conversion of the L-phenylalanine to N-phenylacetyl-L- phenylalanine the enzyme was filtered off. The aqueous phase was acidified to pH 1 using 32 wt.percent aqueous HCl solution, which resulted in precipitation of N-phenylacetyl-L- phenylalanine, phenylacetamide and phenylacetic acid. The precipitates were isolated by filtration. The aqueous phase was evaporated under reduced pressure and the residue was recrystallized from water/ethanol to afford D-phenylalanine. The precipitates were washed by cyclohexane (3.x.20 ml) and recrystallized from ethanol to afford N-phenylacetyl-L-phenylalanine. Stage 1: With recombinant Alcaligenes faecalis penicillin G acylase immobilized on oxirane acrylic carrier, potassium hydroxide in water, Time= 2.33333h, T= 35 °C , pH= 10, Enzymatic reaction Stage 2: With hydrogenchloride in water, pH= 1, optical yield given as percent ee, enantioselective reaction Gong, Xiangyu; Su, Erzheng; Wang, Pixiang; Wei, Dongzhi; Tetrahedron Letters; vol. 52; nb. 41; (2011); p. 5398 - 5402 View in Reaxys

O O

NH 2 HO

NH 2

HO N H

H 2N

Rx-ID: 31677143 View in Reaxys 90/834 Yield

Conditions & References General procedure of enzymatic reaction General procedure: A typical acylation was carried out in a thermostatted cell of a pH-stat at pH 10, 35°C in an aqueous medium (total volume 30 ml) with 0.1 M DL-phenylalanine (3a) and 0.25 M phenylacetamide (2a). The reaction was started by adding 0.1 g of immobilized A. faecalis PGA to the reaction mixture and the pH was kept constant by automatic titration of 2 M KOH solution. The course of reaction was monitored with HPLC. After full conversion of the L-phenylalanine to N-phenylacetyl-L- phenylalanine the enzyme was filtered off. The aqueous phase was acidified to pH 1 using 32 wt.percent aqueous HCl solution, which resulted in precipitation of N-phenylacetyl-L- phenylalanine, phenylacetamide and phenylacetic acid. The precipitates were isolated by filtration. The aqueous phase was evaporated under reduced pressure and the residue was recrystallized from water/ethanol to afford D-phenylalanine. The precipitates were washed by cyclohexane (3.x.20 ml) and recrystallized from ethanol to afford N-phenylacetyl-L-phenylalanine. Stage 1: With recombinant Alcaligenes faecalis penicillin G acylase immobilized on oxirane acrylic carrier, potassium hydroxide in water, Time= 4h, T= 35 °C , pH= 10, Enzymatic reaction Stage 2: With hydrogenchloride in water, pH= 1, optical yield given as percent ee, enantioselective reaction Gong, Xiangyu; Su, Erzheng; Wang, Pixiang; Wei, Dongzhi; Tetrahedron Letters; vol. 52; nb. 41; (2011); p. 5398 - 5402 View in Reaxys

HO O

Rx-ID: 2694874 View in Reaxys 91/834 Yield 98 %

Conditions & References With hydrochlorid acid in water, DMFA, Electrochemical reaction

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Tateno, Hiroyuki; Matsumura, Yoshimasa; Nakabayashi, Koji; Senboku, Hisanori; Atobe, Mahito; RSC Advances; vol. 5; nb. 119; (2015); p. 98721 - 98723 View in Reaxys 90 %

With tetra-n-butylammonium perchlorate in DMFA, T= 5 °C , electrochemical oxidation Sock, Oumar; Troupel, Michel; Perichon, Jacques; Tetrahedron Letters; vol. 26; nb. 12; (1985); p. 1509 - 1512 View in Reaxys

83 %

With Al-anode in DMFA, T= 20 °C , electrocarboxylation Silvestri, Giuseppe; Gambino, Salvatore; Filardo, Giuseppe; Gulotta, Antonio; Angewandte Chemie; vol. 96; nb. 12; (1984); p. 978 - 979 View in Reaxys

69 %

With [NiCl2(1,2-dimethoxyethane)], C15H27P*(x)BF4*H(1+), magnesium chloride, zinc in DMFA, T= 20 °C , p= 760.051Torr , Schlenk technique Leon, Thierry; Correa, Arkaitz; Martin, Ruben; Journal of the American Chemical Society; vol. 135; nb. 4; (2013); p. 1221 - 1224 View in Reaxys With p-GaAs semiconductor photocell with Mg electrode in acetonitrile, Time= 16h, T= 25 °C , Irradiation, var. semiconductor photocells, var. times, Product distribution Ueda, Jo-ji; Nakabayashi, Seiichiro; Ushizaki, Jun-ichi; Uosaki, Kohei; Chemistry Letters; nb. 10; (1993); p. 1747 - 1750 View in Reaxys

208 mg

Stage 1: With magnesium, lithium chloride, zinc(II) chloride in tetrahydrofuran, Time= 1h, T= 25 °C Stage 2: in tetrahydrofuran, Time= 2.5h, T= 25 °C Bernhardt, Sebastian; Metzger, Albrecht; Knochel, Paul; Synthesis; nb. 22; (2010); p. 3802 - 3810; Art.No: T19210SS View in Reaxys

35 %Spectr.

With samarium, samarium diiodide in tetrahydrofuran, Time= 4.5h, T= 20 °C , p= 760.051Torr , UV-irradiation Nomoto, Akihiro; Kojo, Yusuke; Shiino, Go; Tomisaka, Yuri; Mitani, Ikuko; Tatsumi, Masahiko; Ogawa, Akiya; Tetrahedron Letters; vol. 51; nb. 50; (2010); p. 6580 - 6583 View in Reaxys

HO C

O O

Rx-ID: 2694884 View in Reaxys 92/834 Yield

Conditions & References

31 %

With N-benzyl-N,N,N-triethylammonium chloride, pentacarbonyliron(0) in hexane, Time= 48h, p= 760Torr , Ambient temperature, Yield given Tustin, Gerald C.; Hembre, Robert T.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1761 - 1764 View in Reaxys

Rx-ID: 3998846 View in Reaxys 93/834

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Yield

Conditions & References

100 %

With diethylamine, Pd(0) (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) in water, acetonitrile, Time= 1.25h, 2.5 molpercent catalyst Lemaire-Audoire; Lemaire-Audoire, Sandrine; Savignac; Savignac, Monique; Blart; Blart, Errol; Pourcelot; Pourcelot, Guy; Genet; Genet, Jean Pierre; Bernard; Bernard, Jean-Marie; Tetrahedron Letters; vol. 35; nb. 47; (1994); p. 8783 - 8786 View in Reaxys

100 %

With diethylamine, Pd(0) (from Pd(OAc)2 and m.sulf.-Ph3P) in water, acetonitrile, Time= 1.25h, var. solvents, cat. amounts and substrates, Product distribution Lemaire-Audoire; Lemaire-Audoire, Sandrine; Savignac; Savignac, Monique; Blart; Blart, Errol; Pourcelot; Pourcelot, Guy; Genet; Genet, Jean Pierre; Bernard; Bernard, Jean-Marie; Tetrahedron Letters; vol. 35; nb. 47; (1994); p. 8783 - 8786 View in Reaxys

97 %

With Montmorillonite K-10 clay, toluene, Time= 0.333333h, Microwave irradiation, Dealkylation Gajare, Anil S.; Shaikh, Nadim S.; Bonde, Bhushan K.; Deshpande, Vishnu H.; Journal of the Chemical Society, Perkin Transactions 1; nb. 5; (2000); p. 639 - 640 View in Reaxys

94 %

With methoxybenzene in toluene, Time= 10h, Heating Gajare; Shingare; Kulkarni; Barhate; Wakharkar; Synthetic Communications; vol. 28; nb. 1; (1998); p. 25 - 33 View in Reaxys

85 %

With sodium iodide, zirconium tetrachloride in acetonitrile, Time= 1h, Heating Sharma, Gangavaram V. M.; Reddy, Ch. Govardhan; Krishna, Palakodety Radha; Synlett; nb. 11; (2003); p. 1728 - 1730 View in Reaxys

84 %

With toluene-4-sulfonic acid, Time= 0.0666667h, microwave irradiation Lee, Jong Chan; Yoo, Eun Sang; Lee, Jin Seo; Synthetic Communications; vol. 34; nb. 16; (2004); p. 3017 - 3020 View in Reaxys

68 %

With sulphated SnO2 in toluene, Time= 5h, Heating Chavan, Subhash P.; Zubaidha; Dantale, Shubhada W.; Keshavaraja; Ramaswamy; Ravindranathan; Tetrahedron Letters; vol. 37; nb. 2; (1996); p. 237 - 240 View in Reaxys

HO C

O O

Rx-ID: 4429640 View in Reaxys 94/834 Yield 16 %, 72 %

Conditions & References With sodium hydroxide, η6-C6H6BPh3 -Rh(COD)+, tetra-n-hexylammonium hydrogen sulfate in dichloromethane, T= 40 °C , p= 760Torr Amaratunga, Shiyamalie; Alper, Howard; Journal of Organometallic Chemistry; vol. 488; nb. 1-2; (1995); p. 25 28 View in Reaxys

65 %, 32 %

With iPr2NEt3, triphenylphosphine in water, T= 53 °C Jones, Ray V.H.; Lindsell, W. Edward; Palmer, Daniel D.; Preston, Peter N.; Whitton, Alan J.; Tetrahedron Letters; vol. 46; nb. 50; (2005); p. 8695 - 8697 View in Reaxys

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Rx-ID: 4726166 View in Reaxys 95/834 Yield

Conditions & References

45 %

HO Z O

Rx-ID: 9912190 View in Reaxys 96/834 Yield

Conditions & References

65 %

With sodium hydroxide, dihydrogen peroxide in tetrahydrofuran, methanol, Time= 4h, T= 20 °C Bhat, Narayan G.; Caga-Anan, Zerremi; Leija, Reynaldo; Tetrahedron Letters; vol. 46; nb. 31; (2005); p. 5109 5111 View in Reaxys

Rx-ID: 10060511 View in Reaxys 97/834 Yield 95 %, 2 %

Conditions & References With potassium hydroxide, samarium diiodide in tetrahydrofuran, Time= 0.35h, T= 20 °C Kamochi, Yasuko; Kudo, Tadahiro; Masuda, Toshinobu; Takadate, Akira; Chemical and Pharmaceutical Bulletin; vol. 53; nb. 8; (2005); p. 1017 - 1020 View in Reaxys

28 %, 36 %

With potassium hydroxide, samarium diiodide in tetrahydrofuran, Time= 0.133333h, T= 20 °C Kamochi, Yasuko; Kudo, Tadahiro; Masuda, Toshinobu; Takadate, Akira; Chemical and Pharmaceutical Bulletin; vol. 53; nb. 8; (2005); p. 1017 - 1020 View in Reaxys

tungsten 4-hexynyl complex (9b)

Phe-Phe-NH-resin bound Rx-ID: 12152528 View in Reaxys 98/834

Yield

Conditions & References Reaction Steps: 2 1: 64 percent / tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine; [Cu(CH3CN)4]PF6; aq. sodium bicarbonate / aq. sodium ascorbate / 2-methyl-propan-2-ol / 20 °C 2: 60 percent / aq. NaOH / methanol / 90 °C With sodium hydroxide, [Cu(MeCN)4]+[PF6]-, sodium hydrogencarbonate, TBTA, sodium L-ascorbate in methanol, tert-butyl alcohol Cassidy, Michael P.; Raushel, Jessica; Fokin, Valery V.; Angewandte Chemie - International Edition; vol. 45; nb. 19; (2006); p. 3154 - 3157 View in Reaxys

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Rx-ID: 25108109 View in Reaxys 99/834 Yield 42%

Conditions & References 5 : EXAMPLE 5 EXAMPLE 5 Alpha-bromoacetophenone (1 g; 5 m.moles) was dissolved in a nitrogen atmosphere in 10 ml of trimethylorthoformiate. The solution was added with silver tetrafluoroborate (1.2 g; 5.8 m.moles) and BF3.2CH 3 OH (0.66 g; 5m.moles). The mixture was magnetically stirred in the absence of light, in a nitrogen atmosphere, at 50° C. for 1 hour and 30 minutes. The reaction mixture was then treated as described in Example 1. By basic hydrolysis of the raw product, phenylacetic acid (0.28 g) was obtained with a yield of 42percent calculated as in Example 1. With silver tetrafluoroborate Patent; Montedison S.p.A.; US4328356; (1982); (A1) English View in Reaxys

O–

Na +

Rx-ID: 25597002 View in Reaxys 100/834 Yield

Conditions & References 4.7 g. of sodium, 30 ml of absolute toluene and 6 mg of catalyst are put into a stainless-steel preliminary reactor that has a mixer capable of mixing at 10,000 revolutions per minute, a heater, a backflow condenser, a viewing window, and a cooling jacket. All processes are carried out in a dry-nitrogen atmosphere. The reactor is heated up to the toluene boiling point Then the high-speed mixer is switched on for 1-1.5 minutes for sodium crushing.The suspension is then cooled down to 25-30° C. and placed in a phenylsodium-conversion reactor. 5-8 ml of a chlorobenzene and toluene solution, made by mixing the 2 reagents in equal proportion with catalyst, is added to toluene-sodium suspension while mixing and cooling the reactor to 2740° C. The reaction begins immediately and black sediments of phenylsodium are generated in the reactor. The temperature of reaction mixture is kept at 2740° C. The chlorobenzene metallizing reaction takes approximately 1 hour.The suspension of phenylsodium is taken from the pheynylsodium-conversion reactor to a reserve tank, where reaction is completed in a nitrogen atmosphere. In order to transform phenylsodium into benzylsodium, the contents of the reserve tank are placed into a benzylsodium-conversion reactor, where the suspension boils for 1-1.5 hours. While boiling, the solution's color gets brick-red and then black again.Upon completion of the reaction, the hot solution is removed from the benzylsodium-conversion reactor and placed into a cooling tank. Then as soon as possible, the cooled reaction mass is poured into crushed dry ice in a carbonation reactor and mixed. When vaporization of the CO2 is completed, 20 ml of water is added to the residue during cooling and mixing. The water layer is then separated and acidulated with hydrochloric acid to a pH around pH 2. The generated sediment phenylacetic acid is separated by filtration in a vacuum-filter. 12.5 g. of phenylacetic acid (92percent) with melting point 77° C. is produced. The results of other experiments are given in the Table 1. TABLE 1 Experimental results of PhAA production in the absence and presence of catalyst respectively PhAA production in the PhAA yields in the absence of catalyst, percent presence of catalyst, percent Time of Rate of addition of toluene Rate of addition of toluene boiling of solution of chlorobenzene solution of chlorobenzene phenylsodium and toluene suspension of and toluene suspension of in toluene, hr. sodium, 4.3 mole/hr. sodium, 4.3 mole/hr. 2.5 3.5 4.3 5 2.5 3.5 4.3 5 0.5 16.2 18.9 27 33 66 74 75 70 1 34.6 40.5 48 54 83.5 90 94.5 89 2 42.8 44.8 52 58 83.4 89.8 93.7 86.7 3 52.5 60.4 62.5 69 80.8 90.6 90.3 85.9 4 49.6 58.4 66.5 - 76 87 88 80.8 The table shows that including a catalyst greatly increases phenylacetic-acid yield. The highest yield of the product is observed when the time of boiling in toluene equals 1 hour time. Further increase in boiling time causes a decrease in desired product yield. Also, the application of a catalyst improves the stability of the results.It was also observed that the increase in catalyst amount to 0.001percent leads to a rise in yield of the desired product. Further increases in catalyst amount do not generally give an increase of the desired product With hydrogenchloride in water, toluene, pH= 2 Patent; Property Development Corporation International, Ltd, Inc.; US7161026; (2007); (B1) English

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View in Reaxys

Rx-ID: 29653301 View in Reaxys 101/834 Yield

Conditions & References

94 %

With hydrogenchloride in water, acetonitrile, Time= 7h, T= 55 - 65 °C Krohn, Karsten; Cludius-Brandt, Stephan; Synthesis; nb. 15; (2010); p. 2616 - 2620; Art.No: T03610SS View in Reaxys

HO O

O O

Rx-ID: 32403128 View in Reaxys 102/834 Yield

Conditions & References

70 %, 64 %

Rx-ID: 32439885 View in Reaxys 103/834 Yield

Conditions & References

96 %Chromat.

4.8. Preparative photolysis General procedure: A solution of caged compound (4a-h) and (7b-d) (0.05 mmol) in acetonitrile/H2O (75/25) individually was irradiated using the procedure described under deprotection photolysis. The irradiation was monitored by TLC at regular intervals. After completion of photolysis, solvent was removed under vacuum and the photoproducts (3-(hydroxymethyl)perylene, and the corresponding carboxylic acid or alcohol) were isolated by column chromatography using increasing percentage of EtOAc in hexane as an eluant. With water in acetonitrile, Photolysis Jana, Avijit; Ikbal, Mohammed; Singh, N.D. Pradeep; Tetrahedron; vol. 68; nb. 4; (2012); p. 1128 - 1136 View in Reaxys

Rx-ID: 34790046 View in Reaxys 104/834

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Yield

Conditions & References

88%

With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrin)MnCl in water, acetonitrile, Time= 0.166667h, T= 20 °C , Inert atmosphere, Solvent, Reagent/catalyst Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys OH HO

Rx-ID: 437180 View in Reaxys 105/834 Yield

Conditions & References

95 %

With water, hydrogen iodide, Time= 8h, T= 90 °C Aramini, Andrea; Sablone, Manolo R.; Bianchini, Gianluca; Amore, Alessia; Fani, Michela; Perrone, Plinio; Dolce, Alberto; Allegretti, Marcello; Tetrahedron; vol. 65; nb. 10; (2009); p. 2015 - 2021 View in Reaxys With ethanol, hydrazine hydrate, man verseift das Nitril Purgotti; Gazzetta Chimica Italiana; vol. 25 I; (1895); p. 120 View in Reaxys

HO O

Rx-ID: 2694875 View in Reaxys 106/834 Yield

Conditions & References

34 %, 0 %, With cadmium(II) sulphide, triethylamine in DMFA, Time= 8h, T= 20 °C , Irradiation 55 % Fujiwara, Hiroaki; Kanemoto, Masashi; Ankyu, Hirofumi; Murakoshi, Kei; Wada, Yuji; Yanagida, Shozo; Journal of the Chemical Society. Perkin Transactions 2; nb. 2; (1997); p. 317 - 321 View in Reaxys 0 %, 55 %, With cadmium(II) sulphide, triethylamine in DMFA, Time= 8h, T= 20 °C , Irradiation 34 % Fujiwara, Hiroaki; Kanemoto, Masashi; Ankyu, Hirofumi; Murakoshi, Kei; Wada, Yuji; Yanagida, Shozo; Journal of the Chemical Society. Perkin Transactions 2; nb. 2; (1997); p. 317 - 321 View in Reaxys 50 %, 10 %, 2 %

With cobalt-salen complex, product distribution in presence,or absence water, Product distribution Folest, Jean-Claude; Duprilot, Jean-Marc; Perichon, Jacques; Robin, Yvette; Devynck, Jacques; Tetrahedron Letters; vol. 26; nb. 22; (1985); p. 2633 - 2636 View in Reaxys

35%, 17 %, 8 %

With manganese, palladium diacetate, tetra-(n-butyl)ammonium iodide in DMFA, Time= 12h, p= 760.051Torr , Inert atmosphere, Schlenk technique, Reagent/catalyst Zhang, Shuai; Chen, Wei-Qiang; Yu, Ao; He, Liang-Nian; ChemCatChem; vol. 7; nb. 23; (2015); p. 3972 - 3977 View in Reaxys With cadmium(II) sulphide in DMFA, T= 20 °C , Kinetics Fujiwara, Hiroaki; Kanemoto, Masashi; Ankyu, Hirofumi; Murakoshi, Kei; Wada, Yuji; Yanagida, Shozo; Journal of the Chemical Society. Perkin Transactions 2; nb. 2; (1997); p. 317 - 321 View in Reaxys

95 % Chromat.,

With lithium perchlorate, {Co(salen)}NaY in DMFA, Time= 2h, p= 760Torr , Electrochemical reaction, Carboxylation, reduction

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2 % Chromat., 3 % Chromat.

Bessel, Carol A.; Rolison, Debra R.; Journal of the American Chemical Society; vol. 119; nb. 51; (1997); p. 12673 - 12674 View in Reaxys

N H

NH O

NH 2

Rx-ID: 3061479 View in Reaxys 107/834 Yield

Conditions & References

87 %

With pH 7.5, penicillinacylase on Eupergit C beads in water, T= 28 °C Fuganti, Claudio; Grasselli, Piero; Casati, Paolo; Tetrahedron Letters; vol. 27; nb. 27; (1986); p. 3191 - 3194 View in Reaxys

99 % Chromat.

With penicillin amidase, Time= 2.5h, T= 25 °C Stoineva; Galunsky; Lozanov; Ivanov; Petkov; Tetrahedron; vol. 48; nb. 6; (1992); p. 1115 - 1122 View in Reaxys

99 % Chromat.

With penicillin amidase, Time= 2.5h, T= 25 °C , Rate constant, Product distribution Stoineva; Galunsky; Lozanov; Ivanov; Petkov; Tetrahedron; vol. 48; nb. 6; (1992); p. 1115 - 1122 View in Reaxys

O N Z

Rx-ID: 4358237 View in Reaxys 108/834 Yield 72 %, 21 %

Conditions & References With potassium carbonate, CuI * pyridine in N,N-dimethyl-formamide, Time= 5h, Ambient temperature Miura, Masahiro; Enna, Masahiro; Okuro, Kazumi; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 60; nb. 16; (1995); p. 4999 - 5004 View in Reaxys

O O

Rx-ID: 9459468 View in Reaxys 109/834 Yield 70 %

Conditions & References With potassium hydroxide in methanol, Time= 1h, T= 35 °C Khurana, Jitender M.; Chauhan, Sushma; Bansal, Geeti; Monatshefte fur Chemie; vol. 135; nb. 1; (2004); p. 83 87 View in Reaxys

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(1-{benzyl[4-(N'-phenylacetyl-hydrazinomethyl)-benzyl]-amino}ethyl)-terminated poly(acrylamide-co-ethylene glycol)1900 {1-[benzyl-(4-hydrazinomethyl-benzyl)-amino]-ethyl}-terminated poly(acrylamide-co-ethylene glycol)1900

HO O

Rx-ID: 9950717 View in Reaxys 110/834 Yield

Conditions & References

20 %

O O

P O

E O

Rx-ID: 11273274 View in Reaxys 111/834 Yield

Conditions & References

93 %

With hydrogen bromide, Time= 0.166667h, T= 100 °C McNulty, James; Das, Priyabrata; Gosciniak, Don; Tetrahedron Letters; vol. 49; nb. 2; (2008); p. 281 - 285 View in Reaxys

93 %

With water, hydrogen bromide, Time= 0.166667h, T= 100 °C , Inert atmosphere McNulty, James; Das, Priyabrata; Tetrahedron; vol. 65; nb. 37; (2009); p. 7794 - 7800 View in Reaxys

OH O

O O

N E N

Rx-ID: 24003240 View in Reaxys 112/834 Yield

Conditions & References 39 : Intermediate 19: Benzeneacetic acid, 2-[2-[3,4-dihydro-3-oxo-4- (6-hexylphthalimide)-2H-1,4-benzoxazin-2-yl]ethoxy]-, methyl ester Intermediate 19: Benzeneacetic acid, 2-[2-[3,4-dihydro-3-oxo-4- (6-hexylphthalimide)-2H-1,4-benzoxazin-2yl]ethoxy]-, methyl ester A solution of Intermediate 18 (5 g, 11.8 mmol), methyl (2-hydroxyphenyl)acetate (3.9 g, 17.8 mmol), and tributylphosphine (4.4 mL, 17.8 mmol) in 180 mL anhydrous benzene, under N2, was cooled to 4° C. 1,1'-(Azodicarbonyl)dipiperidine (4.5 g, 17.8 mmol) in THF (36 mL) was added in one portion, and the solution was stirred, at room temperature overnight. The organic phase was washed with 4*20 mL 2 N NaOH, 40 mL water and 40 mL brine. The organics were dried (Na2SO4), filtered, and solvent was removed in vacuo. The product was purified by silica gel chromatography with hexane/ethyl acetate. Compound 77 was obtained as a yellow solid (2.6 g, 4.56 mmol). MS: 593 (M+Na) With tributylphosphine in tetrahydrofuran, benzene Patent; Burris, Thomas P.; Combs, Donald W.; Rybczynski, Philip J.; Dudash JR., Joseph; US2003/83329; (2003); (A1) English View in Reaxys

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N O

OH HO

N E N

Rx-ID: 24126220 View in Reaxys 113/834 Yield

Conditions & References 2 : Benzeneacetic Acid, 2-[2-[(2R)-4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl]ethoxy]-, Methyl Ester Benzeneacetic Acid, 2-[2-[(2R)-4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl]ethoxy]-, Methyl Ester A solution of (2H-1,4-benzoxazin-3(4H)-one, 4-hexyl-2-(2-hydroxyethyl)-, (2R)-) (16.7 g, 0.06 mol), (2-hydroxyphenyl)acetic acid (15 g, 0.09 mol), and tributylphosphine (22.4 mL, 0.09 mol) in 1 L anhydrous benzene, under N2, was cooled to 10° C. 1,1'-(Azodicarbonyl)dipiperidine (22.7 g, 0.09 mol) was added in one portion, and the solution was stirred, with an overhead stirrer, at room temperature overnight. 130 mL water was added and stirring continued for 40 minutes. The mixture was transferred to a separatory funnel. The organic phase was washed with 4*100 mL water, and 100 mL brine. The organics were dried (Na2SO4), filtered, and solvent was removed in vacuo. The product was purified by silica gel chromatography with hexane/ethyl acetate. The ester (benzeneacetic acid, 2-[2-[(2R)-4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl]ethoxy]-, methyl ester) was obtained as a colorless oil (24.3 g, 0.057 mol). 1H (CDCl ): 7.28-6.89 (m, 8H), 4.76 (dd, 1H, J=9.4, 4), 4.28-4.21 (m, 2H), 3.92 (t, 2H, J=7.7), 3.60 (two singlets, 5H), 3 2.49 (m, 1H), 2.23 (m, 1H), 1.66 (m, 2H), 1.34 (m, 6H), 0.89 (br t, 3H). With tributylphosphine in water, benzene Patent; Burris, Thomas P.; Rybczynski, Philip J.; US2002/103193; (2002); (A1) English View in Reaxys

O H

H N

O O N

HO O

NH O O

Rx-ID: 25347622 View in Reaxys 114/834 Yield

Conditions & References 10 : Removal of the phenylacetyl group from methyl 2-(2'-R-phenylacetoxy-3'-S-benzoylamino-4'-oxo)azetidinyl-3-methyl-2-butenoate STR24 EXAMPLE 10 Removal of the phenylacetyl group from methyl 2-(2'-R-phenylacetoxy-3'-S-benzoylamino-4'-oxo)azetidinyl-3-methyl-2-butenoate STR24 The methyl 2-(2'R-phenylacetoxy-3'S-benzoylamino-4'-oxo)azetidinyl-3-methyl-2-butenoate (100 mg) is dissolved in absolute ethanol (1 ml) containing pyridine (0.5 ml). This solution is cooled to 0° and then an additional 0.5 ml of ethanol is added, followed by 2N sodium hydroxide (0.5 ml). The mixture is stirred at 0° for 5 min, and is then acidified with ice-cold dilute HCl. Extraction with methylene chloride and evaporation of the dried organic layer affords phenylacetic acid and methyl 2(2'R-hydroxy-3'S-benzoylamino-4'-oxo)azetidinyl-3-methyl-2-butenoate. With pyridine, sodium hydroxide in ethanol Patent; Queen's University at Kingston; US4071512; (1978); (A1) English

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View in Reaxys

–O

HO K+

Rx-ID: 35102405 View in Reaxys 115/834 Yield

Conditions & References

85 %

With [PhCOPd(PtBu3)I], dtbpf in 2-methyl tetrahydrofuran, Time= 18h, T= 80 °C , Inert atmosphere Korsager, Signe; Taaning, Rolf H.; Skrydstrup, Troels; Journal of the American Chemical Society; vol. 135; nb. 8; (2013); p. 2891 - 2894 View in Reaxys

O HO

HO O

Rx-ID: 332919 View in Reaxys 116/834 Yield

Conditions & References

80 %

With iodosylbenzene in 1,4-dioxane, Ambient temperature Moriarty, Robert M.; Gupta, Satish C.; Hu, Henry; Berenschot, Daniel M.; White, Kenneth B.; Journal of the American Chemical Society; vol. 103; nb. 3; (1981); p. 686 - 688 View in Reaxys

76 %

With sodium perborate in water, Time= 48h, Ambient temperature Morrow, Nicholas; Ramsden, Christopher A.; Sargent, Bruce J.; Wallett, Christiaan D.; Tetrahedron; vol. 54; nb. 33; (1998); p. 9603 - 9612 View in Reaxys T= 280 °C Hurd; Raterink; Journal of the American Chemical Society; vol. 56; (1934); p. 1348 View in Reaxys

HO O

Rx-ID: 2040656 View in Reaxys 117/834 Yield

Conditions & References

92 %

With sodium ditelluride in N,N-dimethyl-formamide, Time= 12h, Ambient temperature Suzuki, Hitomi; Padmanabhan, Seetharamaiyer; Ogawa, Takuji; Chemistry Letters; (1989); p. 1017 - 1020 View in Reaxys

87 %

With sodium hydrogen telluride in ethanol, Time= 1h, Ambient temperature Chen, Jian; Zhou, Xun-jun; Synthetic Communications; vol. 17; nb. 2; (1987); p. 161 - 164 View in Reaxys

O HO

H O

Rx-ID: 2071859 View in Reaxys 118/834 Yield 82 %

Conditions & References With sodium periodate, tri-n-butylhexadecylphosphonium bromide in chloroform, water, Time= 3h, Heating

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Ferraboschi, Patrizia; Azadani, Morteza Nasr; Santaniello, Enzo; Trave, Susanna; Synthetic Communications; vol. 16; nb. 1; (1986); p. 43 - 50 View in Reaxys

HO O

Rx-ID: 2659520 View in Reaxys 119/834 Yield 80 %

Conditions & References With hydrogenchloride in tetrahydrofuran, Time= 3h, Heating Takahashi, Kazumasa; Shibasaki, Kenichiro; Ogura, Katsuyuki; Iida, Hirotada; Journal of Organic Chemistry; vol. 48; nb. 20; (1983); p. 3566 - 3569 View in Reaxys O N Z

HO N E

O racemate

Rx-ID: 3363805 View in Reaxys 120/834 Yield

Conditions & References

74 %, 3 %, With copper(l) iodide, water, 1,2-bis-(diphenylphosphino)ethane in N,N-dimethyl-formamide, Time= 4h, other alkyne; 7 %, 9 % var. ligands and reaction times, Product distribution Okuro, Kazumi; Enna, Masahiro; Miura, Masahiro; Nomura, Masakatsu; Journal of the Chemical Society, Chemical Communications; nb. 13; (1993); p. 1107 - 1108 View in Reaxys 74 %, 3 % Chromat., 7 % Chromat., 9 % Chromat.

With CuI-Ph2P(CH2)2PPh2, water, potassium carbonate in N,N-dimethyl-formamide, Time= 4h, T= 80 °C , different ligands in CuI catalyst system, different reaction times, Product distribution Miura, Masahiro; Enna, Masahiro; Okuro, Kazumi; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 60; nb. 16; (1995); p. 4999 - 5004 View in Reaxys

3 %, 7 %, With copper(l) iodide, water, potassium carbonate, 1,2-bis-(diphenylphosphino)ethane in N,N-dimethyl-formamide, 11 %, 74 % Time= 4h, T= 80 °C Okuro, Kazumi; Enna, Masahiro; Miura, Masahiro; Nomura, Masakatsu; Journal of the Chemical Society, Chemical Communications; nb. 13; (1993); p. 1107 - 1108 View in Reaxys 3 % Chromat., 7 % Chromat., 9 % Chromat., 74 % 13 %, 44 %, 33 %, 36 %

With water, potassium carbonate, CuI-Ph2P(CH2)2PPh2 in N,N-dimethyl-formamide, Time= 4h, T= 80 °C Miura, Masahiro; Enna, Masahiro; Okuro, Kazumi; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 60; nb. 16; (1995); p. 4999 - 5004 View in Reaxys With copper(l) iodide, tributylphosphine, water, potassium carbonate in N,N-dimethyl-formamide, Time= 5h, T= 80 °C Okuro, Kazumi; Enna, Masahiro; Miura, Masahiro; Nomura, Masakatsu; Journal of the Chemical Society, Chemical Communications; nb. 13; (1993); p. 1107 - 1108 View in Reaxys

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13 % Chromat., 44 % Chromat., 33 % Chromat., 36 % Chromat.

With water, potassium carbonate, CuI/n-Bu3P complex in N,N-dimethyl-formamide, Time= 5h, T= 80 °C Miura, Masahiro; Enna, Masahiro; Okuro, Kazumi; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 60; nb. 16; (1995); p. 4999 - 5004 View in Reaxys

O N Z

HO N E

racemate

Rx-ID: 4358202 View in Reaxys 121/834 Yield

Conditions & References

22 %, 11 % With water, potassium carbonate, CuI * pyridine in N,N-dimethyl-formamide, Time= 8h, T= 0 °C , Yield given Miura, Masahiro; Enna, Masahiro; Okuro, Kazumi; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 60; nb. 16; (1995); p. 4999 - 5004 View in Reaxys O O

N Z

O N

N O

Rx-ID: 4358230 View in Reaxys 122/834 Yield 58 %, 32 %

H 2N

Rx-ID: 28389140 View in Reaxys 123/834 Yield

Conditions & References

80.4 With (4,5-bis-(di-iso-propylphosphinomethyl)acridine)RuH(CO)Cl, ammonia, water, Time= 36h, T= 135 °C , p= %Chromat. 5700.38Torr , Inert atmosphere Gunanathan, Chidambaram; Milstein, David; Angewandte Chemie - International Edition; vol. 47; nb. 45; (2008); p. 8661 - 8664 View in Reaxys

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Rx-ID: 34790054 View in Reaxys 124/834 Yield

Conditions & References

89%, 91%

With (5,10,15,20-tetramesitylporphyrin)MnCl in water, acetonitrile, Time= 0.166667h, T= 20 °C , Inert atmosphere, Concentration, Reagent/catalyst, Solvent Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

Rx-ID: 34790058 View in Reaxys 125/834 Yield

Conditions & References

90%, 89%

With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrin)MnCl in water, acetonitrile, Time= 0.166667h, T= 20 °C , Inert atmosphere, Concentration, Reagent/catalyst, Solvent Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

O O

HO O

Rx-ID: 1637969 View in Reaxys 126/834 Yield

Conditions & References

97 %, 94 %

With methanol, sodium tetrahydroborate in tetrahydrofuran, Time= 1h, Ambient temperature Soai, Kenso; Yokoyama, Shuji; Mochida, Katsuko; Synthesis; nb. 7; (1987); p. 647 - 648 View in Reaxys

94 %, 97 %

With methanol, sodium tetrahydroborate in tetrahydrofuran, Time= 1h, Ambient temperature Soai, Kenso; Yokoyama, Shuji; Mochida, Katsuko; Synthesis; nb. 7; (1987); p. 647 - 648 View in Reaxys

NH O

H 2N

S K+

O O

H S K+

N O

O–

Rx-ID: 2327914 View in Reaxys 127/834 Yield

Conditions & References With pH 7.5, penicillinacylase on Eupergit C beads in water, T= 28 °C , enzymatic cleavage of phenacetyl group investigated Fuganti, Claudio; Grasselli, Piero; Casati, Paolo; Tetrahedron Letters; vol. 27; nb. 27; (1986); p. 3191 - 3194 View in Reaxys With pH 7.5, penicillinacylase on Eupergit C beads in water, T= 28 °C , Yield given Fuganti, Claudio; Grasselli, Piero; Casati, Paolo; Tetrahedron Letters; vol. 27; nb. 27; (1986); p. 3191 - 3194 View in Reaxys

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2.5. Initial activity and operational stability tests The procedure used to test the activity of the immobilized PGA was as follows. The as‐separated immobilized PGA mentioned above was homogenously mixed with 10 mL deionized water and 5 mL phosphate buffer (0.1 mol/L, pH = 7.8) at 37 °C in a thermostatic bath, and then 30 mL 4percent (m/v) aqueous solution of penicillin G potassium salt kept at 37 °C was added. The mixed solution was automatically titrated with NaOH solution (0.1 mol/L) to maintain pH = 7.8, and the volume of NaOH consumed during the first 10 min was measured. The activity of the immobilized PGA was calculated as follows: A (U/g) = VNaOH ·CNaOH · 103/(m · t) where VNaOH is the volume (mL) of NaOH solution consumed, CNaOH is the concentration (mol/L) of the NaOH solution, m is the amount (g) of dry support, and t is the reaction time (min, i.e., 10 min). With water in aq. phosphate buffer, T= 37 °C , pH= 7.8, Enzymatic reaction Zhan, Wangcheng; Lü, Yongjun; Yang, Ling; Guo, Yanglong; Wang, Yanqin; Guo, Yun; Lu, Guanzhong; Chinese Journal of Catalysis; vol. 35; nb. 10; (2014); p. 1709 - 1715 View in Reaxys

HO HO

Rx-ID: 2393624 View in Reaxys 128/834 Yield

Conditions & References

With carbon monoxide, pentacarbonyliron(0), tetra-n-butyl-ammonium sulfate, Time= 8h, T= 50 °C , p= 45600Torr Tanguy, Guy; Weinberger, Berndt; Abbayes, Herve des; Tetrahedron Letters; vol. 24; nb. 37; (1983); p. 4005 4008 View in Reaxys

HO C

O O

Rx-ID: 2397133 View in Reaxys 129/834 Yield

Conditions & References With sodium hydroxide, pentacarbonyliron(0), tetra-n-butyl-ammonium sulfate in dichloromethane, Time= 4h, T= 10 °C , p= 30400Torr , Yield given. Yields of byproduct given Laurent, Pascale; Tanguy, Guy; Abbayes, Herve des; Journal of the Chemical Society, Chemical Communications; nb. 24; (1986); p. 1754 - 1756 View in Reaxys

H O

Rx-ID: 2401421 View in Reaxys 130/834 Yield

Conditions & References

58 %, 9 %, With sodium hydroxide, cobalt trricarbonyl nitrosyl, carbon monoxide, n-dodecyltrimethylammonium chloride in ben7 %, 4 % zene, p= 760Torr , Ambient temperature Gambarotta, Sandro; Alper, Howard; Journal of Organometallic Chemistry; vol. 212; nb. 1; (1981); p. C23 - C26 View in Reaxys 58 %, 7 %, With sodium hydroxide, cobalt trricarbonyl nitrosyl, carbon monoxide, n-dodecyltrimethylammonium chloride in ben4 %, 9 % zene, p= 760Torr , Ambient temperature Gambarotta, Sandro; Alper, Howard; Journal of Organometallic Chemistry; vol. 212; nb. 1; (1981); p. C23 - C26 View in Reaxys

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N O

Rx-ID: 2571077 View in Reaxys 131/834 Yield

Conditions & References

90 %

With hydrogenchloride in tetrahydrofuran, Time= 6h, Heating Takahashi, Kazumasa; Masuda, Takumi; Ogura, Katsuyuki; Iida, Hirotada; Synthesis; nb. 12; (1983); p. 1043 1045 View in Reaxys N

O HO

Rx-ID: 2665424 View in Reaxys 132/834 Yield

Conditions & References

88 %

With hydrogenchloride in tetrahydrofuran, Time= 6h, Heating Takahashi, Kazumasa; Masuda, Takumi; Ogura, Katsuyuki; Iida, Hirotada; Synthesis; nb. 12; (1983); p. 1043 1045 View in Reaxys N

O HO

O N

Rx-ID: 2668164 View in Reaxys 133/834 Yield

Conditions & References

91 %

With hydrogenchloride in tetrahydrofuran, Time= 6h, Heating Takahashi, Kazumasa; Masuda, Takumi; Ogura, Katsuyuki; Iida, Hirotada; Synthesis; nb. 12; (1983); p. 1043 1045 View in Reaxys

O O

N O

H N

HO O

N O

Rx-ID: 3779734 View in Reaxys 134/834 Yield 69.2 %

Conditions & References With TPP(Cl)MnIIIImH in dichloromethane, T= 25 °C , Rate constant Yuan, Lung-Chi; Bruice, Thomas C.; Journal of the American Chemical Society; vol. 108; nb. 7; (1986); p. 1643 1650 View in Reaxys

69.2 %

With TPPMnIII(ImH)2Cl in dichloromethane, T= 25 °C , Rate constant Yuan, Lung-Chi; Bruice, Thomas C.; Journal of the American Chemical Society; vol. 108; nb. 7; (1986); p. 1643 1650 View in Reaxys

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HO HO

O O

Rx-ID: 4437075 View in Reaxys 135/834 Yield

Conditions & References

95 %

With dihydrogen peroxide, methyltrioxorhenium (VII), Time= 48h, Yields of byproduct given Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 60; nb. 24; (1995); p. 7728 - 7732 View in Reaxys

HO O

Rx-ID: 4437076 View in Reaxys 136/834 Yield

Conditions & References

95 %

Rx-ID: 4437082 View in Reaxys 137/834 Yield 96 %

Conditions & References With dihydrogen peroxide, methyltrioxorhenium (VII), Time= 48h, Yields of byproduct given Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 60; nb. 24; (1995); p. 7728 - 7732 View in Reaxys

HO OH

Rx-ID: 4437134 View in Reaxys 138/834 Yield 94 %

HO O

Rx-ID: 4437139 View in Reaxys 139/834 Yield 21 %, 68 %

Conditions & References With dihydrogen peroxide, methyltrioxorhenium (VII) in dichloromethane, Time= 48h Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 60; nb. 24; (1995); p. 7728 - 7732 View in Reaxys

11 %, 65 % With dihydrogen peroxide, methyltrioxorhenium (VII) in acetone, Time= 48h Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 60; nb. 24; (1995); p. 7728 - 7732 View in Reaxys

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O O

Rx-ID: 5047083 View in Reaxys 140/834 Yield

Conditions & References

40 %, 24 %

With Oxonereg;, sodium hydrogencarbonate in water, acetone, Time= 1h, T= 2 °C , Oxidation Webb, Kevin S.; Ruszkay, Stephen J.; Tetrahedron; vol. 54; nb. 3-4; (1998); p. 401 - 410 View in Reaxys

25 %, 33 %

With Oxonereg;, sodium hydrogencarbonate in water, Time= 1h, T= 2 °C , Oxidation Webb, Kevin S.; Ruszkay, Stephen J.; Tetrahedron; vol. 54; nb. 3-4; (1998); p. 401 - 410 View in Reaxys

HO C

Rx-ID: 8604211 View in Reaxys 141/834 Yield

Conditions & References

41 % Chromat., 29 % Chromat., 25 % Chromat., 5 % Chromat.

With Pd(2-OCOC5H4N)(PPh3)OTs, toluene-4-sulfonic acid, lithium iodide in water, Time= 12h, T= 115 °C , p= 40504.1Torr , Carbonylation, esterification; etherification; iodination Jayasree; Seayad; Chaudhari; Organic Letters; vol. 2; nb. 2; (2000); p. 203 - 206 View in Reaxys

HO O

Rx-ID: 8762437 View in Reaxys 142/834 Yield

Conditions & References

93 %

With carbon tetrabromide in isopropyl alcohol, Time= 2h, Heating Shih-Yuan Lee, Adam; Hu, Yi-Jung; Chu, Shu-Fang; Tetrahedron; vol. 57; nb. 11; (2001); p. 2121 - 2126 View in Reaxys

HO O

Rx-ID: 10060512 View in Reaxys 143/834 Yield 66 %, 16 %

Conditions & References With samarium diiodide, water in tetrahydrofuran, Time= 0.2h, T= 20 °C Kamochi, Yasuko; Kudo, Tadahiro; Masuda, Toshinobu; Takadate, Akira; Chemical and Pharmaceutical Bulletin; vol. 53; nb. 8; (2005); p. 1017 - 1020 View in Reaxys

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HO C

Rx-ID: 10307139 View in Reaxys 144/834 Yield

Conditions & References

60 %, 9 %

With N,N-diethyl-N-isopropylamine, triphenylphosphine in water, T= 71 °C Jones, Ray V.H.; Lindsell, W. Edward; Palmer, Daniel D.; Preston, Peter N.; Whitton, Alan J.; Tetrahedron Letters; vol. 46; nb. 50; (2005); p. 8695 - 8697 View in Reaxys

Rx-ID: 25327211 View in Reaxys 145/834 Yield

Conditions & References

70.5%

2 : EXAMPLE 2 EXAMPLE 2 Into the apparatus described in example 1 and following the same modalities, the following was introduced: Following the modalities of the preceding example, 16.5 g of benzyl chloride were added, whereupon it was operated as in example 1. The raw reaction mixture, after esterification with diazomethane, was subjected to a gas-chromatographic analysis, that revealed a phenylacetic acid yield of 70.5percent calculated on the benzyl chloride introduced. Patent; Montedison S.p.A.; US4128572; (1978); (A1) English View in Reaxys

H O

Rx-ID: 34790047 View in Reaxys 146/834 Yield

Conditions & References

68%, 12%

With (5,10,15,20-tetramesitylporphyrin)MnCl in water, acetonitrile, Time= 0.166667h, T= 20 °C , Inert atmosphere, Solvent, Reagent/catalyst Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

H O

Rx-ID: 34790050 View in Reaxys 147/834 Yield

Conditions & References

95%, With (5,10,15,20-tetramesitylporphyrin)MnCl in acetonitrile, Time= 0.166667h, T= 20 °C , Inert atmosphere, Con6.4%, 68% centration, Reagent/catalyst, Solvent Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

70/258

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H O

Rx-ID: 34790059 View in Reaxys 148/834 Yield

Conditions & References

75%, 25%

With (5,10,15,20-tetramesitylporphyrin)MnCl in toluene, Time= 0.166667h, T= 20 °C , Inert atmosphere, Concentration, Reagent/catalyst, Solvent Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

Rx-ID: 34790065 View in Reaxys 149/834 Yield

Conditions & References

88%, With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrin)MnCl in water, acetonitrile, Time= 0.166667h, T= 20 °C , Inert 8.2%, 39% atmosphere, Concentration, Reagent/catalyst, Solvent Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

–O

HO K+

Rx-ID: 35102373 View in Reaxys 150/834 Yield

Conditions & References

73 %

Rx-ID: 307877 View in Reaxys 151/834 Yield 83 %

Conditions & References With hydrogenchloride, indium, sodium lauryl sulfate, Time= 1h, T= 20 °C Park, Leeyoung; Keum, Gyochang; Kang, Soon Bang; Kim, Kwan Soo; Kim, Youseung; Journal of the Chemical Society, Perkin Transactions 1; nb. 24; (2000); p. 4462 - 4463 View in Reaxys With ammonia, zinc Spiegel; Chemische Berichte; vol. 14; (1881); p. 239 View in Reaxys

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HO O

Rx-ID: 2040651 View in Reaxys 152/834 Yield

Conditions & References

100 %

With sodium hydrogen sulphate, silica gel in dichloromethane, Time= 1.5h, T= 20 °C Ramesh; Ravindranath; Das, Biswanath; Journal of Organic Chemistry; vol. 68; nb. 18; (2003); p. 7101 - 7103 View in Reaxys

94 %

With magnesium bromide in diethyl ether, Time= 1h, Ambient temperature, various protected esters, other time Kim, Sunggak; Park, Young Hee; Kee, In Seo; Tetrahedron Letters; vol. 32; nb. 26; (1991); p. 3099 - 3100 View in Reaxys

Rx-ID: 2077708 View in Reaxys 153/834 Yield

Conditions & References

60 %

With methanol, Irradiation, Yields of byproduct given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

60 %

in methanol, Irradiation, Yield given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

H N

NH 2 O

OH O

Rx-ID: 2121833 View in Reaxys 154/834 Yield

Conditions & References With pH 7.5, penicillinacylase on Eupergit C beads in water, T= 28 °C , Yield given Fuganti, Claudio; Grasselli, Piero; Casati, Paolo; Tetrahedron Letters; vol. 27; nb. 27; (1986); p. 3191 - 3194 View in Reaxys

H O

O O

H 2N

O O

O HN

OH H

Rx-ID: 2163110 View in Reaxys 155/834

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Yield

H N

HO O

Rx-ID: 2293152 View in Reaxys 156/834 Yield

Conditions & References

87 %

With titanium tetrachloride in 1,4-dioxane, water, Time= 20h, Heating Fisher; Caroon; Stabler; Lundberg; Zaidi; Sorensen; Sparacino; Muchowski; Canadian Journal of Chemistry; vol. 72; nb. 1; (1994); p. 142 - 145 View in Reaxys

HO C

H O

Rx-ID: 2394496 View in Reaxys 157/834 Yield

Conditions & References

58 %, 9 %, With sodium hydroxide, cobalt trricarbonyl nitrosyl, n-dodecyltrimethylammonium chloride in benzene, p= 760Torr , 4 %, 7 % Ambient temperature Gambarotta, Sandro; Alper, Howard; Journal of Organometallic Chemistry; vol. 212; nb. 1; (1981); p. C23 - C26 View in Reaxys 9 %, 7 %, 4 %, 58 %

With sodium hydroxide, cobalt trricarbonyl nitrosyl, n-dodecyltrimethylammonium chloride in benzene, p= 760Torr , Ambient temperature Gambarotta, Sandro; Alper, Howard; Journal of Organometallic Chemistry; vol. 212; nb. 1; (1981); p. C23 - C26 View in Reaxys

Rx-ID: 2401392 View in Reaxys 158/834 Yield 87%

Conditions & References 6 : EXAMPLE 6 EXAMPLE 6 Into the apparatus described in example 5 and following the same modalities, there were introduced: Keeping a temperature of 25° C, 1.38 g of benzyl bromide were added in 3.5 hours. At the conclusion of such addition, stirring was continued for 4.5 hours. A sample was drawn and, after acidification, extraction with ethyl ether and esterification with diazomethane, it was subjected to gas-chromatographic analysis. Such gas-chromatographic analysis revealed a phenylacetic acid yield of 87percent calculated on the fed benzyl bromide. Patent; Montedison S.p.A.; US4128572; (1978); (A1) English View in Reaxys With sodium hydroxide, carbon monoxide, NaCo(CO)4, tetrabutyl-ammonium chloride in water, benzene, Ambient temperature, Kinetics, Mechanism Abbayes, Herve des; Bulop, Anne; Tetrahedron Letters; vol. 21; nb. 45; (1980); p. 4343 - 4346 View in Reaxys

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With sodium hydroxide, carbon monoxide, NaCo(CO)4, tetrabutyl-ammonium chloride in dichloromethane, water, Ambient temperature, Kinetics, Mechanism Abbayes, Herve des; Bulop, Anne; Tetrahedron Letters; vol. 21; nb. 45; (1980); p. 4343 - 4346 View in Reaxys With carbon monoxide, NaCo(CO)4, tetrabutyl-ammonium chloride in dichloromethane, water, Ambient temperature, Kinetics, Mechanism Abbayes, Herve des; Bulop, Anne; Tetrahedron Letters; vol. 21; nb. 45; (1980); p. 4343 - 4346 View in Reaxys 5 : EXAMPLE 5 EXAMPLE 5 Into a 50-cc flask, equipped with a water-cooler, a thermometer and a magnetic stirrer, under a CO head, there were introduced: Keeping a temperature of 25° C, 1.38 g of benzyl bromide were added in 2.5 hours. At the conclusion of such addition it was stirred for further 0.5 hours. A sample was drawn and, after acidification, extraction with ethyl ether and esterification with diazomethane, it was subjected to gas-chromatographic analysis. From such gas-chromatographic analysis it resulted a practically quantitative yield of phenylacetic acid. Patent; Montedison S.p.A.; US4128572; (1978); (A1) English View in Reaxys Reaction Steps: 2 1: tetra-n-butylammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / 0 °C / |Electrolysis; |Electrochemical reaction 2: hydrogenchloride / water / 12 h / 20 °C With hydrogenchloride, tetra-n-butylammonium tetrafluoroborate, N-ethyl-N,N-diisopropylamine in water Senboku, Hisanori; Nagakura, Kotaro; Fukuhara, Tsuyoshi; Hara, Shoji; Tetrahedron; vol. 71; nb. 23; (2015); p. 3850 - 3856 View in Reaxys

O O

Rx-ID: 2588924 View in Reaxys 159/834 Yield 95 %

Conditions & References With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane, Time= 18h, Ambient temperature, Yields of byproduct given Kim, C. U.; Misco, P. F.; Tetrahedron Letters; vol. 26; nb. 17; (1985); p. 2027 - 2030 View in Reaxys

Rx-ID: 2697546 View in Reaxys 160/834 Yield 10 %, 85 %

Conditions & References With sodium hydroxide, tetracarbonylcobaltate(1-) ion in methanol, Time= 4h, T= 55 °C Rao, B. Nageswara; Adapa, Srinivas R.; Pardhasaradhi, M.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 27; nb. 1-12; (1988); p. 84 - 85 View in Reaxys

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O O

Rx-ID: 2919751 View in Reaxys 161/834 Yield

Conditions & References

72 %

With methanol, Irradiation, Yields of byproduct given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

O O O

Rx-ID: 2956366 View in Reaxys 162/834 Yield

Conditions & References

59 %

With methanol, Irradiation, Yields of byproduct given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

59 %

in methanol, Irradiation, Yield given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

O O O

HO O

O O

Rx-ID: 2961196 View in Reaxys 163/834 Yield 60 %

Conditions & References With methanol, Irradiation, Yields of byproduct given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

60 %

in methanol, Irradiation, Yield given

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DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

O O

H N

NH 2O

NH H

O HO

Rx-ID: 3058950 View in Reaxys 164/834 Yield

O O

H N

H 2N

O HO

Rx-ID: 3058951 View in Reaxys 165/834 Yield

H N

O O

H N

H 2N

Rx-ID: 3061478 View in Reaxys 166/834 Yield

O H O

H N

H HO

O O

H N

NH 2

Rx-ID: 3061481 View in Reaxys 167/834 Yield

76/258

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H 2N

O N

Rx-ID: 3645607 View in Reaxys 168/834 Yield

Conditions & References

75 %

With sodium hydroxide in methanol, Time= 1.5h, Ambient temperature Jaafar; Francis; Danion-Bougot; Danion; Synthesis; nb. 1; (1994); p. 56 - 60 View in Reaxys O N Z

N E O

N O

Rx-ID: 4358203 View in Reaxys 169/834 Yield

Conditions & References

35 %, 54 %

With potassium carbonate, CuI * pyridine in N,N-dimethyl-formamide, Time= 4h, Ambient temperature Miura, Masahiro; Enna, Masahiro; Okuro, Kazumi; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 60; nb. 16; (1995); p. 4999 - 5004 View in Reaxys

HO O O

Rx-ID: 8915986 View in Reaxys 170/834 Yield

Conditions & References Stage 1: With Cl2(PCy3)2Ru=CHP, ethyl vinyl ether, Time= 0.00694444h Stage 2: With 2,2'-azo-bisisobutyronitrile, tri-n-butyl-tin hydride in benzene, T= 80 °C Stage 3: With lithium hydroxide in tetrahydrofuran, Further stages. Enholm, Eric J.; Gallagher, Maria E.; Organic Letters; vol. 3; nb. 21; (2001); p. 3397 - 3399 View in Reaxys

O N

N O

O NH

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H 2N

O N

Rx-ID: 25612327 View in Reaxys 171/834 Yield

Conditions & References 1 :Compounds 1 and 2 (2 μl of a 10 mM stock solution in DMSO) were dissolved in 98 μl of PBS (pH 7.4) to give a final concentration of 200 μM. Compound 3 (2 μL of a 10 mM stock solution in DMSO: Chremephor EL (1:1)) was dissolved in 98 μl of PBS (pH 7.4) to give a final concentration of 200 μM. All solutions were kept at 37° C. A PGA stock solution in PBS (pH 7.4) was used to activate the dendritic compounds. The UV-Visible spectra of p-nitrophenol and of the tested solutions of Compound 1 and 2 in PBS (pH 7.4) were measured in order to determine the optimal wavelength which will be indicative for following the appearance of released p-nitrophenol and the results are depicted in FIG. 5. As shown in FIG. 5, a wavelength of 405 nm, in which p-nitrophenol has a maximal absorption and the dendritic compounds have minimal absorption was found as indicative for the appearance of a released pnitrophenol. Thus, Compounds 1-3 were incubated with or without PGA in PBS pH 7.4 at 37° C. and the biodegradation of the tested compounds was conveniently monitored by following the formation of 4-nitrophenol with visible spectroscopy at a wavelength of 405 nm. The kinetics of the release of 4-nitrophenol from Compounds 1-3 is shown in FIG. 6. Upon addition of PGA to Compounds 1-3, free 4-nitrophenol was gradually formed, indicating a PGA-induced cleavage of the phenylacetamide substrate and a following degradation that occurs as was predicted. In the absence of PDA, no p-nitrophenol was detected. Expectedly, 4-nitrophenol was released from the G1-dendritic compound (Compound 2) faster then from the G0-dendritic compounds (Compound 1), while the G2-dendritic compound (Compound 3) released it relatively slower. The kinetic constants K(obs) for the three reactions were calculated by linear correlation with the measured plots (e.g., Kobs was calculated as the slop of the linear area of the graphs), and are presented in Table 1 below. Without being bound to any particular theory, it is suggested that the phenomenon of Compound 2 releasing its reporter group faster than Compound 1 occurs since the enzymatic substrate concentration in Compound 2 is twice higher than Compound 1. The following self-cyclization step is relatively fast and therefore, the rate-limiting step is the cleavage of the enzymatic substrate. In Compound 3, additional self-immolative reactions occur in order to complete the release of the reporter group (another intra-cyclization and 1,6-quinone-methide elimination). The overall rate of these reactions is slower than the rate of the enzymatic substrate cleavage and therefore the K(obs) for Compound 3 is relatively smaller. With water, penicillin-G-amidase in Chremephor EL, dimethyl sulfoxide, T= 37 °C , pH= 7.4, Enzymatic reaction, Aqueous phosphate buffer, Kinetics Patent; Ramot At Tel Aviv University Ltd.; US2006/269480; (2006); (A1) English View in Reaxys O HO

O O

Rx-ID: 29761719 View in Reaxys 172/834 Yield

Conditions & References With tetra-n-butylammonium tetrafluoroborate in acetonitrile, T= 0 °C , p= 760.051Torr , Electrochemical reaction Ohkoshi, Masashi; Michinishi, Jun-Ya; Hara, Shoji; Senboku, Hisanori; Tetrahedron; vol. 66; nb. 39; (2010); p. 7732 - 7737 View in Reaxys O HO

O O

Rx-ID: 29761720 View in Reaxys 173/834 Yield

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H O

Rx-ID: 34790048 View in Reaxys 174/834 Yield

Conditions & References

71%, 20%, With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrin)MnCl in toluene, Time= 0.166667h, T= 20 °C , Inert atmos6.8% phere, Reagent/catalyst, Solvent Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

H O

Rx-ID: 34790051 View in Reaxys 175/834 Yield

Conditions & References

88%, 11%, With (5,10,15,20-tetramesitylporphyrin)MnCl in dichloromethane, Time= 0.166667h, T= 20 °C , Inert atmosphere, 63%, 5.2% Concentration, Reagent/catalyst, Solvent Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

H O

Rx-ID: 34790057 View in Reaxys 176/834 Yield

Conditions & References

76%, 15%, With (5,10,15,20-tetramesitylporphyrin)MnCl in acetonitrile, Time= 0.166667h, T= 20 °C , Inert atmosphere, Con30% centration, Reagent/catalyst, Solvent Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

H O

Rx-ID: 34790060 View in Reaxys 177/834 Yield

Conditions & References

79%, 18%, With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrin)MnCl in toluene, Time= 0.166667h, T= 20 °C , Inert atmos7.5% phere, Concentration, Reagent/catalyst, Solvent Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

H O

Rx-ID: 34790063 View in Reaxys 178/834

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Yield

Conditions & References

83%, 11%, 9%, 10%

70%, 18%, With (5,10,15,20-tetramesitylporphyrin)MnCl in acetonitrile, Time= 0.166667h, T= 20 °C , Inert atmosphere, Con5.2%, centration, Reagent/catalyst, Solvent 8.1% Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

H O

Rx-ID: 34790064 View in Reaxys 179/834 Yield

Conditions & References

78%, 12%, With (5,10,15,20-tetramesitylporphyrin)MnCl in water, acetonitrile, Time= 0.166667h, T= 20 °C , Inert atmosphere, 5.2% Concentration, Reagent/catalyst, Solvent Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

Rx-ID: 104103 View in Reaxys 180/834 Yield 80 %

Conditions & References With nickel in ethylene glycol dimethyl ether, Time= 9h, Ambient temperature, Product distribution Inaba, Shin-ichi; Matsumoto, Hideyuki; Rieke, Reuben D.; Journal of Organic Chemistry; vol. 49; nb. 12; (1984); p. 2093 - 2098 View in Reaxys

65 %

With bismuth, ammonium hydrogen fluoride in water, Time= 1h, T= 20 °C Lee, Yoon Joo; Chan, Tak Hang; Canadian Journal of Chemistry; vol. 82; nb. 2; (2004); p. 71 - 74 View in Reaxys

38 %

in n-heptane, Heating Polivin, Yu. N.; Vinokurov, V. A.; Makarshin, S. V.; Karakhanov, R. A.; Silin, M. A.; Ageev, E. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 39; nb. 7.2; (1990); p. 1528 - 1530; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 7; (1990); p. 1682 - 1684 View in Reaxys With sodium amalgam, ethanol Glaser; Radziszewski; ; (1868); p. 142 View in Reaxys

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HO O

Rx-ID: 1622343 View in Reaxys 181/834 Yield

Conditions & References

20 %, 10 %, 55 %

With Al(III) salt, tetrabutylammomium bromide in N,N-dimethyl-formamide, p= 18240Torr , anode = Al 99.9percent ; cathode = Zn 99percent ; cathodic current density 100 A m-2 Silvestri, G.; Gambino, S.; Filardo, G.; Greco, G.; Gulotta, A.; Tetrahedron Letters; vol. 25; nb. 38; (1984); p. 4307 - 4308 View in Reaxys

28 %, 30 %, 29 %

With Al(III) salt, tetrabutylammomium bromide in N,N-dimethyl-formamide, p= 5320Torr , anode = Al 99.9percent ; cathode = Zn 99percent ; cathodic current density 100 A m-2 Silvestri, G.; Gambino, S.; Filardo, G.; Greco, G.; Gulotta, A.; Tetrahedron Letters; vol. 25; nb. 38; (1984); p. 4307 - 4308 View in Reaxys

28 %, 29 %, 30 %

Br Br

Rx-ID: 2032086 View in Reaxys 182/834 Yield

Conditions & References

95 %

With PEG-400, sodium hydroxide, bis[1,2-bis(diphenylphosphino)ethane]palladium(0) in dichloromethane, Time= 17h, T= 60 - 65 °C Li, Pei; Alper, Howard; Journal of Organic Chemistry; vol. 51; nb. 23; (1986); p. 4354 - 4356 View in Reaxys

95 %

With PEG-400, sodium hydroxide, bis[1,2-bis(diphenylphosphino)ethane]palladium(0) in dichloromethane, Time= 17h, T= 60 - 65 °C , var. vinylic dibromides, Mechanism Li, Pei; Alper, Howard; Journal of Organic Chemistry; vol. 51; nb. 23; (1986); p. 4354 - 4356 View in Reaxys

HO C

Rx-ID: 2395351 View in Reaxys 183/834 Yield

Conditions & References

9 %, 12 %, With sodium tetracarbonyl cobaltate, tetra-n-butyl-ammonium sulfate in sodium hydroxide, dichloromethane, Time= 20 %, 50 40h, T= 20 °C , p= 760Torr , Further byproducts given % Tanguy, Guy; Weinberger, Berndt; Abbayes, Herve des; Tetrahedron Letters; vol. 24; nb. 37; (1983); p. 4005 4008 View in Reaxys

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HO C

Rx-ID: 2694881 View in Reaxys 184/834 Yield 32 %

Conditions & References With N-benzyl-N,N,N-triethylammonium chloride, pentacarbonyliron(0) in sodium hydroxide, toluene, Time= 48h, p= 760Torr , Ambient temperature, other temperature, other reaction times, other or without solvents Tustin, Gerald C.; Hembre, Robert T.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1761 - 1764 View in Reaxys

31 %

With N-benzyl-N,N,N-triethylammonium chloride, pentacarbonyliron(0) in sodium hydroxide, hexane, Time= 48h, p= 760Torr , Ambient temperature Tustin, Gerald C.; Hembre, Robert T.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1761 - 1764 View in Reaxys

31 %

With N-benzyl-N,N,N-triethylammonium chloride, pentacarbonyliron(0) in sodium hydroxide, hexane, Time= 48h, p= 760Torr , Ambient temperature, Yield given Tustin, Gerald C.; Hembre, Robert T.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1761 - 1764 View in Reaxys

19 %, 13 %

With tetrabutylammomium bromide, pentacarbonyliron(0) in sodium hydroxide, Time= 48h, p= 760Torr , Ambient temperature, Product distribution Tustin, Gerald C.; Hembre, Robert T.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1761 - 1764 View in Reaxys

13 %, 19 %

With tetrabutylammomium bromide, pentacarbonyliron(0) in sodium hydroxide, Time= 48h, p= 760Torr , Ambient temperature Tustin, Gerald C.; Hembre, Robert T.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1761 - 1764 View in Reaxys

19 %, 13 %

12 %

With N-benzyl-N,N,N-triethylammonium chloride, Fe2(CO)9 in sodium hydroxide, Time= 72h, p= 760Torr , Ambient temperature, or Fe3(CO)12 (other reaction time) Tustin, Gerald C.; Hembre, Robert T.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1761 - 1764 View in Reaxys F

NH 2

NH F F

Rx-ID: 2951125 View in Reaxys 185/834 Yield 77 %

Conditions & References With tetra-fluorophthalic anhydride, Time= 120h, T= 145 °C Eaton, Jefferson T.; Rounds, William D.; Urbanowicz, John H.; Gribble, Gordon W.; Tetrahedron Letters; vol. 29; nb. 50; (1988); p. 6553 - 6556 View in Reaxys

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Rx-ID: 3567965 View in Reaxys 186/834 Yield

Conditions & References

92 %

With sodium hydrogen telluride in ethanol, Time= 0.0333333h, Ambient temperature Chen, Jian; Zhou, Xun-jun; Synthetic Communications; vol. 17; nb. 2; (1987); p. 161 - 164 View in Reaxys

HO O

Rx-ID: 4348522 View in Reaxys 187/834 Yield

Conditions & References

70 %

With sulphated SnO2, methoxybenzene in toluene, Time= 5h, Heating Chavan, Subhash P.; Zubaidha; Dantale, Shubhada W.; Keshavaraja; Ramaswamy; Ravindranathan; Tetrahedron Letters; vol. 37; nb. 2; (1996); p. 237 - 240 View in Reaxys O N Z

Rx-ID: 4358205 View in Reaxys 188/834 Yield

Conditions & References

25 %, 73 %

With potassium carbonate, CuI * pyridine in N,N-dimethyl-formamide, Time= 2h, Ambient temperature Miura, Masahiro; Enna, Masahiro; Okuro, Kazumi; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 60; nb. 16; (1995); p. 4999 - 5004 View in Reaxys Cl

O Cl

N Z

E N

N O

Rx-ID: 4358207 View in Reaxys 189/834 Yield 27 %, 69 %

Conditions & References With potassium carbonate, CuI * pyridine in N,N-dimethyl-formamide, Time= 3h, Ambient temperature Miura, Masahiro; Enna, Masahiro; Okuro, Kazumi; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 60; nb. 16; (1995); p. 4999 - 5004 View in Reaxys O N Z

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E N

N O

Rx-ID: 4358229 View in Reaxys 190/834 Yield

Conditions & References

31 %, 65 %

With potassium carbonate, CuI * pyridine in N,N-dimethyl-formamide, Time= 3h, Ambient temperature Miura, Masahiro; Enna, Masahiro; Okuro, Kazumi; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 60; nb. 16; (1995); p. 4999 - 5004 View in Reaxys

HO C

Rx-ID: 4713454 View in Reaxys 191/834 Yield

Conditions & References

48 % Spectr., 27 % Spectr.

With tetrakis(triphenylphosphine) palladium(0), hydrogen iodide in acetone, Time= 46h, T= 90 °C , p= 68400Torr Lin, Yong-Shou; Yamamoto, Akio; Tetrahedron Letters; vol. 38; nb. 21; (1997); p. 3747 - 3750 View in Reaxys

HO O

Rx-ID: 4900540 View in Reaxys 192/834 Yield 98 %

Conditions & References With methoxybenzene in toluene, Time= 10h, Heating Gajare; Shingare; Kulkarni; Barhate; Wakharkar; Synthetic Communications; vol. 28; nb. 1; (1998); p. 25 - 33 View in Reaxys

/PBSAB018-1380/

HO O

Rx-ID: 6715122 View in Reaxys 193/834 Yield

Conditions & References

6% Spectr., 6 % Spectr., 53 % Spectr., 36 %

With sodium hydroxide in dichloromethane, water, Time= 0.5h, T= 20 °C

6% Spectr., 6 % Spectr., 36 % Spectr., 53 % Spectr.

With sodium hydroxide in dichloromethane, water, Time= 0.5h, T= 20 °C

Tanguy, Guy; Weinberger, Bernd; Abbayes, Hevre des; Tetrahedron Letters; vol. 25; nb. 48; (1984); p. 5529 5532 View in Reaxys

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HO O O

Rx-ID: 8622722 View in Reaxys 194/834 Yield

Conditions & References

88 %

With water, InI3, silica gel, Time= 0.616667h, Irradiation, Hydrolysis Ranu; Dutta; Sarkar; Synthetic Communications; vol. 30; nb. 22; (2000); p. 4167 - 4171 View in Reaxys

H N

HO O

Rx-ID: 25203927 View in Reaxys 195/834 Yield

Conditions & References 14 : EXAMPLE 14 EXAMPLE 14 205 g (1 mol) of N-t.-pentyl-phenylacetamide (melting point: 96° C.) are stirred with 293 g of 15percent strength NaOH (1.1 mols) for 5 hours at 255° C., analogously to Example 12. After distillation, 85.2 g of t.-pentylamine of 97percent purity are obtained, corresponding to a yield of 95percent. 123 g of phenylacetic acid are obtained by acidifying the distillation bottom product. Yield 90.4percent. With sodium hydroxide Patent; Bayer Aktiengesellschaft; US4496736; (1985); (A1) English View in Reaxys

HO HO

Cl O

Rx-ID: 25274166 View in Reaxys 196/834 Yield

Conditions & References 1.B : p-Chloromethylphenylacetyl chloride B. A mixture of 1 g of p-chloromethylphenylacetic acid and 6 ml of thionyl chloride is stirred at room temperature for 25 hours after which the excess thionyl chloride is removed under vacuum to yield p-chloromethylphenylacetyl chloride. When in Example 1 (A) an acid selected from Table I is substituted for phenylacetic acid the respective chloromethyl derivative listed in Table I is obtained which can be converted to the acid chloride by the procedure of Example 1 (B). With thionyl chloride Patent; Yeda Research and Development Co. Ltd.; US3948904; (1976); (A1) English View in Reaxys Patent; Yeda Research and Development Co. Ltd.; US4045438; (1977); (A1) English View in Reaxys Rx-ID: 25612336 View in Reaxys 197/834

Yield

Conditions & References 8 :Aminoquinoline release protocol and fluorescence measurements: A PGA solution (56 mg/ml) was diluted with PBS pH 7.4 to give a 5.6 mg/ml solution. Stock solutions of dendritic Compounds 20 and 21 were prepared in DMSO with 20percent Chremophor EL to yield a 250 μM stock solution of Compound 20 and a 125 μM stock solution of Compound 21. The stock solutions (100 μl) were diluted either with 900 μl PBS pH 7.4 (control), or with a mixture of 882 μl PBS pH 7.4 and 18 μl PGA (5.6 mg/ml in PBS pH 7.4), to give final concentrations of 25 μM of Compound 20 and 12.5 μM of Compound 21. The final concentration of PGA was 0.1 mg/ml (1.4 μM). All solutions were kept at 37° C. and their fluorescence spectra were measured by SpectraMax M2 spectrophotometer (Molecular Devices).

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Standard Costar 96-wells plates were used with sample volumes of 150 μl. The spectra were measured by excitation at 250 nm and the emitting fluorescence between 360 nm-660 nm was recorded. The RFU values at 390 nm and 460 nm were used for the kinetic analysis of 6-aminoquinoline release from the dendritic compounds. Incubation with PGA: In order to prepare aqueous solutions of dendritic Compounds 20 and 21, the compounds were initially dissolved in DMSO/Chremophor EL (4/1) and then diluted into water. The final composition of the solution was 10percent organic and 90percent aqueous. Dendritic Compounds 20 and 21 were then incubated with PGA in phosphate buffered saline (PBS, pH 7.4) at 37° C. Control solutions were incubated in the buffer without the enzyme. With water, penicillin-G-amidase in Chremephor EL, dimethyl sulfoxide, T= 37 °C , pH= 7.4, Enzymatic reaction, Aqueous phosphate buffer, Kinetics Patent; Ramot At Tel Aviv University Ltd.; US2006/269480; (2006); (A1) English View in Reaxys O HO

O O

N O

Rx-ID: 29710712 View in Reaxys 198/834 Yield

Conditions & References

97 %

With isopropyl alcohol in acetonitrile, Irradiation, Inert atmosphere Kammari, Laxminarayana; Solomek, Tomas; Ngoy, Bokolombe Pitchou; Heger, Dominik; Klan, Petr; Journal of the American Chemical Society; vol. 132; nb. 33; (2010); p. 11431 - 11433 View in Reaxys

H O

O HO

Rx-ID: 34790049 View in Reaxys 199/834 Yield

Conditions & References

76%, 9.3%, 5%, 43%

Rx-ID: 34790055 View in Reaxys 200/834 Yield

Conditions & References

82%, 73%, With (5,10,15,20-tetramesitylporphyrin)MnCl in water, acetonitrile, Time= 0.166667h, T= 20 °C , Inert atmosphere, 6.9%, Concentration, Reagent/catalyst, Solvent 9.5% Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys HO

HO O

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H O

Rx-ID: 34790056 View in Reaxys 201/834 Yield

Conditions & References

81%, 15%, With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrin)MnCl in acetonitrile, Time= 0.166667h, T= 20 °C , Inert at6.5%, 10% mosphere, Concentration, Reagent/catalyst, Solvent Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

HO O

Rx-ID: 63779 View in Reaxys 202/834 Yield 83 %

Conditions & References With sodium periodate, 2C16H13N2O10Ru2 (1-)*Ca(2+) in water, Time= 16h, T= 45 °C , Green chemistry Lee, Chia-Han; Wu, Cai-Ling; Hua, Shao-An; Liu, Yi-Hung; Peng, Shie-Ming; Liu, Shiuh-Tzung; European Journal of Inorganic Chemistry; vol. 2015; nb. 8; (2015); p. 1417 - 1423 View in Reaxys Ozonolyse Henne; Hill; Journal of the American Chemical Society; vol. 65; (1943); p. 753 View in Reaxys Briner; Ryffel; Perrottet; Helvetica Chimica Acta; vol. 22; (1939); p. 927,928, 933 View in Reaxys

Rx-ID: 2013377 View in Reaxys 203/834 Yield 37 %, 2 % Spectr.

Conditions & References With 1H-imidazole, [bis(acetoxy)iodo]benzene in dichloromethane, Time= 1h, T= 20 °C Karimipour, Gholam Reza; Shadegan, Hamid Asadpour; Ahmadpour, Roxana; Journal of Chemical Research; nb. 4; (2007); p. 252 - 256 View in Reaxys

5 %, 26 %

With diphenylether, Fe(TAML)Li, [bis(acetoxy)iodo]benzene, water in acetone, Time= 1h, T= 25 °C , Green chemistry Napoly, Francois; Jean-Gerard, Ludivine; Goux-Henry, Catherine; Draye, Micheline; Andrioletti, Bruno; European Journal of Organic Chemistry; vol. 2014; nb. 4; (2014); p. 781 - 787 View in Reaxys

13 % Chromat., 87 % Chromat.

With sodium hypochlorite, 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical, tetrabutyl-ammonium chloride, sodium hydrogencarbonate, sodium chloride, potassium bromide in dichloromethane, water, 1) 0 deg C, 1h, 20 deg C, 20 min Siedlecka; Skarzewski; Mlochowski; Tetrahedron Letters; vol. 31; nb. 15; (1990); p. 2177 - 2180 View in Reaxys

87 % Chromat., 13 % Chromat.

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Siedlecka; Skarzewski; Mlochowski; Tetrahedron Letters; vol. 31; nb. 15; (1990); p. 2177 - 2180 View in Reaxys With tert.-butylhydroperoxide, [O-Cu4(triethanolamine)4(BOH)4][BF4]2 in acetonitrile, Time= 19h, T= 69.84 °C , Title compound not separated from byproducts. Zhu, Mingxia; Li, Bodong; He, Ping; Wei, Xin; Yuan, Youzhu; Tetrahedron; vol. 64; nb. 39; (2008); p. 9239 - 9243 View in Reaxys With CpMo(CO)3(CCPh), dihydrogen peroxide in water, Time= 8h, T= 80 °C , chemoselective reaction Biradar, Ankush V.; Dongare, Mohan K.; Umbarkar, Shubhangi B.; Tetrahedron Letters; vol. 50; nb. 24; (2009); p. 2885 - 2888 View in Reaxys Stage 1: With 2,2,6,6-tetramethyl-piperidine-N-oxyl, carbon, Sonication Stage 2: With nitric acid in water, Time= 5h, T= 50 °C Kuang, Yongbo; Rokubuichi, Hodaka; Nabae, Yuta; Hayakawa, Teruaki; Kakimoto, Masa-Aki; Advanced Synthesis and Catalysis; vol. 352; nb. 14-15; (2010); p. 2635 - 2642 View in Reaxys With Gluconobacter oxydans DSM 2343 in water, Time= 5h, T= 28 °C , pH= 7.5, phosphate buffer, Enzymatic reaction Zambelli, Paolo; Pinto, Andrea; Romano, Diego; Crotti, Elena; Conti, Paola; Tamborini, Lucia; Villa, Raffaella; Molinari, Francesco; Green Chemistry; vol. 14; nb. 8; (2012); p. 2158 - 2161 View in Reaxys With (n-Bu4N)4W10O32, dihydrogen peroxide in water, acetonitrile, Time= 0.25h, T= 135 - 140 °C , p= 25502.6 27002.7Torr , Microwave irradiation, Catalytic behavior, Temperature, Pressure, Time Galica, Mateusz; Kasprzyk, Wiktor; Bednarz, Szczepan; Bogdal, Dariusz; Chemical Papers; vol. 67; nb. 9; (2013); p. 1240 - 1244 View in Reaxys With E. coli perisplasmic aldehyde oxidase, F. graminearum galactose oxidase, catalase in aq. phosphate buffer, acetonitrile, T= 37 °C , pH= 7, Enzymatic reaction McKenna, Shane M.; Leimkühler, Silke; Herter, Susanne; Turner, Nicholas J.; Carnell, Andrew J.; Green Chemistry; vol. 17; nb. 6; (2015); p. 3271 - 3275 View in Reaxys

HO O

Rx-ID: 2013386 View in Reaxys 204/834 Yield

Conditions & References

17 %, 51 %

With dihydrogen peroxide, methyltrioctylammonium tetrakis(oxodiperoxotungsto)phosphate, Time= 6h, T= 90 °C Venturello, Carlo; Gambaro, Mario; Journal of Organic Chemistry; vol. 56; nb. 20; (1991); p. 5924 - 5931 View in Reaxys OH

Rx-ID: 2126753 View in Reaxys 205/834 Yield 86 %, 3 %

Conditions & References With 3-chloro-benzenecarboperoxoic acid in methanol, Time= 3h, Heating Uemura, Sakae; Ohe, Kouichi; Yamauchi, Takayoshi; Mizutaki, Shoichi; Tamaki, Kentaro; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1990); p. 907 - 910

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View in Reaxys

HO C

Rx-ID: 2394492 View in Reaxys 206/834 Yield

Conditions & References

35 %, 45 %

With sodium hydroxide, [(1,5-cyclooctadiene)Rh(triphenylphosphine)2]PF6, tetra-n-hexylammonium hydrogen sulfate in dichloromethane, T= 40 °C , p= 760Torr Amaratunga, Shiyamalie; Alper, Howard; Journal of Organometallic Chemistry; vol. 488; nb. 1-2; (1995); p. 25 28 View in Reaxys

11 %, 6 %

With N-benzyl-N,N,N-triethylammonium chloride, pentacarbonyliron(0) in sodium hydroxide, Time= 168h, p= 760Torr , Ambient temperature, Product distribution Tustin, Gerald C.; Hembre, Robert T.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1761 - 1764 View in Reaxys

6 %, 11 %

With N-benzyl-N,N,N-triethylammonium chloride, pentacarbonyliron(0) in sodium hydroxide, Time= 168h, p= 760Torr , Ambient temperature Tustin, Gerald C.; Hembre, Robert T.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1761 - 1764 View in Reaxys

11 %, 6 %

Br Br

HO O

O HO

Rx-ID: 2394509 View in Reaxys 207/834 Yield

Conditions & References

15 %, 18 With sodium hydroxide, dicobalt octacarbonyl, N-hexadecyl-N,N,N-trimethylammonium bromide in benzene, Time= %, 5 %, 15 20h, T= 20 °C , Further byproducts given % Miura, Masahiro; Akase, Fumiaki; Nomura, Masakatsu; Journal of the Chemical Society, Chemical Communications; nb. 3; (1986); p. 241 - 242 View in Reaxys 15 %, 15 With sodium hydroxide, dicobalt octacarbonyl, N-hexadecyl-N,N,N-trimethylammonium bromide in benzene, Time= %, 5 %, 18 20h, T= 20 °C , Further byproducts given % Miura, Masahiro; Akase, Fumiaki; Nomura, Masakatsu; Journal of the Chemical Society, Chemical Communications; nb. 3; (1986); p. 241 - 242 View in Reaxys

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5 %, 18 %, With sodium hydroxide, dicobalt octacarbonyl, N-hexadecyl-N,N,N-trimethylammonium bromide in benzene, Time= 15 %, 15 20h, T= 20 °C , p= 760Torr , Further byproducts given % Miura, Masahiro; Akase, Fumiaki; Nomura, Masakatsu; Journal of the Chemical Society, Chemical Communications; nb. 3; (1986); p. 241 - 242 View in Reaxys

O O

Rx-ID: 2774658 View in Reaxys 208/834 Yield

Conditions & References

80 %

With sodium hydroxide, sodium tetrahydroborate, dithienylditelluride in ethanol, Time= 0.0833333h, Ambient temperature Silveira; Lenardao; Comasseto; Synthetic Communications; vol. 24; nb. 4; (1994); p. 575 - 582 View in Reaxys

O O O

O O

Rx-ID: 2956513 View in Reaxys 209/834 Yield

Conditions & References

38 %

With methanol, Irradiation, Yields of byproduct given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

38 %

in methanol, Irradiation, Yield given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

HN NH O

S O

Rx-ID: 3162459 View in Reaxys 210/834 Yield 75 %

Conditions & References With CuCl2*2H2O in tetrahydrofuran, water, Time= 6h, Ambient temperature Attanasi, Orazio; Serra-Zanetti, Franco; Journal fuer Praktische Chemie (Leipzig); vol. 325; nb. 6; (1983); p. 901 907 View in Reaxys

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N+

I–

Rx-ID: 3893911 View in Reaxys 211/834 Yield

Conditions & References

84 %

in acetone, Time= 24h, T= 25 °C Katritzky, Alan R.; Khan, Ghulam R.; Schwarz, Otto A.; Tetrahedron Letters; vol. 25; nb. 12; (1984); p. 1223 1226 View in Reaxys

carbonate

Rx-ID: 6330955 View in Reaxys 212/834 Yield 59 %

Conditions & References With potassium-2-ethoxide in tetrahydrofuran, toluene, Time= 13h, Ambient temperature Screttas, Constantinos G.; Micha-Screttas, Maria; Journal of Organometallic Chemistry; vol. 290; (1985); p. 1 14 View in Reaxys

phenylthioacetic acid morpholide

Rx-ID: 6330959 View in Reaxys 213/834 Yield

Conditions & References With sulfuric acid Schwenk; Bloch; Journal of the American Chemical Society; vol. 64; (1942); p. 3051 View in Reaxys King; McMillan; Journal of the American Chemical Society; vol. 68; (1946); p. 2335,2338 View in Reaxys With potassium hydroxide Schwenk; Bloch; Journal of the American Chemical Society; vol. 64; (1942); p. 3051 View in Reaxys King; McMillan; Journal of the American Chemical Society; vol. 68; (1946); p. 2335,2338 View in Reaxys With potassium hydroxide Schwenk; Bloch; Journal of the American Chemical Society; vol. 64; (1942); p. 3051 View in Reaxys King; McMillan; Journal of the American Chemical Society; vol. 68; (1946); p. 2335,2338 View in Reaxys

Krsaquo;Fe(CO)3 NO

Rx-ID: 25112993 View in Reaxys 214/834

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Yield

Conditions & References 2 : EXAMPLE 2 EXAMPLE 2 A suspension of 66 g (1.18 moles) of calcium oxide in 90 g of water was first added to a solution of 21 g (0.1 mole) of KFe(CO)3 NO! and 125 g of methanol, and thereafter 126 g (1 mole) of benzyl chloride were added under a carbon monoxide pressure of 1.7 bars at 45° C., with vigorous stirring. After two hours, the reaction mixture was acidified with hydrochloric acid and then extracted with ether. After conventional working up, the yield of phenylacetic acid was 78percent. In addition, 11percent of methyl phenylacetate were formed. in methanol, water Patent; BASF Aktiengesellschaft; US4424394; (1984); (A1) English View in Reaxys

HO O

B O

O O

Rx-ID: 33692030 View in Reaxys 215/834 Yield

Conditions & References Stage 1: in tetrahydrofuran, toluene, T= 70 °C , p= 760.051Torr Stage 2: With hydrogenchloride in tetrahydrofuran, water, toluene Grigg, R. David; Rigoli, Jared W.; Van Hoveln, Ryan; Neale, Samuel; Schomaker, Jennifer M.; Chemistry - A European Journal; vol. 18; nb. 30; (2012); p. 9391 - 9396 View in Reaxys

H O

Rx-ID: 34790052 View in Reaxys 216/834 Yield

Conditions & References

76%, 5.8%, 60%, 5.6%, 7.1%

H O

Rx-ID: 34790053 View in Reaxys 217/834 Yield 73%, 5.8%, 61%, 6%

Conditions & References With (5,10,15,20-tetramesitylporphyrin)MnCl in water, acetonitrile, Time= 0.166667h, T= 20 °C , Inert atmosphere, Concentration, Reagent/catalyst, Solvent Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

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H O

Rx-ID: 34790062 View in Reaxys 218/834 Yield

Conditions & References

64%, 24%, With (5,10,15,20-tetramesitylporphyrin)MnCl in dichloromethane, Time= 0.166667h, T= 20 °C , Inert atmosphere, 5% Concentration, Reagent/catalyst, Solvent Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

(v4)

N N(v2) –2+ Fe – O O B TB-5 H (v3) (v5) N N

(v4)

N N

(v4)

Rx-ID: 39897414 View in Reaxys 219/834 Yield

Conditions & References

58 %Chromat., 33 %Chromat., 8 %Chromat.

(v4) (v4)

N N

With oxygen in acetonitrile, T= 20 °C Sheet, Debobrata; Bhattacharya, Shrabanti; Paine, Tapan Kanti; Chemical Communications (Cambridge, United Kingdom); vol. 51; nb. 36; (2015); p. 7681 - 7684 View in Reaxys

N N

(v2) –

2+ Fe – O BH O TB-5 (v5) (v4)

N N

(v3)

Rx-ID: 39897417 View in Reaxys 220/834 Yield

Conditions & References With oxygen in acetonitrile, T= 20 °C Sheet, Debobrata; Bhattacharya, Shrabanti; Paine, Tapan Kanti; Chemical Communications (Cambridge, United Kingdom); vol. 51; nb. 36; (2015); p. 7681 - 7684 View in Reaxys O HO

HO O

Rx-ID: 750315 View in Reaxys 221/834 Yield

Conditions & References With 1-chloro-4-methylbutane, sodium, Petroleum ether, Einleiten von Kohlendioxid in das Reaktionsgemisch Morton; Hechenbleikner; Journal of the American Chemical Society; vol. 58; (1936); p. 2599,2604 View in Reaxys With sodium, (nC5H11)2Hg, Einleiten von Kohlendioxid in das Reaktionsgemisch Morton; Hechenbleikner; Journal of the American Chemical Society; vol. 58; (1936); p. 1024,2599,2604 View in Reaxys With phenyl-sodium, benzene, Einleiten von Kohlendioxid in das Reaktionsgemisch

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Morton; Fallwell; Palmer; Journal of the American Chemical Society; vol. 60; (1938); p. 1426 View in Reaxys

Rx-ID: 2393587 View in Reaxys 222/834 Yield

Conditions & References

15 % Spectr., 12 % Spectr., 23 % Spectr.

With NADPH tetrasodium salt, oxygen, cyclohexanone oxygenase in methanol, T= 15 °C , glycine, NaOH, pH=9.0, Rate constant Branchaud, Bruce P.; Walsh, Christopher T.; Journal of the American Chemical Society; vol. 107; (1985); p. 2153 - 2161 View in Reaxys

N N N

N N

N O

N N N

Rx-ID: 2466136 View in Reaxys 223/834 Yield

Conditions & References

92 %

With sulfuric acid in tetrahydrofuran, Time= 48h, T= 50 °C Katritzky, Alan R.; Yang, Zhijun; Lam, Jamshed N.; Synthesis; nb. 8; (1990); p. 666 - 669 View in Reaxys

92 %

With sulfuric acid in tetrahydrofuran, Time= 48h, T= 50 °C , other trisbenzotriazolyl derivatives Katritzky, Alan R.; Yang, Zhijun; Lam, Jamshed N.; Synthesis; nb. 8; (1990); p. 666 - 669 View in Reaxys

O O

Rx-ID: 2587789 View in Reaxys 224/834 Yield 97 %

Conditions & References With ammonium cerium(IV) nitrate in water, acetonitrile, Time= 4h, T= 0 °C Kim, C. U.; Misco, P. F.; Tetrahedron Letters; vol. 26; nb. 17; (1985); p. 2027 - 2030 View in Reaxys With ammonium cerium(IV) nitrate in water, acetonitrile, Time= 4h, T= 0 °C , with or without buffers, or with other oxidant (MnO2), Product distribution Kim, C. U.; Misco, P. F.; Tetrahedron Letters; vol. 26; nb. 17; (1985); p. 2027 - 2030 View in Reaxys

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O O O

O O

Rx-ID: 2974994 View in Reaxys 225/834 Yield

Conditions & References

29 %

With methanol, Irradiation, Yields of byproduct given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

29 %

in methanol, Irradiation, Yield given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

O O HO

Rx-ID: 2979296 View in Reaxys 226/834 Yield

Conditions & References

33 %

With methanol, Irradiation, Yields of byproduct given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

33 %

in methanol, Irradiation, Yield given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys O

O HN

S NH

HO O

Rx-ID: 3153633 View in Reaxys 227/834 Yield 65 %

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HO O

Rx-ID: 4437093 View in Reaxys 228/834 Yield

Conditions & References

50 %, 47 %

With dihydrogen peroxide, methyltrioxorhenium (VII), Time= 48h Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 60; nb. 24; (1995); p. 7728 - 7732 View in Reaxys O HO

Rx-ID: 4779937 View in Reaxys 229/834 Yield 100 %

Conditions & References With N,N,N',N'-tetramethylbenzidine in acetonitrile, Time= 2h, Irradiation, further reagents Banerjee, Anamitro; Falvey, Daniel E.; Journal of Organic Chemistry; vol. 62; nb. 18; (1997); p. 6245 - 6251 View in Reaxys

79 %

With N,N-dimethyl-aniline in acetonitrile, Time= 2h, Irradiation, sensitized deprotection; further phenacyl esters, Mechanism, Product distribution Banerjee, Anamitro; Falvey, Daniel E.; Journal of Organic Chemistry; vol. 62; nb. 18; (1997); p. 6245 - 6251 View in Reaxys With isopropyl alcohol in acetonitrile, Irradiation, other solvent; other H-atom donors; also in the neat solvent, Mechanism Banerjee, Anamitro; Falvey, Daniel E.; Journal of the American Chemical Society; vol. 120; nb. 12; (1998); p. 2965 - 2966 View in Reaxys With 2-aminoanthracene in acetonitrile, Time= 2h, Irradiation, protecting group release upon photolysis using various photosensitizers, Mechanism Banerjee, Anamitro; Lee, Kwangjoo; Yu, Qing; Fang, Albert G.; Falvey, Daniel E.; Tetrahedron Letters; vol. 39; nb. 26; (1998); p. 4635 - 4638 View in Reaxys

/PBSAB018-1380/

HO O

O O

Rx-ID: 6208665 View in Reaxys 230/834 Yield 30 % Spectr., 8 %, 7 % Spectr., 16 % Spectr. 16 % Spectr., 8 %, 7 %

Conditions & References With calcium hydroxide powder in dichloromethane, water, Time= 3.5h, T= 35 °C Tanguy, Guy; Weinberger, Bernd; Abbayes, Hevre des; Tetrahedron Letters; vol. 25; nb. 48; (1984); p. 5529 5532 View in Reaxys With calcium hydroxide powder in dichloromethane, water, Time= 3.5h, T= 35 °C Tanguy, Guy; Weinberger, Bernd; Abbayes, Hevre des; Tetrahedron Letters; vol. 25; nb. 48; (1984); p. 5529 5532 View in Reaxys

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Spectr., 30 % Spectr. 16 % Spectr., 8 %, 30 % Spectr., 7 % Spectr.

With calcium hydroxide powder in dichloromethane, water, Time= 3.5h, T= 35 °C Tanguy, Guy; Weinberger, Bernd; Abbayes, Hevre des; Tetrahedron Letters; vol. 25; nb. 48; (1984); p. 5529 5532 View in Reaxys

(v2)

Rx-ID: 25330535 View in Reaxys 231/834 Yield

Conditions & References 21 : EXAMPLE 21 EXAMPLE 21 The same autoclave as used in Example 17 is charged with 20 grams of benzyl formate, and 20 grams of N-methyl-2-pyrrolidone and 1.4 grams of mercurous iodide are added thereto. Carbon monoxide is introduced into the autoclave under pressure and the reaction is conducted at a pressure of 300 kg./cm.2 gauge and a temperature of 210° C. for 2 hours. As a result there is obtained phenyl acetic acid in a yield of 12.6 grams, which corresponds to a conversion of 63percent based on the starting benzyl formate. With carbon monoxide Patent; Mitsubishi Gas Chemical Company, Inc.; US29981; (1979); (E1) English View in Reaxys

NH 2

S OH

N H

OH O

S O OH

N H

Rx-ID: 28501472 View in Reaxys 232/834 Yield

Conditions & References With penicillin G acylase, water, sodium carbonate in methanol, T= 20 °C , pH= 8.0, Resolution of racemate, Enzymatic reaction, optical yield given as percent ee, enantioselective reaction Grundmann, Peter; Fessner, Wolf-Dieter; Advanced Synthesis and Catalysis; vol. 350; nb. 11-12; (2008); p. 1729 - 1735 View in Reaxys

O N H

OH O

H 2N O

O N H

OH O

Rx-ID: 28501474 View in Reaxys 233/834 Yield

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H O

Rx-ID: 34790061 View in Reaxys 234/834 Yield

Conditions & References

58%, 17%, With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrin)MnCl in toluene, Time= 0.166667h, T= 20 °C , Inert atmos5.5%, 13% phere, Concentration, Reagent/catalyst, Solvent Hyun, Min Young; Jo, Young Dan; Lee, Jun Ho; Lee, Hong Gyu; Park, Hyun Min; Hwang, In Hong; Kim, Kyeong Beom; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 19; nb. 5; (2013); p. 1810 1818 View in Reaxys

N O NH

Rx-ID: 38198779 View in Reaxys 235/834 Yield 44 %

Conditions & References With trifluoroacetic acid, sodium nitrite in chloroform, Time= 1h, T= 0 - 5 °C Mochalov; Gazzaeva; Kadzhaeva; Fedotov; Trofimova; Chemistry of Heterocyclic Compounds; vol. 47; nb. 11; (2012); p. 1415 - 1429; Khim. Geterotsikl. Soedin.; vol. 47; nb. 11; (2011); p. 1702 - 1717,15 View in Reaxys

O O

Rx-ID: 41958372 View in Reaxys 236/834 Yield

Conditions & References With oxygen, sodium t-butanolate in tris(dimethylamino)phosphine oxide, Time= 16h, T= 20 °C , p= 750.075Torr , Solvent, Overall yield = 76 percent; chemoselective reaction Kim, Sun Min; Shin, Hun Yi; Kim, Dong Wan; Yang, Jung Woon; ChemSusChem; vol. 9; nb. 3; (2016); p. 241 245 View in Reaxys

Rx-ID: 278124 View in Reaxys 237/834 Yield

Conditions & References With sodium, Petroleum ether, anschliessendes Behandeln mit festem Kohlendioxid Gilman; Pacevitz; Baine; Journal of the American Chemical Society; vol. 62; (1940); p. 1514,1519 View in Reaxys Gilman; Pacevitz; Journal of the American Chemical Society; vol. 62; (1940); p. 673 View in Reaxys With sodium, toluene, anschliessendes Behandeln mit festem Kohlendioxid Gilman; Pacevitz; Baine; Journal of the American Chemical Society; vol. 62; (1940); p. 1514,1519 View in Reaxys Gilman; Pacevitz; Journal of the American Chemical Society; vol. 62; (1940); p. 673

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View in Reaxys

Rx-ID: 818380 View in Reaxys 238/834 Yield

Conditions & References With carbon dioxide Austin; Johnson; Journal of the American Chemical Society; vol. 54; (1932); p. 647,656 View in Reaxys Gilman; Kirby; Journal of the American Chemical Society; vol. 54; (1932); p. 345,352 View in Reaxys Kinney; Mayhue; Journal of the American Chemical Society; vol. 53; (1931); p. 190,194, 198 View in Reaxys

N Z

N E

N O racemate

Rx-ID: 1554821 View in Reaxys 239/834 Yield 28 %, 40 %, 51 %

Conditions & References With copper(l) iodide, 1,10-phenanthroline, water, potassium carbonate, phenylacetylene in N,N-dimethyl-formamide, Time= 3h, T= 80 °C Okuro, Kazumi; Enna, Masahiro; Miura, Masahiro; Nomura, Masakatsu; Journal of the Chemical Society, Chemical Communications; nb. 13; (1993); p. 1107 - 1108 View in Reaxys

O O

Rx-ID: 1581079 View in Reaxys 240/834 Yield 84 %, 58 %, 16 %

Conditions & References T= 20 °C , Irradiation, Rate constant, Quantum yield Hilborn, James W.; Pincock, James A.; Journal of the American Chemical Society; vol. 113; nb. 7; (1991); p. 2683 - 2686 View in Reaxys

60 %

Irradiation, rate constant of electron transfer (kET X) for radical pair generated in this reaction, Mechanism DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

60 %

Irradiation, Yield given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

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84 % Chromat., 16 % Chromat.

Irradiation

84 % Chromat., 16 % Chromat.

Irradiation, rate of decarboxylation k(CO2), Rate constant, Quantum yield, Mechanism

Hilborn, James W.; Pincock, James A.; Canadian Journal of Chemistry; vol. 70; nb. 3; (1992); p. 992 - 999 View in Reaxys

16 % Chromat., 84 % Chromat.

Irradiation, other substituted naphthalenes Hilborn, James W.; Pincock, James A.; Canadian Journal of Chemistry; vol. 70; nb. 3; (1992); p. 992 - 999 View in Reaxys

HO HO

Rx-ID: 1992682 View in Reaxys 241/834 Yield

Conditions & References

72 %, 38 %

Stage 1: With Corey's ylide in tetrahydrofuran, Time= 0.666667h, T= 20 °C , Inert atmosphere Stage 2: With hydrogenchloride, water in ethyl acetate, pH= 2, Inert atmosphere Leggio, Antonella; De Marco, Rosaria; Perri, Francesca; Spinella, Mariagiovanna; Liguori, Angelo; European Journal of Organic Chemistry; nb. 1; (2012); p. 114 - 118 View in Reaxys With sodium hydroxide in 1,4-dioxane, water, T= 25 °C , effect of the medium, ΔG(S), Thermodynamic data, Rate constant Finkel'shtein, B. L.; Eliseeva, G. D.; Bazhenov, B. N.; Journal of Organic Chemistry USSR (English Translation); vol. 21; (1985); p. 1699 - 1703; Zhurnal Organicheskoi Khimii; vol. 21; nb. 9; (1985); p. 1858 - 1862 View in Reaxys OH HO

Rx-ID: 2126751 View in Reaxys 242/834 Yield 7%

Conditions & References With 3-chloro-benzenecarboperoxoic acid in methanol, Time= 5h, T= 25 °C Uemura, Sakae; Ohe, Kouichi; Yamauchi, Takayoshi; Mizutaki, Shoichi; Tamaki, Kentaro; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1990); p. 907 - 910 View in Reaxys

Rx-ID: 2393577 View in Reaxys 243/834 Yield 3 %, 6 %, 19 %, 56 %

Conditions & References With dihydrogen peroxide, methyltrioctylammonium tetrakis(oxodiperoxotungsto)phosphate, Time= 2h, T= 90 °C Venturello, Carlo; Gambaro, Mario; Journal of Organic Chemistry; vol. 56; nb. 20; (1991); p. 5924 - 5931 View in Reaxys

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O HO

O H N

O OH

Rx-ID: 3264503 View in Reaxys 244/834 Yield 50 %, 53.6 %

Conditions & References With dihydrogen peroxide in acetic acid, heating Funakoshi, Kazuhisa; Mizuoka, Masae; Wada, Kazuko; Saeki, Seitaro; Hamana, Masatomo; Chemical & Pharmaceutical Bulletin; vol. 32; nb. 10; (1984); p. 3886 - 3891 View in Reaxys

53.6 %, 50 %

With dihydrogen peroxide in acetic acid, Time= 3h, heating Funakoshi, Kazuhisa; Mizuoka, Masae; Wada, Kazuko; Saeki, Seitaro; Hamana, Masatomo; Chemical & Pharmaceutical Bulletin; vol. 32; nb. 10; (1984); p. 3886 - 3891 View in Reaxys

HO N E

N O racemate

Rx-ID: 3365710 View in Reaxys 245/834 Yield 28 %, 51 %, 40 %

Conditions & References With copper(l) iodide, 1,10-phenanthroline, water, potassium carbonate, N-phenyl-C-phenyl nitrone in N,N-dimethylformamide, Time= 3h, T= 80 °C Okuro, Kazumi; Enna, Masahiro; Miura, Masahiro; Nomura, Masakatsu; Journal of the Chemical Society, Chemical Communications; nb. 13; (1993); p. 1107 - 1108 View in Reaxys

H O

Rx-ID: 3379485 View in Reaxys 246/834 Yield 35 %, 20 %

Conditions & References With sodium carbonate in 1,2-dichloro-ethane, Time= 24h, Heating Ganem, Bruce; Heggs, Richard P.; Biloski, Alan J.; Schwartz, Daniel R.; Tetrahedron Letters; vol. 21; (1980); p. 685 - 688 View in Reaxys

20 %, 35 %

With sodium carbonate in 1,2-dichloro-ethane, Time= 24h, Heating Ganem, Bruce; Heggs, Richard P.; Biloski, Alan J.; Schwartz, Daniel R.; Tetrahedron Letters; vol. 21; (1980); p. 685 - 688 View in Reaxys O N Z

O O

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N E

N O

O racemate

racemate

Rx-ID: 4358250 View in Reaxys 247/834 Yield

Conditions & References

11 %

With potassium carbonate, CuI * pyridine in N,N-dimethyl-formamide, Time= 2h, Ambient temperature, Yield given. Yields of byproduct given Miura, Masahiro; Enna, Masahiro; Okuro, Kazumi; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 60; nb. 16; (1995); p. 4999 - 5004 View in Reaxys

HO C

Rx-ID: 4429641 View in Reaxys 248/834 Yield 72 %, 16 %, 45 %

Conditions & References With sodium hydroxide, η6-C6H6BPh3 -Rh(COD)+, tetra-n-hexylammonium hydrogen sulfate in dichloromethane, T= 40 °C , p= 760Torr , other substituted benzylic and allylic bromides; var. phase transfer catalysts; var. rhodium catalysts, Mechanism, Product distribution Amaratunga, Shiyamalie; Alper, Howard; Journal of Organometallic Chemistry; vol. 488; nb. 1-2; (1995); p. 25 28 View in Reaxys

O O

Rx-ID: 4437092 View in Reaxys 249/834 Yield 47 %, 41 %, 5 %

H 2N

H N

HO O

O O

Rx-ID: 4504240 View in Reaxys 250/834 Yield 76 %

Conditions & References With [bis(acetoxy)iodo]benzene, Time= 6h, T= 10 °C Prakash, Om; Sharma, Vijay; Sadana, Anil; Journal of Chemical Research - Part S; nb. 2; (1996); p. 100 - 101 View in Reaxys

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H N

Rx-ID: 4580454 View in Reaxys 251/834 Yield

Conditions & References With hydrogenchloride in water, Time= 1h, T= 100 °C Revelle, Larry K.; D'Avignon, D. Andre; Wilson, Joe A.; Journal of Pharmaceutical Sciences; vol. 85; nb. 10; (1996); p. 1049 - 1052 View in Reaxys

Rx-ID: 5230427 View in Reaxys 252/834 Yield

Conditions & References

75 %, 60 %

in methanol, Time= 1.5h, Irradiation, Decomposition Pirrung, Michael C.; Lee, Yong Rok; Park, Kaapjoo; Springer, James B.; Journal of Organic Chemistry; vol. 64; nb. 14; (1999); p. 5042 - 5047 View in Reaxys

Rx-ID: 8747376 View in Reaxys 253/834 Yield

Conditions & References

95 %

With sodium hydroxide, Time= 0.0166667h, microwave irradiation Matloubi Moghaddam; Ghaffarzadeh; Synthetic Communications; vol. 31; nb. 2; (2001); p. 317 - 321 View in Reaxys With sodium hydroxide, N-benzyl-N,N,N-triethylammonium chloride, Time= 8h, T= 100 °C Alam, Mujahid; Adapa, Srinivas R.; Synthetic Communications; vol. 33; nb. 1; (2003); p. 59 - 63 View in Reaxys

H O

Rx-ID: 9132925 View in Reaxys 254/834 Yield

Conditions & References With trans-cyclooctene, [Fe(III)(tmp)]Cl in dichloromethane, Time= 0.166667h, T= 20 °C , Product distribution, Further Variations: Reagents, Catalysts Suzuki, Noriyuki; Higuchi, Tsunehiko; Nagano, Tetsuo; Journal of the American Chemical Society; vol. 124; nb. 32; (2002); p. 9622 - 9628 View in Reaxys

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HO O

O OH

Rx-ID: 9954329 View in Reaxys 255/834 Yield

Conditions & References With sodium hexamethyldisilazane in tetrahydrofuran, T= -20 °C Dittmer, Donald C.; Li, Qun; Avilov, Dimitry V.; Journal of Organic Chemistry; vol. 70; nb. 12; (2005); p. 4682 4686 View in Reaxys

HO O

Rx-ID: 11244584 View in Reaxys 256/834 Yield

Conditions & References With sodium hydroxide in methanol, dichloromethane, Time= 4h, T= 20 °C Theodorou, Vassiliki; Skobridis, Konstantinos; Tzakos, Andreas G.; Ragoussis, Valentine; Tetrahedron Letters; vol. 48; nb. 46; (2007); p. 8230 - 8233 View in Reaxys

N-BOC-(L)-3,4-dimethoxyphenylalanine on Merrifield resin Rx-ID: 16559051 View in Reaxys 257/834

Yield

Conditions & References Reaction Steps: 2 1: 3 percent / aq. HI / [Pd(PPh3)4] / acetone / 42 h / 100 °C / 76000 Torr 2: 98 percent / aq. HI / [Pd(PPh3)4] / acetone / 42 h / 100 °C / 76000 Torr With hydrogen iodide, tetrakis(triphenylphosphine) palladium(0) in acetone, 1: Carbonylation / 2: Carbonylation Lin, Yong-Shou; Yamamoto, Akio; Bulletin of the Chemical Society of Japan; vol. 71; nb. 3; (1998); p. 723 - 734 View in Reaxys

OH H

O O

Rx-ID: 20832617 View in Reaxys 258/834 Yield

Conditions & References Reaction Steps: 4 1: H2 / Raney nickel 2: NaHSO3 3: H(+) 4: KOH / ethanol With potassium hydroxide, hydrogen, hydrogen cation, sodium hydrogensulfite, nickel in ethanol Matthews, Barry R.; Gountzos, Helen; Jackson, W. Roy; Watson, Keith G.; Tetrahedron Letters; vol. 30; nb. 38; (1989); p. 5157 - 5158 View in Reaxys

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O O

Rx-ID: 20841191 View in Reaxys 259/834 Yield

Conditions & References Reaction Steps: 2 1: 75 percent 2: pH 7.5 / penicillinacylase on Eupergit C beads / H2O / 28 °C With pH 7.5, penicillinacylase on Eupergit C beads in water Fuganti, Claudio; Grasselli, Piero; Casati, Paolo; Tetrahedron Letters; vol. 27; nb. 27; (1986); p. 3191 - 3194 View in Reaxys

Rx-ID: 21185594 View in Reaxys 260/834 Yield

Conditions & References Reaction Steps: 2 1: 80 percent / KH / tetrahydrofuran / 2 h / Ambient temperature 2: 80 percent / 10percent aq. HCl / tetrahydrofuran / 3 h / Heating With hydrogenchloride, potassium hydride in tetrahydrofuran Takahashi, Kazumasa; Shibasaki, Kenichiro; Ogura, Katsuyuki; Iida, Hirotada; Journal of Organic Chemistry; vol. 48; nb. 20; (1983); p. 3566 - 3569 View in Reaxys Reaction Steps: 2 1: 1.)BuLi / 1.)THF, hexane, -78 deg C, 1 h; 2.)a.)THF, -78 deg C, 2 h, b.)r.t., 2 h 2: 3 percent / meta-chloroperbenzoic acid / 3 h / Heating With n-butyllithium, 3-chloro-benzenecarboperoxoic acid Uemura, Sakae; Ohe, Kouichi; Yamauchi, Takayoshi; Mizutaki, Shoichi; Tamaki, Kentaro; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1990); p. 907 - 910 View in Reaxys Reaction Steps: 2 1: 1.)BuLi / 1.)THF, hexane, -78 deg C, 1 h; 2.)a.)THF, -78 deg C, 2 h, b.)r.t., 2 h 2: 3 percent / meta-chloroperbenzoic acid / methanol / 3 h / Heating With n-butyllithium, 3-chloro-benzenecarboperoxoic acid in methanol Uemura, Sakae; Ohe, Kouichi; Yamauchi, Takayoshi; Mizutaki, Shoichi; Tamaki, Kentaro; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1990); p. 907 - 910 View in Reaxys O HO

N O

Rx-ID: 21244610 View in Reaxys 261/834 Yield

Conditions & References Reaction Steps: 2 1: 68 percent / 50percent aq. NaOH / triethylbenzylammonium chloride / CH2Cl2 / 6 h / Ambient temperature 2: 90 percent / 10percent aq. hydrochloric acid / tetrahydrofuran / 6 h / Heating With hydrogenchloride, sodium hydroxide, N-benzyl-N,N,N-triethylammonium chloride in tetrahydrofuran, dichloromethane

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Takahashi, Kazumasa; Masuda, Takumi; Ogura, Katsuyuki; Iida, Hirotada; Synthesis; nb. 12; (1983); p. 1043 1045 View in Reaxys

HO O

Rx-ID: 37381818 View in Reaxys 262/834 Yield

Conditions & References

30 %, 28 %, 45 %

With Pseudomonas sp. isolated from coastal waters and soils of the Absheron peninsula at the Caspian Sea in water, T= 28 °C , Microbiological reaction Veliev; Salmanov; Babashly; Alieva; Bektashi; Petroleum Chemistry; vol. 53; nb. 6; (2013); p. 426 - 430; Neftekhimiya; vol. 53; nb. 6; (2013); p. 476 - 480,4 View in Reaxys

O HO

HO O

NH 2

Rx-ID: 2020653 View in Reaxys 263/834 Yield

Conditions & References With N-hexadecyl-N,N,N-trimethylammonium bromide, coenzyme PQQ, Time= 24h, T= 30 °C , Yield given. Yields of byproduct given Itoh, Shinobu; Kato, Nobuyuki; Ohshiro, Yoshiki; Agawa, Toshio; Tetrahedron Letters; vol. 25; nb. 42; (1984); p. 4753 - 4756 View in Reaxys

HO O

Rx-ID: 2032077 View in Reaxys 264/834 Yield

Conditions & References

93 %

With sulfuric acid, Ambient temperature Hayashi, Sei-ichi; Nakai, Takeshi; Ishikawa, Nobuo; Chemistry Letters; (1980); p. 651 - 654 View in Reaxys

HO O

O O

Rx-ID: 2395352 View in Reaxys 265/834 Yield

Conditions & References

75 %, 3 %, With pentacarbonyliron(0), tetra-n-butyl-ammonium sulfate in sodium hydroxide, benzene, Time= 15h, T= 20 °C , p= 14 %, 6 %, 760Torr , variation of solvent, temperature, catalyst, pressure, reaction time and ratio of catalyst and substrate, ex2% aminations with further benzyl halides, Product distribution Tanguy, Guy; Weinberger, Berndt; Abbayes, Herve des; Tetrahedron Letters; vol. 24; nb. 37; (1983); p. 4005 4008 View in Reaxys

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N N N

Rx-ID: 2964001 View in Reaxys 266/834 Yield 12 %

12 %

in methanol, Irradiation, Yield given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

H O

Rx-ID: 3365753 View in Reaxys 267/834 Yield 2 % Chromat., 97 % Chromat.

Conditions & References With methyl(trifluoromethyl)dioxirane in various solvent(s), Time= 0.116667h, T= 0 °C Curci, Ruggero; Fiorentino, Michele; Fusco, Caterina; Mello, Rossella; Ballistreri, Francesco; et al.; Tetrahedron Letters; vol. 33; nb. 51; (1992); p. 7929 - 7932 View in Reaxys

O HO

O O O

Rx-ID: 4437083 View in Reaxys 268/834 Yield 40 %, 15 %, 30 %, 11 % 40 %, 15 %, 11 %, 30 %

Conditions & References With dihydrogen peroxide, methyltrioxorhenium (VII), Time= 48h Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 60; nb. 24; (1995); p. 7728 - 7732 View in Reaxys With dihydrogen peroxide, methyltrioxorhenium (VII), Time= 48h Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 60; nb. 24; (1995); p. 7728 - 7732 View in Reaxys

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O HO

O O

Rx-ID: 4437128 View in Reaxys 269/834 Yield

Conditions & References

38 %, 17 With dihydrogen peroxide, methyltrioxorhenium (VII), Time= 48h %, 30 %, 8 Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 60; nb. 24; (1995); p. 7728 - 7732 % View in Reaxys 38 %, 17 With dihydrogen peroxide, methyltrioxorhenium (VII), Time= 48h %, 8 %, 30 Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 60; nb. 24; (1995); p. 7728 - 7732 % View in Reaxys

HO O

Rx-ID: 4437132 View in Reaxys 270/834 Yield

Conditions & References

30 %, 60 %

With dihydrogen peroxide, methyltrioxorhenium (VII), Time= 48h Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 60; nb. 24; (1995); p. 7728 - 7732 View in Reaxys

HO O

Rx-ID: 4477796 View in Reaxys 271/834 Yield 8.3 %, 89.8 %

Conditions & References With cobalt-salen complex, tetra-n-butylammonium perchlorate, water in acetonitrile, T= 25 °C , electrochemical reaction Isse, Abdirisak Ahmed; Gennaro, Armando; Vianello, Elio; Journal of the Chemical Society - Dalton Transactions; nb. 8; (1996); p. 1613 - 1618 View in Reaxys

77 %, 23 %

With dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine, manganese, palladium diacetate, magnesium chloride in DMFA, Time= 12h, p= 760.051Torr , Inert atmosphere, Schlenk technique, Reagent/catalyst Zhang, Shuai; Chen, Wei-Qiang; Yu, Ao; He, Liang-Nian; ChemCatChem; vol. 7; nb. 23; (2015); p. 3972 - 3977 View in Reaxys

34.6 %, 53.4 %

With cobalt-salen complex, tetra-n-butylammonium perchlorate in acetonitrile, T= 25 °C , E=-1.52 V (vs. SCE); var. potential; ΔGo(excit.), Product distribution, Mechanism, Rate constant Isse, Abdirisak Ahmed; Gennaro, Armando; Vianello, Elio; Journal of the Chemical Society - Dalton Transactions; nb. 8; (1996); p. 1613 - 1618 View in Reaxys

49.3 %, 43.7 %

With cobalt-salen complex, tetra-n-butylammonium perchlorate in acetonitrile, T= 25 °C , electrochemical reaction Isse, Abdirisak Ahmed; Gennaro, Armando; Vianello, Elio; Journal of the Chemical Society - Dalton Transactions; nb. 8; (1996); p. 1613 - 1618 View in Reaxys

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mandelate sodium

Rx-ID: 6330958 View in Reaxys 272/834 Yield

Conditions & References With nickel oxide, T= 280 °C , p= 63840Torr , Hydrogenation Ipatjew; Rasuwajew; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 58; (1926); p. 128; Chemische Berichte; vol. 59; (1926); p. 310 View in Reaxys

HO O

Rx-ID: 10132010 View in Reaxys 273/834 Yield 47 %, 36 %

Conditions & References With tetra-n-butylammonium tetrafluoroborate in acetonitrile, Electrolysis Otero, M. Dolores; Batanero, Belen; Barba, Fructuoso; Tetrahedron Letters; vol. 47; nb. 13; (2006); p. 2171 2173 View in Reaxys

Cl O

Rx-ID: 10148014 View in Reaxys 274/834 Yield

Conditions & References With water in acetone, T= 0 °C , Kinetics Bentley, T. William; Harris, H. Carl; Ryu, Zoon Ha; Lim, Gui Taek; Sung, Dae Dong; Szajda, Stanley R.; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 8963 - 8970 View in Reaxys Reaction Steps: 2 1: 85 percent / 40percent aqueous NaOH / 1.5 h / 15 °C 2: acetone / 24 h / 25 °C With sodium hydroxide in acetone Katritzky, Alan R.; Khan, Ghulam R.; Schwarz, Otto A.; Tetrahedron Letters; vol. 25; nb. 12; (1984); p. 1223 1226 View in Reaxys Reaction Steps: 2 1: 76 percent / CH3COONa / dioxane / 1) 0.5 deg C, 4 h, 2) r.t., 1 h 2: 56 percent / benzene / 24 h / Irradiation With sodium acetate in 1,4-dioxane, benzene Parshad; Sharma; Journal of the Indian Chemical Society; vol. 67; nb. 2; (1990); p. 150 - 152 View in Reaxys Reaction Steps: 2 1: 76 percent / CH3COONa / dioxane / 1) 0.5 deg C, 4 h, 2) r.t., 1 h 2: 17 percent / propan-2-ol / 40 h / Irradiation With sodium acetate in 1,4-dioxane, isopropyl alcohol Parshad; Sharma; Journal of the Indian Chemical Society; vol. 67; nb. 2; (1990); p. 150 - 152 View in Reaxys Reaction Steps: 3 1: triethylamine / dichloromethane / 20 °C

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2: methanol / |Reflux 3: ascorbic acid powder; sodium sulfate / acetonitrile; chloroform-d1; water-d2 / 1 h / 20 °C / |UV-irradiation With sodium sulfate, triethylamine, ascorbic acid powder in methanol, chloroform-d1, dichloromethane, water-d2, acetonitrile Kunsberg, David J.; Kipping, Allison H.; Falvey, Daniel E.; Organic Letters; vol. 17; nb. 14; (2015); p. 3454 3457 View in Reaxys

O O

Rx-ID: 29175790 View in Reaxys 275/834 Yield

Conditions & References With oxygen, T= -103.16 °C Zhou, Ling; Gorin, Craig F.; Madix, Robert J.; Journal of the American Chemical Society; vol. 132; nb. 2; (2010); p. 434 - 435 View in Reaxys HO

O Br

Rx-ID: 33927778 View in Reaxys 276/834 Yield 62 %

Conditions & References With methanesulfonic acid, trifluoromethanesulfonic anhydride, T= 100 °C , Inert atmosphere, Fries rearrangement, regioselective reaction Jeon, Ingyu; Mangion, Ian K.; Synlett; vol. 23; nb. 13; (2012); p. 1927 - 1930 View in Reaxys

H O

Rx-ID: 38068157 View in Reaxys 277/834 Yield

Conditions & References With tert.-butylhydroperoxide in toluene, Time= 8h, T= 99.84 °C Fang, Yiyun; Chen, Yuanzhe; Li, Xinzhe; Zhou, Xingchun; Li, Jing; Tang, Weijie; Huang, Jingwei; Jin, Jun; Ma, Jiantai; Journal of Molecular Catalysis A: Chemical; vol. 392; (2014); p. 16 - 21 View in Reaxys With dihydrogen peroxide in toluene, Time= 8h, T= 99.84 °C , Solvent Fang, Yiyun; Chen, Yuanzhe; Li, Xinzhe; Zhou, Xingchun; Li, Jing; Tang, Weijie; Huang, Jingwei; Jin, Jun; Ma, Jiantai; Journal of Molecular Catalysis A: Chemical; vol. 392; (2014); p. 16 - 21 View in Reaxys

H O

Rx-ID: 38068158 View in Reaxys 278/834 Yield

Conditions & References With oxygen in toluene, Time= 8h, T= 99.84 °C Fang, Yiyun; Chen, Yuanzhe; Li, Xinzhe; Zhou, Xingchun; Li, Jing; Tang, Weijie; Huang, Jingwei; Jin, Jun; Ma, Jiantai; Journal of Molecular Catalysis A: Chemical; vol. 392; (2014); p. 16 - 21

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View in Reaxys

HO O

Rx-ID: 2131095 View in Reaxys 279/834 Yield

Conditions & References With benzonitrile, (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride, T= 30 °C , Rate constant Yuan, Lung-Chi; Bruice, Thomas C.; Journal of the American Chemical Society; vol. 108; nb. 7; (1986); p. 1643 1650 View in Reaxys

HO O

Rx-ID: 2131098 View in Reaxys 280/834 Yield

Conditions & References

9 %, 61 %, With 5,10,15,20-tetrakisphenylporphyrinatoiron(III) chloride, 2,4,6-tri-(tert-butyl)phenol in benzene, Time= 24 % 0.166667h, T= 25 °C , other peroxy acid; also var. iron(III) porphyrin-deriv. - ligand complexes, Product distribution Higuchi, Tsunehiko; Shimada, Kousei; Maruyama, Naho; Hirobe, Masaaki; Journal of the American Chemical Society; vol. 115; nb. 16; (1993); p. 7551 - 7552 View in Reaxys

Si O

Rx-ID: 2538540 View in Reaxys 281/834 Yield

Conditions & References With hydrogenchloride, n-butyllithium, water, methyllithium, Yield given. Multistep reaction. Yields of byproduct given Kowalski, Conrad J.; Fields, Kevin W.; Journal of the American Chemical Society; vol. 104; nb. 1; (1982); p. 321 323 View in Reaxys

HO O

Rx-ID: 2542015 View in Reaxys 282/834 Yield

Conditions & References With mercury(II) diacetate in formic acid, Time= 3h, T= 50 °C , Yield given Fortes, Carlos C.; Fortes, Helena C.; Goncalves, Dioneia C. R. G.; Journal of the Chemical Society, Chemical Communications; nb. 15; (1982); p. 857 - 858 View in Reaxys

HO C

Rx-ID: 2694883 View in Reaxys 283/834 Yield 20 %

Conditions & References With N-benzyl-N,N,N-triethylammonium chloride, pentacarbonyliron(0) in sodium hydroxide, hexane, Time= 48h, p= 760Torr , Ambient temperature, Product distribution

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Tustin, Gerald C.; Hembre, Robert T.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1761 - 1764 View in Reaxys O HO

Rx-ID: 5277785 View in Reaxys 284/834 Yield

Conditions & References

90 - 96 %

With 9,10-bis(chlorodimethyl)anthracene in acetonitrile, Time= 2h, UV-irradiation Patent; University of Maryland; US6392089; (2002); (B1) English View in Reaxys

88 %

With 9-methyl carbazole in acetonitrile, Time= 3h, UV-irradiation Patent; University of Maryland; US6392089; (2002); (B1) English View in Reaxys

86 %

With potassium hydroxide, 9-phenanthrolate, ascorbic acid powder in methanol, water, Time= 3.5h, UV-irradiation Patent; University of Maryland; US6392089; (2002); (B1) English View in Reaxys

78 - 83 %

With 9-methyl anthracene in acetonitrile, Time= 2 - 2.5h, UV-irradiation Patent; University of Maryland; US6392089; (2002); (B1) English View in Reaxys

76 %

With N,N,N',N'-tetramethyl-para-phenylenediamine in acetonitrile, Time= 2h, UV-irradiation Patent; University of Maryland; US6392089; (2002); (B1) English View in Reaxys

70 %

With potassium hydroxide, 2-naphthoxide ion, ascorbic acid powder in methanol, water, Time= 3h, UV-irradiation Patent; University of Maryland; US6392089; (2002); (B1) English View in Reaxys

70 - 97 %

With 2-aminoanthracene in acetonitrile, Time= 5 - 15h, UV-irradiation Patent; University of Maryland; US6392089; (2002); (B1) English View in Reaxys With 9,10-bis(chlorodimethyl)anthracene in acetonitrile-D3, Time= 2h, UV-irradiation, Decomposition, Quantum yield Banerjee, Anamitro; Lee, Kwangjoo; Falvey, Daniel E.; Tetrahedron; vol. 55; nb. 44; (1999); p. 12699 - 12710 View in Reaxys

O O

O OH

O O

HO O

Rx-ID: 9051744 View in Reaxys 285/834

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Yield

Conditions & References

5 mg, 8 mg With sodium hydroxide in acetone, Time= 2.5h, T= 50 °C Hu, Lin; Gao, Jin-Ming; Liu, Ji-Kai; Helvetica Chimica Acta; vol. 84; nb. 11; (2001); p. 3342 - 3349 View in Reaxys

H N O

Rx-ID: 9742378 View in Reaxys 286/834 Yield

Conditions & References

35 %, 30 %

in tert-butyl alcohol, Time= 168h, T= 130 °C Henry-Riyad, Huda; Tidwell, Thomas T.; Canadian Journal of Chemistry; vol. 81; nb. 6; (2003); p. 697 - 704 View in Reaxys

C (v4) H 2 Zr

Cl 2OZr

CH 2

Rx-ID: 26631352 View in Reaxys 287/834 Yield

Conditions & References

50 %, 50 %

With hydrogenchloride in diethyl ether, CO2 was bubbled through a cold (-78°C) soln. of compound in ether in the absence of light for 3-4 h, aq. HCl was added; Bougeard, Peter; McCullough, John J.; Sayer, Brian G.; McGlinchey, Michael J.; Inorganica Chimica Acta; vol. 89; (1984); p. 133 - 138 ; (from Gmelin) View in Reaxys

O O

Rx-ID: 29175791 View in Reaxys 288/834 Yield

Conditions & References With oxygen, T= -103.16 °C Zhou, Ling; Gorin, Craig F.; Madix, Robert J.; Journal of the American Chemical Society; vol. 132; nb. 2; (2010); p. 434 - 435 View in Reaxys O O

O O

HO O

H HO

H O

Rx-ID: 29836107 View in Reaxys 289/834

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Yield

Conditions & References

12.5 %Chromat., 12.5 %Chromat.

Stage 1: With tris(dibenzylideneacetone)dipalladium(0) chloroform complex, (S)-Cl,MeO-BIPHEP, lithium chloride, lithium diisopropyl amide in tetrahydrofuran, Time= 40h, T= -78 °C , Claisen rearrangement Stage 2: With ammonium chloride in tetrahydrofuran, water, optical yield given as percent ee, enantioselective reaction Braun, Manfred; Meletis, Panos; Schrader, Wolfgang; European Journal of Organic Chemistry; nb. 28; (2010); p. 5369 - 5372 View in Reaxys

I HO

Rx-ID: 31428068 View in Reaxys 290/834 Yield

Conditions & References

59 %, 18 %Spectr.

Stage 1: With potassium tert-butylate in dimethyl sulfoxide, Time= 0.166667h, Inert atmosphere Stage 2: in dimethyl sulfoxide, Time= 2h, Inert atmosphere, Irradiation Stage 3: With ammonium nitrate, nitric acid in water Guastavino, Javier F.; Buden, Maria E.; Garcia, Carolina S.; Rossi, Roberto A.; Arkivoc; vol. 2011; nb. 7; (2011); p. 389 - 405 View in Reaxys

HO O

N H

O N

O O

Rx-ID: 38436326 View in Reaxys 291/834 Yield 91%

Conditions & References in chloroform-d1, Time= 18h, Irradiation Szymanski, Wiktor; Velema, Willem A.; Feringa, Ben L.; Angewandte Chemie - International Edition; vol. 53; nb. 33; (2014); p. 8682 - 8686; Angew. Chem.; vol. 126; nb. 33; (2014); p. 8826 - 8830,5 View in Reaxys

HO HO

HO O

Rx-ID: 40660990 View in Reaxys 292/834 Yield 55 %, 12 %

Conditions & References With caesium carbonate in water, Time= 1h, UV-irradiation, Inert atmosphere Ravelli, Davide; Protti, Stefano; Fagnoni, Maurizio; Journal of Organic Chemistry; vol. 80; nb. 2; (2015); p. 852 858 View in Reaxys

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N+

HO O

I–

Rx-ID: 40681508 View in Reaxys 293/834 Yield

Conditions & References Reaction Steps: 2 1: methanol / |Reflux 2: ascorbic acid powder; sodium sulfate / acetonitrile; chloroform-d1; water-d2 / 1 h / 20 °C / |UV-irradiation With sodium sulfate, ascorbic acid powder in methanol, chloroform-d1, water-d2, acetonitrile Kunsberg, David J.; Kipping, Allison H.; Falvey, Daniel E.; Organic Letters; vol. 17; nb. 14; (2015); p. 3454 3457 View in Reaxys

O O

Rx-ID: 41542157 View in Reaxys 294/834 Yield

Conditions & References With water, potassium carbonate in DME, Time= 16h, T= 25 °C Schwieter, Kenneth E.; Johnston, Jeffrey N.; Chemical Communications; vol. 52; nb. 1; (2016); p. 152 - 155 View in Reaxys O

OH O

Rx-ID: 750316 View in Reaxys 295/834 Yield

Conditions & References With octane, pentyl sodium, Eintragen des Reaktionsgemisches in festes Kohlendioxid Morton; Little; Strong; Journal of the American Chemical Society; vol. 65; (1943); p. 1339,1345 View in Reaxys

Cl HO

HO C

O O

HO O

Rx-ID: 1629120 View in Reaxys 296/834 Yield

Conditions & References

3.7 % Chromat., 87.4 % Chromat.

With sodium hydroxide, dicobalt octacarbonyl in water, Time= 24h, T= 65 °C , p= 1471.02Torr , Irradiation, Product distribution Kashimura, Tsugunori; Kudo, Kiyoshi; Mori, Sadayuki; Sugita, Nobuyuki; Chemistry Letters; (1986); p. 299 302 View in Reaxys

O O

Rx-ID: 2070891 View in Reaxys 297/834

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Yield

Conditions & References

51.6 mg, 153.0 mg, 4.0 mg, 139.7 mg

With (4-methylphenyl)sulfonyl bromide in benzene, Time= 40h, T= 70 °C , Further byproducts given

139.7 mg, 153.0 mg, 4.0 mg, 51.6 mg

With (4-methylphenyl)sulfonyl bromide in benzene, Time= 40h, T= 70 °C , Further byproducts given

139.7 mg, 51.6 mg, 4.0 mg, 153.0 mg

With (4-methylphenyl)sulfonyl bromide in benzene, Time= 40h, T= 70 °C , Further byproducts given

da Silva Correa, Carlos M.M.; Oliveira, Maria Augusta B.C.S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1987); p. 811 - 814 View in Reaxys

O HO

Rx-ID: 2206233 View in Reaxys 298/834 Yield

Conditions & References With sodium hydroxide, water in ethanol, T= 30 °C , Rate constant Jackman; Petrei; Smith; Journal of the American Chemical Society; vol. 113; nb. 9; (1991); p. 3451 - 3458 View in Reaxys

O NH O

S N

O O

H 2N

Rx-ID: 2629643 View in Reaxys 299/834 Yield

Conditions & References

15 %

in water, acetonitrile, T= 23 °C , penicillin acylase; pH=7.3 Baldaro; Faiardi; Fuganti; Grasselli; Lazzarini; Tetrahedron Letters; vol. 29; nb. 36; (1988); p. 4623 - 4624 View in Reaxys

N N

O O

Rx-ID: 2971157 View in Reaxys 300/834 Yield 75 %

Conditions & References With ammonium hydroxide, other reagents and conditions Garcia, Jordi; Vilarrasa, Jaume; Tetrahedron Letters; vol. 28; nb. 3; (1987); p. 341 - 342 View in Reaxys

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O HO

O O

Rx-ID: 2971700 View in Reaxys 301/834 Yield

Conditions & References

43 %, 67.4 %

67.4 %, 43 %

With dibenzo-18-crown-6 in benzene Grebenyuk, A. D.; Kosareva, L. V.; Chemistry of Natural Compounds; vol. 18; nb. 4; (1982); p. 483 - 484; Khimiya Prirodnykh Soedinenii; vol. 18; nb. 4; (1982); p. 515 - 516 View in Reaxys With sulfuric acid, periodate(1-), ruthenium(III) cation in acetic acid, T= 50 °C , Mechanism, Rate constant Swarnalakshmi, N.; Uma, V.; Sethuram, B.; Navaneeth Rao, T.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 23; nb. 5; (1984); p. 386 - 388 View in Reaxys With sulfuric acid, acetic acid, ruthenium trichloride, T= 24.85 - 39.85 °C , Catalytic oxidation, Kinetics Annapoorna; Prasad Rao; Sethuram; International Journal of Chemical Kinetics; vol. 32; nb. 10; (2000); p. 581 588 View in Reaxys

O O

Rx-ID: 3259587 View in Reaxys 302/834 Yield

Conditions & References With chromium(VI) oxide, sulfuric acid, water in acetone, Time= 0.0833333h, T= 1 °C , Yield given. Yields of byproduct given Warnhoff, E.W.; Yerhoff, F.W.; Heterocycles; vol. 15; nb. 2; (1981); p. 777 - 784 View in Reaxys

O O

Rx-ID: 3365786 View in Reaxys 303/834 Yield 43 %, 7 %

Conditions & References With Oxonereg;, (ethylenedinitrilo)tetraacetic acid disodium salt, sodium hydrogencarbonate in acetone, acetonitrile, Time= 15h, T= 10 °C , Product distribution, Further Variations: time Zeller, Klaus-Peter; Kowallik, Meike; Haiss, Peter; Organic and Biomolecular Chemistry; vol. 3; nb. 12; (2005); p. 2310 - 2318 View in Reaxys

36 % Chromat., 17 % Chromat.

With PMP in acetonitrile, Time= 4h, Ambient temperature, Product distribution Ogata, Yoshiro; Sawaki, Yasuhiko; Ohno, Takashi; Journal of the American Chemical Society; vol. 104; nb. 1; (1982); p. 216 - 219 View in Reaxys

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HO O

Rx-ID: 3962310 View in Reaxys 304/834 Yield

Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, Time= 2h, T= -20 °C Larson, Gerald L.; Ortiz, Margarita; Roca, Marisol Rodriguez de; Synthetic Communications; vol. 11; nb. 7; (1981); p. 583 - 590 View in Reaxys

O O

Rx-ID: 4437086 View in Reaxys 305/834 Yield

Conditions & References

10 %, 85 %

With dihydrogen peroxide, methyltrioxorhenium (VII), Time= 48h Zhu, Zuolin; Espenson, James H.; Journal of Organic Chemistry; vol. 60; nb. 24; (1995); p. 7728 - 7732 View in Reaxys

O–

N+ O O

Cl OO

Rx-ID: 10013448 View in Reaxys 306/834 Yield 73 %

Conditions & References With N,N-dimethyl-aniline in methanol, Time= 2h, Irradiation, Quantum yield, Further Variations: Reagents Sundararajan, Chitra; Falvey, Daniel E.; Organic Letters; vol. 7; nb. 13; (2005); p. 2631 - 2634 View in Reaxys

Cl O

Ala ester

N-BOC-(L)-3,4-dimethoxyphenylalanine on Merrifield resin

Rx-ID: 16273476 View in Reaxys 307/834 Yield

Conditions & References Reaction Steps: 2 1: 89 percent / 4-(dimethylamino)pyridine; pyridine / CH2Cl2 / 0 - 20 °C 2: 75 percent / methanol / 1.5 h / Irradiation With pyridine, 4-(N,N-dimethlyamino)pyridine in methanol, dichloromethane, 1: Addition / 2: Decomposition Pirrung, Michael C.; Lee, Yong Rok; Park, Kaapjoo; Springer, James B.; Journal of Organic Chemistry; vol. 64; nb. 14; (1999); p. 5042 - 5047 View in Reaxys

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3t-<2>naphthyl-acrylaldehyde

Rx-ID: 17764703 View in Reaxys 308/834 Yield

Conditions & References Reaction Steps: 3 1: 86 percent / CH2Cl2 / 16 h / Ambient temperature 2: 98 percent / KF / dimethylsulfoxide / 2 h / 100 °C 3: 70 percent / HgSO4, 2N H2SO4 / acetic acid / 24 h / 80 °C With potassium fluoride, sulfuric acid, mercuric sulphate in dichloromethane, acetic acid, dimethyl sulfoxide Schmitz, Carole; Rouanet-Dreyfuss, Anne-Claire; Tueni, Marie; Biellmann, Jean-Francois; Journal of Organic Chemistry; vol. 61; nb. 5; (1996); p. 1817 - 1821 View in Reaxys

3t-<2>naphthyl-acrylaldehyde

Rx-ID: 17774624 View in Reaxys 309/834 Yield

Conditions & References Reaction Steps: 2 1: 98 percent / KF / dimethylsulfoxide / 2 h / 100 °C 2: 70 percent / HgSO4, 2N H2SO4 / acetic acid / 24 h / 80 °C With potassium fluoride, sulfuric acid, mercuric sulphate in acetic acid, dimethyl sulfoxide Schmitz, Carole; Rouanet-Dreyfuss, Anne-Claire; Tueni, Marie; Biellmann, Jean-Francois; Journal of Organic Chemistry; vol. 61; nb. 5; (1996); p. 1817 - 1821 View in Reaxys

H N

O O

Rx-ID: 21114615 View in Reaxys 310/834 Yield

Conditions & References Reaction Steps: 2 1: 87 percent / triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h / 25 °C 2: 91 percent / 1.0 N lithium hydroxide / tetrahydrofuran / 1 h / 25 °C With 4-(N,N-dimethlyamino)pyridine, lithium hydroxide, triethylamine in tetrahydrofuran, dichloromethane Flynn, Daniel L.; Zelle, Robert E.; Grieco, Paul A.; Journal of Organic Chemistry; vol. 48; nb. 14; (1983); p. 2424 2426 View in Reaxys

Cl HN

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O N

O O

Z N

Rx-ID: 27962142 View in Reaxys 311/834 Yield

Conditions & References

30 %, 19 %, 9 %, 9 %

With sodium nitrite, Time= 1h, T= 25 °C , Further byproducts. Loeppky, Richard N.; Shi, Jianzheng; Barnes, Charles L.; Geddam, Sailaja; Chemical Research in Toxicology; vol. 21; nb. 2; (2008); p. 295 - 307 View in Reaxys

H O

Rx-ID: 29530791 View in Reaxys 312/834 Yield

Conditions & References

53.5 With 4CH4O*C92H64Mn4N20O12Re4Se4*8H2O, 3-chloro-benzenecarboperoxoic acid in dichloromethane, acetonitrile, %ChroTime= 0.166667h, T= 20 °C , Air atmosphere mat., 54.7 %Chromat. Lee, Sun Hwa; Xu, Li; Park, Byeong Kwon; Mironov, Yuri V.; Kim, Soo Hyun; Song, Young Ju; Kim, Cheal; Kim, Youngmee; Kim, Sung-Jin; Chemistry - A European Journal; vol. 16; nb. 15; (2010); p. 4678 - 4685 View in Reaxys

O O

N O

O O

N O

Rx-ID: 29710715 View in Reaxys 313/834 Yield

Conditions & References

88 %

in acetonitrile, Irradiation Kammari, Laxminarayana; Solomek, Tomas; Ngoy, Bokolombe Pitchou; Heger, Dominik; Klan, Petr; Journal of the American Chemical Society; vol. 132; nb. 33; (2010); p. 11431 - 11433 View in Reaxys

O Cl

Rx-ID: 29852368 View in Reaxys 314/834 Yield

Conditions & References

23 %, 67 %

With indium, ND4Cl, deuterated ammonium chloride in THF-d8 (tetrahydrofuran-d8), Time= 30h, Reflux Mineno, Tomoko; Hirayama, Haruyasu; Nakahara, Kazuhide; Yamashita, Mitsuaki; Kansui, Hisao; Moriwaki, Hiroshi; Tetrahedron Letters; vol. 51; nb. 46; (2010); p. 6045 - 6048 View in Reaxys

O HO

HO NH 2

Rx-ID: 31007021 View in Reaxys 315/834

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Yield

Conditions & References Stage 1: With C18H18FeN2O4, sodium hydroxide in water, Time= 24h, T= 20 °C , Inert atmosphere Stage 2: With hydrogenchloride in water, pH= 2 - 3 Klacanova, Katarina; Fodran, Peter; Rosenberg, Michal; Monatshefte fur Chemie; vol. 141; nb. 7; (2010); p. 823 - 828 View in Reaxys

HO O

Rx-ID: 32042942 View in Reaxys 316/834 Yield

Conditions & References With oxygen in N,N-dimethyl-formamide, Time= 6h, T= 100 °C Cui, Haitao; Zhang, Ye; Zhao, Liangfu; Zhu, Yulei; Catalysis Communications; vol. 12; nb. 6; (2011); p. 417 - 420 View in Reaxys

O O

Rx-ID: 40562092 View in Reaxys 317/834 Yield

Conditions & References With Boc-L-(π-Me)-His-AGly-L-Cha-L-Phe-NH-TEMPO, 3-chloro-benzenecarboperoxoic acid in toluene, Time= 15h, T= 20 °C Hofmann, Christine; Schümann, Jan M.; Schreiner, Peter R.; Journal of Organic Chemistry; vol. 80; nb. 3; (2015); p. 1972 - 1978 View in Reaxys

HO HO

HO O

O O

Rx-ID: 40660988 View in Reaxys 318/834 Yield

Conditions & References

50 %, 13 %

With caesium carbonate in water, Time= 1h, UV-irradiation, Inert atmosphere Ravelli, Davide; Protti, Stefano; Fagnoni, Maurizio; Journal of Organic Chemistry; vol. 80; nb. 2; (2015); p. 852 858 View in Reaxys

O HO

O I

C– N

Na +

Rx-ID: 223337 View in Reaxys 319/834 Yield

Conditions & References With toluene, Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge und Erhitzen der erhaltenen Saeure auf 210grad Case; Journal of the American Chemical Society; vol. 55; (1933); p. 2927,2930 View in Reaxys

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HO O

Rx-ID: 2025984 View in Reaxys 320/834 Yield

Conditions & References With 5,10,15,20-tetrakisphenylporphyrinatoiron(III) chloride in methanol, dichloromethane, T= 30 °C , oxygen transfer to (TPP)Fe(III)(Cl) with/without buffer, Rate constant Lee, William A.; Yuan, Lung-Chi; Bruice, Thomas C.; Journal of the American Chemical Society; vol. 110; nb. 13; (1988); p. 4277 - 4283 View in Reaxys

HO O

O HO

Rx-ID: 2401325 View in Reaxys 321/834 Yield

Conditions & References

15 %, 18 With sodium hydroxide, dicobalt octacarbonyl, N-hexadecyl-N,N,N-trimethylammonium bromide in benzene, Time= %, 15 %, 5 20h, T= 20 °C , Further byproducts given % Miura, Masahiro; Akase, Fumiaki; Nomura, Masakatsu; Journal of the Chemical Society, Chemical Communications; nb. 3; (1986); p. 241 - 242 View in Reaxys

NH 2

Rx-ID: 2409719 View in Reaxys 322/834 Yield

Conditions & References With immobilized activated nitrilase in water, Time= 30h, Ambient temperature, effect of β-cyclodextrin, Rate constant Geresh, Shimona; Giron, Yakir; Gilboa, Ygal; Glaser, Robert; Tetrahedron; vol. 49; nb. 44; (1993); p. 10099 10102 View in Reaxys With potassium phosphate buffer, lyophilized Zea mays nitrilase ZmNIT2 EC 3.5.5.1 in water, Time= 14h, T= 30 °C , pH= 7.15, Title compound not separated from byproducts Mukherjee, Chandrani; Zhu, Dunming; Biehl, Edward R.; Parmar, Rajiv R.; Hua, Ling; Tetrahedron; vol. 62; nb. 26; (2006); p. 6150 - 6154 View in Reaxys With recombinant nitrilase from Pseudomonas fluorescens EBC 191 in methanol, phosphate buffer, Time= 4h, T= 10 °C , pH= 6, Kinetics, Product distribution, Further Variations: pH-values, Temperatures Fernandes, Bruno C. M.; Mateo, Cesar; Kiziak, Christoph; Chmura, Andrzej; Wacker, Jan; Van Rantwijk, Fred; Stolz, Andreas; Sheldon, Roger A.; Advanced Synthesis and Catalysis; vol. 348; nb. 18; (2006); p. 2597 - 2603 View in Reaxys

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O O

O HO

Rx-ID: 4437133 View in Reaxys 323/834 Yield

Conditions & References

10 %, 84 %

Rx-ID: 5207132 View in Reaxys 324/834 Yield

Conditions & References

50 %

With BF3·2HOAc in hexane, Time= 2.5h, Heating, Aldol-Grob reaction Kabalka; Li; Tejedor; Malladi; Gao; Trotman; Synthetic Communications; vol. 29; nb. 16; (1999); p. 2783 - 2787 View in Reaxys

HO O

Fmoc-L-Val-(p-methylbenzhydrylamine resin)

Rx-ID: 13426333 View in Reaxys 325/834 Yield

Conditions & References Reaction Steps: 2 1: 72 percent / pTsOH*H2O / CH2Cl2 / 6 h / 60 °C 2: 71 percent / H2O2 / H2O; tetrahydrofuran / 1 h / 20 °C With dihydrogen peroxide, toluene-4-sulfonic acid in tetrahydrofuran, dichloromethane, water Tiecco, Marcello; Testaferri, Lorenzo; Temperini, Andrea; Bagnoli, Luana; Marini, Francesca; Santi, Claudio; Terlizzi, Raffaella; European Journal of Organic Chemistry; nb. 16; (2004); p. 3447 - 3458 View in Reaxys

O O

Rx-ID: 21440832 View in Reaxys 326/834 Yield

Conditions & References Reaction Steps: 2 1: 65 percent / Et3N / dimethylformamide / 24 h / 23 °C 2: H2O; acetonitrile / 23 °C / penicillin acylase; pH=7.3 With triethylamine in water, N,N-dimethyl-formamide, acetonitrile Baldaro; Faiardi; Fuganti; Grasselli; Lazzarini; Tetrahedron Letters; vol. 29; nb. 36; (1988); p. 4623 - 4624 View in Reaxys Reaction Steps: 2 1: 65 percent / Et3N / dimethylformamide / 24 h / 23 °C 2: H2O; acetonitrile / 23 °C / penicillin acylase; pH=7.3 With triethylamine in water, N,N-dimethyl-formamide, acetonitrile Baldaro; Faiardi; Fuganti; Grasselli; Lazzarini; Tetrahedron Letters; vol. 29; nb. 36; (1988); p. 4623 - 4624

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View in Reaxys

O O

Rx-ID: 22842345 View in Reaxys 327/834 Yield

Conditions & References

49.8 g

With sodium hydroxide in methanol, water, T= 20 °C Patent; THE WELLCOME FOUNDATION LIMITED; EP1199307; (2002); (A1) English View in Reaxys

(v3) (v3)

O Co O O (v5) P

(v3)

(v4)

Rx-ID: 26737107 View in Reaxys 328/834 Yield

Conditions & References With iodine in methanol, decompn. with iodine in methanol; Nagy-Magos; Bor; Marko; Journal of Organometallic Chemistry; vol. 14; nb. 1; (1968); p. 205 - 209 ; (from Gmelin) View in Reaxys With I2 in methanol, decompn. with iodine in methanol; vol. Co: Org.Verb.1; 1.1.4.4.1.2.1, page 87 - 93 ; (from Gmelin) View in Reaxys

HO C

Rx-ID: 28959580 View in Reaxys 329/834 Yield

Conditions & References

54.2 With water, palladium diacetate, Time= 2h, T= 110 °C , p= 3750.38Torr , Ionic liquid %Chromat., 12.8 Lapidus, Albert L.; Eliseev, Oleg L.; Bondarenko, Tatyana N.; Chau, Nguen H.; Kazantsev, Ruslan V.; Mende%Chromat. leev Communications; vol. 19; nb. 5; (2009); p. 256 - 257 View in Reaxys

H O

Rx-ID: 33354753 View in Reaxys 330/834 Yield

Conditions & References With [Co(bpc)Cl2][Et4N], PPAA in dichloromethane, acetonitrile, Time= 0.166667h, T= 20 °C Song, Young Joo; Hyun, Min Young; Lee, Jun Ho; Lee, Hong Gyu; Kim, Jin Hoon; Jang, Seung Pyo; Noh, Jin Young; Kim, Youngmee; Kim, Sung-Jin; Lee, Suk Joong; Kim, Cheal; Chemistry - A European Journal; vol. 18; nb. 19; (2012); p. 6094 - 6101 View in Reaxys

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Rx-ID: 33354755 View in Reaxys 331/834 Yield

H O

Rx-ID: 33354757 View in Reaxys 332/834 Yield

H O

Rx-ID: 33354759 View in Reaxys 333/834 Yield

O O O

HO HO

Rx-ID: 1592587 View in Reaxys 334/834 Yield 59 %

Conditions & References Irradiation, Yield given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

59 %

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View in Reaxys 74 % Chromat., 59 %, 24 % Chromat.

T= 25 °C , Irradiation, Rate constant, Quantum yield DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 115; nb. 6; (1993); p. 2180 - 2190 View in Reaxys

O O

Rx-ID: 2070889 View in Reaxys 335/834 Yield

Conditions & References

139.7 mg, 51.6 mg, 153.0 mg, 20.5 mg

With (4-methylphenyl)sulfonyl bromide in benzene, Time= 40h, T= 70 °C , Further byproducts given da Silva Correa, Carlos M.M.; Oliveira, Maria Augusta B.C.S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1987); p. 811 - 814 View in Reaxys

O Si O

Rx-ID: 2183779 View in Reaxys 336/834 Yield

Conditions & References With KHF2, dihydrogen peroxide in acetic anhydride, N,N-dimethyl-formamide, Time= 20h, Ambient temperature, Yield given Tamao, Kohei; Kumada, Makoto; Maeda, Kimio; Tetrahedron Letters; vol. 25; nb. 3; (1984); p. 321 - 324 View in Reaxys

N+

Cl –

Rx-ID: 2241050 View in Reaxys 337/834 Yield 95 %

Conditions & References With sodium hydroxide, Co(CO)8, methyl iodide in benzene, Ambient temperature, other quaternaryammonium salts, Mechanism Gambarotta, Sandro; Alper, Howard; Journal of Organometallic Chemistry; vol. 194; nb. 1; (1980); p. C19 - C21 View in Reaxys Cl

HO O

NH 2

Cl Cl

Rx-ID: 2409709 View in Reaxys 338/834 Yield 12 %, 76 %

Conditions & References With tetrachloro-phthalic acid, Time= 144h, T= 140 °C Eaton, Jefferson T.; Rounds, William D.; Urbanowicz, John H.; Gribble, Gordon W.; Tetrahedron Letters; vol. 29; nb. 50; (1988); p. 6553 - 6556 View in Reaxys

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N S

Rx-ID: 3132492 View in Reaxys 339/834 Yield

Conditions & References

55 %

With hydrogenchloride, Heating, 50 deg C, 180 min, 100 deg C, 180 min Jonczyk, Andrzej; Owczarczyk, Zbyslaw; Makosza, Mieczyslaw; Winiarski, Jerzy; Bulletin des Societes Chimiques Belges; vol. 96; nb. 4; (1987); p. 303 - 310 View in Reaxys

Rx-ID: 3202405 View in Reaxys 340/834 Yield

Conditions & References

93 %

With sodium amalgam, water in methanol, Time= 12h, Ambient temperature, Heating, Product distribution Kuo; Aoyama; Shioiri; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 3; (1983); p. 883 - 886 View in Reaxys With sodium amalgam, water, 1.) methanol, room temperature, 9 h, 2.) reflux, 3 h, Yield given. Multistep reaction Kuo; Aoyama; Shioiri; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 3; (1983); p. 883 - 886 View in Reaxys

O Si

O S

O Si

Rx-ID: 3382938 View in Reaxys 341/834 Yield

Conditions & References in dichloromethane, Time= 8h, T= -30 °C , Yield given. Yields of byproduct given Camporeale, Michele; Fiorani, Tiziana; Troisi, Luigino; Adam, Waldemar; Curci, Ruggero; Edwards, John O.; Journal of Organic Chemistry; vol. 55; nb. 1; (1990); p. 93 - 98 View in Reaxys

Rx-ID: 3808709 View in Reaxys 342/834 Yield 64 %

Conditions & References With hydrogenchloride, Time= 18h, Heating Shatzmiller, Shimon; Bercovici, Sorin; Liebigs Annalen der Chemie; nb. 10; (1992); p. 997 - 1004 View in Reaxys

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HO O

Rx-ID: 3935136 View in Reaxys 343/834 Yield

Conditions & References With 4,4'-diphenylsulfide, 3-chloro-benzenecarboperoxoic acid in chlorobenzene, Time= 7h, T= 100 °C , Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts Perkel', A. L.; Freidin, B. G.; Voronina, S. G.; Ginter, S. V.; Fokin, A. A.; J. Appl. Chem. USSR (Engl. Transl.); vol. 62; nb. 11.2; (1989); p. 2560 - 2565,2378 - 2382 View in Reaxys OH

HO HO

Rx-ID: 10058946 View in Reaxys 344/834 Yield 53 %

Conditions & References With [bis(acetoxy)iodo]benzene, sulfuric acid, Time= 72h, T= 20 °C , Further byproducts given Yusubov; Zholobova; Filimonova; Chi, Ki-Whan; Russian Chemical Bulletin; vol. 53; nb. 8; (2004); p. 1735 - 1742 View in Reaxys

NH 2

Fmoc-L-Val-(p-methylbenzhydrylamine resin) Rx-ID: 13391655 View in Reaxys 345/834

Yield

Conditions & References Reaction Steps: 2 1: 45 percent / Alcaligenes faecalis penicillin acylase; potassium hydroxide / H2O / 0.42 h / 25 °C / pH 10 2: Alkaligenes faecalis penicillin acylase / 25 °C / pH 7.5 With potassium hydroxide, Alcaligenes faecalis penicillin acylase, Alkaligenes faecalis penicillin acylase in water Guranda, Dorel T.; Khimiuk, Andrey I.; Van Langen, Luuk M.; Van Rantwijk, Fred; Sheldon, Roger A.; Svedas, Vytas K.; Tetrahedron Asymmetry; vol. 15; nb. 18; (2004); p. 2901 - 2906 View in Reaxys

Cl O

(+-)-5-phenyl-2-aza-bicyclo<3.3.1>nonane

phosphorus

Rx-ID: 18466025 View in Reaxys 346/834 Yield

Conditions & References Reaction Steps: 2 1: Et3N / CH2Cl2 / 0 - 20 °C 2: 87 percent / TiCl4 / dioxane; H2O / 20 h / Heating With titanium tetrachloride, triethylamine in 1,4-dioxane, dichloromethane, water Fisher; Caroon; Stabler; Lundberg; Zaidi; Sorensen; Sparacino; Muchowski; Canadian Journal of Chemistry; vol. 72; nb. 1; (1994); p. 142 - 145 View in Reaxys Reaction Steps: 2 1: aq. NH4OH / CH2Cl2 / 0 - 20 °C 2: 91 percent / TiCl4 / dioxane; H2O / 17 h / Heating With ammonium hydroxide, titanium tetrachloride in 1,4-dioxane, dichloromethane, water

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Fisher; Caroon; Stabler; Lundberg; Zaidi; Sorensen; Sparacino; Muchowski; Canadian Journal of Chemistry; vol. 72; nb. 1; (1994); p. 142 - 145 View in Reaxys

O N N

Rx-ID: 20827573 View in Reaxys 347/834 Yield

Conditions & References Reaction Steps: 3 1: Zn / 1)10 - 15 grad C, 2) 40 - 50 grad C 2: N2O4 / CH2Cl2 3: NH4OH / other reagents and conditions With ammonium hydroxide, dinitrogen tetraoxide, zinc in dichloromethane Garcia, Jordi; Vilarrasa, Jaume; Tetrahedron Letters; vol. 28; nb. 3; (1987); p. 341 - 342 View in Reaxys

HO O

Rx-ID: 20839444 View in Reaxys 348/834 Yield

Conditions & References Reaction Steps: 3 1: NaHSO3 2: H(+) 3: KOH / ethanol With potassium hydroxide, hydrogen cation, sodium hydrogensulfite in ethanol Matthews, Barry R.; Gountzos, Helen; Jackson, W. Roy; Watson, Keith G.; Tetrahedron Letters; vol. 30; nb. 38; (1989); p. 5157 - 5158 View in Reaxys

O N

Rx-ID: 20841428 View in Reaxys 349/834 Yield

Conditions & References Reaction Steps: 2 1: H(+) 2: KOH / ethanol With potassium hydroxide, hydrogen cation in ethanol Matthews, Barry R.; Gountzos, Helen; Jackson, W. Roy; Watson, Keith G.; Tetrahedron Letters; vol. 30; nb. 38; (1989); p. 5157 - 5158 View in Reaxys

HO O

N HN O

Rx-ID: 20844347 View in Reaxys 350/834 Yield

Conditions & References Reaction Steps: 2 1: N2O4 / CH2Cl2

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2: NH4OH / other reagents and conditions With ammonium hydroxide, dinitrogen tetraoxide in dichloromethane Garcia, Jordi; Vilarrasa, Jaume; Tetrahedron Letters; vol. 28; nb. 3; (1987); p. 341 - 342 View in Reaxys

O P

O O

Rx-ID: 28894266 View in Reaxys 351/834 Yield

Conditions & References With water, hydrogen bromide, Time= 0.05h, T= 100 °C , Inert atmosphere, Microwave irradiation McNulty, James; Das, Priyabrata; Tetrahedron; vol. 65; nb. 37; (2009); p. 7794 - 7800 View in Reaxys

racemate

Rx-ID: 33354754 View in Reaxys 352/834 Yield

H O

Rx-ID: 33354756 View in Reaxys 353/834 Yield

H 2N

NH 2

Rx-ID: 34485738 View in Reaxys 354/834 Yield

Conditions & References With tert -butyl hydrogen peroxide, zinc dibromide in pyridine, water, Time= 16h, T= 80 °C Wu, Xiao-Feng; Bheeter, Charles Beromeo; Neumann, Helfried; Dixneuf, Pierre H.; Beller, Matthias; Chemical Communications; vol. 48; nb. 100; (2012); p. 12237 - 12239 View in Reaxys

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H N O

S N

H 2N

O N

Rx-ID: 2626846 View in Reaxys 355/834 Yield

Conditions & References in water, acetonitrile, T= 23 °C , penicillin acylase; pH=7.3, Yield given Baldaro; Faiardi; Fuganti; Grasselli; Lazzarini; Tetrahedron Letters; vol. 29; nb. 36; (1988); p. 4623 - 4624 View in Reaxys

H N O

S N

H 2N

Rx-ID: 2626915 View in Reaxys 356/834 Yield

H N O

S N

H 2N

O N

O OH

Rx-ID: 2628827 View in Reaxys 357/834 Yield

/PXHEA341--525/

Rx-ID: 5801224 View in Reaxys 358/834

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Yield

Conditions & References

With N-benzyl-N,N,N-triethylammonium chloride in sodium hydroxide, hexane, Time= 24h, p= 760Torr , Ambient temperature, Product distribution Tustin, Gerald C.; Hembre, Robert T.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1761 - 1764 View in Reaxys

With tetrabutylammomium bromide in sodium hydroxide, Time= 24h, p= 760Torr , Ambient temperature Tustin, Gerald C.; Hembre, Robert T.; Journal of Organic Chemistry; vol. 49; nb. 10; (1984); p. 1761 - 1764 View in Reaxys

dibenzyl ketoxime-benzenesulfonate

Rx-ID: 6330956 View in Reaxys 359/834 Yield

Conditions & References With ammonia, T= 0 °C Neber; Uber; Justus Liebigs Annalen der Chemie; vol. 467; (1928); p. 54,62 View in Reaxys F

F F

F F F F

F F

F F F

Rx-ID: 8985029 View in Reaxys 360/834 Yield

Conditions & References

100 %

With trifluoroacetic acid, Time= 15h, Product distribution Pardo, Juan; Cobas, Agustin; Guitian, Enrique; Castedo, Luis; Organic Letters; vol. 3; nb. 23; (2001); p. 3711 3714 View in Reaxys

F F

F F F F F

F F F F

F F F

F F

HO O

F F

Rx-ID: 8985568 View in Reaxys 361/834 Yield 100 %

Conditions & References With trifluoroacetic acid, Time= 15h, Product distribution Pardo, Juan; Cobas, Agustin; Guitian, Enrique; Castedo, Luis; Organic Letters; vol. 3; nb. 23; (2001); p. 3711 3714 View in Reaxys

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O O N+

O– Cl O OO

O– O

N+

Cl OO

Rx-ID: 10009645 View in Reaxys 362/834 Yield

Conditions & References

92 % Spectr.

With pyrene, cyclohexa-1,4-diene in methanol, Time= 2h, T= 20 °C , Photolysis, Quantum yield, Further Variations: Reagents, Solvents Sundararajan, Chitra; Falvey, Daniel E.; Journal of Organic Chemistry; vol. 69; nb. 17; (2004); p. 5547 - 5554 View in Reaxys

100 % Spectr.

With coumarin-540, cyclohexa-1,4-diene in acetonitrile, Time= 0.333333h, visible light irradiation, Product distribution, Further Variations: Reagents, reaction time Sundararajan, Chitra; Falvey, Daniel E.; Journal of the American Chemical Society; vol. 127; nb. 22; (2005); p. 8000 - 8001 View in Reaxys

copolymer, Mn = 9080, Mw = 17630, PDI = 1.9, prepared by thermal free-radical copolymerization; monomer(s): styrene, 80 wt; 2[(4-vinylphenyl)methoxy]ethyl phenylacetate, 20 wt

HO O

Rx-ID: 11267936 View in Reaxys 363/834 Yield

Conditions & References With phosphate buffer, penicillin G acylase (EC 3.5.1.11) immobilized on Eupergit C in N,N-dimethyl-formamide, T= 37 °C , pH= 8, Kinetics, Further Variations: Reagents, Solvents Pasini, Dario; Filippini, Marco; Pianetti, Ilaria; Pregnolato, Massimo; Advanced Synthesis and Catalysis; vol. 349; nb. 6; (2007); p. 971 - 978 View in Reaxys Cl

HO O

metal oxide

Rx-ID: 19357706 View in Reaxys 364/834 Yield

Conditions & References Reaction Steps: 2 1: HCl/AcOH / 240 h / Ambient temperature 2: CrO3/H2SO4/H2O / acetone / 0.08 h / 1 °C With chromium(VI) oxide, hydrogenchloride, sulfuric acid, water, acetic acid in acetone Warnhoff, E.W.; Yerhoff, F.W.; Heterocycles; vol. 15; nb. 2; (1981); p. 777 - 784 View in Reaxys Reaction Steps: 3 1: HCl/AcOH / 240 h / Ambient temperature 2: CrO3/H2SO4/H2O / acetone / 0.08 h / 1 °C 3: KOH / methanol / 1.) RT,2h, 2.) reflux, 2h With chromium(VI) oxide, hydrogenchloride, potassium hydroxide, sulfuric acid, water, acetic acid in methanol, acetone Warnhoff, E.W.; Yerhoff, F.W.; Heterocycles; vol. 15; nb. 2; (1981); p. 777 - 784 View in Reaxys

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metal oxide

Rx-ID: 19359914 View in Reaxys 365/834 Yield

Conditions & References Reaction Steps: 2 1: HClO4/AcOH / 1.) RT, 1.5 h, 2.) 70 deg C, 3.5 h 2: CrO3/H2SO4/H2O / acetone / 0.08 h / 1 °C With chromium(VI) oxide, perchloric acid, sulfuric acid, water, acetic acid in acetone Warnhoff, E.W.; Yerhoff, F.W.; Heterocycles; vol. 15; nb. 2; (1981); p. 777 - 784 View in Reaxys Reaction Steps: 3 1: HClO4/AcOH / 1.) RT, 1.5 h, 2.) 70 deg C, 3.5 h 2: CrO3/H2SO4/H2O / acetone / 0.08 h / 1 °C 3: KOH / methanol / 1.) RT,2h, 2.) reflux, 2h With chromium(VI) oxide, potassium hydroxide, perchloric acid, sulfuric acid, water, acetic acid in methanol, acetone Warnhoff, E.W.; Yerhoff, F.W.; Heterocycles; vol. 15; nb. 2; (1981); p. 777 - 784 View in Reaxys

metal oxide

Rx-ID: 19360119 View in Reaxys 366/834 Yield

Conditions & References Reaction Steps: 2 1: HCl/HOAc 2: CrO3/H2SO4/H2O / acetone / 0.08 h / 1 °C With chromium(VI) oxide, hydrogenchloride, sulfuric acid, water, acetic acid in acetone Warnhoff, E.W.; Yerhoff, F.W.; Heterocycles; vol. 15; nb. 2; (1981); p. 777 - 784 View in Reaxys Reaction Steps: 3 1: HCl/HOAc 2: CrO3/H2SO4/H2O / acetone / 0.08 h / 1 °C 3: KOH / methanol / 1.) RT,2h, 2.) reflux, 2h With chromium(VI) oxide, hydrogenchloride, potassium hydroxide, sulfuric acid, water, acetic acid in methanol, acetone Warnhoff, E.W.; Yerhoff, F.W.; Heterocycles; vol. 15; nb. 2; (1981); p. 777 - 784 View in Reaxys Br

HO O

metal oxide

Rx-ID: 19360126 View in Reaxys 367/834 Yield

Conditions & References Reaction Steps: 2 1: HBr/HOAc / 96 h / Ambient temperature 2: CrO3/H2SO4/H2O / acetone / 0.08 h / 1 °C With chromium(VI) oxide, sulfuric acid, water, hydrogen bromide, acetic acid in acetone Warnhoff, E.W.; Yerhoff, F.W.; Heterocycles; vol. 15; nb. 2; (1981); p. 777 - 784 View in Reaxys

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Reaction Steps: 3 1: HBr/HOAc / 96 h / Ambient temperature 2: CrO3/H2SO4/H2O / acetone / 0.08 h / 1 °C 3: KOH / methanol / 1.) RT,2h, 2.) reflux, 2h With chromium(VI) oxide, potassium hydroxide, sulfuric acid, water, hydrogen bromide, acetic acid in methanol, acetone Warnhoff, E.W.; Yerhoff, F.W.; Heterocycles; vol. 15; nb. 2; (1981); p. 777 - 784 View in Reaxys

ethanolic solution

metal oxide

Rx-ID: 19526297 View in Reaxys 368/834 Yield

Conditions & References Reaction Steps: 2 1: 26.4 percent / Ac2O / dimethylformamide / 1.) 0 degC, 3 h, 2.) r.t., 3 h 2: 50 percent / 30percent H2O2 / acetic acid / 3 h / heating With dihydrogen peroxide, acetic anhydride in acetic acid, N,N-dimethyl-formamide Funakoshi, Kazuhisa; Mizuoka, Masae; Wada, Kazuko; Saeki, Seitaro; Hamana, Masatomo; Chemical & Pharmaceutical Bulletin; vol. 32; nb. 10; (1984); p. 3886 - 3891 View in Reaxys

CaCO3

ammonium carbonate

Rx-ID: 20163267 View in Reaxys 369/834 Yield

Conditions & References Reaction Steps: 2 1: n-BuLi / tetrahydrofuran; hexane / -70 - 25 °C 2: mercuric sulfate/2N H2SO4 / 80 °C With n-butyllithium, sulfuric acid, mercuric sulphate in tetrahydrofuran, hexane Abrams, Suzanne R.; Canadian Journal of Chemistry; vol. 61; (1983); p. 2423 - 2424 View in Reaxys

H O

racemate

Rx-ID: 33354752 View in Reaxys 370/834 Yield

O O

Rx-ID: 72815 View in Reaxys 371/834

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Yield

Conditions & References T= 165 - 210 °C , p= 14Torr Hurd; Christ; Thomas; Journal of the American Chemical Society; vol. 55; (1933); p. 2589,2591 View in Reaxys Kalnin; ; vol. 1; (1930); p. 455 View in Reaxys

Rx-ID: 156363 View in Reaxys 372/834 Yield

Conditions & References With sulfur, T= 190 - 200 °C , Erwaermen des Reaktionsprodukts mit wss. Schwefelsaeure Stanek; Collection of Czechoslovak Chemical Communications; vol. 12; (1947); p. 675 View in Reaxys

HO O

NH 2

Rx-ID: 716470 View in Reaxys 373/834 Yield

Conditions & References With (NH4)2S, T= 200 - 220 °C , im Druckrohr Willgerodt; Merk; Journal fuer Praktische Chemie (Leipzig); vol. <2> 80; (1909); p. 193 View in Reaxys Willgerodt; Chemische Berichte; vol. 21; (1888); p. 534; Journal fuer Praktische Chemie (Leipzig); vol. <2> 80; (1909); p. 183 View in Reaxys

Rx-ID: 1980240 View in Reaxys 374/834 Yield

Conditions & References With water, T= 26 °C , Rate constant Bothe,E. et al.; Angewandte Chemie; vol. 88; nb. 12; (1976); p. 413 View in Reaxys With water, sodium chloride, sodium hydroxide, T= 25 °C , solvent isotope effect determinated, Rate constant Allen, Annette D.; Kresge, A. Jerry; Schepp, Norman P.; Tidwell, Thomas T.; Canadian Journal of Chemistry; vol. 65; (1987); p. 1719 - 1723 View in Reaxys With water, Rate constant Allen, Annette D.; Andraos, John; Kresge, A. J.; McAllister, Michael A.; Tidwell, Thomas T.; Journal of the American Chemical Society; vol. 114; nb. 5; (1992); p. 1878 - 1879 View in Reaxys

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O O

O racemate

racemate

Rx-ID: 2504378 View in Reaxys 375/834 Yield

Conditions & References

55 %

electrochemically induced cation radical Diels-Alder dimerization, Yield given. Yields of byproduct given Mlcoch, Jiri; Steckhan, Eberhard; Tetrahedron Letters; vol. 28; nb. 10; (1987); p. 1081 - 1084 View in Reaxys With 2,4,6-triphenylpyrylium-tetrafluoroborate in dichloromethane, Time= 0.166667h, Irradiation, Yield given. Yields of byproduct given Mlcoch, Jiri; Steckhan, Eberhard; Angewandte Chemie; vol. 97; nb. 5; (1985); p. 429 - 431 View in Reaxys 2 Na +

HO O

O–O

O O– O

Rx-ID: 2525487 View in Reaxys 376/834 Yield

Conditions & References With potassium maleate buffer, water, T= 37 °C , pH 6.2, Rate constant Kluger, Ronald; Huang, Zheng; Journal of the American Chemical Society; vol. 113; nb. 13; (1991); p. 5124 - 5125 View in Reaxys

Rx-ID: 2772064 View in Reaxys 377/834 Yield

Conditions & References With abzyme 27B5, ATE buffer (0.1 M ACES, 0.052 M Tris, and 0.052 M ethanolamine), dimethyl sulfoxide, T= 25 °C , other abzymes; enantioselectivity via antibody controlled enantioface protonation, Rate constant, Product distribution Fujii, Ikuo; Lerner, Richard A.; Janda, Kim D.; Journal of the American Chemical Society; vol. 113; nb. 22; (1991); p. 8528 - 8529 View in Reaxys

HO O

Rx-ID: 2817272 View in Reaxys 378/834 Yield

Conditions & References With 2,4,6-triphenylpyrylium-tetrafluoroborate in dichloromethane, Time= 0.25h, Irradiation, Yield given Mlcoch, Jiri; Steckhan, Eberhard; Angewandte Chemie; vol. 97; nb. 5; (1985); p. 429 - 431 View in Reaxys

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O HO

O O

O N

NH 2 O

Rx-ID: 2839433 View in Reaxys 379/834 Yield

Conditions & References With potassium hydroxide in ethanol Matthews, Barry R.; Gountzos, Helen; Jackson, W. Roy; Watson, Keith G.; Tetrahedron Letters; vol. 30; nb. 38; (1989); p. 5157 - 5158 View in Reaxys

S O

Rx-ID: 2880525 View in Reaxys 380/834 Yield

Conditions & References With sulfuric acid, mercuric sulphate, T= 80 °C , Yield given Abrams, Suzanne R.; Canadian Journal of Chemistry; vol. 61; (1983); p. 2423 - 2424 View in Reaxys O O

HO O

Rx-ID: 8588418 View in Reaxys 381/834 Yield

Conditions & References

91 %

in benzene, UV-irradiation, Disproportionation, Quantum yield Klan, Petr; Zabadal, Miroslav; Heger, Dominik; Organic Letters; vol. 2; nb. 11; (2000); p. 1569 - 1571 View in Reaxys

HO O

phosphorus Rx-ID: 18606814 View in Reaxys 382/834

Yield

Conditions & References Reaction Steps: 2 1: 86 percent / SO2Cl2, pyridine / CCl4 / 1) r.t., 2) 1 h, reflux 2: Hg(OAc)2 / formic acid / 3 h / 50 °C With pyridine, sulfuryl dichloride, mercury(II) diacetate in tetrachloromethane, formic acid Fortes, Carlos C.; Fortes, Helena C.; Goncalves, Dioneia C. R. G.; Journal of the Chemical Society, Chemical Communications; nb. 15; (1982); p. 857 - 858 View in Reaxys

HO O

metal oxide

Rx-ID: 19375003 View in Reaxys 383/834

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Yield

Conditions & References Reaction Steps: 2 1: CrO3/H2SO4/H2O / acetone / 0.08 h / 1 °C 2: KOH / methanol / 1.) RT,2h, 2.) reflux, 2h With chromium(VI) oxide, potassium hydroxide, sulfuric acid, water in methanol, acetone Warnhoff, E.W.; Yerhoff, F.W.; Heterocycles; vol. 15; nb. 2; (1981); p. 777 - 784 View in Reaxys

O O

ammonium carbonate

Rx-ID: 19713579 View in Reaxys 384/834 Yield

Conditions & References Reaction Steps: 3 1: 70 percent / hydroxylamine hydrochloride, KOH / methanol / 0.5 h / Ambient temperature 2: 1.) K2CO3 / 1.)MeOH, H2O, 15 min, r.t., 2.a) 5 to 10 deg C, 15 min, b) 24 h, r.t. 3: 64 percent / conc. HCl / 18 h / Heating With hydrogenchloride, potassium hydroxide, hydroxylamine hydrochloride, potassium carbonate in methanol Shatzmiller, Shimon; Bercovici, Sorin; Liebigs Annalen der Chemie; nb. 10; (1992); p. 997 - 1004 View in Reaxys

HO (v2)

Rx-ID: 31234078 View in Reaxys 385/834 Yield

Conditions & References Reaction Steps: 2 1: not given 2: H2O2 With H2O2 in not given vol. Co: Org.Verb.2; 3.1.3.5, page 152 - 167 View in Reaxys

H (v3) (v3) (v3)

O O Co (v6) O

O O

(v6)

(v3)

Rx-ID: 31234129 View in Reaxys 386/834 Yield

Conditions & References Reaction Steps: 2 1: not given 2: H2O2 With H2O2 in not given vol. Co: Org.Verb.2; 3.1.3.5, page 152 - 167 View in Reaxys

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HO O

Rx-ID: 31718500 View in Reaxys 387/834 Yield

Conditions & References With hydrogenchloride, water, T= 60 °C Romer, Duane R.; Synthesis; nb. 17; (2011); p. 2721 - 2723; Art.No: M54911SS View in Reaxys O

H O

Rx-ID: 33354758 View in Reaxys 388/834 Yield

Rx-ID: 651932 View in Reaxys 389/834 Yield

Conditions & References With copper, T= 180 - 200 °C , man verseift den Aethylester mit alkoh. Kali Zincke; Chemische Berichte; vol. 2; (1869); p. 739; Justus Liebigs Annalen der Chemie; vol. 159; (1871); p. 368 View in Reaxys O

O N

O OH

Rx-ID: 2047986 View in Reaxys 390/834 Yield

Conditions & References With sulfuric acid, periodate(1-), ruthenium(III) cation in acetic acid, T= 50 °C , Mechanism, Rate constant Swarnalakshmi, N.; Uma, V.; Sethuram, B.; Navaneeth Rao, T.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 23; nb. 5; (1984); p. 386 - 388 View in Reaxys

Rx-ID: 2131097 View in Reaxys 391/834 Yield

Conditions & References With EDTA ferric sodium salt in methanol, Product distribution Balasubramanian, P. N.; Bruice, Thomas C.; Journal of the American Chemical Society; vol. 108; nb. 18; (1986); p. 5495 - 5503

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View in Reaxys O

O HO

Rx-ID: 2144347 View in Reaxys 392/834 Yield

Conditions & References Yield given. Multistep reaction Satoh; Mizu; Hayashi; Yamakawa; Tetrahedron Letters; vol. 35; nb. 1; (1994); p. 133 - 134 View in Reaxys With sodium hydroxide, tert.-butyl lithium, potassium hydride, 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C, 20 min, 3) THF, H2O, -78 deg C, 10 min; 0 deg C, 10 min, Yield given. Multistep reaction Satoh, Tsuyoshi; Unno, Hideaki; Mizu, Yasuhiro; Hayashi, Yasumasa; Tetrahedron; vol. 53; nb. 23; (1997); p. 7843 - 7854 View in Reaxys

NH O

(v1)

N N

Rx-ID: 3049332 View in Reaxys 393/834 Yield

Conditions & References

56 %, 9.0 %, 12.0 %

in benzene, Time= 24h, Irradiation, Further byproducts given Parshad; Sharma; Journal of the Indian Chemical Society; vol. 67; nb. 2; (1990); p. 150 - 152 View in Reaxys

HO O

Rx-ID: 3263165 View in Reaxys 394/834 Yield

Conditions & References With potassium hydroxide in methanol, 1.) RT,2h, 2.) reflux, 2h, Yield given. Yields of byproduct given Warnhoff, E.W.; Yerhoff, F.W.; Heterocycles; vol. 15; nb. 2; (1981); p. 777 - 784 View in Reaxys

Rx-ID: 3384242 View in Reaxys 395/834 Yield 6%

Conditions & References With iodosylbenzene, silver(l) oxide in chloroform, Time= 24h, T= 60 °C Joergensen, Karl Anker; Larsen, Erik; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 3; (1990); p. 1053 - 1056 View in Reaxys Stage 1: With morpholine, sulfur, Time= 48h, T= 130 °C , Willgerodt reaction Stage 2: With sodium hydroxide, water, Time= 24h, T= 130 °C Stage 3: With hydrogenchloride in water

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Usui, Satoshi; Tsuboya, Shoko; Umezawa, Yukthiro; Hazama, Ken; Okamura, Mutsuo; Bulletin of the Chemical Society of Japan; vol. 82; nb. 2; (2009); p. 254 - 260 View in Reaxys O HO

O HO

Rx-ID: 3576656 View in Reaxys 396/834 Yield

HO O

Rx-ID: 3935120 View in Reaxys 397/834 Yield

Conditions & References With air, cobalt naphthenate in chlorobenzene, T= 100 °C , other catalyst: manganese naphthenate, without catalyst, Mechanism, Product distribution Perkel', A. L.; Voronia, S. G.; Shimko, E. I.; Freiden, B. G.; J. Appl. Chem. USSR (Engl. Transl.); vol. 64; nb. 3.2; (1991); p. 592 - 599,530 - 535 View in Reaxys With oxygen in benzene, Time= 0.5h, Irradiation, Product distribution, Mechanism Felder, Bruno; Schumacher, Rolf; Sitek, Franciszek; Helvetica Chimica Acta; vol. 63; nb. 1; (1980); p. 132 - 147 View in Reaxys

Cl E

Rx-ID: 5000581 View in Reaxys 398/834 Yield

Conditions & References With boron trifluoride in hexane, Time= 5h, Heating, Yield given. Yields of byproduct given Kabalka, George W.; Tejedor, David; Li, Nan-Sheng; Malladi, Rama R.; Trotman, Sarah; Tetrahedron; vol. 54; nb. 51; (1998); p. 15525 - 15532 View in Reaxys

Z E

Rx-ID: 5003092 View in Reaxys 399/834 Yield

Conditions & References With boron trifluoride in hexane, Time= 3h, Heating, Yield given. Yields of byproduct given Kabalka, George W.; Tejedor, David; Li, Nan-Sheng; Malladi, Rama R.; Trotman, Sarah; Tetrahedron; vol. 54; nb. 51; (1998); p. 15525 - 15532 View in Reaxys

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Cl E

Rx-ID: 5007106 View in Reaxys 400/834 Yield

H 2N

H N

N H

O H

OH O

Rx-ID: 5026592 View in Reaxys 401/834 Yield

Conditions & References With sodium acetate, T= 37 °C , var. pH values, Rate constant Smith, Robert M.; Hansen, David E.; Journal of the American Chemical Society; vol. 120; nb. 35; (1998); p. 8910 8913 View in Reaxys

H 2N

Rx-ID: 9730250 View in Reaxys 402/834 Yield

Conditions & References With potassium hydroxide, potassium dihydrogenphosphate, Alcaligenes faecalis penicillin acylase in water, Time= 5h, T= 25 °C , pH= 7.5 Guranda, Dorel T.; Khimiuk, Andrey I.; Van Langen, Luuk M.; Van Rantwijk, Fred; Sheldon, Roger A.; Svedas, Vytas K.; Tetrahedron Asymmetry; vol. 15; nb. 18; (2004); p. 2901 - 2906 View in Reaxys With Alkaligenes faecalis penicillin acylase, T= 25 °C , pH= 7.5, Kinetics Guranda, Dorel T.; Khimiuk, Andrey I.; Van Langen, Luuk M.; Van Rantwijk, Fred; Sheldon, Roger A.; Svedas, Vytas K.; Tetrahedron Asymmetry; vol. 15; nb. 18; (2004); p. 2901 - 2906 View in Reaxys With Escherichia coli penicillin acylase, potassium chloride, water, T= 24.84 °C , Enzymatic reaction, Equilibrium constant Guranda, Dorel T.; Ushakov, Gennadij A.; Yolkin, Petr G.; Svedas, Vytas K.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 48 - 53 View in Reaxys HO

HO O

O HO

Rx-ID: 10048940 View in Reaxys 403/834

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Yield

Conditions & References

22 % Spectr., 78 % Spectr.

With bismuth, ZnF2 in water-d2, Time= 6h Lee, Yoon Joo; Chan, Tak Hang; Canadian Journal of Chemistry; vol. 81; nb. 11; (2003); p. 1406 - 1412 View in Reaxys

Rx-ID: 38196101 View in Reaxys 404/834 Yield

Conditions & References

55 %Spectr.

With silver(I) acetate, sodium acetate, palladium dichloride, Time= 24h, T= 130 °C , Schlenk technique, Inert atmosphere, Reagent/catalyst Wu, Guo-Jie; Guan, Jing; Han, Fu-She; Zhao, Yu-Long; ChemCatChem; vol. 6; nb. 6; (2014); p. 1589 - 1593 View in Reaxys

HO HO

O HO

Rx-ID: 40660994 View in Reaxys 405/834 Yield

Conditions & References

16 %, 7 %, With caesium carbonate in water, Time= 1h, UV-irradiation, Inert atmosphere 26 %, 16 Ravelli, Davide; Protti, Stefano; Fagnoni, Maurizio; Journal of Organic Chemistry; vol. 80; nb. 2; (2015); p. 852 % 858 View in Reaxys

Rx-ID: 2000321 View in Reaxys 406/834 Yield

Conditions & References With magnesium, 1.) THF, reflux, 4 days, 2.) RT, 3 h, Yield given. Multistep reaction Burns, Timothy P.; Rieke, Reuben D.; Journal of Organic Chemistry; vol. 52; nb. 16; (1987); p. 3674 - 3680 View in Reaxys

NH 2

S– K+

O O

Rx-ID: 2202886 View in Reaxys 407/834 Yield

Conditions & References With hydrogenchloride, sodium hydroxide, sodium nitrite, Yield given. Multistep reaction Pendergast; Johnson; Dickerson; Dev; Duch; Ferone; Hall; Humphreys; Kelly; Wilson; Journal of Medicinal Chemistry; vol. 36; nb. 16; (1993); p. 2279 - 2291 View in Reaxys

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NH 2 –S

K+

S O

Rx-ID: 2202888 View in Reaxys 408/834 Yield

HO O

Rx-ID: 2394489 View in Reaxys 409/834 Yield

Conditions & References

33 % Chromat., 13 % Chromat., 27 %

With tetra-n-butylammonium tetrafluoroborate, (bpy)NiBr2 in various solvent(s), Ambient temperature, electrolysis, -1.6 V; further solvent and electrolyte, Product distribution, Mechanism Garnier, L.; Rollin, Y.; Perichon, J.; Journal of Organometallic Chemistry; vol. 367; (1989); p. 347 - 358 View in Reaxys

HO O

Rx-ID: 4681222 View in Reaxys 410/834 Yield

Conditions & References

16 %, 12 %, 23 %

16 %, 23 %, 12 %

23 %, 12 %, 16 %

With cadmium(II) sulphide, triethylamine in N,N-dimethyl-formamide, Time= 1h, T= 20 °C , Irradiation Fujiwara, Hiroaki; Kanemoto, Masashi; Ankyu, Hirofumi; Murakoshi, Kei; Wada, Yuji; Yanagida, Shozo; Journal of the Chemical Society. Perkin Transactions 2; nb. 2; (1997); p. 317 - 321 View in Reaxys With cadmium(II) sulphide in N,N-dimethyl-formamide, T= 20 °C , Kinetics Fujiwara, Hiroaki; Kanemoto, Masashi; Ankyu, Hirofumi; Murakoshi, Kei; Wada, Yuji; Yanagida, Shozo; Journal of the Chemical Society. Perkin Transactions 2; nb. 2; (1997); p. 317 - 321 View in Reaxys O

O O

H N

HO N

Rx-ID: 4688674 View in Reaxys 411/834 Yield

Conditions & References in acetonitrile, T= 25 °C , Rate constant, Product distribution

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Cho, Bong Rae; Kim, Yong Kwan; Yoon, Choon-Ock Maing; Journal of the American Chemical Society; vol. 119; nb. 4; (1997); p. 691 - 697 View in Reaxys O

H N

O O

HO N

Rx-ID: 4688675 View in Reaxys 412/834 Yield

Conditions & References in acetonitrile, T= 25 °C , Rate constant, Product distribution Cho, Bong Rae; Kim, Yong Kwan; Yoon, Choon-Ock Maing; Journal of the American Chemical Society; vol. 119; nb. 4; (1997); p. 691 - 697 View in Reaxys

HO C

Rx-ID: 4713453 View in Reaxys 413/834 Yield

Conditions & References

90 % Spectr., 3 % Spectr., 1% Spectr.

With tetrakis(triphenylphosphine) palladium(0), hydrogen iodide in acetone, Time= 44h, T= 90 °C , p= 68400Torr , var. Pd complex, quant. and qual. promoter, time, temp., press., solvent, Product distribution, Mechanism Lin, Yong-Shou; Yamamoto, Akio; Tetrahedron Letters; vol. 38; nb. 21; (1997); p. 3747 - 3750 View in Reaxys

Rx-ID: 5043421 View in Reaxys 414/834 Yield

Conditions & References With diethyl ether Houben; Kesselkaul; Chemische Berichte; vol. 35; (1902); p. 2521 View in Reaxys Tiffeneau; Delange; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 137; (1903); p. 574 View in Reaxys Zelinsky; Chemische Berichte; vol. 35; (1902); p. 2691 View in Reaxys Zaburdaeva; Stepovik; Dodonov; Martynova; Russian Journal of General Chemistry; vol. 67; nb. 12; (1997); p. 1902 - 1908 View in Reaxys

O O

Rx-ID: 5074057 View in Reaxys 415/834 Yield

Conditions & References in acetonitrile, Photolysis, Decomposition

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Shi, Yijian; Corrie, John E.T.; Wan, Peter; Journal of Organic Chemistry; vol. 62; nb. 24; (1997); p. 8278 - 8279 View in Reaxys

acetylmandelic acid

Rx-ID: 6330954 View in Reaxys 416/834 Yield

Conditions & References With Pd-BaSO4, 1,2,3,4-tetrahydro-naphthalene, Hydrogenation Rosenmund; Schindler; Archiv der Pharmazie (Weinheim, Germany); (1928); p. 281 View in Reaxys With Pd-BaSO4, isopropyl-benzene, Hydrogenation Rosenmund; Schindler; Archiv der Pharmazie (Weinheim, Germany); (1928); p. 281 View in Reaxys

Rx-ID: 8941984 View in Reaxys 417/834 Yield

Conditions & References With potassium fluoride, thiophenol in chloroform-d1, T= 80 °C , Kinetics, Further Variations: Solvents Sung Soo Kim; Tuchkin; Chun Soo Kim; Journal of Organic Chemistry; vol. 66; nb. 23; (2001); p. 7738 - 7740 View in Reaxys O

I HO

Rx-ID: 31428054 View in Reaxys 418/834 Yield

Conditions & References

86 %Spectr., 13 %Spectr.

Stage 1: With potassium tert-butylate in dimethyl sulfoxide, Time= 0.166667h, Inert atmosphere Stage 2: in dimethyl sulfoxide, Time= 1h, Inert atmosphere, Irradiation Stage 3: With ammonium nitrate, nitric acid in water Guastavino, Javier F.; Buden, Maria E.; Garcia, Carolina S.; Rossi, Roberto A.; Arkivoc; vol. 2011; nb. 7; (2011); p. 389 - 405 View in Reaxys OH

O HO

Rx-ID: 31428063 View in Reaxys 419/834 Yield 22 %Spectr., 65 %Spectr.

Conditions & References Stage 1: With potassium tert-butylate in dimethyl sulfoxide, Time= 0.166667h, Inert atmosphere Stage 2: in dimethyl sulfoxide, Time= 2h, Inert atmosphere, Irradiation Stage 3: With ammonium nitrate, nitric acid in water Guastavino, Javier F.; Buden, Maria E.; Garcia, Carolina S.; Rossi, Roberto A.; Arkivoc; vol. 2011; nb. 7; (2011); p. 389 - 405 View in Reaxys

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O I

Rx-ID: 31428065 View in Reaxys 420/834 Yield

Conditions & References

55 %Spectr., 45 %Spectr.

Rx-ID: 31428066 View in Reaxys 421/834 Yield

Conditions & References

57 %Spectr., 25 %Spectr.

Stage 1: With potassium tert-butylate in dimethyl sulfoxide, Time= 0.166667h, Inert atmosphere Stage 2: in dimethyl sulfoxide, Time= 2h, Inert atmosphere, Irradiation Stage 3: With ammonium nitrate, nitric acid in water, regiospecific reaction Guastavino, Javier F.; Buden, Maria E.; Garcia, Carolina S.; Rossi, Roberto A.; Arkivoc; vol. 2011; nb. 7; (2011); p. 389 - 405 View in Reaxys I

OH O

Rx-ID: 31428069 View in Reaxys 422/834 Yield 24 %Spectr., 41 %Spectr.

Conditions & References Stage 1: With potassium tert-butylate in dimethyl sulfoxide, Time= 0.166667h, Inert atmosphere Stage 2: in dimethyl sulfoxide, Time= 2h, Inert atmosphere, Irradiation Stage 3: With ammonium nitrate, nitric acid in water, regiospecific reaction Guastavino, Javier F.; Buden, Maria E.; Garcia, Carolina S.; Rossi, Roberto A.; Arkivoc; vol. 2011; nb. 7; (2011); p. 389 - 405 View in Reaxys

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O O

O HO

OH HOOO

O OH O OH

O O

OH O

HO O

Rx-ID: 36250299 View in Reaxys 423/834 Yield

Conditions & References Stage 1: in aq. buffer, Sonication Stage 2: in aq. buffer, Time= 1.5h, Irradiation, Inert atmosphere Jayaraj, Nithyanandhan; Jagadesan, Pradeepkumar; Samanta, Shampa R.; Da Silva, Jose P.; Ramamurthy; Organic Letters; vol. 15; nb. 17; (2013); p. 4374 - 4377 View in Reaxys

Cl HO

HO O

Rx-ID: 40660989 View in Reaxys 424/834 Yield 7 %, 5 %, 14 %, 23 %

Conditions & References With caesium carbonate in aq. buffer, Time= 1h, UV-irradiation, Inert atmosphere Ravelli, Davide; Protti, Stefano; Fagnoni, Maurizio; Journal of Organic Chemistry; vol. 80; nb. 2; (2015); p. 852 858 View in Reaxys

Rx-ID: 1569534 View in Reaxys 425/834 Yield 6%

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H 2N

Rx-ID: 2020866 View in Reaxys 426/834 Yield

Conditions & References

43 %

With ruthenium trichloride, sodium periodate in tetrachloromethane, water, acetonitrile, Time= 8h Ranganathan, Subramania; Ranganathan, Darshan; Bhattacharyya, Dipti; Journal of the Chemical Society, Chemical Communications; nb. 14; (1987); p. 1085 - 1086 View in Reaxys With uranyl sulphate, sulfuric acid in water, Irradiation, Mechanism Bhatt, R.; Shrimali, P. S.; Ameta, S. C.; Chowdhry, H. C.; Zeitschrift fuer Physikalische Chemie (Leipzig); vol. 267; nb. 4; (1986); p. 817 - 820 View in Reaxys

HO O

O OH HO

HO OH

O HO O

O OH

H HO

OH OH

OH H

O O

HO OH

OH HO

OHHO

H O H

H H

H O HO

HO OH

Rx-ID: 4732339 View in Reaxys 427/834 Yield

Conditions & References With phosphate buffer in water-d2, T= 25 °C , standard molar enthalpy ΔrH0, standard molar Gibbs energy ΔrG0, standard molar entropy ΔrS0, Equilibrium constant, Thermodynamic data Rekharsky, Mikhail V.; Mayhew, Martin P.; Goldberg, Robert N.; Ross, Philip D.; Yamashoji, Yuko; Inoue, Yoshihisa; Journal of Physical Chemistry B; vol. 101; nb. 1; (1997); p. 87 - 100 View in Reaxys

O Cl

HO O

Rx-ID: 4832358 View in Reaxys 428/834 Yield 14 %, 18 %, 47 %

Conditions & References With methyloxirane in water, acetonitrile, Time= 4h, Irradiation Dhavale, Dilip D.; Mali, Vasant P.; Sudrik, Surendra G.; Sonawane, Harikisan R.; Tetrahedron; vol. 53; nb. 49; (1997); p. 16789 - 16794 View in Reaxys

37 %, 24 %, 29 %

With methyloxirane in water, acetone, Time= 4h, Irradiation, other α-chloro acetophenones, other solvents, other reaction time, Mechanism, Product distribution Dhavale, Dilip D.; Mali, Vasant P.; Sudrik, Surendra G.; Sonawane, Harikisan R.; Tetrahedron; vol. 53; nb. 49; (1997); p. 16789 - 16794 View in Reaxys

37 %, 24 %, 29 %

With methyloxirane in water, acetone, Time= 4h, Irradiation

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Dhavale, Dilip D.; Mali, Vasant P.; Sudrik, Surendra G.; Sonawane, Harikisan R.; Tetrahedron; vol. 53; nb. 49; (1997); p. 16789 - 16794 View in Reaxys

HO O

Rx-ID: 9140558 View in Reaxys 429/834 Yield

Conditions & References

71 %, 22 %, 5 %

in acetonitrile, T= 25 °C , Electrochemical reaction, Product distribution, Further Variations: Reagents, electrode material Isse, Abdirisak A.; Gennaro, Armando; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 42; nb. 4; (2003); p. 751 - 757 View in Reaxys With N(Et)4ClO4 in acetonitrile, Electrochemical reaction, Product distribution, Further Variations: cathode materials Isse, Abdirisak A.; Gennaro, Armando; Chemical Communications; nb. 23; (2002); p. 2798 - 2799 View in Reaxys

H O

HO O

Rx-ID: 10141296 View in Reaxys 430/834 Yield

Conditions & References

5 %, 51 %, With 3,3-dimethyldioxirane in acetone, Time= 22h, T= 4 °C , Product distribution, Further Variations: time 13 %, 5 % Zeller, Klaus-Peter; Kowallik, Meike; Haiss, Peter; Organic and Biomolecular Chemistry; vol. 3; nb. 12; (2005); p. 2310 - 2318 View in Reaxys

HO O

H O

Rx-ID: 10505513 View in Reaxys 431/834 Yield

Conditions & References

87.51 % Chromat., 7.61 % Chromat., 2.13 % Chromat., 1.21 % Chromat.

With dihydrogen peroxide, polystyrene-anchored K[VO2(fsal-ohyba)] in acetonitrile, T= 80 °C , Product distribution, Further Variations: Catalysts, Temperatures, reagent ratios Maurya, Mannar R.; Kumar, Umesh; Manikandan; Dalton Transactions; nb. 29; (2006); p. 3561 - 3575 View in Reaxys

O O

Rx-ID: 22005631 View in Reaxys 432/834 Yield

Conditions & References Reaction Steps: 3 1: 20 - 40 Torr / bei der Destillation 2: water; alcoholic sodium ethylate

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3: beim Schmelzen With water, sodium ethanolate Wislicenus,W.; Chemische Berichte; vol. 27; (1894); p. 1094 View in Reaxys Reaction Steps: 3 1: 12 h / 170 - 180 °C 2: water; potassium hydroxide / 51 - 73 °C 3: Heating With water, potassium hydroxide Malki, Fatiha; Touati, Abdelkader; Rahal, Said; Moulay, Saad; Asian Journal of Chemistry; vol. 23; nb. 3; (2011); p. 961 - 967 View in Reaxys O HO

O O

Rx-ID: 22026196 View in Reaxys 433/834 Yield

Conditions & References Reaction Steps: 2 1: water; alcoholic sodium ethylate 2: beim Schmelzen With water, sodium ethanolate Wislicenus,W.; Chemische Berichte; vol. 27; (1894); p. 1094 View in Reaxys Reaction Steps: 2 1: water; potassium hydroxide / 51 - 73 °C 2: Heating With water, potassium hydroxide Malki, Fatiha; Touati, Abdelkader; Rahal, Said; Moulay, Saad; Asian Journal of Chemistry; vol. 23; nb. 3; (2011); p. 961 - 967 View in Reaxys

H O

Rx-ID: 26042720 View in Reaxys 434/834 Yield

Conditions & References

36 % Chromat., 30 % Chromat., 29 % Chromat., 5 % Chromat.

With water, oxygen, dichloro bis(acetonitrile) palladium(II), Time= 2h, T= 80 °C , p= 3800.26Torr , Wacker oxidation, Product distribution, Further Variations: Temperatures, Catalysts, Reagents Andreeva; Maksimov; Zhuchkova; Predeina; Filippova; Karakhanov; Petroleum Chemistry; vol. 47; nb. 5; (2007); p. 331 - 336 View in Reaxys

N (v4) Mn N N (v5) (v4) N

N Cl (v7) Mn N (v4) O N

(v4)

Rx-ID: 26502857 View in Reaxys 435/834

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Yield

Conditions & References in benzonitrile, Kinetics, the soln. under anaerobic conditions at 30°C Yuan, Lung-Chi; Bruice, Thomas C.; Inorganic Chemistry; vol. 24; (1985); p. 986 - 987 ; (from Gmelin) View in Reaxys

(v3)

O O

(v6)

O (v3) (v3) Co O (v6) Co

(v6)

(v3)

Rx-ID: 26629957 View in Reaxys 436/834 Yield

Conditions & References With dihydrogen peroxide Krueerke; Huebel; Chemistry and Industry (London, United Kingdom); (1960); p. 1264 ; (from Gmelin) View in Reaxys With H2O2 vol. Co: Org.Verb.2; 3.1.3.5, page 152 - 167 ; (from Gmelin) View in Reaxys

O N

HO O HN

Z N

H N

HO O

Rx-ID: 27962132 View in Reaxys 437/834 Yield

Conditions & References

0.55 %, 0.14 %, 0.05 %, 0.05 %

With Nitrite in acetate buffer, Time= 1h, T= 37 °C , pH= 3, Product distribution, Further Variations: pH-values, reaction time Loeppky, Richard N.; Shi, Jianzheng; Barnes, Charles L.; Geddam, Sailaja; Chemical Research in Toxicology; vol. 21; nb. 2; (2008); p. 295 - 307 View in Reaxys

OH HO

H O

N H

NH 2

NH 2 H

OH N H

OH O

Rx-ID: 28501467 View in Reaxys 438/834 Yield

Conditions & References With penicillin G acylase, water, sodium carbonate, Time= 0.333333h, pH= 8.0, Resolution of racemate, Enzymatic reaction, optical yield given as percent ee, enantioselective reaction Grundmann, Peter; Fessner, Wolf-Dieter; Advanced Synthesis and Catalysis; vol. 350; nb. 11-12; (2008); p. 1729 - 1735 View in Reaxys

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Rx-ID: 37867797 View in Reaxys 439/834 Yield 90 %

Conditions & References in water, acetonitrile, Time= 6.66667h, Photolysis, Inert atmosphere, Quantum yield Ikbal; Saha, Biswajit; Barman, Shrabani; Atta, Sanghamitra; Banerjee, Deb Ranjan; Ghosh, Sudip Kumar; Singh, N. D. Pradeep; Organic and Biomolecular Chemistry; vol. 12; nb. 21; (2014); p. 3459 - 3469 View in Reaxys

Rx-ID: 1592439 View in Reaxys 440/834 Yield 72 %

Conditions & References Irradiation, Yield given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

72 %

Irradiation, rate constant of electron transfer (kET x) for radical pair generated in this reaction, Mechanism DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

O O

HO HO

O O

Rx-ID: 1592594 View in Reaxys 441/834 Yield 31 % Chromat., 38 %, 52 % Chromat., 8 % Chromat.

Conditions & References T= 25 °C , Irradiation, excited-singlet-state energy (S); other var. substituted 1-naphthyl esters of phenylacetic acid, 3-phenylpropanoic acid, and 9-methylfluorene-9-carboxylic acid, Mechanism, Quantum yield, Rate constant DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 115; nb. 6; (1993); p. 2180 - 2190 View in Reaxys

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HO O

Rx-ID: 2000351 View in Reaxys 442/834 Yield

Conditions & References With Cs/Na/K alloy, 1) NH3, -75 deg C, 2 h, 2) H2O, Yield given. Multistep reaction. Yields of byproduct given Sengupta, Dibyendu; Grovenstein, E.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 185 - 186 View in Reaxys With Cs/Na/K alloy, multistep reaction: 1.) THF, -75 deg C, 2 h, rate of cleavage relative to bibenzyl, Product distribution, Rate constant Grovenstein, Erling; Bhatti, Amjad M.; Quest, Dean E.; Sengupta, Dibyendu; VanDerveer, Don; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6290 - 6299 View in Reaxys With Cs/Na/K alloy, multistep reaction, reaction also with other methyl-substituted bibenzyls, Product distribution, Mechanism Sengupta, Dibyendu; Grovenstein, E.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 185 - 186 View in Reaxys

HO O

Rx-ID: 2000504 View in Reaxys 443/834 Yield

Conditions & References With Cs/Na/K alloy, 1) NH3, -75 deg C, 2 h, 2) H2O, Yield given. Multistep reaction. Yields of byproduct given Sengupta, Dibyendu; Grovenstein, E.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 185 - 186 View in Reaxys With Cs/Na/K alloy, 1) NH3(l), -75 deg C, 2 h, 2) H2O, Yield given. Multistep reaction. Yields of byproduct given Sengupta, Dibyendu; Grovenstein, E.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 185 - 186 View in Reaxys With Cs/Na/K alloy, multistep reaction: 1.) THF, -75 deg C, 2 h, rate of cleavage relative to bibenzyl, Product distribution, Rate constant Grovenstein, Erling; Bhatti, Amjad M.; Quest, Dean E.; Sengupta, Dibyendu; VanDerveer, Don; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6290 - 6299 View in Reaxys

H 2N

O O

N H H 2N

HO O

Rx-ID: 2095188 View in Reaxys 444/834 Yield

Conditions & References With hydrogenchloride, Time= 0.583333h, Yield given. Yields of byproduct given Chakraborty, D. P.; Mandal, Anchal Kanti; Roy, Swapan Kumar; Synthesis; nb. 12; (1981); p. 977 - 979

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View in Reaxys H 2N

O HO

HN O

Rx-ID: 2096023 View in Reaxys 445/834 Yield

Conditions & References With hydrogenchloride, Time= 0.583333h Chakraborty, D. P.; Mandal, Anchal Kanti; Roy, Swapan Kumar; Synthesis; nb. 12; (1981); p. 977 - 979 View in Reaxys

Rx-ID: 2158070 View in Reaxys 446/834 Yield

Conditions & References With buffer pH 8.0 in acetonitrile, T= 37 °C , half-life time of hydrolysis at different pH Schwenker; Stiefvater; Archiv der Pharmazie; vol. 324; nb. 9; (1991); p. 547 - 550 View in Reaxys

O O

Rx-ID: 3843203 View in Reaxys 447/834 Yield

Conditions & References With sodium hydroxide, Yield given Moriarty, Robert M.; Vaid, Radhe K.; Duncan, Michael P.; Vaid, Beena K.; Tetrahedron Letters; vol. 28; nb. 25; (1987); p. 2845 - 2848 View in Reaxys

α-phenyl-acetoacetic acid ester

Rx-ID: 6330952 View in Reaxys 448/834 Yield

Conditions & References With potassium hydroxide Beckh; Chemische Berichte; vol. 31; (1898); p. 3163 View in Reaxys

2-phenyl-4-benzyliden-oxazolone

Rx-ID: 6330953 View in Reaxys 449/834 Yield

Conditions & References With sodium hydroxide, Oxydation des Reaktionsprodukts in alkal. Loesung mit Wasserstoffsuperoxyd Mauthner; Justus Liebigs Annalen der Chemie; vol. 370; (1909); p. 374 View in Reaxys

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hydrazine salt of hydrazono-phenyl-acetic acid

Rx-ID: 6330957 View in Reaxys 450/834 Yield

Conditions & References With potassium hydroxide Lock; ; vol. 51; (1950); p. 77 View in Reaxys

NH 2

H N H

Rx-ID: 9549634 View in Reaxys 451/834 Yield

Conditions & References With hydrogenchloride, sodium hydroxide, E. coli penicillin acylase in water, T= 5 °C , pH= 5, Equilibrium constant Chilov, Ghermes G.; Moody, Harold M.; Boesten, Wilhelmus H. J.; Svedas, Vytas K.; Tetrahedron Asymmetry; vol. 14; nb. 17; (2003); p. 2613 - 2617 View in Reaxys

HO O

Rx-ID: 10144893 View in Reaxys 452/834 Yield 11 %

Conditions & References With tetra-n-butylammonium tetrafluoroborate, Electrolysis Otero, M. Dolores; Batanero, Belen; Barba, Fructuoso; Tetrahedron Letters; vol. 47; nb. 13; (2006); p. 2171 2173 View in Reaxys

copolymer, Mn = 8610, Mw = 15800, PDI = 1.8, prepared by thermal free-radical copolymerization; monomer(s): styrene, 80 wt; 3[(4-vinylphenyl)methoxy]propyl phenylacetate, 20 wt

HO O

Rx-ID: 11267937 View in Reaxys 453/834 Yield

Conditions & References With phosphate buffer, T= 37 °C , pH= 8, Kinetics Pasini, Dario; Filippini, Marco; Pianetti, Ilaria; Pregnolato, Massimo; Advanced Synthesis and Catalysis; vol. 349; nb. 6; (2007); p. 971 - 978 View in Reaxys

copolymer, Mn = 9190, Mw = 17420, PDI = 1.9, prepared by thermal free-radical copolymerization; monomer(s): styrene, 80 wt; 4[(4-vinylphenyl)methoxy]butyl phenylacetate, 20 wt

HO O

Rx-ID: 11267938 View in Reaxys 454/834 Yield

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O–

Cl OO

N+

HO O

Rx-ID: 25994025 View in Reaxys 455/834 Yield

Conditions & References

100 % Chromat.

With phosphate buffer, DTT in water-d2, acetonitrile, Time= 1h, pH= 7.0, UV-irradiation, Product distribution, Quantum yield, Further Variations: Reagents Borak, J. Brian; Lopez-Sola, Susana; Falvey, Daniel E.; Organic Letters; vol. 10; nb. 3; (2008); p. 456 - 460 View in Reaxys

Rx-ID: 279966 View in Reaxys 456/834 Yield

Conditions & References With potassium hydroxide, beim Schmelzen Kraut; Justus Liebigs Annalen der Chemie; vol. 148; (1868); p. 240 View in Reaxys

HO O

Rx-ID: 316823 View in Reaxys 457/834 Yield

Conditions & References With potassium permanganate, water, sodium carbonate Mazza; ; vol. 21; (1935); p. 320,326 View in Reaxys

HO O

Rx-ID: 416134 View in Reaxys 458/834 Yield

Conditions & References With alcoholic alkali Nef; Justus Liebigs Annalen der Chemie; vol. 308; (1899); p. 325 View in Reaxys

E O

O O

HO O

Rx-ID: 588171 View in Reaxys 459/834 Yield

Conditions & References With barium dihydroxide Moeller; Strecker; Justus Liebigs Annalen der Chemie; vol. 113; (1860); p. 68 View in Reaxys

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Br HO

Rx-ID: 736935 View in Reaxys 460/834 Yield

Conditions & References With magnesium, durch Verseifung Salkind; Baskow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 46; (1914); p. 477; Chem. Zentralbl.; vol. 85; nb. II; (1914); p. 1268 View in Reaxys

O O O

HO HO

O O

Rx-ID: 1592635 View in Reaxys 461/834 Yield

Conditions & References

60 %

Irradiation, Yield given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

60 %

HO O

O HO

Rx-ID: 2000349 View in Reaxys 462/834 Yield

Conditions & References With n-butyllithium, nickel, Multistep reaction Cabiddu, Salvatore; Fattuoni, Claudia; Floris, Costantino; Gelli, Gioanna; Melis, Stefana; Sotgiu, Francesca; Tetrahedron; vol. 46; nb. 3; (1990); p. 861 - 884 View in Reaxys

HO O

Rx-ID: 2000503 View in Reaxys 463/834 Yield

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With Cs/Na/K alloy, multistep reaction: 1.) THF, -75 deg C, 2 h, rate of cleavage relative to bibenzyl, Product distribution, Rate constant Grovenstein, Erling; Bhatti, Amjad M.; Quest, Dean E.; Sengupta, Dibyendu; VanDerveer, Don; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6290 - 6299 View in Reaxys

HO O

Rx-ID: 2084480 View in Reaxys 464/834 Yield

Conditions & References With water, Irradiation, Rate constant, Mechanism Chiang, Y.; Kresge, A. J.; Hochstrasser, R.; Wirz, J.; Journal of the American Chemical Society; vol. 111; nb. 6; (1989); p. 2355 - 2357 View in Reaxys

HO O

Rx-ID: 2124964 View in Reaxys 465/834 Yield

Conditions & References With perchloric acid, water in 1,4-dioxane, T= 25 °C , ΔH(excit.), ΔS(excit.) var. temperature and H2O/dioxane ratio, Rate constant, Thermodynamic data Motie, Richard E..; Satchell, Derek P. N.; Wassef, Wasfy N.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 6; (1993); p. 1087 - 1090 View in Reaxys

O O

HO O

O O

Rx-ID: 2193047 View in Reaxys 466/834 Yield

Conditions & References With pyridine hydrochloride Baiocchi, Leandro; Giannangeli, Marilena; Bonanomi, Michele; Picconi, Giuseppe; Ridolfi, Pietro; Gazzetta Chimica Italiana; vol. 115; nb. 4; (1985); p. 199 - 216 View in Reaxys

O O

Cl –

N+

Rx-ID: 2444925 View in Reaxys 467/834 Yield

Conditions & References in water, T= 37 °C , pH 7.4; plasma hydrolysis (dog plasma), Rate constant Bodor; Woods; Raper; et al.; Journal of Medicinal Chemistry; vol. 23; nb. 5; (1980); p. 474 - 480 View in Reaxys

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O Cl

O O

Rx-ID: 2817273 View in Reaxys 468/834 Yield

Conditions & References With dihydrogen peroxide, sodium hydrogencarbonate in methanol, Time= 1h, T= 47 - 53 °C , Yield given. Yields of byproduct given Buyck, L. De; Verhe, R.; Kimpe, N. De; Courtheyn, D.; Schamp, N.; Bulletin des Societes Chimiques Belges; vol. 89; nb. 6; (1980); p. 441 - 458 View in Reaxys With dihydrogen peroxide, sodium carbonate in water, Time= 2h, T= 55 - 65 °C , other base, solvent, time, temperature, Product distribution Buyck, L. De; Verhe, R.; Kimpe, N. De; Courtheyn, D.; Schamp, N.; Bulletin des Societes Chimiques Belges; vol. 89; nb. 6; (1980); p. 441 - 458 View in Reaxys

H H H O

O H

H H

H HO H

Rx-ID: 2996818 View in Reaxys 469/834 Yield

Conditions & References in N,N,N',N',N'',N''-hexamethylphosphoric triamide, water, Time= 5h, Irradiation, Yield given. Yields of byproduct given Portella, C.; Deshayes, H.; Pete, J. P.; Scholler, D.; Tetrahedron; vol. 40; nb. 19; (1984); p. 3635 - 3644 View in Reaxys

N O

O O

Rx-ID: 3581343 View in Reaxys 470/834 Yield

Conditions & References With barium dihydroxide, N-hexadecyl-N,N,N-trimethylammonium bromide in water, T= 30 °C , dependence of rate constant on concentration of cetyltrimethylammonium bromide, Rate constant, Mechanism Broxton, Trevor J.; Duddy, Neil W.; Australian Journal of Chemistry; vol. 33; nb. 7; (1980); p. 1771 - 1781 View in Reaxys

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O O

Rx-ID: 3661770 View in Reaxys 471/834 Yield

O O

Rx-ID: 3663799 View in Reaxys 472/834 Yield

O O

Rx-ID: 3664071 View in Reaxys 473/834 Yield

O HO

Rx-ID: 4273105 View in Reaxys 474/834 Yield

Conditions & References With oxygen in ethanol, Time= 240h, T= 25 °C , other solvent; determinations of half-lives, Mechanism Muller; Gawlik; Wiegrebe; Archiv der Pharmazie; vol. 328; nb. 4; (1995); p. 359 - 362 View in Reaxys

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O O

O N

Rx-ID: 4872658 View in Reaxys 475/834 Yield

Conditions & References With phosphate-buffered saline, antibodies 12G2 in acetonitrile, Km, Rate constant Grynszpan, Flavio; Keinan, Ehud; Chemical Communications; nb. 8; (1998); p. 865 - 866 View in Reaxys

O O

P O

Rx-ID: 4983680 View in Reaxys 476/834 Yield

Conditions & References With hydrogenchloride, Time= 0.5h, Heating, Yield given Dufrechou; Combret; Malhiac; Collignon; Phosphorus, Sulfur and Silicon and Related Elements; vol. 127; (1997); p. 1 - 14 View in Reaxys

tellurium

Rx-ID: 6731571 View in Reaxys 477/834 Yield

Conditions & References With water Laishev, V. Z.; Petrov, M. L.; Petrov, A. A.; Journal of Organic Chemistry USSR (English Translation); vol. 17; (1981); p. 1842 - 1847; Zhurnal Organicheskoi Khimii; vol. 17; nb. 10; (1981); p. 2064 - 2071 View in Reaxys O HO

O N

Rx-ID: 8618303 View in Reaxys 478/834 Yield

Conditions & References With sulfuric acid, acetic acid, ruthenium trichloride, T= 24.85 - 39.85 °C , Catalytic oxidation, Kinetics Annapoorna; Prasad Rao; Sethuram; International Journal of Chemical Kinetics; vol. 32; nb. 10; (2000); p. 581 588 View in Reaxys O

O O

Cl HO

Rx-ID: 8637186 View in Reaxys 479/834 Yield

Conditions & References With sulfuric acid, acetic acid, ruthenium trichloride, T= 24.85 - 39.85 °C , Catalytic oxidation, Kinetics

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Annapoorna; Prasad Rao; Sethuram; International Journal of Chemical Kinetics; vol. 32; nb. 10; (2000); p. 581 588 View in Reaxys O HO

Rx-ID: 8639070 View in Reaxys 480/834 Yield

NH H 2 O

H N

NH H

N O HO

Rx-ID: 9120460 View in Reaxys 481/834 Yield

Conditions & References With acetic acid n-butyl ester, phosphoric acid, penicillin acylase from E. coli in water, T= 20 °C , pH= 3.4, Enzymatic reaction, Kinetics, Further Variations: pH-values Chilov, Ghermes G.; Svedas, Vytas K.; Canadian Journal of Chemistry; vol. 80; nb. 6; (2002); p. 699 - 707 View in Reaxys

NHH 2 H O

NHH H

O O

Rx-ID: 9154193 View in Reaxys 482/834 Yield

Conditions & References With potassium hydroxide, acetic acid n-butyl ester, penicillin acylase from E. coli in water, T= 20 °C , pH= 3.4, Enzymatic reaction, Kinetics, Further Variations: pH-values Chilov, Ghermes G.; Svedas, Vytas K.; Canadian Journal of Chemistry; vol. 80; nb. 6; (2002); p. 699 - 707 View in Reaxys

O O

Rx-ID: 9935971 View in Reaxys 483/834 Yield 44 %, 51 %

Conditions & References With carbon tetrabromide, Time= 1h, T= 20 °C , Irradiation, Product distribution, Further Variations: Solvents, Temperatures, irradiation in part time

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Lee, Adam Shih-Yuan; Su, Feng-Yih; Tetrahedron Letters; vol. 46; nb. 37; (2005); p. 6305 - 6309 View in Reaxys O HO

phosphorus

Rx-ID: 18568485 View in Reaxys 484/834 Yield

Conditions & References Reaction Steps: 2 2: pyridinium chloride With pyridine hydrochloride Baiocchi, Leandro; Giannangeli, Marilena; Bonanomi, Michele; Picconi, Giuseppe; Ridolfi, Pietro; Gazzetta Chimica Italiana; vol. 115; nb. 4; (1985); p. 199 - 216 View in Reaxys

H N

HO O

ammonium carbonate Rx-ID: 19677375 View in Reaxys 485/834

Yield

Conditions & References Reaction Steps: 2 1: 1.) K2CO3 / 1.)MeOH, H2O, 15 min, r.t., 2.a) 5 to 10 deg C, 15 min, b) 24 h, r.t. 2: 64 percent / conc. HCl / 18 h / Heating With hydrogenchloride, potassium carbonate Shatzmiller, Shimon; Bercovici, Sorin; Liebigs Annalen der Chemie; nb. 10; (1992); p. 997 - 1004 View in Reaxys

Rx-ID: 22184362 View in Reaxys 486/834 Yield

Conditions & References Reaction Steps: 4 1: potash; alcohol / 110 - 130 °C 2: absolute ether solution; sulfuryl chloride 3: sodium ethylate 4: alcoholic alkali With sulfuryl dichloride, diethyl ether, ethanol, sodium ethanolate, potassium carbonate Nef; Justus Liebigs Annalen der Chemie; vol. 308; (1899); p. 325 View in Reaxys

Rx-ID: 22184388 View in Reaxys 487/834 Yield

Conditions & References Reaction Steps: 2 1: sodium ethylate 2: alcoholic alkali With sodium ethanolate Nef; Justus Liebigs Annalen der Chemie; vol. 308; (1899); p. 325 View in Reaxys

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Rx-ID: 22184434 View in Reaxys 488/834 Yield

Conditions & References Reaction Steps: 4 1: zinc dust; alcohol 2: absolute ether solution; sulfuryl chloride 3: sodium ethylate 4: alcoholic alkali With sulfuryl dichloride, diethyl ether, ethanol, sodium ethanolate, zinc Nef; Justus Liebigs Annalen der Chemie; vol. 308; (1899); p. 325 View in Reaxys

HO O

Rx-ID: 22186533 View in Reaxys 489/834 Yield

Conditions & References Reaction Steps: 4 1: potassium hydroxide; absolute alcohol / 130 - 135 °C 2: absolute ether solution; sulfuryl chloride 3: sodium ethylate 4: alcoholic alkali With potassium hydroxide, sulfuryl dichloride, diethyl ether, ethanol, sodium ethanolate Nef; Justus Liebigs Annalen der Chemie; vol. 308; (1899); p. 325 View in Reaxys

O O

Rx-ID: 22186885 View in Reaxys 490/834 Yield

Conditions & References Reaction Steps: 5 1: natrium carbonate 2: potassium hydroxide; absolute alcohol / 130 - 135 °C 3: absolute ether solution; sulfuryl chloride 4: sodium ethylate 5: alcoholic alkali With potassium hydroxide, sulfuryl dichloride, diethyl ether, ethanol, sodium ethanolate, sodium carbonate Nef; Justus Liebigs Annalen der Chemie; vol. 308; (1899); p. 325 View in Reaxys

O N

O H

HO O

OH racemate

Rx-ID: 22235770 View in Reaxys 491/834 Yield

Conditions & References Reaction Steps: 2 1: aq. barium hydroxide solution / 100 °C 2: potassium hydroxide / beim Schmelzen With barium dihydroxide, potassium hydroxide

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Kraut; Justus Liebigs Annalen der Chemie; vol. 148; (1868); p. 240 View in Reaxys O

(v3) O

O (v6)O Pd OPd O (v6) (v3)

(v3)

(v6)O Pd Pd O O(v6) O

(v3) OO

Rx-ID: 26479467 View in Reaxys 492/834 Yield

Conditions & References in toluene, byproducts: CO2, isomeric tolyl acids; thermolysis at 110°C in a glass container Stromnova, Tatyana A.; Busygina, Irina N.; Kochubey, Dmitry I.; Moiseev, Ilya I.; Journal of Organometallic Chemistry; vol. 417; nb. 1/2; (1991); p. 193 - 204 ; (from Gmelin) View in Reaxys

HO O

Rx-ID: 336525 View in Reaxys 493/834 Yield

Conditions & References T= 315 - 320 °C Hibbert; Burt; Journal of the American Chemical Society; vol. 47; (1925); p. 2243 View in Reaxys

O O O

O O

Rx-ID: 363133 View in Reaxys 494/834 Yield

Conditions & References T= 250 °C Hurd; Raterink; Journal of the American Chemical Society; vol. 55; (1953); p. 1541,1543, 1544 View in Reaxys

O O

Rx-ID: 381183 View in Reaxys 495/834 Yield

Conditions & References With sodium hydroxide Ivanoff; Popoff; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1547,1550 View in Reaxys

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Br HO

O HO

Rx-ID: 512382 View in Reaxys 496/834 Yield

Conditions & References With sodium hydroxide Ivanoff; Popoff; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1547,1550 View in Reaxys

HO O

Rx-ID: 669114 View in Reaxys 497/834 Yield

Conditions & References T= 435 - 545 °C Hurd; Blunck; Journal of the American Chemical Society; vol. 60; (1938); p. 2419,2422 View in Reaxys

OH O

H 2N 2

Rx-ID: 818356 View in Reaxys 498/834 Yield

Conditions & References With diethyl ether Iwanow; Bulletin de la Societe Chimique de France; vol. <4>37; (1925); p. 289,293; Bulletin de la Societe Chimique de France; vol. <4>43; (1928); p. 443 View in Reaxys

H O

Rx-ID: 1546466 View in Reaxys 499/834 Yield

Conditions & References

15 %, 2 %, With iodosylbenzene, silver(l) oxide in chloroform, Time= 24h, T= 60 °C , further alkenes, other epoxidation systems 2 %, 2 %, Joergensen, Karl Anker; Larsen, Erik; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry 10 % (1972-1999); nb. 3; (1990); p. 1053 - 1056 View in Reaxys OH Se HO

O O

Rx-ID: 1581983 View in Reaxys 500/834 Yield 3 %, 86 %

Conditions & References With 3-chloro-benzenecarboperoxoic acid, Time= 3h, Heating Uemura, Sakae; Ohe, Kouichi; Yamauchi, Takayoshi; Mizutaki, Shoichi; Tamaki, Kentaro; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1990); p. 907 - 910 View in Reaxys

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HO O

Rx-ID: 2048402 View in Reaxys 501/834 Yield

Conditions & References With base in 1,4-dioxane, water, T= 19.9 - 39.9 °C , entalpy and entropy of activation, Kinetics, Thermodynamic data, Rate constant Nassar, Ahmed M. G.; El-Kholy, Ali E.; Kasem, Taher S.; Fathallah, Magda F. A. M.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 32; nb. 10; (1993); p. 1079 - 1082 View in Reaxys

O O OH

Rx-ID: 2207258 View in Reaxys 502/834 Yield

HO O

Rx-ID: 2954085 View in Reaxys 503/834 Yield

Conditions & References With Cs/Na/K alloy, 1) NH3, -75 deg C, 2 h, 2) H2O, Yield given. Multistep reaction Sengupta, Dibyendu; Grovenstein, E.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 185 - 186 View in Reaxys

H O

Rx-ID: 3365755 View in Reaxys 504/834 Yield

Conditions & References

2 % Chromat., 64 % Chromat., 5 % Chromat., 20 % Chromat.

With 3,3-dimethyldioxirane in acetone, Time= 6h, T= 0 °C , other dioxirane (in another solvent), other alkynes, other temperature, other times, Product distribution Curci, Ruggero; Fiorentino, Michele; Fusco, Caterina; Mello, Rossella; Ballistreri, Francesco; et al.; Tetrahedron Letters; vol. 33; nb. 51; (1992); p. 7929 - 7932 View in Reaxys

HO O

LiClO4 (d)

Rx-ID: 6683248 View in Reaxys 505/834

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Yield

Conditions & References With cobalt-salen complex, 1.) electrolysis, THF, HMPA, 2.) aq. HCl, Yield given. Multistep reaction Folest, Jean-Claude; Duprilot, Jean-Marc; Perichon, Jacques; Robin, Yvette; Devynck, Jacques; Tetrahedron Letters; vol. 26; nb. 22; (1985); p. 2633 - 2636 View in Reaxys

(v4)

Rx-ID: 7446953 View in Reaxys 506/834 Yield

Conditions & References T= -40 - -30 °C , anschliessende Behandlung mit heissem Wasser Jacobs; Journal of the American Chemical Society; vol. 58; (1936); p. 2272 View in Reaxys T= -40 - -30 °C , anschliessende Behandlung mit kalter wss. KMnO4-Loesung Johnson; Jacobs; Schwartz; Journal of the American Chemical Society; vol. 60; (1938); p. 1885,1888 View in Reaxys

O H

Rx-ID: 7541328 View in Reaxys 507/834 Yield

Conditions & References T= 96 °C , Racemisierung Campbell; Campbell; Journal of the American Chemical Society; vol. 54; (1932); p. 4581,4583 View in Reaxys Cl

aqueous propan-1-ol

OH Cl

Rx-ID: 8236641 View in Reaxys 508/834 Yield

Conditions & References T= 55 °C , sowie bei 65grad und 75grad, Rate constant, racemat of mp: 213-214.5 degree Rondestvedt; Rowley; Journal of the American Chemical Society; vol. 78; (1956); p. 3804,3805 View in Reaxys T= 55 °C , sowie bei 65grad und 75grad, Rate constant, racemat of mp: 202-202.5 degree Rondestvedt; Rowley; Journal of the American Chemical Society; vol. 78; (1956); p. 3804,3805 View in Reaxys

aqueous ammonium polysulfide HS

NH 2

Rx-ID: 8255572 View in Reaxys 509/834

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Yield

Conditions & References T= 200 °C King; McMillan; Journal of the American Chemical Society; vol. 68; (1946); p. 1372 View in Reaxys

aqueous propan-1-ol

OH Cl

Rx-ID: 8258588 View in Reaxys 510/834 Yield

Conditions & References T= 65 °C , Rate constant, racemat of mp: 188-189 degree Rondestvedt; Rowley; Journal of the American Chemical Society; vol. 78; (1956); p. 3804,3805 View in Reaxys T= 65 °C , sowie bei 75grad, Rate constant, racemat of mp: 192-193 degree Rondestvedt; Rowley; Journal of the American Chemical Society; vol. 78; (1956); p. 3804,3805 View in Reaxys

O N O

N O

Rx-ID: 9277176 View in Reaxys 511/834 Yield

Conditions & References With water-d2 in acetonitrile-D3, Photolysis, Quantum yield Ma, Chicheng; Steinmetz, Mark G.; Cheng, Qing; Jayaraman, Vasanthi; Organic Letters; vol. 5; nb. 1; (2003); p. 71 - 74 View in Reaxys O HO

O O

Rx-ID: 11267944 View in Reaxys 512/834 Yield

OH HO

Rx-ID: 11267949 View in Reaxys 513/834 Yield

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View in Reaxys O

Rx-ID: 11267953 View in Reaxys 514/834 Yield

HO O

Rx-ID: 29509487 View in Reaxys 515/834 Yield

Conditions & References With water, Photolysis Hagen, Volker; Kilic, Funda; Schaal, Janina; Dekowski, Brigitte; Schmidt, Reinhard; Kotzur, Nico; Journal of Organic Chemistry; vol. 75; nb. 9; (2010); p. 2790 - 2797 View in Reaxys

O Br

HO HO

N O

O N

OH O

Rx-ID: 29509499 View in Reaxys 516/834 Yield

172/258

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O O O

Rx-ID: 1592593 View in Reaxys 517/834 Yield

Conditions & References

38 %

Irradiation, Yield given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

38 %

HO O

Rx-ID: 1980455 View in Reaxys 518/834 Yield

Conditions & References With Cs/Na/K alloy, multistep reaction: 1.) THF, -75 deg C, 2 h, rate of cleavage relative to bibenzyl, Product distribution, Rate constant Grovenstein, Erling; Bhatti, Amjad M.; Quest, Dean E.; Sengupta, Dibyendu; VanDerveer, Don; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6290 - 6299 View in Reaxys

HO O

Rx-ID: 2000274 View in Reaxys 519/834 Yield

HO O

Rx-ID: 2000493 View in Reaxys 520/834 Yield

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View in Reaxys

HO O

Rx-ID: 2001584 View in Reaxys 521/834 Yield

HO O

Rx-ID: 2001644 View in Reaxys 522/834 Yield

HO O

Rx-ID: 2954086 View in Reaxys 523/834 Yield

Conditions & References With Cs/Na/K alloy, multistep reaction: 1.) THF, -75 deg C, 2 h; further substituted bibenzyls, Product distribution Grovenstein, Erling; Bhatti, Amjad M.; Quest, Dean E.; Sengupta, Dibyendu; VanDerveer, Don; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6290 - 6299 View in Reaxys

NH N

NH O

O N

(v1)

N N

Rx-ID: 3049331 View in Reaxys 524/834 Yield 56 %, 12.0 %, 9 %

Conditions & References Time= 24h, Irradiation, Further byproducts given Parshad; Sharma; Journal of the Indian Chemical Society; vol. 67; nb. 2; (1990); p. 150 - 152 View in Reaxys

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N N

HO O

NH 2

NH 2 Cl

OH Cl

H O

Rx-ID: 3055136 View in Reaxys 525/834 Yield

Conditions & References

96 %

With hydrogenchloride, Time= 15h, Heating Crilley, Martine M. L.; Stoodley, Richard J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1984); p. 1127 - 1132 View in Reaxys

NH 2

(-)-enantiomer,L-isomer

Rx-ID: 3672635 View in Reaxys 526/834 Yield

Conditions & References With manganese sulphate, cerium(IV) sulphate, sulfuric acid in water, T= 34.9 °C , variation of substrate and H2SO4 concentrations, ΔE (excit.), ΔS (excit.), Kinetics, Mechanism, Thermodynamic data Khandia, B. L.; Vaidya, V. K.; Ameta, S. C.; Journal of the Indian Chemical Society; vol. 64; nb. 2; (1987); p. 91 92 View in Reaxys

NH 2

Rx-ID: 5818186 View in Reaxys 527/834 Yield

Conditions & References T= 250 - 280 °C , Pyrolysis Davidson; Karten; Journal of the American Chemical Society; vol. 78; (1956); p. 1066 View in Reaxys

H O

Rx-ID: 5819734 View in Reaxys 528/834 Yield

Conditions & References T= 250 °C Hurd; Raterink; Journal of the American Chemical Society; vol. 55; (1933); p. 1541,1543 View in Reaxys Angus; Owen; Journal of the Chemical Society; (1943); p. 249 View in Reaxys

HO O

Rx-ID: 5855682 View in Reaxys 529/834

175/258

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Yield

Conditions & References With diethylzinc, sodium Schorigin; Chemische Berichte; vol. 41; (1908); p. 2717,2723; Chemische Berichte; vol. 43; (1910); p. 1931 View in Reaxys

sodium

petroleum ether

Rx-ID: 6799994 View in Reaxys 530/834 Yield

Conditions & References Siedetemperatur, Leiten von CO2 in das Reaktionsgemisch Morton; Le Fevre; Hechenbleikner; Journal of the American Chemical Society; vol. 58; (1936); p. 754 View in Reaxys Gilman; Pacevitz; Baine; Journal of the American Chemical Society; vol. 62; (1940); p. 1514,1519 View in Reaxys Morton; Stevens; Journal of the American Chemical Society; vol. 53; (1931); p. 4028,4031 View in Reaxys Ziegler; Angewandte Chemie; vol. 49; (1936); p. 455,457 View in Reaxys

O Cl

aqueous propan-1-ol HO

Rx-ID: 7154805 View in Reaxys 531/834 Yield

Conditions & References T= 65 °C , sowie bei 75grad, Rate constant Rondestvedt; Rowley; Journal of the American Chemical Society; vol. 78; (1956); p. 3804,3805 View in Reaxys

aqueous propan-1-ol

Rx-ID: 7446241 View in Reaxys 532/834 Yield

Conditions & References T= 55 °C , sowie bei 65grad und 75grad, Rate constant Rondestvedt; Rowley; Journal of the American Chemical Society; vol. 78; (1956); p. 3804,3805 View in Reaxys OH

aqueous propan-1-ol

O O

S O

Rx-ID: 7987560 View in Reaxys 533/834 Yield

Conditions & References T= 65 °C , sowie bei 75grad, Rate constant

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Rondestvedt; Rowley; Journal of the American Chemical Society; vol. 78; (1956); p. 3804,3805 View in Reaxys

HO Cl

aqueous propan-1-ol

Rx-ID: 8258648 View in Reaxys 534/834 Yield

Conditions & References T= 65 °C , sowie bei 75grad und 80grad, Rate constant Rondestvedt; Rowley; Journal of the American Chemical Society; vol. 78; (1956); p. 3804,3805 View in Reaxys Cl

aqueous propan-1-ol

OH Cl

Cl Cl

O O

Rx-ID: 8259864 View in Reaxys 535/834 Yield

Conditions & References T= 65 °C , sowie bei 75grad, Rate constant Rondestvedt; Rowley; Journal of the American Chemical Society; vol. 78; (1956); p. 3804,3805 View in Reaxys OH

aqueous propan-1-ol

O HO

HO O

Rx-ID: 8261911 View in Reaxys 536/834 Yield

Conditions & References T= 55 °C , sowie bei 65grad und 75grad, Rate constant Rondestvedt; Rowley; Journal of the American Chemical Society; vol. 78; (1956); p. 3804,3805 View in Reaxys

aqueous propan-1-ol HO

HO O

Rx-ID: 8262392 View in Reaxys 537/834 Yield

Conditions & References T= 65 °C , sowie bei 75grad und 80grad, Rate constant Rondestvedt; Rowley; Journal of the American Chemical Society; vol. 78; (1956); p. 3804,3805 View in Reaxys

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O HO O

Rx-ID: 57260 View in Reaxys 538/834 Yield

Conditions & References T= 65 °C , sowie bei 75grad, Rate constant Rondestvedt; Rowley; Journal of the American Chemical Society; vol. 78; (1956); p. 3804,3805 View in Reaxys

HO N

Rx-ID: 604998 View in Reaxys 539/834 Yield

Conditions & References man verseift das Nitril Cannizzaro; Justus Liebigs Annalen der Chemie; vol. 96; (1855); p. 246 View in Reaxys Mann; Chemische Berichte; vol. 14; (1881); p. 1646 View in Reaxys Staedel; Chemische Berichte; vol. 19; (1886); p. 1948 View in Reaxys Hofmann,A. W.; Chemische Berichte; vol. 7; (1874); p. 519 View in Reaxys

HO O

OH O

H 2N 2

Rx-ID: 669139 View in Reaxys 540/834 Yield

Conditions & References T= 625 °C Hurd; Blunck; Journal of the American Chemical Society; vol. 60; (1938); p. 2419,2422 View in Reaxys

O HO

O O

Rx-ID: 1588625 View in Reaxys 541/834 Yield 95 %, 94 %

Conditions & References Time= 0.5h, Irradiation, Product distribution Iwamura, Michiko; Ishikawa, Touru; Koyama, Yukiyoshi; Sakuma, Keisuke; Iwamura, Hiizu; Tetrahedron Letters; vol. 28; nb. 6; (1987); p. 679 - 682 View in Reaxys

80 %

Time= 2h, Irradiation, Quantum yield Iwamura, Michiko; Tokuda, Kazuko; Koga, Noboru; Iwamura, Hiizu; Chemistry Letters; (1987); p. 1729 - 1732 View in Reaxys

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O O O

O O

Rx-ID: 1592765 View in Reaxys 542/834 Yield 29 %

Conditions & References Irradiation, Yield given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

29 %

O O HO

Rx-ID: 1592845 View in Reaxys 543/834 Yield 33 %

Conditions & References Irradiation, Yield given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

33 %

Na +

I –O

HO O

O O

Rx-ID: 1793642 View in Reaxys 544/834 Yield

Conditions & References With toluene-4-sulfonic acid, iron(II) sulfate, 1.) NH3 (liquid), 20 min, 2.) H2O, reflux, 4 h, Yield given. Multistep reaction. Yields of byproduct given Leeuwen, Milko van; McKillop, Alexander; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1993); p. 2433 - 2440 View in Reaxys

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H N

HO O

Rx-ID: 1987932 View in Reaxys 545/834 Yield

Conditions & References With sulfuric acid, water, T= 49.8 °C , Equilibrium constant, Rate constant Buglass, A. J.; Dorr, M.; Juffkins, M.; Tetrahedron Letters; vol. 28; nb. 28; (1987); p. 3283 - 3284 View in Reaxys

O E

HO O

Rx-ID: 2143504 View in Reaxys 546/834 Yield

Conditions & References With sodium hydroxide, sodium metasilicate, diethylenetriamine-N,N,N',N'',N''-pentaacetic acid, dihydrogen peroxide in water, Time= 1h, T= 40 °C , pH 10.0, Mechanism Gellerstedt, Goeran; Hardell, Hanne-Lise; Lindfors, Eva-Lisa; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 34; nb. 9; (1980); p. 669 - 674 View in Reaxys

O HO

O O

Rx-ID: 2598248 View in Reaxys 547/834 Yield

Conditions & References Yield given Kim, C. U.; Misco, P. F.; Tetrahedron Letters; vol. 26; nb. 17; (1985); p. 2027 - 2030 View in Reaxys

F F

Rx-ID: 3755865 View in Reaxys 548/834 Yield

Conditions & References

77 %

Time= 24h, T= 105 °C , effect of the presence of TFAA, other reaction time, Product distribution Tabor, Derrick C.; Evans, Slayton A.; Kenan, William Rand; Synthetic Communications; vol. 12; nb. 11; (1982); p. 855 - 864 View in Reaxys

O O

180/258

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O O

Rx-ID: 3843190 View in Reaxys 549/834 Yield

Conditions & References With lithium diisopropyl amide, 1.) -78 deg C, 20 min, THF, hexane, 2.) room temperature, overnight, Yield given. Multistep reaction. Yields of byproduct given Ramage, Robert; McCleery, Patrick P.; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); nb. 7; (1984); p. 1555 - 1560 View in Reaxys

N H

sulfur

NH 2

Rx-ID: 5855929 View in Reaxys 550/834 Yield

Conditions & References T= 170 °C Dauben et al.; Journal of the American Chemical Society; vol. 68; (1946); p. 2117 View in Reaxys

sodium

Rx-ID: 6799992 View in Reaxys 551/834 Yield

sodium

Rx-ID: 6799993 View in Reaxys 552/834 Yield

181/258

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Cl HO

O O

Rx-ID: 10148001 View in Reaxys 553/834 Yield

Conditions & References With water, T= 0 °C , Kinetics Bentley, T. William; Harris, H. Carl; Ryu, Zoon Ha; Lim, Gui Taek; Sung, Dae Dong; Szajda, Stanley R.; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 8963 - 8970 View in Reaxys

Rx-ID: 10148002 View in Reaxys 554/834 Yield

HO O

Rx-ID: 40002968 View in Reaxys 555/834 Yield

Conditions & References

41 %Chromat., 28 %Chromat., 15 %Chromat., 11 %Chromat.

With FeIII(meso-(tetrakis(pentafluorophenyl)porphyrinato))OTf, dihydrogen peroxide in 1,4-dioxane, Time= 5h, T= 20 °C , Mechanism, chemoselective reaction Du, Yi-Dan; Tse, Chun-Wai; Xu, Zhen-Jiang; Liu, Yungen; Che, Chi-Ming; Chemical Communications; vol. 50; nb. 84; (2014); p. 12669 - 12672 View in Reaxys

HO O

Rx-ID: 2000388 View in Reaxys 556/834 Yield

Conditions & References With Cs/Na/K alloy, multistep reaction: 1.) THF, -75 deg C, 2 h, rate of cleavage relative to bibenzyl, Product distribution Grovenstein, Erling; Bhatti, Amjad M.; Quest, Dean E.; Sengupta, Dibyendu; VanDerveer, Don; Journal of the American Chemical Society; vol. 105; nb. 20; (1983); p. 6290 - 6299 View in Reaxys

O O

182/258

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Rx-ID: 2025849 View in Reaxys 557/834 Yield

Conditions & References With 2,2'-azo-bisisobutyronitrile, oxygen in chlorobenzene, T= 60 °C , Product distribution, Mechanism Voronina, S. G.; Perkel', A. L.; Freidin, B. G.; J. Appl. Chem. USSR (Engl. Transl.); vol. 65; nb. 9.2; (1992); p. 2084 - 2090,1705 - 1710 View in Reaxys

Rx-ID: 2393578 View in Reaxys 558/834 Yield

Conditions & References With oxygen, anhydrous cobalt diacetate in acetic acid, Time= 2h, T= 30 °C , other reagents; var. temperature and var. reaction time, Product distribution, Mechanism Pritzkow, Wilhelm; Voerckel, Volkmar; Weber, Heike; Journal fuer Praktische Chemie/Chemiker-Zeitung; vol. 335; nb. 8; (1993); p. 705 - 707 View in Reaxys O O O

O HO

O O

Rx-ID: 4795969 View in Reaxys 559/834 Yield

Conditions & References With N,N-dimethyl-aniline in acetonitrile, Time= 2h, Irradiation, sensitized deprotection; competing bromide and carboxylate elimination, Mechanism Banerjee, Anamitro; Falvey, Daniel E.; Journal of Organic Chemistry; vol. 62; nb. 18; (1997); p. 6245 - 6251 View in Reaxys

O N

O O

Rx-ID: 5100592 View in Reaxys 560/834 Yield 28 % Chromat., 11 % Chromat., 25 % Chromat.

Conditions & References With potassium tert-butylate, Time= 1h, T= 190 °C , other temperature, reaction time, effect of cosolvents; various ratios of base and substrate, various amounts of MeOH as cosolvent, Product distribution Selva, Maurizio; Tundo, Pietro; Journal of Organic Chemistry; vol. 63; nb. 25; (1998); p. 9540 - 9544 View in Reaxys

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CO; peroxy acids; O

O OH

Rx-ID: 6727267 View in Reaxys 561/834 Yield

Conditions & References With oxygen in 1,2-dichloro-benzene, T= 130 °C , other temperature; activation energy; cobalt naphthenate as catal.;, Product distribution, Mechanism, Kinetics Voroshilova; Voroshilov; Perkel'; Fredin; Orlova; Journal of applied chemistry of the USSR; vol. 57; nb. 7 pt 2; (1984); p. 1455 - 1460 View in Reaxys

HO O

Rx-ID: 9321063 View in Reaxys 562/834 Yield

Conditions & References

26 %, 9 %, in acetonitrile, T= 25 °C , Electrochemical reaction, Product distribution, Further Variations: Reagents, electrode ma44 % terial Isse, Abdirisak A.; Gennaro, Armando; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 42; nb. 4; (2003); p. 751 - 757 View in Reaxys O HO

Rx-ID: 11187139 View in Reaxys 563/834 Yield 67 % Chromat.

Conditions & References in tetrahydrofuran, water, Time= 3h, T= 20 °C , Photolysis, 350 nm, Quantum yield Khade, Prashant K.; Singh, Anil K.; Tetrahedron Letters; vol. 48; nb. 39; (2007); p. 6920 - 6923 View in Reaxys

O O

Rx-ID: 30032217 View in Reaxys 564/834 Yield

Conditions & References With water in acetonitrile, Time= 0.2h, pH= 7.5, UV-irradiation, aq. buffer, Kinetics, Quantum yield, Time, Wavelength Jana, Avijit; Atta, Sanghamitra; Sarkar, Sujan K.; Singh, N.D. Pradeep; Tetrahedron; vol. 66; nb. 52; (2010); p. 9798 - 9807 View in Reaxys

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N N N

HO HO

Rx-ID: 1592674 View in Reaxys 565/834 Yield

Conditions & References

12 %

Irradiation, Yield given DeCosta, Dayal P.; Pincock, James A.; Journal of the American Chemical Society; vol. 111; nb. 24; (1989); p. 8948 - 8950 View in Reaxys

12 %

N+

CH –

O O

Rx-ID: 1834074 View in Reaxys 566/834 Yield

Conditions & References With oxygen in benzene, Time= 10h, T= 40 °C , Irradiation, other solvent cyclohexane, without O2, other temp., time, Product distribution Rao, T. S. S.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 329; nb. 4; (1987); p. 617 - 625 View in Reaxys

HO O

O O

Rx-ID: 3935121 View in Reaxys 567/834 Yield

Conditions & References With 4,4'-diphenylsulfide, 3-chloro-benzenecarboperoxoic acid in chlorobenzene, Time= 7h, T= 100 °C , Kinetics, Mechanism, Product distribution Perkel', A. L.; Freidin, B. G.; Voronina, S. G.; Ginter, S. V.; Fokin, A. A.; J. Appl. Chem. USSR (Engl. Transl.); vol. 62; nb. 11.2; (1989); p. 2560 - 2565,2378 - 2382 View in Reaxys

185/258

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HO Br

HBr

Rx-ID: 8450205 View in Reaxys 568/834 Yield

Conditions & References in various solvent(s), T= -125.1 - -120.1 °C , Kinetics Clark, David R.; Emsley, John; Hibbert, Frank; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1989); p. 1455 - 1458 View in Reaxys

HO O

Z O

HO O

Rx-ID: 28643966 View in Reaxys 569/834 Yield

Conditions & References With aluminum tri-bromide, Time= 0.5h, T= 60 °C , Sonication Golounin; Marakushina; Khramenko; Russian Journal of Applied Chemistry; vol. 81; nb. 12; (2008); p. 2137 2140 View in Reaxys

HO O

Rx-ID: 30999954 View in Reaxys 570/834 Yield

Conditions & References With 6-hydroxy-2-methyl-benzoxazole, 2,2'-azo-bisisobutyronitrile, oxygen, T= 69.84 °C , Kinetics, Concentration, Reagent/catalyst, Temperature Khizhan; Nikolaevskii; Kniga; Ivleva; Tikhonova; Russian Journal of General Chemistry; vol. 81; nb. 1; (2011); p. 122 - 127 View in Reaxys

S O

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Rx-ID: 1583514 View in Reaxys 571/834 Yield

Conditions & References

32 %, 4 %, With Ba(ClO4)2, Time= 72h, T= 20 °C , anodic oxidation, Mechanism 30 %, 5 %, Ismail, M.T.; El-Khawaga, A.M.; El-Zohry, M.F.; Abdel-Wahab, A.A.; Bulletin de la Societe Chimique de France; 4% nb. 5; (1986); p. 726 - 728 View in Reaxys

Rx-ID: 2043290 View in Reaxys 572/834 Yield

Conditions & References in cyclohexane, Irradiation, Quantum yield, Rate constant Kasper; Nash; Morrison; Journal of Organic Chemistry; vol. 59; nb. 10; (1994); p. 2792 - 2798 View in Reaxys

H N O

H 2N

S N

O O

Rx-ID: 2572072 View in Reaxys 573/834 Yield

Conditions & References With PEG 20000, potassium phosphate, penicillin acylase, T= 37 °C , Product distribution Andersson; Mattiasson; Hahn Hagerdal; ; vol. 37; nb. 8 B; (1983); p. 749 - 753 View in Reaxys

H N O

H 2N

O HO

S N

Rx-ID: 2572073 View in Reaxys 574/834 Yield

Conditions & References With sodium hydroxide, T= 28 °C , penicillin G amidase (E.C. 3.5.1.11) immobilized on polyacrylamide, pH 8; var. substrate concentrations, Equilibrium constant Danzig, Joachim; Tischer, Wilhelm; Wandrey, Christian; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 32; nb. 1; (1993); p. 40 - 43 View in Reaxys

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O O

Rx-ID: 2885216 View in Reaxys 575/834 Yield

Conditions & References With zeolite HZSM5, T= 259.9 °C , p= 37.5Torr , unexpected improvement of the selectivity to o-hydroxyacetophenone by passivation of the external acid sites of HZSM5 Neves, Isabel; Jayat, Francois; Magnoux, Patrick; Perot, Guy; Ribeiro, Fernando R.; et al.; Journal of the Chemical Society, Chemical Communications; nb. 6; (1994); p. 717 - 718 View in Reaxys

HO O

potassium

Rx-ID: 5801222 View in Reaxys 576/834 Yield

Conditions & References Morton; Ramsden; Journal of the American Chemical Society; vol. 70; (1948); p. 3132,3134 View in Reaxys

H N

sulfur

Rx-ID: 7154421 View in Reaxys 577/834 Yield

Conditions & References Erhitzen des Reaktionsprodukts mit wss. H2SO4 McMillan; King; Journal of the American Chemical Society; vol. 70; (1948); p. 4143,4149 View in Reaxys O

aqueous ethyl hydroperoxide solution

aqueous NaOH

Rx-ID: 7156305 View in Reaxys 578/834 Yield

Conditions & References Barnes; Lewis; Journal of the American Chemical Society; vol. 58; (1936); p. 947 View in Reaxys

O HO

Rx-ID: 7541329 View in Reaxys 579/834 Yield

Conditions & References Sobin; Bachmann; Journal of the American Chemical Society; vol. 57; (1935); p. 2458 View in Reaxys

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Br O

aqueous sodium hydrogencarbonate solution

O O

compound C23H16O5 of mp: 218-219 degree

Rx-ID: 7922214 View in Reaxys 580/834 Yield

Conditions & References Sobin; Bachmann; Journal of the American Chemical Society; vol. 57; (1935); p. 2458 View in Reaxys N

O HO

potassium hydroxide

Rx-ID: 7980207 View in Reaxys 581/834 Yield

Conditions & References substance of bp 0,5: 142 degree Whyte; Cope; Journal of the American Chemical Society; vol. 65; (1943); p. 1999,2002 View in Reaxys substance of bp 2: 162 degree Whyte; Cope; Journal of the American Chemical Society; vol. 65; (1943); p. 1999,2002 View in Reaxys

N E

aqueous alkali

N H

Rx-ID: 8255300 View in Reaxys 582/834 Yield

Conditions & References Kohler, Shohan; Journal of the American Chemical Society; vol. 48; (1926); p. 2433 View in Reaxys Kohler, Goodwin; Journal of the American Chemical Society; vol. 49; (1927); p. 222 View in Reaxys

HO O

alkaline KMnO4

O O

Rx-ID: 8265094 View in Reaxys 583/834 Yield

Conditions & References Kohler, Rao; Journal of the American Chemical Society; vol. 41; (1919); p. 1703 View in Reaxys

O N

O O

Rx-ID: 9912529 View in Reaxys 584/834 Yield

Conditions & References in water, acetonitrile, Photolysis, Quantum yield

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Ma, Chicheng; Steinmetz, Mark G.; Kopatz, Erica J.; Rathore, Rajendra; Journal of Organic Chemistry; vol. 70; nb. 11; (2005); p. 4431 - 4442 View in Reaxys

O O

Rx-ID: 9914651 View in Reaxys 585/834 Yield

Conditions & References in water, acetonitrile, Photolysis, Quantum yield Ma, Chicheng; Steinmetz, Mark G.; Kopatz, Erica J.; Rathore, Rajendra; Journal of Organic Chemistry; vol. 70; nb. 11; (2005); p. 4431 - 4442 View in Reaxys

O N

O O

Rx-ID: 9987226 View in Reaxys 586/834 Yield

HO O N

HO O

O O

Rx-ID: 28169807 View in Reaxys 587/834 Yield

Conditions & References With potassium hydroxide, HEPES buffer in acetonitrile, pH= 7.2, UV-irradiation, Quantum yield Hagen, Volker; Dekowski, Brigitte; Kotzur, Nico; Lechler, Ralf; Wiesner, Burkhard; Briand, Benoit; Beyermann, Michael; Chemistry - A European Journal; vol. 14; nb. 5; (2008); p. 1621 - 1627 View in Reaxys

O HO

H N

HO O

NH 2 O

Rx-ID: 32974448 View in Reaxys 588/834 Yield

Conditions & References With Escherichia coli penicillin acylase, potassium chloride, water, T= 24.84 °C , pH= 7.05, Enzymatic reaction, Equilibrium constant Guranda, Dorel T.; Ushakov, Gennadij A.; Yolkin, Petr G.; Svedas, Vytas K.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 48 - 53

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View in Reaxys H N

S O

O O

NH 2

Rx-ID: 32974450 View in Reaxys 589/834 Yield

Conditions & References With Escherichia coli penicillin acylase, potassium chloride, water, T= 24.84 °C , Enzymatic reaction, Equilibrium constant Guranda, Dorel T.; Ushakov, Gennadij A.; Yolkin, Petr G.; Svedas, Vytas K.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 48 - 53 View in Reaxys H N

NH 2

HO O

O HO

Rx-ID: 32974452 View in Reaxys 590/834 Yield

Conditions & References With Escherichia coli penicillin acylase, potassium chloride, water, T= 24.84 °C , pH= 4.3, Enzymatic reaction, Equilibrium constant Guranda, Dorel T.; Ushakov, Gennadij A.; Yolkin, Petr G.; Svedas, Vytas K.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 48 - 53 View in Reaxys

H N

O HO

O H 2N

H 2N O

H 2N

Rx-ID: 32974454 View in Reaxys 591/834 Yield

Conditions & References With Escherichia coli penicillin acylase, potassium chloride, water, T= 24.84 °C , pH= 5.47, Enzymatic reaction, Equilibrium constant Guranda, Dorel T.; Ushakov, Gennadij A.; Yolkin, Petr G.; Svedas, Vytas K.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 48 - 53 View in Reaxys

H N O

OH HO

H 2N O

Rx-ID: 32974456 View in Reaxys 592/834 Yield

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H N

H 2N

Rx-ID: 32974458 View in Reaxys 593/834 Yield

Conditions & References With Escherichia coli penicillin acylase, potassium chloride, water, T= 24.84 °C , pH= 4.4, Enzymatic reaction, Equilibrium constant Guranda, Dorel T.; Ushakov, Gennadij A.; Yolkin, Petr G.; Svedas, Vytas K.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 48 - 53 View in Reaxys H N

O N

NH 2

Rx-ID: 32974460 View in Reaxys 594/834 Yield

H N

H 2N

Rx-ID: 32974462 View in Reaxys 595/834 Yield

H N

NH 2 Cl

Rx-ID: 32974464 View in Reaxys 596/834 Yield

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O O

H 2N

Rx-ID: 32974466 View in Reaxys 597/834 Yield

Conditions & References With Escherichia coli penicillin acylase, potassium chloride, water, T= 24.84 °C , pH= 6.67, Enzymatic reaction, Equilibrium constant Guranda, Dorel T.; Ushakov, Gennadij A.; Yolkin, Petr G.; Svedas, Vytas K.; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 48 - 53 View in Reaxys

H N

H 2N

Rx-ID: 32974469 View in Reaxys 598/834 Yield

Cl Cl

O O

Rx-ID: 61074 View in Reaxys 599/834 Yield

Conditions & References Kharasch; Kane; Brown; Journal of the American Chemical Society; vol. 64; (1942); p. 1621,1623 View in Reaxys O

HO Na

OH O

Rx-ID: 749607 View in Reaxys 600/834 Yield

Conditions & References anschliessende Umsetztung mit CO2; mit o-, m- und p-Xylol entstehen vorwiegend die entsprechenden Phenylendiessigsaeuren Morton; Hechenbleikner; Journal of the American Chemical Society; vol. 58; (1936); p. 1024,2599,2604 View in Reaxys Morton; Little; Strong; Journal of the American Chemical Society; vol. 65; (1943); p. 1339,1345 View in Reaxys

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HO S S

Rx-ID: 2205651 View in Reaxys 601/834 Yield

Conditions & References With sulfur, Time= 8h, T= 240 °C , Mechanism Abdel-Wahab, Aboel-Magd A.; El-Khawaga, Ahmed M.; Ismail, Mohamed T.; Canadian Journal of Chemistry; vol. 60; (1982); p. 2870 - 2875 View in Reaxys

O N N N

N HO

NH N

(v1)

N N N

Rx-ID: 3049334 View in Reaxys 602/834 Yield

Conditions & References

56 %, 9.0 in benzene, Time= 24h, Irradiation, Mechanism %, 12.0 %, Parshad; Sharma; Journal of the Indian Chemical Society; vol. 67; nb. 2; (1990); p. 150 - 152 4.0 % View in Reaxys

Rx-ID: 3407460 View in Reaxys 603/834 Yield

Conditions & References With potassium fluoride, DOWEX resin H+, Mercury, benzenesulfenyl chloride, multistep reaction; other substrates Schmitz, Carole; Rouanet-Dreyfuss, Anne-Claire; Tueni, Marie; Biellmann, Jean-Francois; Tetrahedron Letters; vol. 33; nb. 34; (1992); p. 4911 - 4912 View in Reaxys Yield given. Multistep reaction Schmitz, Carole; Rouanet-Dreyfuss, Anne-Claire; Tueni, Marie; Biellmann, Jean-Francois; Tetrahedron Letters; vol. 33; nb. 34; (1992); p. 4911 - 4912 View in Reaxys

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HO O

O O

Rx-ID: 3628553 View in Reaxys 604/834 Yield

Conditions & References

2 %, 12 %, in benzene, Time= 72h, T= 150 °C , thermolysis; var. temp., time and solvent, Product distribution, Mechanism 77 % McCullough, Kevin J.; Morgan, Alistair R.; Nonhebel, Derek C.; Pauson, Peter L.; Journal of Chemical Research, Miniprint; nb. 2; (1980); p. 651 - 676 View in Reaxys OH

O HO

Rx-ID: 4168934 View in Reaxys 605/834 Yield

Conditions & References T= 215 °C , p= 3040Torr , other nitriles, other dicarboxylic acids; var. temp. and pressure, conventional and microwave heating; Ea, Kinetics, Thermodynamic data, Mechanism Chemat, Farid; Poux, Martine; Berlan, Jacques; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 12; (1994); p. 2597 - 2602 View in Reaxys

potassium

Rx-ID: 5801223 View in Reaxys 606/834 Yield

Conditions & References Morton; Ramsden; Journal of the American Chemical Society; vol. 70; (1948); p. 3132,3134 View in Reaxys

N2O

Rx-ID: 5857155 View in Reaxys 607/834 Yield

Conditions & References T= 300 °C , p= 367754Torr Buckley; Levy; Journal of the Chemical Society; (1951); p. 3016 View in Reaxys O O

OH HO

sodium phenylmalonic acid ester O

O O

O OH

Rx-ID: 7047242 View in Reaxys 608/834

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Yield

Conditions & References Case; Journal of the American Chemical Society; vol. 55; (1933); p. 2927,2930 View in Reaxys

carbon dioxide(solid)

Rx-ID: 7976175 View in Reaxys 609/834 Yield

Conditions & References Gilman; Pacevitz; Baine; Journal of the American Chemical Society; vol. 62; (1940); p. 1514,1519 View in Reaxys

N E

alkali

Rx-ID: 7976791 View in Reaxys 610/834 Yield

Conditions & References Kohler, Shohan; Journal of the American Chemical Society; vol. 48; (1926); p. 2433 View in Reaxys

N E

O HO

alkali

O O

Rx-ID: 8255299 View in Reaxys 611/834 Yield

Conditions & References Kohler, Goodwin; Journal of the American Chemical Society; vol. 49; (1927); p. 222 View in Reaxys

O O

N E

KOH-solution

Rx-ID: 8255301 View in Reaxys 612/834 Yield

Conditions & References Kohler, Goodwin; Journal of the American Chemical Society; vol. 49; (1927); p. 222 View in Reaxys

H N

(v1)

O N

O O

Rx-ID: 1928265 View in Reaxys 613/834 Yield

Conditions & References With oxygen in benzene, Time= 0.5h, Irradiation, var. solvents, Product distribution, Mechanism

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Felder, Bruno; Schumacher, Rolf; Sitek, Franciszek; Helvetica Chimica Acta; vol. 63; nb. 1; (1980); p. 132 - 147 View in Reaxys

O N O

H O

O O

Rx-ID: 2062734 View in Reaxys 614/834 Yield

Conditions & References

1.7 % Chromat., 3.4 % Chromat., 0.4 % Chromat., 0.2 % Chromat., 0.6 % Chromat., 0.2 % Chromat.

With sodium sulfide, sodium hydroxide in ethanol, water, Time= 3h, Heating, var. sodium polysulfides, also 4-nitrostyrene, Product distribution Ogata, Yoshiro; Nakagawa, Yoshiaki; Inaishi, Morio; Bulletin of the Chemical Society of Japan; vol. 55; nb. 2; (1982); p. 625 - 626 View in Reaxys

HO OH

Rx-ID: 2409165 View in Reaxys 615/834 Yield

Conditions & References With sulfuric acid, T= 190 °C , exchange reaction between (+)-(S)-2-methylbutanoic acid (95percent optical purity) and phenylacetonitrile, optical yield, racemization; stereoselective formation of nitrile by the reaction with chlorosulfonylisocyanate under mild conditions, Product distribution Botteghi, C.; Chelucci, G.; Marchetti, M.; Synthetic Communications; vol. 12; nb. 1; (1982); p. 25 - 34 View in Reaxys

H racemate

Rx-ID: 2658959 View in Reaxys 616/834 Yield

Conditions & References in hexane, Irradiation, Mechanism Rej, R. N.; Taylor, C.; Eadon, G.; Journal of Organic Chemistry; vol. 45; nb. 1; (1980); p. 126 - 130 View in Reaxys

O H

racemate

H racemate

Rx-ID: 2658960 View in Reaxys 617/834 Yield

Conditions & References in hexane, Irradiation, Mechanism

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Rej, R. N.; Taylor, C.; Eadon, G.; Journal of Organic Chemistry; vol. 45; nb. 1; (1980); p. 126 - 130 View in Reaxys

N HO

NH 2

N N

Rx-ID: 3049333 View in Reaxys 618/834 Yield

Conditions & References

17.0 %, 30.0 %, 5.0 %, 31 %

in isopropyl alcohol, Time= 40h, Irradiation Parshad; Sharma; Journal of the Indian Chemical Society; vol. 67; nb. 2; (1990); p. 150 - 152 View in Reaxys

17.0 %, 30.0 %, 5.0 %, 31.0 %

in isopropyl alcohol, Time= 40h, Irradiation, Mechanism Parshad; Sharma; Journal of the Indian Chemical Society; vol. 67; nb. 2; (1990); p. 150 - 152 View in Reaxys

17.0 %, 30.0 %, 31.0 %, 5 %

in isopropyl alcohol, Time= 40h, Irradiation Parshad; Sharma; Journal of the Indian Chemical Society; vol. 67; nb. 2; (1990); p. 150 - 152 View in Reaxys

O O P O

Rx-ID: 4675980 View in Reaxys 619/834 Yield

Conditions & References in water, acetonitrile, Ambient temperature, Irradiation, Mechanism Givens, Richard S.; Park, Chan-Ho; Tetrahedron Letters; vol. 37; nb. 35; (1996); p. 6259 - 6262 View in Reaxys

petroleum ether

O HO

HO O

Rx-ID: 5809936 View in Reaxys 620/834 Yield

Conditions & References Morton; Hechenbleikner; Journal of the American Chemical Society; vol. 58; (1936); p. 2599,2604 View in Reaxys

petroleum ether

OH O

Rx-ID: 5811476 View in Reaxys 621/834 Yield

Conditions & References Morton; Little; Strong; Journal of the American Chemical Society; vol. 65; (1943); p. 1339,1345

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View in Reaxys

HO H

N2O

Rx-ID: 5857156 View in Reaxys 622/834 Yield

Conditions & References T= 300 °C , p= 367754Torr Buckley; Levy; Journal of the Chemical Society; (1951); p. 3016 View in Reaxys O HO

aqueous NaOH

O O

Rx-ID: 7063307 View in Reaxys 623/834 Yield

Conditions & References Barnes; Lewis; Journal of the American Chemical Society; vol. 58; (1936); p. 947 View in Reaxys O

aqueous NaOH

Rx-ID: 7156304 View in Reaxys 624/834 Yield

Conditions & References Barnes; Journal of the American Chemical Society; vol. 57; (1935); p. 937,938 View in Reaxys

O O

O HO

aqueous KOH-solution

Rx-ID: 7976185 View in Reaxys 625/834 Yield

Conditions & References Erhitzen auf Schmelztemperatur Ivanoff; Mihova; Christova; Bulletin de la Societe Chimique de France; vol. <4> 51; (1932); p. 1321,1324 View in Reaxys Erhitzen auf Siedetemperatur Ivanoff; Mihova; Christova; Bulletin de la Societe Chimique de France; vol. <4> 51; (1932); p. 1321,1324 View in Reaxys T= 35 - 50 °C , Rate constant Spassoff; Bulletin de la Societe Chimique de France; vol. <5> 12; (1945); p. 275,278 View in Reaxys

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O O

CrO3

O O

Rx-ID: 8259420 View in Reaxys 626/834 Yield

Conditions & References Kohler, Barnes; Journal of the American Chemical Society; vol. 56; (1934); p. 211,214 View in Reaxys

HO (v2)

sodium

Rx-ID: 8259741 View in Reaxys 627/834 Yield

Conditions & References Behandlung der Reaktionsloesung mit Kohlendioxyd und anschliessend mit Wasser Bachmann; Clarke; Journal of the American Chemical Society; vol. 49; (1927); p. 2093 View in Reaxys O

Br H

aqueous alkaline solution

O O

Rx-ID: 8265315 View in Reaxys 628/834 Yield

Conditions & References Barnes; Payton; Journal of the American Chemical Society; vol. 58; (1936); p. 1300 View in Reaxys

H N

NH 2

Rx-ID: 669060 View in Reaxys 629/834 Yield

Conditions & References Underwood; Baril; Journal of the American Chemical Society; vol. 57; (1935); p. 2729 View in Reaxys

Rx-ID: 2131096 View in Reaxys 630/834 Yield 60 % Chromat., 27 % Chromat., 9 % Chromat., 5 % Chromat., 2 % Chromat.

Conditions & References in benzene, T= 100 °C , also in cyclohexane, Product distribution, Mechanism, Rate constant Fossey, Jacques; Lefort, Daniel; Massoudi, Massoud; Nedelec, Jean-Yves; Sorba, Jeanine; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1986); p. 781 - 786 View in Reaxys

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H 2N

HO O

NH 2

Rx-ID: 4078586 View in Reaxys 631/834 Yield

Conditions & References With α-chymotrypsin chemically modified with monomethoxypolyethylene glycol (α-CT-PEG), enzymatic hydrolysis at pH 8.0 (phosphate buffer), Km value, Rate constant Dominguez; Cabezas; Sanchez - Montero; Sinisterra; Tetrahedron; vol. 51; nb. 6; (1995); p. 1827 - 1844 View in Reaxys

O O

H 2N

NH 2 OH

Rx-ID: 4097925 View in Reaxys 632/834 Yield

O O

Rx-ID: 4259832 View in Reaxys 633/834 Yield

Conditions & References T= 20 °C , reactions under var. conditions, Product distribution, Mechanism Bravo, Anna; Fontana, Francesca; Fronza, Giovanni; Minisci, Francesco; Serri, Anna; Tetrahedron Letters; vol. 36; nb. 38; (1995); p. 6945 - 6948 View in Reaxys T= 60 °C , Yield given. Yields of byproduct given Bravo, Anna; Fontana, Francesca; Fronza, Giovanni; Minisci, Francesco; Serri, Anna; Tetrahedron Letters; vol. 36; nb. 38; (1995); p. 6945 - 6948 View in Reaxys O HO O

HO O

Rx-ID: 5809935 View in Reaxys 634/834 Yield

Conditions & References Morton; Hechenbleikner; Journal of the American Chemical Society; vol. 58; (1936); p. 2599,2604 View in Reaxys O

HO O

OH O

Rx-ID: 5811475 View in Reaxys 635/834 Yield

Conditions & References Morton; Little; Strong; Journal of the American Chemical Society; vol. 65; (1943); p. 1339,1345

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View in Reaxys OO

OH HO

aqueous KOH-solution

Rx-ID: 7987251 View in Reaxys 636/834 Yield

Conditions & References Spassoff; Bulletin de la Societe Chimique de France; vol. <5> 12; (1945); p. 275,278 View in Reaxys T= 55 - 75 °C , Rate constant Spassoff; Bulletin de la Societe Chimique de France; vol. <5> 12; (1945); p. 275,278 View in Reaxys Spasow; ; 36 Chimija <1940> 211, 218; ; (1943); p. 4000 View in Reaxys OO

aqueous KOH-solution

Rx-ID: 8261827 View in Reaxys 637/834 Yield

Conditions & References Ivanoff; Mihova; Christova; Bulletin de la Societe Chimique de France; vol. <4> 51; (1932); p. 1321,1324 View in Reaxys Spassoff; Bulletin de la Societe Chimique de France; vol. <5> 12; (1945); p. 275,278 View in Reaxys T= 70 - 85 °C , Rate constant Spassoff; Bulletin de la Societe Chimique de France; vol. <5> 12; (1945); p. 275,278 View in Reaxys O O

N O HO

O N

Rx-ID: 9999223 View in Reaxys 638/834 Yield 100 % Chromat.

Conditions & References in water, acetonitrile, Time= 6h, Photolysis, Quantum yield Singh, Anil K.; Khade, Prashant K.; Tetrahedron; vol. 61; nb. 42; (2005); p. 10007 - 10012 View in Reaxys

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Rx-ID: 10000050 View in Reaxys 639/834 Yield

Conditions & References

43 % Chromat.

in water, acetonitrile, Time= 0.333333h, Photolysis, Quantum yield Singh, Anil K.; Khade, Prashant K.; Tetrahedron Letters; vol. 46; nb. 33; (2005); p. 5563 - 5566 View in Reaxys

H 2N

Rx-ID: 30337675 View in Reaxys 640/834 Yield

Conditions & References With thia-containing Schiff-base iron(III) complex adsorbed on glassy carbon electrode, Electrochemical reaction, aq. buffer, Kinetics Saghatforoush, Lotfali; Hasanzadeh, Mohammad; Shadjou, Nasrin; Khalilzadeh, Balal; Electrochimica Acta; vol. 56; nb. 3; (2011); p. 1051 - 1061 View in Reaxys

O N

N+

O O

CH –

O O

Rx-ID: 1834073 View in Reaxys 641/834 Yield

Conditions & References in benzene, Time= 10h, T= 40 °C , Irradiation, other solvent cyclohexane, Product distribution Rao, T. S. S.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 329; nb. 4; (1987); p. 617 - 625 View in Reaxys

steam

thorium oxide

Rx-ID: 5412192 View in Reaxys 642/834 Yield

Conditions & References T= 420 °C Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 171; (1920); p. 247; Bulletin de la Societe Chimique de France; vol. <4>27; (1920); p. 756 View in Reaxys

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H N

sulfur

Rx-ID: 5801226 View in Reaxys 643/834 Yield

Conditions & References T= 200 °C , Erwaermen des Reaktionsprodukts mit wss. Schwefelsaeure Stanek; Collection of Czechoslovak Chemical Communications; vol. 12; (1947); p. 675 View in Reaxys

sulfur H 2N

Rx-ID: 5801227 View in Reaxys 644/834 Yield

Conditions & References T= 190 - 200 °C , Kochen des Reaktionsprodukts mit wss. Schwefelsaeure Stanek; Collection of Czechoslovak Chemical Communications; vol. 12; (1947); p. 675 View in Reaxys

sulfur

Rx-ID: 7154420 View in Reaxys 645/834 Yield

Conditions & References T= 190 - 200 °C , Kochen des Reaktionsprodukts mit wss. Schwefelsaeure Stanek; Collection of Czechoslovak Chemical Communications; vol. 12; (1947); p. 675 View in Reaxys

ethanolic KOH

2-cyclohexyl-1-phenyl-ethanol-(2)

Rx-ID: 7434831 View in Reaxys 646/834 Yield

Conditions & References T= 145 °C Wenus-Danilowa; Bolschuchin; Zhurnal Obshchei Khimii; vol. 9; (1939); p. 975,982; Chem. Zentralbl.; vol. 111; nb. I; (1940); p. 1190 View in Reaxys

OO OH

aqueous KOH-solution OH

Rx-ID: 7976358 View in Reaxys 647/834 Yield

Conditions & References T= 60 - 75 °C , Rate constant Spassoff; Bulletin de la Societe Chimique de France; vol. <5> 12; (1945); p. 275,278 View in Reaxys Spassoff; Bulletin de la Societe Chimique de France; vol. <5> 12; (1945); p. 275,278

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View in Reaxys

O N

O O

HO N

Rx-ID: 9901747 View in Reaxys 648/834 Yield

Conditions & References in water, acetonitrile, Photolysis, Quantum yield Ma, Chicheng; Steinmetz, Mark G.; Kopatz, Erica J.; Rathore, Rajendra; Tetrahedron Letters; vol. 46; nb. 6; (2005); p. 1045 - 1048 View in Reaxys

O N O

Rx-ID: 29710713 View in Reaxys 649/834 Yield

Conditions & References in acetonitrile, Irradiation, Quantum yield Kammari, Laxminarayana; Solomek, Tomas; Ngoy, Bokolombe Pitchou; Heger, Dominik; Klan, Petr; Journal of the American Chemical Society; vol. 132; nb. 33; (2010); p. 11431 - 11433 View in Reaxys

O O N O

Rx-ID: 29710719 View in Reaxys 650/834 Yield

HO S

Rx-ID: 2205652 View in Reaxys 651/834 Yield

Conditions & References Time= 8h, T= 240 °C , Yields of byproduct given Abdel-Wahab, Aboel-Magd A.; El-Khawaga, Ahmed M.; Ismail, Mohamed T.; Canadian Journal of Chemistry; vol. 60; (1982); p. 2870 - 2875 View in Reaxys Time= 8h, T= 240 °C , Mechanism Abdel-Wahab, Aboel-Magd A.; El-Khawaga, Ahmed M.; Ismail, Mohamed T.; Canadian Journal of Chemistry; vol. 60; (1982); p. 2870 - 2875 View in Reaxys

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OH HO

H O

OH Cl

Rx-ID: 2326763 View in Reaxys 652/834 Yield

Conditions & References T= 120 °C , degradation also in aq. solution and with aq. HCl and aq. KOH (6 h, reflux), Mechanism Martin, Elisabeth; Pohloudek-Fabini, R.; Pharmazie; vol. 36; nb. 7; (1981); p. 480 - 482 View in Reaxys

N+

O N O–

(v2)

Rx-ID: 3137427 View in Reaxys 653/834 Yield

Conditions & References in N,N-dimethyl-formamide, Ambient temperature, Equilibrium constant Jaworski, Jan S.; Krawczyk, Irena; Monatshefte fuer Chemie; vol. 123; nb. 1/2; (1992); p. 43 - 50 View in Reaxys

KOH-solution

HO O

OH O

H 2N 2

α.α'-diphenyl-acetone Rx-ID: 5683931 View in Reaxys 654/834

Yield

Conditions & References T= 150 - 160 °C , im Rohr Wedekind; Justus Liebigs Annalen der Chemie; vol. 378; (1911); p. 283 View in Reaxys

alcoholic KOH-solution

Rx-ID: 5929635 View in Reaxys 655/834 Yield

Conditions & References T= 100 - 120 °C Nef; Justus Liebigs Annalen der Chemie; vol. 308; (1899); p. 325 View in Reaxys

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sodium sulfide

sulfur

O O

Rx-ID: 5957969 View in Reaxys 656/834 Yield

Conditions & References T= 220 °C , unter Druck Willgerodt; Merk; Journal fuer Praktische Chemie (Leipzig); vol. <2> 80; (1909); p. 193 View in Reaxys

alcoholic KOH-solution

Rx-ID: 7157807 View in Reaxys 657/834 Yield

Conditions & References T= 125 - 130 °C Orechow; Bulletin de la Societe Chimique de France; vol. <4> 25; (1919); p. 114 View in Reaxys

copper OH

NH 2

Rx-ID: 7450167 View in Reaxys 658/834 Yield

Conditions & References T= 200 °C Yamaguchi; Bulletin of the Chemical Society of Japan; vol. 1; (1926); p. 38; Memoirs of the College of Science, Kyoto Imperial University; vol. <A> 9; (1926); p. 431; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 3538 View in Reaxys

alcoholic KOH-solution

Rx-ID: 7542846 View in Reaxys 659/834 Yield

Conditions & References T= 125 - 130 °C Orechow; Bulletin de la Societe Chimique de France; vol. <4> 25; (1919); p. 188 View in Reaxys

O HO

O O OH

HO O

NH 2

N H

Rx-ID: 7542853 View in Reaxys 660/834

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Yield

Conditions & References T= 150 °C , im Druckrohr Erlenmeyer junior; Kunlin; Justus Liebigs Annalen der Chemie; vol. 307; (1899); p. 152,154, 158 View in Reaxys Erlenmeyer junior; Chemische Berichte; vol. 30; (1897); p. 2977; Chemische Berichte; vol. 31; (1898); p. 2238 View in Reaxys O OH

hydrogen

copper-oxide-chromium oxide

racemate

HO O

Rx-ID: 7976176 View in Reaxys 661/834 Yield

Conditions & References T= 200 °C Davies; Morris; Journal of the Chemical Society; (1947); p. 1697 View in Reaxys

O O O

Rx-ID: 34500706 View in Reaxys 662/834 Yield

Conditions & References in acetonitrile, Time= 4.25h, Irradiation, Photolysis, Quantum yield Ikbal, Mohammed; Banerjee, Rakesh; Atta, Sanghamitra; Dhara, Dibakar; Anoop, Anakuthil; Singh, N. D. Pradeep; Journal of Organic Chemistry; vol. 77; nb. 23; (2012); p. 10557 - 10567 View in Reaxys

O– Na +

Rx-ID: 724727 View in Reaxys 663/834 Yield

Conditions & References T= 100 - 120 °C Nef; Justus Liebigs Annalen der Chemie; vol. 308; (1899); p. 325 View in Reaxys

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O HO

H 2N

Rx-ID: 5412183 View in Reaxys 664/834 Yield

Conditions & References T= 140 - 150 °C , im Rohr Schoettle et al.; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 60; (1928); p. 1521,1525, 1531; Chem. Zentralbl.; vol. 100; nb. I; (1929); p. 2989 View in Reaxys

NH 2

HO O

Rx-ID: 5412185 View in Reaxys 665/834 Yield

O HO

H 2N

Rx-ID: 5412186 View in Reaxys 666/834 Yield

HO N O

nickel-aluminium-alloy

Rx-ID: 5801213 View in Reaxys 667/834 Yield

Conditions & References Papa; Schwenk; Ginsberg; Journal of Organic Chemistry; vol. 14; (1949); p. 723,729 View in Reaxys

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C O

Rx-ID: 7072757 View in Reaxys 668/834 Yield

Conditions & References T= 130 - 140 °C Walther; Schickler; Journal fuer Praktische Chemie (Leipzig); vol. <2> 55; (1897); p. 323 View in Reaxys O HO

H 2N O HO

aqueous alkaline solution

N H

HO O

Rx-ID: 8255179 View in Reaxys 669/834 Yield

Conditions & References T= 20 °C Schreiber; Annales de Chimie (Cachan, France); vol. <12> 2; (1947); p. 84,120 View in Reaxys

H H

(v5)

–O

P H

B– PH H

Rx-ID: 28922802 View in Reaxys 670/834 Yield

Conditions & References T= 57.84 °C , Gas phase, Equilibrium constant Hurtado, Marcela; Yanez, Manuel; Herrero, Rebeca; Guerrero, Andres; Juan Z. Davalos; Jose-Luis, M. Abboud; Khater, Brahim; Guillemin, Jean-Claude; Chemistry - A European Journal; vol. 15; nb. 18; (2009); p. 4622 4629 View in Reaxys Rx-ID: 35295617 View in Reaxys 671/834

Yield

Conditions & References Time= 0.5h, pH= 5, UV-irradiation, Darkness Xu, Xiang; Shen, Xiaoping; Zhou, Hu; Qiu, Dezhou; Zhu, Guoxing; Chen, Kangmin; Applied Catalysis A: General; vol. 455; (2013); p. 183 - 192 View in Reaxys

S OO

dichromate

Rx-ID: 7441838 View in Reaxys 672/834 Yield

Conditions & References Patent; Grignard; DE164883 View in Reaxys Walbaum; Chemische Berichte; vol. 33; (1900); p. 2300 View in Reaxys Grimal; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 144; (1907); p. 434 View in Reaxys v. Soden; Rojahn; Chemische Berichte; vol. 33; (1900); p. 1723 View in Reaxys Radziszewski; Chemische Berichte; vol. 9; (1876); p. 373 View in Reaxys

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Grignard; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 30; Chem. Zentralbl.; vol. 76; nb. II; (1905); p. 1751 View in Reaxys Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 141; (1905); p. 45; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 30; Chem. Zentralbl.; vol. 76; nb. II; (1905); p. 1751 View in Reaxys

NH O

Rx-ID: 7443663 View in Reaxys 673/834 Yield

Conditions & References T= 125 °C , im Rohr Gupta; Journal of the Chemical Society; vol. 119; (1921); p. 303 View in Reaxys

aqueous KOH-solution

E HO O

HO O

Rx-ID: 7448930 View in Reaxys 674/834 Yield

Conditions & References T= 200 - 210 °C Schemjakin; Red'kin; Zhurnal Obshchei Khimii; vol. 11; (1941); p. 1163,1167; ; (1943); p. 4054 View in Reaxys O

OH HO

HO N

OH O

H 2N 2

Rx-ID: 8256227 View in Reaxys 675/834 Yield

Conditions & References T= 90 - 100 °C Hopkins; Chisholm; Canadian Journal of Research, Section B: Chemical Sciences; vol. 24; (1946); p. 89,91 View in Reaxys

HO O

Rx-ID: 418814 View in Reaxys 676/834

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Yield

Conditions & References bei der Ozonspaltung Thiele; Henle; Justus Liebigs Annalen der Chemie; vol. 347; (1906); p. 304 View in Reaxys Kuhn; Winterstein; Helvetica Chimica Acta; vol. 11; (1928); p. 113; Helvetica Chimica Acta; vol. 12; (1929); p. 493 View in Reaxys

OH H 2N 2

Br–

Mg+

Rx-ID: 678865 View in Reaxys 677/834 Yield

Conditions & References Houben; Kesselkaul; Chemische Berichte; vol. 35; (1902); p. 2521 View in Reaxys Tiffeneau; Delange; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 137; (1903); p. 574 View in Reaxys Zelinsky; Chemiker-Zeitung, Chemische Apparatur; (1902); p. 531; Chemische Berichte; vol. 35; (1902); p. 2694 View in Reaxys

OH H 2N 2

Cl –

Mg+

Rx-ID: 678866 View in Reaxys 678/834 Yield

aqueous KOH-solution

Rx-ID: 5412190 View in Reaxys 679/834 Yield

Conditions & References Cannizzaro; Justus Liebigs Annalen der Chemie; vol. 96; (1855); p. 246 View in Reaxys Mann; Chemische Berichte; vol. 14; (1881); p. 1646 View in Reaxys

OH H

Rx-ID: 5690842 View in Reaxys 680/834 Yield

Conditions & References T= 95 °C Cattaneo; Gazzetta Chimica Italiana; vol. 64; (1934); p. 509,510 View in Reaxys

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liver

H 2N

Rx-ID: 5801212 View in Reaxys 681/834 Yield

Conditions & References Guggenheim; Loeffler; Biochemische Zeitschrift; vol. 72; (1916); p. 337 View in Reaxys Loeffler; Biochemische Zeitschrift; vol. 85; (1918); p. 292 View in Reaxys

O HO

NH 2

oxygen

blood coal

OH O

H 2N 2

Rx-ID: 7445534 View in Reaxys 682/834 Yield

Conditions & References T= 38 °C Wieland; Bergel; Justus Liebigs Annalen der Chemie; vol. 439; (1924); p. 205 View in Reaxys N HO

aq.-ethanolic NaOH-solution

H 2N O

Rx-ID: 7976174 View in Reaxys 683/834 Yield

Conditions & References Keller; Helvetica Chimica Acta; vol. 20; (1937); p. 436,443 View in Reaxys

Rx-ID: 340171 View in Reaxys 684/834 Yield

Conditions & References Ozonolyse Zaki; Iskander; Journal of the Chemical Society; (1943); p. 68 View in Reaxys

N Cl

Rx-ID: 342369 View in Reaxys 685/834 Yield

Conditions & References Ozonolyse Zaki; Iskander; Journal of the Chemical Society; (1943); p. 68 View in Reaxys

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HO O

Rx-ID: 459545 View in Reaxys 686/834 Yield

Conditions & References bei der Ozonspaltung Grignard; Tcheoufaki; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 188; (1929); p. 1532; Recueil des Travaux Chimiques des Pays-Bas; vol. 48; (1929); p. 902 View in Reaxys

O O

O S

Rx-ID: 534221 View in Reaxys 687/834 Yield

Conditions & References bei der Kalischmelze Perkin; Journal of the Chemical Society; vol. 28; (1875); p. 12 View in Reaxys

E O

Rx-ID: 641011 View in Reaxys 688/834 Yield

Conditions & References beim Ozonisieren und folgend Kochen mit Wasserstoffperoxyd Kuhn; Winterstein; Helvetica Chimica Acta; vol. 11; (1928); p. 113; Helvetica Chimica Acta; vol. 12; (1929); p. 493 View in Reaxys

E O

Rx-ID: 641032 View in Reaxys 689/834 Yield

Conditions & References bei der Ozonisierung und folgend Kochen mit Perhydrol Kuhn; Winterstein; Helvetica Chimica Acta; vol. 11; (1928); p. 113; Helvetica Chimica Acta; vol. 12; (1929); p. 493 View in Reaxys

alcoholic KOH-solution

Rx-ID: 5412187 View in Reaxys 690/834 Yield

Conditions & References Hofmann,A. W.; Chemische Berichte; vol. 7; (1874); p. 519 View in Reaxys

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O HO

NH N

N H

alkali hypochlorite

Rx-ID: 5412188 View in Reaxys 691/834 Yield

Conditions & References Bougault; Daniel; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 186; (1928); p. 151,1216 View in Reaxys

N HO

aqueous KOH-solution

Rx-ID: 5412189 View in Reaxys 692/834 Yield

Conditions & References Chase et al.; Journal of the Chemical Society; (1951); p. 3439,3442 View in Reaxys

H N

H S

penicillin-amidase

N O HO

H 2N

penicillium chrysogenum-stems

H S N

O O

Rx-ID: 5446836 View in Reaxys 693/834 Yield

Conditions & References Hydrolysis Murao; Nippon Nogei Kagaku Kaishi; vol. 29; (1955); p. 404; ; (1957); p. 8160 View in Reaxys Sakaguchi; Murao; Nippon Nogei Kagaku Kaishi; vol. 23; (1950); p. 411; ; (1951) View in Reaxys

aq. barium hydroxide solution

Rx-ID: 5801211 View in Reaxys 694/834 Yield

Conditions & References Volhard; Justus Liebigs Annalen der Chemie; vol. 296; (1897); p. 29 View in Reaxys

aqueous ammonium sulfide

NH 2

Rx-ID: 5855928 View in Reaxys 695/834 Yield

Conditions & References Willgerodt; Merk; Journal fuer Praktische Chemie (Leipzig); vol. <2> 80; (1909); p. 193 View in Reaxys

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Willgerodt; Chemische Berichte; vol. 21; (1888); p. 534; Journal fuer Praktische Chemie (Leipzig); vol. <2> 80; (1909); p. 183 View in Reaxys

H N

bromine water

Rx-ID: 6799990 View in Reaxys 696/834 Yield

Conditions & References de Paolini; Gazzetta Chimica Italiana; vol. 56; (1926); p. 758; Gazzetta Chimica Italiana; vol. 62; (1932); p. 1053 View in Reaxys H N O

H N

alcoholic KOH-solution

Rx-ID: 7154416 View in Reaxys 697/834 Yield

Conditions & References im Druckrohr Hepp; Chemische Berichte; vol. 10; (1877); p. 1651 View in Reaxys H N

alcoholic potash

Rx-ID: 7154417 View in Reaxys 698/834 Yield

Conditions & References Wolff; Justus Liebigs Annalen der Chemie; vol. 394; (1912); p. 44 View in Reaxys

hydrogen

nickel

alkali

Rx-ID: 7154418 View in Reaxys 699/834 Yield

Conditions & References Kinetics, dl-phenylchloroacetic acid Kelber; Chemische Berichte; vol. 54; (1921); p. 2257 View in Reaxys O HO

palladium-barium sulfate

HO O

Rx-ID: 7154419 View in Reaxys 700/834 Yield

Conditions & References Hydrogenation Rosenmund; Schindler; Archiv der Pharmazie (Weinheim, Germany); (1928); p. 281 View in Reaxys

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OH HO

K+

N HO

O S

O–

Rx-ID: 7976171 View in Reaxys 701/834 Yield

Conditions & References Schultz; Gmelin; Archiv der Pharmazie (Weinheim, Germany); vol. 287; (1954); p. 342,346 View in Reaxys O

OH HO

60 percent aqueous hydrobromic acid

Rx-ID: 7976172 View in Reaxys 702/834 Yield

Conditions & References Kuehlung Hopkins; Chisholm; Canadian Journal of Research, Section B: Chemical Sciences; vol. 24; (1946); p. 89,91 View in Reaxys

alcoholic potash

Rx-ID: 7976173 View in Reaxys 703/834 Yield

Conditions & References Nef; Justus Liebigs Annalen der Chemie; vol. 308; (1899); p. 325 View in Reaxys O HO

KOH-solution

O HO

Rx-ID: 7976177 View in Reaxys 704/834 Yield

Conditions & References Alexander; Justus Liebigs Annalen der Chemie; vol. 258; (1890); p. 76,86 View in Reaxys

OH HO

hydrogen

nickel

diluted KOH-solution

Rx-ID: 7976179 View in Reaxys 705/834 Yield

Conditions & References Kinetics Kelber; Chemische Berichte; vol. 54; (1921); p. 2257 View in Reaxys

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O O

OH O

aqueous barium hydroxide

O O

N O

Rx-ID: 7981587 View in Reaxys 706/834 Yield

Conditions & References Ruggli; Caspar; Hegedues; Helvetica Chimica Acta; vol. 20; (1937); p. 250,257 View in Reaxys

O O

ethanolic KOH-solution

O O

Rx-ID: 8259388 View in Reaxys 707/834 Yield

Conditions & References 3-benzoyloxy-2,3-diphenyl-acrylic acid ethyl ester of mp: 103 degree and mp: 112 degree Adickes; Meister; Chemische Berichte; vol. 68; (1935); p. 2191,2199 View in Reaxys Scheibler; Emden; Krabbe; Chemische Berichte; vol. 63; (1930); p. 1562,1569 View in Reaxys

Rx-ID: 211495 View in Reaxys 708/834 Yield

Conditions & References bei der Ozonspaltung Staudinger; Kreis; Schilt; Helvetica Chimica Acta; vol. 5; (1922); p. 750 View in Reaxys O

HO N

Rx-ID: 266878 View in Reaxys 709/834 Yield

Conditions & References Ivanoff; Mihova; Christova; Bulletin de la Societe Chimique de France; vol. <4> 51; (1932); p. 1321,1324 View in Reaxys

O N O

N O

HO O

Rx-ID: 283558 View in Reaxys 710/834 Yield

Conditions & References nachfolgend Behandeln mit Wasserstoffperoxyd

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Mauthner; Justus Liebigs Annalen der Chemie; vol. 370; (1909); p. 374 View in Reaxys

OH O

O O

Rx-ID: 381823 View in Reaxys 711/834 Yield

Conditions & References Erhitzen auf Schmelztemperatur Ivanoff; Mihova; Christova; Bulletin de la Societe Chimique de France; vol. <4> 51; (1932); p. 1321,1324 View in Reaxys

O– Na +

Rx-ID: 416133 View in Reaxys 712/834 Yield

Conditions & References Nef; Justus Liebigs Annalen der Chemie; vol. 308; (1899); p. 325 View in Reaxys HO O

HO OH O

Rx-ID: 428564 View in Reaxys 713/834 Yield

Conditions & References Erhitzen auf Schmelztemperatur Ivanoff; Mihova; Christova; Bulletin de la Societe Chimique de France; vol. <4> 51; (1932); p. 1321,1324 View in Reaxys

H 2N 2

Rx-ID: 537047 View in Reaxys 714/834 Yield

Conditions & References de Postis; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 222; (1946); p. 398 View in Reaxys

S N

O O

HO O

O HO

HO O

Rx-ID: 1599664 View in Reaxys 715/834

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Yield

Conditions & References With antimony(V) pentachloride, water, 1.) CH2Cl2, -60 deg C, 2.) r.t.; variable temperatures, Product distribution, Mechanism Helwig, Reinhard; Hanack, Michael; Chemische Berichte; vol. 118; nb. 3; (1985); p. 1008 - 1021 View in Reaxys

H N

Rx-ID: 5412182 View in Reaxys 716/834 Yield

Conditions & References Pinner; Chemische Berichte; vol. 30; (1897); p. 1885; Justus Liebigs Annalen der Chemie; vol. 298; (1897); p. 45 View in Reaxys

chromic acid

Rx-ID: 5412191 View in Reaxys 717/834 Yield

Conditions & References Linstead; Williams; Journal of the Chemical Society; (1926); p. 2745 View in Reaxys

OH O

aq.-ethanolic KOH-solution

O O

Rx-ID: 5412193 View in Reaxys 718/834 Yield

Conditions & References Ivanoff; Bulletin de la Societe Chimique de France; vol. <4> 53; (1933); p. 321 View in Reaxys

aq. barium hydroxide solution O

HO O

OH O

Rx-ID: 5423256 View in Reaxys 719/834 Yield

Conditions & References Dimroth; Eble; Chemische Berichte; vol. 39; (1906); p. 3928 View in Reaxys

aq. barium hydroxide solution

HO O

O OH

Rx-ID: 5423266 View in Reaxys 720/834 Yield

Conditions & References Dimroth; Feuchter; Chemische Berichte; vol. 36; (1903); p. 2239 Anm.5 View in Reaxys

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O O

concentrated KOH-solution

O O

O OH

Rx-ID: 5589078 View in Reaxys 721/834 Yield

Conditions & References Hesse; Chemische Berichte; vol. 13; (1880); p. 1817; Journal fuer Praktische Chemie (Leipzig); vol. <2> 58; (1898); p. 538 View in Reaxys

H 2N

alkali

Rx-ID: 5687966 View in Reaxys 722/834 Yield

Conditions & References beim Schmelzen Auwers; Czerny; Chemische Berichte; vol. 31; (1898); p. 2696 View in Reaxys

OH O

Cl OO

palladium

Rx-ID: 5801214 View in Reaxys 723/834 Yield

Conditions & References Hydrogenation Kindler; Kwok; Justus Liebigs Annalen der Chemie; vol. 554; (1943); p. 9,10, 12, 14 View in Reaxys

OH HO

S OO

palladium

Rx-ID: 5801215 View in Reaxys 724/834 Yield

Conditions & References Hydrogenation Kindler; Kwok; Justus Liebigs Annalen der Chemie; vol. 554; (1943); p. 9,10, 12, 14 View in Reaxys

palladium

Rx-ID: 5801218 View in Reaxys 725/834 Yield

Conditions & References Hydrogenation Kindler; Kwok; Justus Liebigs Annalen der Chemie; vol. 554; (1943); p. 9,10, 12, 14 View in Reaxys

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HO I

phosphorus

Rx-ID: 5801220 View in Reaxys 726/834 Yield

Conditions & References racemic mandelic acid Crum Brown; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1865); p. 340,443 View in Reaxys HO OH

palladium(II)-chloride

HO O

platinum/charcoal-catalyst

Rx-ID: 5801221 View in Reaxys 727/834 Yield

Conditions & References Hydrogenation Zelinsky; Packendorff; Leder-Packendorff; Chemische Berichte; vol. 67; (1934); p. 300 View in Reaxys O HO

diluted NaOH-solution

Rx-ID: 5803371 View in Reaxys 728/834 Yield

Conditions & References α-form Wislicenus,W.; Chemische Berichte; vol. 20; (1887); p. 2931; Chemische Berichte; vol. 28; (1895); p. 771 View in Reaxys β-form Wislicenus,W.; Chemische Berichte; vol. 20; (1887); p. 2931; Chemische Berichte; vol. 28; (1895); p. 771 View in Reaxys

liver

H 2N

O NH 2

Rx-ID: 5956999 View in Reaxys 729/834 Yield

Conditions & References Loeffler; Biochemische Zeitschrift; vol. 85; (1918); p. 292 View in Reaxys O

diluted acid

O O

Rx-ID: 5957968 View in Reaxys 730/834 Yield

Conditions & References Walther; Schickler; Journal fuer Praktische Chemie (Leipzig); vol. <2> 55; (1897); p. 323 View in Reaxys

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sodium amalgam

Rx-ID: 6330960 View in Reaxys 731/834 Yield

Conditions & References Glaser; Radziszewski; ; (1868); p. 142 View in Reaxys

O H 2N

substituted benzoic acid

Rx-ID: 6731462 View in Reaxys 732/834 Yield

Conditions & References Roullier; American Chemical Journal; vol. 47; (1912); p. 479 View in Reaxys -2

(v1)

2 Na +

N + CH –

(v1)

S O

silver oxide

O O

Rx-ID: 6799991 View in Reaxys 733/834 Yield

Conditions & References Wolff; Justus Liebigs Annalen der Chemie; vol. 394; (1912); p. 44 View in Reaxys N

Rx-ID: 7154414 View in Reaxys 734/834 Yield

Conditions & References Wol'pin et al.; Zhurnal Obshchei Khimii; vol. 28; (1958); p. 330,332; engl. Ausg. S. 326, 328 View in Reaxys H N

H N

Rx-ID: 7154415 View in Reaxys 735/834 Yield

Conditions & References im Druckrohr Hepp; Chemische Berichte; vol. 10; (1877); p. 1651 View in Reaxys O HO

alcoholic potash O

OH O

Rx-ID: 7155819 View in Reaxys 736/834 Yield

Conditions & References Metzner; Justus Liebigs Annalen der Chemie; vol. 298; (1897); p. 379 View in Reaxys

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O HO

alkali

Rx-ID: 7441811 View in Reaxys 737/834 Yield

Conditions & References Harding; Haworth; Journal of the Chemical Society; vol. 97; (1910); p. 497 View in Reaxys O HO

alcoholic KOH-solution

Rx-ID: 7444861 View in Reaxys 738/834 Yield

Conditions & References Beckh; Chemische Berichte; vol. 31; (1898); p. 3163 View in Reaxys

alcoholic KOH-solution

O HO

Rx-ID: 7446683 View in Reaxys 739/834 Yield

Conditions & References Blaise; Courtot; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 141; (1905); p. 725; Bulletin de la Societe Chimique de France; vol. <3>35; (1906); p. 589 View in Reaxys O O

0.5 percent aqueous ammonia O

Rx-ID: 7541330 View in Reaxys 740/834 Yield

Conditions & References Sonn; Litten; Chemische Berichte; vol. 66; (1933); p. 1512,1518 View in Reaxys

alcoholic NaOH-solution O

OH H

Rx-ID: 7541473 View in Reaxys 741/834 Yield

Conditions & References Wislicenus; v. Schroetter; Justus Liebigs Annalen der Chemie; vol. 424; (1921); p. 226 View in Reaxys HO

aq.-ethanolic KOH-solution OH

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Rx-ID: 7541877 View in Reaxys 742/834 Yield

Conditions & References Ivanoff; Bulletin de la Societe Chimique de France; vol. <4> 53; (1933); p. 321 View in Reaxys O HO

aqueous ammonia higher concentration O

O O

Rx-ID: 7916175 View in Reaxys 743/834 Yield

Conditions & References Sonn; Litten; Chemische Berichte; vol. 66; (1933); p. 1512,1518 View in Reaxys O HO

concentrated alcoholic KOH-solution

O O

Rx-ID: 7919140 View in Reaxys 744/834 Yield

Conditions & References Wislicenus; Eichert; Marquardt; Justus Liebigs Annalen der Chemie; vol. 436; (1924); p. 93 View in Reaxys N

concentrated aqueous alkali

O O

Rx-ID: 7919193 View in Reaxys 745/834 Yield

Conditions & References Bodroux; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 151; (1910); p. 235; Bulletin de la Societe Chimique de France; vol. <4> 7; (1910); p. 847,850 View in Reaxys

O HN

Rx-ID: 7976170 View in Reaxys 746/834 Yield

Conditions & References Curtius; Kenngott; Journal fuer Praktische Chemie (Leipzig); vol. <2> 112; (1926); p. 325 View in Reaxys

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lead (IV)-oxide

H N

Rx-ID: 7976178 View in Reaxys 747/834 Yield

Conditions & References Rodd; Linch; Journal of the Chemical Society; (1927); p. 2187 View in Reaxys

HO OH

HO H

sodium amalgam

Rx-ID: 7976180 View in Reaxys 748/834 Yield

Conditions & References Radziszewski; Chemische Berichte; vol. 2; (1869); p. 209; Chemische Berichte; vol. 3; (1870); p. 648 View in Reaxys

HO H

zinc dust

Rx-ID: 7976181 View in Reaxys 749/834 Yield

Conditions & References Spiegel; Chemische Berichte; vol. 14; (1881); p. 239 View in Reaxys

OH HO

S OO

zinc-powder

racemate

Rx-ID: 7976182 View in Reaxys 750/834 Yield

Conditions & References Schoeberl; Berninger; Harren; Chemische Berichte; vol. 67; (1934); p. 1545,1550 View in Reaxys

zinc

OH HO

Rx-ID: 7976183 View in Reaxys 751/834 Yield

Conditions & References Ulpiani; Ciancarelli; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 12 II; (1903); p. 224 View in Reaxys

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HO E

alcoholic KOH-solution

NH 2

Rx-ID: 7976184 View in Reaxys 752/834 Yield

Conditions & References Atkinson; Ingham; Thorpe; Journal of the Chemical Society; vol. 91; (1907); p. 591 View in Reaxys OH HO

alkali

OH H

Rx-ID: 7976790 View in Reaxys 753/834 Yield

Conditions & References Boerner; Chem. Zentralbl.; vol. 71; nb. I; (1900); p. 123 View in Reaxys

Z N

aqueous KOH-solution

NH 2

OH O

Rx-ID: 7979290 View in Reaxys 754/834 Yield

Conditions & References Best; Thorpe; Journal of the Chemical Society; vol. 95; (1909); p. 14 View in Reaxys N HO

aqueous potash NH 2

OH O

Rx-ID: 7979291 View in Reaxys 755/834 Yield

Conditions & References Smith; Thorpe; Journal of the Chemical Society; vol. 91; (1907); p. 1903 View in Reaxys

O HO

aqueous alkaline solution O

OH NHO2

Rx-ID: 7989500 View in Reaxys 756/834 Yield

Conditions & References Cordier; Moreau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 217; (1943); p. 199 View in Reaxys

H H

aqueous KOH-solution

H O

racemate

Rx-ID: 8251793 View in Reaxys 757/834

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Yield

Conditions & References Ivanoff; Bulletin de la Societe Chimique de France; vol. <4> 53; (1933); p. 321 View in Reaxys

methanolic potash

O O

Rx-ID: 8262371 View in Reaxys 758/834 Yield

Conditions & References Smith; Thorpe; Journal of the Chemical Society; vol. 91; (1907); p. 1903 View in Reaxys O

O– Na +

Rx-ID: 44013 View in Reaxys 759/834 Yield

Conditions & References Bertho; Nuessel; Justus Liebigs Annalen der Chemie; vol. 457; (1927); p. 292 View in Reaxys

N O

HN O

O OH

Rx-ID: 146884 View in Reaxys 760/834 Yield

Conditions & References bei Siedetemperatur Volhard; Henke; Justus Liebigs Annalen der Chemie; vol. 282; (1894); p. 66,81 View in Reaxys

HO O

Rx-ID: 266729 View in Reaxys 761/834 Yield

Conditions & References Ivanoff; Popoff; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1547,1550 View in Reaxys HO

O HO

N O

Rx-ID: 266761 View in Reaxys 762/834 Yield

Conditions & References Ivanoff; Popoff; Bulletin de la Societe Chimique de France; vol. <4> 49; (1931); p. 1547,1550 View in Reaxys

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O– Na +

O O

Rx-ID: 372335 View in Reaxys 763/834 Yield

Conditions & References Hannach; v. Kostanecki; Chemische Berichte; vol. 35; (1902); p. 867 View in Reaxys

H O

Rx-ID: 639673 View in Reaxys 764/834 Yield

Conditions & References Ozonolyse; anschliessende Behandlung mit Zink-Pulver Treibs; Chemische Berichte; vol. 80; (1947); p. 97,98, 100 View in Reaxys O N

N H

Rx-ID: 784499 View in Reaxys 765/834 Yield

Conditions & References Vuylsteke; Bulletin de la Classe des Sciences, Academie Royale de Belgique; vol. <5> 12; (1926); p. 535; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 888 View in Reaxys

Al3+ HO

3 O

–O

O HO

Rx-ID: 4858991 View in Reaxys 766/834 Yield

Conditions & References With sulfuric acid, multistep reaction; various temperature and reaction time, Product distribution Stepovik; Zaburdaeva; Dodonov; Russian Journal of General Chemistry; vol. 67; nb. 2; (1997); p. 264 - 269 View in Reaxys

OH HO

S OO

HO H

Rx-ID: 5412184 View in Reaxys 767/834 Yield

Conditions & References Staedel; Chemische Berichte; vol. 19; (1886); p. 1948 View in Reaxys

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O O

aq. barium hydroxide solution

O O

Rx-ID: 5589079 View in Reaxys 768/834 Yield

Conditions & References Moeller; Strecker; Justus Liebigs Annalen der Chemie; vol. 113; (1860); p. 68 View in Reaxys

alkaline solution O

HO O

OH H 2N 2

HN H 2N

Rx-ID: 5687990 View in Reaxys 769/834 Yield

Conditions & References Rupe; Labhardt; Chemische Berichte; vol. 33; (1900); p. 245 View in Reaxys

HO O O

concentrated KOH-solution

O O

OH HO

HO O

Rx-ID: 5714869 View in Reaxys 770/834 Yield

Conditions & References Asano; Kameda; Chemische Berichte; vol. 68; (1935); p. 1568,1569; Yakugaku Zasshi; vol. 55; (1935); p. 1235,1240 View in Reaxys

HO OH O

Cl OO

palladium

Rx-ID: 5801216 View in Reaxys 771/834 Yield

Conditions & References Hydrogenation Kindler; Kwok; Justus Liebigs Annalen der Chemie; vol. 554; (1943); p. 9,10, 12, 14 View in Reaxys

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HO OH

S OO

palladium

Rx-ID: 5801217 View in Reaxys 772/834 Yield

Conditions & References Hydrogenation Kindler; Kwok; Justus Liebigs Annalen der Chemie; vol. 554; (1943); p. 9,10, 12, 14 View in Reaxys

palladium

Rx-ID: 5801219 View in Reaxys 773/834 Yield

Conditions & References Hydrogenation Kindler; Kwok; Justus Liebigs Annalen der Chemie; vol. 554; (1943); p. 9,10, 12, 14 View in Reaxys

HO O

(v2)

sodium

Rx-ID: 5801225 View in Reaxys 774/834 Yield

Conditions & References Schorigin; Chemische Berichte; vol. 41; (1908); p. 2717,2723; Chemische Berichte; vol. 43; (1910); p. 1931 View in Reaxys

aqueous NaOH

O O

Rx-ID: 5957967 View in Reaxys 775/834 Yield

Conditions & References Ruggli; Zeller; Helvetica Chimica Acta; vol. 28; (1945); p. 741,746 View in Reaxys

OH O

palladium/barium sulfate

Cl OO O

HO O

(2RS:3RS(?))-3-hydroxy-2.4-diphenyl-butyric acid

phenethyl alcohol(?) Rx-ID: 6218261 View in Reaxys 776/834

Yield

Conditions & References anschliessende Hydrolyse Davies; Morris; Journal of the Chemical Society; (1947); p. 1697 View in Reaxys

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aqueous NaOH

O HO

Rx-ID: 6676389 View in Reaxys 777/834 Yield

Conditions & References Baker; Jukes; Subrahmanyam; Journal of the Chemical Society; (1934); p. 1681,1683 View in Reaxys O

H N

HO O

NH 2 O

Rx-ID: 6683265 View in Reaxys 778/834 Yield

Conditions & References Salkowski,E.; Salkowski,H.; Chemische Berichte; vol. 12; (1879); p. 653; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 7; (1882); p. 162 View in Reaxys

oxygen

Rx-ID: 6683390 View in Reaxys 779/834 Yield

Conditions & References Licht Fortey; Journal of the Chemical Society; vol. 75; (1899); p. 871 View in Reaxys

OH HO

S OO

K2cr2O7

Rx-ID: 6800510 View in Reaxys 780/834 Yield

Conditions & References Mueller; ; vol. 17; (1931); p. 498 View in Reaxys N

O HO

OH S OO

Rx-ID: 7441810 View in Reaxys 781/834 Yield

Conditions & References Harding; Haworth; Journal of the Chemical Society; vol. 97; (1910); p. 497 View in Reaxys

NH O HN

alcoholic KOH-solution

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Rx-ID: 7443664 View in Reaxys 782/834 Yield

Conditions & References Gupta; Journal of the Chemical Society; vol. 119; (1921); p. 303 View in Reaxys

permanganate

HO O

alkali

Rx-ID: 7447159 View in Reaxys 783/834 Yield

Conditions & References lower-melting form Stoermer; Thier; Chemische Berichte; vol. 58; (1925); p. 2613 View in Reaxys

KMnO4

Rx-ID: 7447239 View in Reaxys 784/834 Yield

Conditions & References Dieckmann; Kaemmerer; Chemische Berichte; vol. 39; (1906); p. 3049 View in Reaxys

O OH HO

H N

S OO

HO O

H 2N

NH 2 O OH

Rx-ID: 7542060 View in Reaxys 785/834 Yield

Conditions & References Thierfelder; Sherwin; Chemische Berichte; vol. 47; (1914); p. 2632; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 94; (1915); p. 5 View in Reaxys N HO

alkali

HO O

Rx-ID: 7918017 View in Reaxys 786/834 Yield

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H N

O O

HO O

NH 2

Rx-ID: 7918116 View in Reaxys 787/834 Yield

Conditions & References Ruhemann; Priestley; Journal of the Chemical Society; vol. 95; (1909); p. 452 View in Reaxys

H 2N

OH NH 2

O OH

Rx-ID: 7978664 View in Reaxys 788/834 Yield

Conditions & References Totani; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 68; (1910); p. 76 View in Reaxys

O OH

O O

KMnO4

OH O

Rx-ID: 7979292 View in Reaxys 789/834 Yield

Conditions & References Riiber; Chemische Berichte; vol. 37; (1904); p. 3123 View in Reaxys N HO

Z O

potash

OH O

NH 2

Rx-ID: 7979293 View in Reaxys 790/834 Yield

Conditions & References Atkinson; Thorpe; Journal of the Chemical Society; vol. 89; (1906); p. 1922 View in Reaxys

O O O

O OO

alkali

OH O

Rx-ID: 7979297 View in Reaxys 791/834 Yield

Conditions & References Schott; Chemische Berichte; vol. 29; (1896); p. 1989 View in Reaxys

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Rx-ID: 7981564 View in Reaxys 792/834 Yield

Conditions & References Krollpfeiffer; Justus Liebigs Annalen der Chemie; vol. 462; (1928); p. 62; Chemische Berichte; vol. 56; (1923); p. 2363 View in Reaxys

acid

E N

O N

Rx-ID: 8259433 View in Reaxys 793/834 Yield

Conditions & References Buelow; Grotowsky; Chemische Berichte; vol. 34; (1901); p. 1485 View in Reaxys

alkali

E N

O N

Rx-ID: 8259434 View in Reaxys 794/834 Yield

Conditions & References Buelow; Grotowsky; Chemische Berichte; vol. 34; (1901); p. 1485 View in Reaxys OH O

permanganate

O O

Rx-ID: 8259748 View in Reaxys 795/834 Yield

Conditions & References Ingold; Piggott; Journal of the Chemical Society; vol. 121; (1922); p. 2386 View in Reaxys

S OO

H N

O O

O OH

Rx-ID: 8264134 View in Reaxys 796/834 Yield

Conditions & References Cornforth; View in Reaxys

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H N

aldehyde

Rx-ID: 8267838 View in Reaxys 797/834 Yield

Conditions & References Bernthsen; Justus Liebigs Annalen der Chemie; vol. 184; (1877); p. 300 View in Reaxys

carbon monoxide

Rx-ID: 8270821 View in Reaxys 798/834 Yield

Conditions & References Diels; Justus Liebigs Annalen der Chemie; vol. 432; (1923); p. 39 View in Reaxys O

H O

compound C20H17O5N

compound C20H19O5N Rx-ID: 8272300 View in Reaxys 799/834

Yield

Conditions & References Diels; Justus Liebigs Annalen der Chemie; vol. 432; (1923); p. 39 View in Reaxys

Cl – Mg+

magnesium bromide salt of carbonic acid monoethyl ester

Rx-ID: 8470041 View in Reaxys 800/834 Yield

Conditions & References Iwanow; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 189; (1929); p. 931 View in Reaxys

E N

O N

Rx-ID: 192674 View in Reaxys 801/834 Yield

Conditions & References Buelow; Grotowsky; Chemische Berichte; vol. 34; (1901); p. 1485 View in Reaxys

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Rx-ID: 639914 View in Reaxys 802/834 Yield

Conditions & References beim Ozonisieren, lower-melting form Stoermer; Thier; Chemische Berichte; vol. 58; (1925); p. 2613 View in Reaxys

O O

Rx-ID: 640530 View in Reaxys 803/834 Yield

Conditions & References Harries; Justus Liebigs Annalen der Chemie; vol. 390; (1912); p. 264 View in Reaxys

Rx-ID: 731434 View in Reaxys 804/834 Yield

Conditions & References anschliessend Erwaermen auf dem Dampfbad Pfeiffer; Boettcher; Journal fuer Praktische Chemie (Leipzig); vol. <2> 148; (1937); p. 126,133 View in Reaxys 2 Ca 2+

O–

3 H

4 O

Rx-ID: 844257 View in Reaxys 805/834 Yield

Conditions & References Behandeln mit Kaliumpermanganat Riiber; Chemische Berichte; vol. 38; (1905); p. 2743 View in Reaxys

O O

aq. barium hydroxide solution O H OH

O HO

HO O

OH OO

Rx-ID: 5564866 View in Reaxys 806/834

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Yield

Conditions & References Claisen; Ewan; Justus Liebigs Annalen der Chemie; vol. 284; (1895); p. 281 View in Reaxys

Na2O2

NH 2

Rx-ID: 5678969 View in Reaxys 807/834 Yield

Conditions & References Deinert; Journal fuer Praktische Chemie (Leipzig); vol. <2> 52; (1895); p. 431 View in Reaxys

HO O

N O

H 2N 2

HN H 2N

Rx-ID: 5687989 View in Reaxys 808/834 Yield

Conditions & References Rupe; Labhardt; Chemische Berichte; vol. 33; (1900); p. 245 View in Reaxys

HO O

(v2)

sodium

Rx-ID: 5855683 View in Reaxys 809/834 Yield

Conditions & References Schorigin; Chemische Berichte; vol. 41; (1908); p. 2717,2723; Chemische Berichte; vol. 43; (1910); p. 1931 View in Reaxys

HO H

NH 2

Rx-ID: 6679967 View in Reaxys 810/834 Yield

Conditions & References Bernthsen; Justus Liebigs Annalen der Chemie; vol. 184; (1877); p. 300 View in Reaxys

S OO

O OH

Rx-ID: 6683936 View in Reaxys 811/834 Yield

Conditions & References Soliman; West; Journal of the Chemical Society; (1944); p. 53 View in Reaxys

O– Na +

OH H

Rx-ID: 7541472 View in Reaxys 812/834 Yield

Conditions & References Wislicenus; v. Schroetter; Justus Liebigs Annalen der Chemie; vol. 424; (1921); p. 226

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View in Reaxys HO Cl Cl

PCl Cl

O O

Rx-ID: 7919192 View in Reaxys 813/834 Yield

Conditions & References Behandeln des Reaktionsprodukts mit wss. NaOH Taylor; Journal of the Chemical Society; (1931); p. 2018,2026 View in Reaxys

natrium carbonate

H 2N O

compound C9H9ON3

Rx-ID: 7922322 View in Reaxys 814/834 Yield

Conditions & References Stoermer; Kirchner; Chemische Berichte; vol. 53; (1920); p. 1299 View in Reaxys

Rx-ID: 8255225 View in Reaxys 815/834 Yield

Conditions & References Hill; Short; Journal of the Chemical Society; (1935); p. 1123,1125 View in Reaxys

H 2N H

H 2N

NH 2

Rx-ID: 8258026 View in Reaxys 816/834 Yield

Conditions & References Dixon; Taylor; Journal of the Chemical Society; vol. 9; (1857); p. 924 View in Reaxys N H N

OH HO

S OO

OH O

H 2N

Rx-ID: 8258162 View in Reaxys 817/834 Yield

Conditions & References Smith; Thorpe; Journal of the Chemical Society; vol. 91; (1907); p. 1903 View in Reaxys

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NH 2

H N

NH 2 O

Rx-ID: 8259236 View in Reaxys 818/834 Yield

Conditions & References Finger; Zeh; Journal fuer Praktische Chemie (Leipzig); vol. <2> 82; (1910); p. 55 View in Reaxys

KMnO4

HO O

O O

Rx-ID: 8259449 View in Reaxys 819/834 Yield

Conditions & References Pudowik; Arbusow; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1948); p. 246,248; ; (1948); p. 4973 View in Reaxys O

HO O

carbon monoxide

Rx-ID: 8270829 View in Reaxys 820/834 Yield

Conditions & References Diels; Justus Liebigs Annalen der Chemie; vol. 432; (1923); p. 39 View in Reaxys

oxygen

O O

OH O

H 2N 2

phenylacetic acid-peroxide

Rx-ID: 8284970 View in Reaxys 821/834 Yield

Conditions & References Wieland; Hintermaier; Dennstedt; Justus Liebigs Annalen der Chemie; vol. 452; (1927); p. 10 View in Reaxys

O– Na +

alkaline water

nickel-anode

Rx-ID: 8481819 View in Reaxys 822/834

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Yield

Conditions & References weiteres Produkt: Kohlendioxid.Electrolysis Tommila; Annales Academiae Scientiarum Fennicae, Series A; vol. 46; nb. 6; (1936); p. 83; Chem. Zentralbl.; vol. 108; nb. II; (1937); p. 204 View in Reaxys

N O

Rx-ID: 714285 View in Reaxys 823/834 Yield

Conditions & References anschliessend Erwaermen auf dem Dampfbad Pfeiffer; Boettcher; Journal fuer Praktische Chemie (Leipzig); vol. <2> 148; (1937); p. 126,133 View in Reaxys

O O

O– Na +

O O O

Rx-ID: 848461 View in Reaxys 824/834 Yield

Conditions & References 3-benzoyloxy-2,3-diphenyl-acrylic acid ethyl ester of mp: 103 degree and mp: 112 degree Scheibler; Emden; Krabbe; Chemische Berichte; vol. 63; (1930); p. 1562,1569 View in Reaxys

O HO

oxygen

cellulose coal

Rx-ID: 7447174 View in Reaxys 825/834 Yield

Conditions & References Wieland; Justus Liebigs Annalen der Chemie; vol. 436; (1924); p. 256; Justus Liebigs Annalen der Chemie; vol. 445; (1925); p. 199 View in Reaxys

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O HO

oxygen

palladium black

Rx-ID: 7447175 View in Reaxys 826/834 Yield

Conditions & References Wieland; Justus Liebigs Annalen der Chemie; vol. 436; (1924); p. 256; Justus Liebigs Annalen der Chemie; vol. 445; (1925); p. 199 View in Reaxys OH HO

nickel-anode

N O

O OH

Rx-ID: 8264284 View in Reaxys 827/834 Yield

Conditions & References Electrolysis Tommila; Annales Academiae Scientiarum Fennicae, Series A; vol. 46; nb. 6; (1936); p. 83; Chem. Zentralbl.; vol. 108; nb. II; (1937); p. 204 View in Reaxys

Br O

O Br

Rx-ID: 4717460 View in Reaxys 828/834 Yield

Conditions & References Irradiation, other 1-naphthylmethyl phenylacetates, Mechanism Nevill; Pincock; Canadian Journal of Chemistry; vol. 75; nb. 2; (1997); p. 232 - 247 View in Reaxys

(v4)

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OH O

HO OH

Rx-ID: 8259603 View in Reaxys 829/834 Yield

Conditions & References Zerlegen des entstandenen Ozonids mit Wasser, 3-<β-phenyl-ethylidene>-d-camphor Rupe; Iselin; Chemische Berichte; vol. 49; (1916); p. 30 View in Reaxys

HO O

Rx-ID: 6330951 View in Reaxys 830/834 Yield 99 %

Conditions & References III-2.4 Patent; National University Corporation Nara Institute of Science and Technology; US2011/28738; (2011); (A1) English View in Reaxys

96.4%

9 : Example 9 Example 9 4-chloromethylphenylacetic acid was prepared in the same manner as in Example 1 except for using 30 g of 4-methyl phenylacetic acid instead of 2-methyl phenylacetic acid and using 90 g of monochlorobenzene. When reaction solution after the completion of the reaction was analyzed on gas chromatography, 6.8percent of 4methyl phenylacetic acid as the raw material, 74.8percent of 4-chloromethylphenylacetic acid, the desired compound, and 0.5percent of 4-methyl-α-chlorophenylacetic acid, 5.8percent of 4-dichloromethylphenylacetic acid and 7.7percent of 4-chloromethyl-α-chlorophenylacetic acid, as by-products, were present. The selectivity to 4-chloromethylphenylacetic acid was 80.2percent. After the completion of the reaction, the reaction solution was cooled to 20° C., and precipitates were filtered and separated to obtain 26.2 g of 4-chloromehtyl phenylacetic acid (purity: 96.4percent, yield: 71percent). Patent; Ihara Chemical Industry Co., Ltd.; US6414186; (2002); (B1) English View in Reaxys

92%

87 : 4-[1-[3-chloro-4(N'-phenylureido)phenylacetyl]-(4S)-fluoro-(2S)-pyrrolidinyl]methoxybenzoic Acid To a stirred solution of methyl 3-chloro-4-(N'-phenylureido)phenylacetate (1.79 g, 5.62 mmol) in THF (30 ml) was added 0.25 N NaOH (30 ml). After stirring at room temperature for 20 h, the solvent was concentrated in vacuo. The residue was triturated by the addition of 1 N HCl and dried at 60° C. for 2 days under a reduced pressure to give 3-chloro-4N'-phenylureido) phenylacetic acid (1.58 g, 92percent) as pale brown solid 1H-NMR (DMSO-d6) δ 3.55 (s, 2H), 6.99 (t, J 7.3 Hz, 1H), 7.17 (d, J=8.3 Hz, 1H), 7.29 (t, J=7.6 Hz, 2H), 7.36 (s, 1H), 7.46 (d, J=8.0 Hz, 2H), 8.07 (d, J=8.3 Hz, 1H), 8.28 (s, 1H), 9.37 (s, 1H), 12.37 (br, 1H). Patent; Daiichi Pharmaceutical Co., LTD.; US2003/78249; (2003); (A1) English View in Reaxys

83%

5 : EXAMPLE 5 EXAMPLE 5 The operation was carried out in the same equipment and according to the same modalities as in Example 1. Under a CO head, there were charged 100 ml of CH3 OH, 10 ml of catalyst solution prepared as in Example 1, and 7 g of resin AMBERLYST A 27 type (III). It was stirred for 15 minutes whereupon operating as in Example 1, 44 g of benzyl chloride were carbonylated. The solution filtered from the resin at the end of the test was treated as described in Example 1, thus obtaining 39.3 g of phenylacetic acid (yield=83percent). Patent; Montedison S.p.A.; US4435575; (1984); (A1) English View in Reaxys

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81.6%

6 : EXAMPLE 6 EXAMPLE 6 The operation was carried out in the same equipment and with the same modalities as in Example 1. 100 ml of CH3 OH, 10 ml of a catalyst solution prepared as in Example 1 and 7 g of resin AMBERLYST A 29 type (IV) were charged under a CO head. The whole was stirred for 15 minutes, whereupon operating as in Example 1, 44 g of benzyl chloride were carbonylated. The solution filtered from the resin at the end of the test was treated as described in Example 1, thus obtaining 38.6 g of phenylacetic acid (yield: 81.6percent). Patent; Montedison S.p.A.; US4435575; (1984); (A1) English View in Reaxys

65%

25 : Benzeneacetic acid, 4-[2-(bis[(1,1-dimethylethoxy)carbonyl]amino]ethoxy]-,hydrazide Example 25 Benzeneacetic acid, 4-[2-(bis[(1,1-dimethylethoxy)carbonyl]amino]ethoxy]-,hydrazide To a round-bottomed flask containing imidodicarbonic acid, [2-[4-[2-[[(1,1-dimethylethoxy)carbonyl]methylamino]-2oxoethyl]phenoxy]ethyl]-, bis(1,1-dimethylethyl)ester (3.10 g, 6.09 mmol) in methanol (30 ml) was added hydrazine monohydrate (1.03 ml, 21.3 mmol) dropwise. The resulting solution was allowed to stir at room temperature overnight, and was then concentrated in vacuo to an oil. The residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate, and extracted with methylene chloride. The crude material was purified by column chromatography (silica gel; methylene chloride to 5percent methanol/ methylene chloride) to afford 1.63 g (65percent yield) of the desired product as an oil which crystallized upon standing. Patent; Day, Robert F.; Lafontaine, Jennifer A.; US2002/52392; (2002); (A1) English View in Reaxys

33.0%

5 : EXAMPLE 5 EXAMPLE 5 Example 1 was repeated, 24 wt. percent aqueous NaOH being used, and 35 mols of NaOH being metered in throughout the reaction time. After working up, a total yield of phenylpyruvic acids of 62.9percent and of phenylacetic acid of 33.0percent was obtained. Patent; Dynamit Nobel AG; US4447644; (1984); (A1) English View in Reaxys

5.8%

2 : (B) (2) The NaOH solution was acidified and extracted with ether. Here only phenylacetic acid was obtained, in an amount of 126 g. (Yield, 5.8percent) Patent; Dynamit Nobel AG; US4447644; (1984); (A1) English View in Reaxys Herstellung von Phenyl-<1-14 C>essigsaeure Dauben et al.; ; (1958); p. 72 View in Reaxys Herstellung von Phenyl-<2-14 C>essigsaeure Montgomery et al.; ; (1958); p. 74 View in Reaxys Wittmann,H. et al.; Monatshefte fuer Chemie; vol. 99; (1968); p. 1982 - 1989 View in Reaxys Raap,R.; Micetich,R.G.; Canadian Journal of Chemistry; vol. 46; (1968); p. 1057 - 1063 View in Reaxys Ruechardt,C. et al.; Chemische Berichte; vol. 102; (1969); p. 3922 - 3946

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View in Reaxys Wenkert,E.; McPherson,C.A.; Journal of the American Chemical Society; vol. 94; nb. 23; (1972); p. 8084 - 8090 View in Reaxys Bestmann,H.J. et al.; Justus Liebigs Annalen der Chemie; vol. 709; (1967); p. 105 - 112 View in Reaxys Schoellkopf,U. et al.; Justus Liebigs Annalen der Chemie; vol. 766; (1972); p. 130 - 141 View in Reaxys Schoellkopf,U.; Schroeder,R.; Angewandte Chemie; vol. 84; (1972); p. 289 - 290 View in Reaxys Zymalkowski,F. et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 302; (1969); p. 272 - 284 View in Reaxys Colau,R.; Viel,C.; Bulletin de la Societe Chimique de France; vol. <II>; (1979); p. 362 - 365 View in Reaxys Minato,H. et al.; Chemistry Letters; (1976); p. 593 - 596 View in Reaxys Ferris,A.F.; Journal of Organic Chemistry; vol. 25; (1960); p. 12 - 18 View in Reaxys Bailey,W.J.; Daly,J.J.; Journal of Organic Chemistry; vol. 29; (1964); p. 1249 - 1251 View in Reaxys Takano,S. et al.; Synthetic Communications; vol. 6; (1976); p. 349 - 355 View in Reaxys Bestmann,H.J. et al.; Tetrahedron Letters; (1974); p. 1275 - 1276 View in Reaxys Canonica,L. et al.; Gazzetta Chimica Italiana; vol. 91; (1961); p. 1400 - 1412 View in Reaxys Lochmann,L.; Lim,D.; Journal of Organometallic Chemistry; vol. 28; (1971); p. 153 - 158 View in Reaxys Dauth,C.; Becker,H.G.O.; Journal fuer Praktische Chemie (Leipzig); vol. 313; (1971); p. 686 - 698 View in Reaxys Sakota; Koine; Okita; Nippon Kagaku Zasshi; vol. 90; (1969); p. 77,78; ; vol. 70; (1969); p. 115517 View in Reaxys Delaby et al.; Bulletin de la Societe Chimique de France; (1961); p. 2067,2068; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 246; (1958); p. 2906 View in Reaxys Vaughn; Robbins; Journal of Organic Chemistry; vol. 40; (1975); p. 1187 View in Reaxys Dickstein; Miller; Journal of Organic Chemistry; vol. 37; (1972); p. 2175,2176 View in Reaxys Eisch; Kaska; Journal of Organic Chemistry; vol. 27; (1962); p. 3745,3751 View in Reaxys Rapoport; Chen; Journal of Organic Chemistry; vol. 25; (1960); p. 313 View in Reaxys Gillis; Dain; Journal of Organic Chemistry; vol. 36; (1971); p. 518 View in Reaxys Patent; Lemieux; Raap (R and L Molecular Research); US3654294; (1972); ; vol. 77; nb. 5448b View in Reaxys Kennedy; Stock; Journal of Organic Chemistry; vol. 25; (1960); p. 1901,1905 View in Reaxys Plieninger et al.; Chemische Berichte; vol. 98; (1965); p. 1774 View in Reaxys Yukawa; Ibata; Nippon Kagaku Zasshi; vol. 88; (1967); p. 1223,1228 View in Reaxys Asinger; Halcour; Monatshefte fuer Chemie; vol. 95; (1964); p. 24,28 View in Reaxys Johnson; Riggs; Australian Journal of Chemistry; vol. 24; (1971); p. 1643,1647,1654 View in Reaxys Ho et al.; Synthesis; (1972); p. 562 View in Reaxys Kharasch et al.; Chemistry and Industry (London, United Kingdom); (1962); p. 1720 View in Reaxys

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McDonald et al.; Journal of the American Chemical Society; vol. 86; (1964); p. 4866,4870 View in Reaxys Castaneda; Marini-Bettolo; Gazzetta Chimica Italiana; vol. 93; (1963); p. 345,347 View in Reaxys De Pasquale; Vogel; Journal of Organic Chemistry; vol. 35; (1970); p. 1057 View in Reaxys Ivanov; Bojilowa; Chemische Berichte; vol. 111; (1978); p. 3755,3761 View in Reaxys Edwards; Gill; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1973); p. 1529,1537 View in Reaxys Olah; Welch; Journal of the American Chemical Society; vol. 100; (1978); p. 5396,5397 View in Reaxys Friedman; Berger; Journal of the American Chemical Society; vol. 82; (1960); p. 5758 View in Reaxys Heyns; Blazejewicz; Tetrahedron; vol. 9; (1960); p. 67,73 View in Reaxys Kharasch; Goethlich; Angewandte Chemie; vol. 74; (1962); p. 651 View in Reaxys Zweifel; Backlund; Journal of the American Chemical Society; vol. 99; (1977); p. 3184 View in Reaxys Hara et al.; Chemical and Pharmaceutical Bulletin; vol. 20; (1972); p. 1063 View in Reaxys Baiocchi et al.; Synthesis; (1979); p. 434 View in Reaxys Scarpati; Sica; Rendiconto dell'Accademia delle Scienze Fisiche e Matematiche, Naples; vol. 28; (1961); p. 70,71-80; ; vol. 62; nb. 6425; (1965) View in Reaxys Marcot et al.; Revue Roumaine de Chimie; vol. 20; nb. 1; (1975); p. 91,92-106 View in Reaxys Yukawa et al.; Bulletin of the Chemical Society of Japan; vol. 40; (1967); p. 2618,2619 View in Reaxys Patent; Rhone-Poulenc S.A.; DE2136481; (1970); ; vol. 76; nb. 112913a; (1972) View in Reaxys Southwick; Synthesis; (1970); p. 628,630, 634 View in Reaxys Reitsema; Allphin; Journal of Organic Chemistry; vol. 27; (1962); p. 27 View in Reaxys Arita et al.; Kogyo Kagaku Zasshi; vol. 73; (1970); p. 175,176; ; vol. 72; nb. 128054; (1970) View in Reaxys Collignon; Journal of Organometallic Chemistry; vol. 96; (1975); p. 139,141 View in Reaxys Ogura; Tsuchihashi; Tetrahedron Letters; (1972); p. 1383 View in Reaxys Kasai et al.; Kogyo Kagaku Zasshi; vol. 74; (1971); p. 961,963 View in Reaxys Lanchow University et al.; Huaxue Xuebao; vol. 34; (1976); p. 295,299; ; vol. 88; nb. 104848r View in Reaxys Screttas; Journal of the Chemical Society, Chemical Communications; (1972); p. 752 View in Reaxys Neuman; Behar; Journal of the American Chemical Society; vol. 91; (1969); p. 6024,6026 View in Reaxys Ullman et al.; Journal of the American Chemical Society; vol. 91; (1969); p. 5792,5796 View in Reaxys des Abbayes; Buloup; Journal of the Chemical Society, Chemical Communications; (1978); p. 1090 View in Reaxys Sooma; Sano; Kogyo Kagaku Zasshi; vol. 73; (1970); p. 2723; ; vol. 74; nb. 111515; (1971) View in Reaxys Patent; Sagami Chem. Research Center; DE2248592; (1972); ; vol. 79; nb. 5140 View in Reaxys Patent; Ihara; DE2633204; (1977); ; vol. 86; nb. 155377

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View in Reaxys Alper; Des Abbayes; Journal of Organometallic Chemistry; vol. 134; (1977); p. C11,C12-C14 View in Reaxys Cassar; Foa; Journal of Organometallic Chemistry; vol. 134; (1977); p. C15 View in Reaxys Hope; Wiles; Journal of the Chemical Society; (1965); p. 5386,5390 View in Reaxys Petrov et al.; Zhurnal Organicheskoi Khimii; vol. 11; (1975); p. 267,261 View in Reaxys Ho; Olah; Synthesis; (1977); p. 417 View in Reaxys Jain; Chandalia; Journal of Applied Chemistry and Biotechnology; vol. 24; (1974); p. 105,107, 108, 109 View in Reaxys Brown; Darwent; Journal of the Chemical Society, Chemical Communications; (1979); p. 169 View in Reaxys Labunski; J. Gen. Chem. USSR (Engl. Transl.); vol. 31; (1961); p. 1580,1467; ; nb. 22250; (1961) View in Reaxys Joshi; Bose; Journal of Scientific and Industrial Research, Section B: Physical Sciences; vol. 21; (1962); p. 284 View in Reaxys Castaneda; Bettolo; Rendiconti Istituto Superiore di Sanita (English Edition); vol. 27; (1964); p. 94,97; ; vol. 92; nb. 14614 View in Reaxys Ganushchak et al.; Zhurnal Organicheskoi Khimii; vol. 8; (1972); p. 2356,2403,2406 View in Reaxys Cornforth; Tetrahedron; vol. 30; (1974); p. 3933 View in Reaxys Madoery et al.; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 63; (1975); p. 95,101 View in Reaxys Smith; Nickel; Organic Preparations and Procedures International; vol. 7; (1975); p. 277,279 View in Reaxys Miles; Huang; Journal of Organic Chemistry; vol. 41; (1976); p. 208,210,213 View in Reaxys Heiba; Dessau; Journal of the American Chemical Society; vol. 93; (1971); p. 995,996 View in Reaxys Walling; Lepley; Journal of the American Chemical Society; vol. 94; (1972); p. 2007,2013 View in Reaxys Collignon; Normant; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 271; (1970); p. 1185 View in Reaxys Dombrowskii; Naidan; J. Gen. Chem. USSR (Engl. Transl.); vol. 32; (1962); p. 1282,1256 View in Reaxys Badger et al.; Australian Journal of Chemistry; vol. 17; (1964); p. 778,782, 786 View in Reaxys Asinger; Halcour; Monatshefte fuer Chemie; vol. 94; (1963); p. 1029,1034 View in Reaxys Najdan; Dombrowskii; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 1469,1474 View in Reaxys Bestmann; Schulz; Justus Liebigs Annalen der Chemie; vol. 674; (1964); p. 11,16 View in Reaxys Corey; Tius; Tetrahedron Letters; (1977); p. 2081 View in Reaxys Sonoda; Tsutsumi; Bulletin of the Chemical Society of Japan; vol. 33; (1960); p. 1440 View in Reaxys Lee; Spitzer; Journal of Organic Chemistry; vol. 34; (1969); p. 1493 View in Reaxys Nagai; Sammes; Journal of the Chemical Society [Section] C: Organic; (1967); p. 2230 View in Reaxys Smith; Waters; Journal of the Chemical Society [Section] B: Physical Organic; (1969); p. 462 View in Reaxys Karube; Onada; Nippon Kagaku Kaishi; (1973); p. 2166,2167,2169 View in Reaxys

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Bojko et al.; Zhurnal Organicheskoi Khimii; vol. 4; (1968); p. 1355,1307 View in Reaxys Palazzo; Baiocchi; Tetrahedron Letters; (1968); p. 4739 View in Reaxys Blagoev; Blagoi; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 268; (1969); p. 543 View in Reaxys 13 : Compound 90 of Table 1: Benzeneacetic acid, 2-[2-14-(6-fluorohexyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl]ethoxy]-, methyl ester EXAMPLE 13 Compound 90 of Table 1: Benzeneacetic acid, 2-[2-14-(6-fluorohexyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2yl]ethoxy]-, methyl ester Prepared from Intermediate 7 (1.8 g, 0.006 mol) in a manner analogous to Method C. Compound 90 was obtained as a colorless oil (2.2 g, 0.005 mol). 1H (CDCl ): 7.28-6.89 (m, 8H), 4.76 (dd, 1H, J=9.5, 4.0), 4.44 (dt, 2H, J=47.3, 6.0), 4.19 (m, 2H), 3.93 (br t, 2H), 3.61 3 and 3.60 (two singlets, 5H), 2.50 (m, 3H), 2.22 (m, 1H), 1.68 (m, 4H), 1.57 (m, 4H) Patent; Burris, Thomas P.; Combs, Donald W.; Rybczynski, Philip J.; Dudash JR., Joseph; US2003/83329; (2003); (A1) English View in Reaxys 19 : Intermediate 10: Benzeneacetic acid, 2- [2- (4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl)ethoxy]-, methyl ester EXAMPLE 19 Intermediate 10: Benzeneacetic acid, 2- [2- (4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl)ethoxy]-, methyl ester Prepared from Intermediate 9 (11.16 g, 0.04 mol) in a manner analogous to Method C. Intermediate 10 was obtained as a colorless oil (9.7 g, 0.023 mol). 1H (CDCl ): 7.28-6.89 (m, 8H), 4.76 (dd, 1H, J=9.4, 4), 4.28-4.21 (m, 2H), 3.92 (t, 2H, J=7.7), 3.60 (two singlets, 5H), 3 2.49 (m, 1H), 2.23 (m, 1H), 1.66 (m, 2H), 1.34 (m, 6H), 0.89 (br t, 3H). Patent; Burris, Thomas P.; Combs, Donald W.; Rybczynski, Philip J.; Dudash JR., Joseph; US2003/83329; (2003); (A1) English View in Reaxys 22 : Compound 12 of Table 1: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2yl)ethoxy]-a-oxo-, methyl ester EXAMPLE 22 Compound 12 of Table 1: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl)ethoxy]-aoxo-, methyl ester Prepared from Intermediate 9 (0.61 g, 0.0022 mol) and 2-hydroxy-α-oxo-bezeneacetic acid, methyl ester (0.4 g, 0.0022 mol). Compound 12 was obtained as a colorless oil (0.48 g, 0.0011 mol). 1H(CDCl ): 7.88 (d, 1H, J=7.4), 7.58 (t, 1H, J=6.5), 6.99 (m, 6H), 4.65 (dd, 1H, J=9.6, 3.9), 4.57 (t, 2H, J=7.4), 4.32 3 (m, 1H), 3.87 (s and m, 4H), 2.49 (m, 1H), 2.24 (m, 1H), 1.62 (m, 2H), 1.32 (m, 6H), 0.88 (br t, 3H). Patent; Burris, Thomas P.; Combs, Donald W.; Rybczynski, Philip J.; Dudash JR., Joseph; US2003/83329; (2003); (A1) English View in Reaxys 36 : Compound 127 of Table 2: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazin-2-yl)ethoxy]-, methyl ester EXAMPLE 36 Compound 127 of Table 2: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazin-2yl)ethoxy]-, methyl ester Intermediate 11 (0.26 g, 0.0006 mol) was dissolved in 10 ml THF and cooled to 0° C. Sodium hexamethyldisilazide (1.8 mL, 1.0 M) was added, then the reaction was stirred at room temperature for 30 minutes. The reaction was cooled to 0° C., iodomethane (0.07 mL, 1.2 mmol) was added, and the reaction was stirred at room temperature overnight. The reaction was diluted with water and extracted with CH2Cl2. The organics were dried (Na2SO4), filtered, and solvent was removed in vacuo.

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The crude mixture, DMAP (0.004 g, 0.00003 mol) and methanol (0.05 mL, 0.001 mol) were dissolved in 20 mL CH2Cl2. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 0.059 g, 0.0003 mol) was added and the reaction stirred overnight at room temperature. Solvent was removed and the product was purified by silica gel chromatography. Compound 119 was obtained as a colorless oil (0.1 g, 0.00023 mol). 1H (CDCl ): 7.3-6.9 (m, 8H), 4.3-4.1 (m, 2H), 3.92 (m, 2H), 3.66 and 3.62 (two singlets, 5H), 2.49 (m, 1H), 2.25 (m, 3 1H), 1.66 (m, 2H), 1.51 (s, 3H), 1.33 (m, 6H), 0.89 (br t, 3H). Patent; Burris, Thomas P.; Combs, Donald W.; Rybczynski, Philip J.; Dudash JR., Joseph; US2003/83329; (2003); (A1) English View in Reaxys 39 : Intermediate 20: Benzeneacetic acid, 2-[2-[3,4-dihydro-3-oxo-4-(6-methylsulfonamidohexyl)-2H-1,4-benzoxazin-2-yl]ethoxy]-, methyl ester Intermediate 20: Benzeneacetic acid, 2-[2-[3,4-dihydro-3-oxo-4-(6-methylsulfonamidohexyl)-2H-1,4-benzoxazin-2yl]ethoxy]-, methyl ester To a suspension of intermediate 19 (1.0 g, 1.75 mmol) in 3.5 mL EtOH and 2 mL THF was added hydrazine (0.07 mL, 2.1 mmol). The reaction was stirred overnight at room temperature, then diluted with MeOH and filtered. The solvent is evaporated in vacuo to give a white solid. To the white solid (0.2 g, 0.45 mmol) in 4 mL of CH2Cl2 is added methanesulfonyl chloride (0.04 mL, 0.6 mmol) and triethylamine (0.1 mL, 0.74 mmol). The reaction is stirred for 17 h at room temperature, then quenched with 2 mL of 1N HCl and diluted with 8 mL of EtOAc. The organic layer is washed with water and brine, dried (Na2SO4) and concentrated in vacuo. Purification by reverse-phase HPLC gave intermediate 20 as an orange oil (0.038 g, 0.07 mmol). MS: 541 (M+Na). Patent; Burris, Thomas P.; Combs, Donald W.; Rybczynski, Philip J.; Dudash JR., Joseph; US2003/83329; (2003); (A1) English View in Reaxys 8 : Compound 81 of Table 1: Benzeneacetic acid, 2-[2-[3,4-dihydro-4-(5-hydroxyhexyl)-3-oxo-2H-1,4-benzoxazin-2-yl]ethoxy]-, methyl ester EXAMPLE 8 Compound 81 of Table 1: Benzeneacetic acid, 2-[2-[3,4-dihydro-4-(5-hydroxyhexyl)-3-oxo-2H-1,4-benzoxazin-2yl]ethoxy]-, methyl ester A slurry of Compound 78 (0.2 g, 0.00046 mol) in 10 mL ethanol was treated with sodium borohydride (0.012 mg, 0.00031 mol), then stirred for 1 hour at room temperature. The reaction was diluted with water and extracted with ethyl acetate. The organics were dried (Na2SO4), filtered, and solvent was evaporated. Compound 81 was obtained as a colorless oil (0.052 g, 0.00012 mol). 1H (CDCl ): 7.25 (m, 2H), 6.95 (m, 6H), 4.76 (dd, 1H, J=9.4, 3.9), 4.23 (m, 2H), 3.94 (t, 2H, J=7.5), 3.80 (m, 1H), 3 3.61 and 3.60 (two singlets, 5H), 2.49 (m, 1H), 2.23 (m, 1H), 1.70 (m, 2H), 1.47 (m, 4H), 1.19 (d, 3H, J=6.0). Patent; Burris, Thomas P.; Combs, Donald W.; Rybczynski, Philip J.; US2002/165228; (2002); (A1) English View in Reaxys Patent; Burris, Thomas P.; Combs, Donald W.; Rybczynski, Philip J.; Dudash JR., Joseph; US2003/83329; (2003); (A1) English View in Reaxys 19 : Intermediate 10: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl)ethoxy]-, methyl ester EXAMPLE 19 Intermediate 10: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl)ethoxy]-, methyl ester Prepared from Intermediate 9 (11.16 g, 0.04 mol) in a manner analogous to Method C. Intermediate 10 was obtained as a colorless oil (9.7 g, 0.023 mol). 1H (CDCl ): 7.28-6.89 (m, 8H), 4.76 (dd, 1H, J=9.4, 4), 4.28-4.21 (m, 2H), 3.92 (t, 2H, J=7.7), 3.60 (two singlets, 5H), 3 2.49 (m, 1H), 2.23 (m, 1H), 1.66 (m, 2H), 1.34 (m, 6H), 0.89 (br t, 3H). Patent; Burris, Thomas P.; Combs, Donald W.; Rybczynski, Philip J.; US2002/165228; (2002); (A1) English View in Reaxys 22 : 5,5-Dioxo-2,3,3a,4-tetrahydro-1 H-pyrrolo[2,1-c][1,2,4]-benzothiadiazin-7-yl phenylacetate

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EXAMPLE 22 5,5-Dioxo-2,3,3a,4-tetrahydro-1 H-pyrrolo[2,1-c][1,2,4]-benzothiadiazin-7-yl phenylacetate Melting point: 169-171° C. Patent; Cordi, Alex; Desos, Patrice; Lefoulon, Francois; Lestage, Pierre; US2002/37894; (2002); (A1) English View in Reaxys 22 : Compound 12 of Table 1: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2yl)ethoxy]-a-oxo-, methyl ester EXAMPLE 22 Compound 12 of Table 1: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl)ethoxy]-aoxo-, methyl ester Prepared from Intermediate 9 (0.61 g, 0.0022 mol) and 2-hydroxy-α-oxo-bezeneacetic acid, methyl ester (0.4 g, 0.0022 mol). Compound 12 was obtained as a colorless oil (0.48 g, 0.0011 mol). 1H(CDCl ): 7.88 (d, 1H, J=7.4), 7.58 (t, 1H, J=6.5), 6.99 (m, 6H), 4.65 (dd, 1H, J=9.6, 3.9), 4.57 (t, 2H, J=7.4), 4.32 3 (m, 1H), 3.87 (s and m, 4H), 2.49 (m, 1H), 2.24 (m, 1H), 1.62 (m, 2H), 1.32 (m, 6H), 0.88 (br t, 3H) Patent; Burris, Thomas P.; Combs, Donald W.; Rybczynski, Philip J.; US2002/165228; (2002); (A1) English View in Reaxys 36 : Compound 127 of Table 2: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazin-2-yl)ethoxy]-, methyl ester EXAMPLE 36 Compound 127 of Table 2: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazin-2yl)ethoxy]-, methyl ester Intermediate 11 (0.26 g, 0.0006 mol) was dissolved in 10 ml THF and cooled to 0° C. Sodium hexamethyldisilazide (1.8 mL, 1.0 M) was added, then the reaction was stirred at room temperature for 30 minutes. The reaction was cooled to 0° C., iodomethane (0.07 mL, 1.2 mmol) was added, and the reaction was stirred at room temperature overnight. The reaction was diluted with water and extracted with CH2Cl2. The organics were dried (Na2SO4), filtered, and solvent was removed in vacuo. The crude mixture, DMAP (0.004 g, 0.00003 mol) and methanol (0.05 mL, 0.001 mol) were dissolved in 20 mL CH2Cl2. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 0.059 g, 0.0003 mol) was added and the reaction stirred overnight at room temperature. Solvent was removed and the product was purified by silica gel chromatography. Compound 119 was obtained as a colorless oil (0.1 g, 0.00023 mol). 1H (CDCl ) 7.3-6.9 (m, 8H), 4.3-4.1 (m, 2H), 3.92 (m, 2H), 3.66 and 3.62 (two singlets, 5H), 2.49 (m, 1H), 2.25 (m, 3 1H), 1.66 (m, 2H), 1.51 (s, 3H), 1.33 (m, 6H), 0.89 (br t, 3H). Patent; Burris, Thomas P.; Combs, Donald W.; Rybczynski, Philip J.; US2002/165228; (2002); (A1) English View in Reaxys 13.33 g (90%)

R.4 : Synthesis of Phenylacetic Acid (18) Synthesis of Phenylacetic Acid (18) To 14.00 g (F.W. 348.196, 40.0 mmol) of nitrile compound (17) were added 33.6 mL of ethanol and 33.6 mL of a 6N sodium hydroxide aqueous solution [8.06 g (F.W. 40.00, 201.5 mmol) of sodium hydroxide being dissolved in water] and stirred at 110° C. overnight. To the reaction solution was added ice and the resulting solution was made pH 2 with concentrated hydrochloric acid. The reaction solution thus obtained was extracted with ethyl acetate and the extract was washed with water and then with a saturated sodium chloride aqueous solution. After drying with anhydrous magnesium sulfate, the solvent was completely removed and the residue was crystallized from benzene-hexane to obtain 13.33 g (90percent) of phenylacetic acid (18). (TLC; ethyl acetate:hexane=1:2 or 1:1). NMR (CDCl3): 3.70 (3H, s, CH3), 3.90 (3H, s, CH3), 3.95 (1H, s, CH2), 6.26 (1H, d, J=2.5 Hz, Ar-H), 6.46 (1H, d, J=2.5; Hz, Ar-H), 7.08 (1H, d, J=8.5 Hz, Ar-H), 7.33 (1H, dd, J=8.5, 2.3 Hz, Ar-H), 7.41 (1H, d, J=2.3 Hz, Ar-H), 12.91; (1H, s, OH). Patent; Nippon Suisan Kaisha, Ltd.; US6602898; (2003); (B1) English View in Reaxys 164 : Synthesis of Phenylacetic Acid (72)

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Synthesis of Phenylacetic Acid (72) To a mixture of 27.0 g (F.W. 313.41, 77.2 mmol) of crude ethylated compound (71) and 66 mL of ethylene glycol was added a 30percent sodium hydroxide aqueous solution (42.7 g). The resulting solution was stirred at 150° C. overnight. To the reaction solution was added ice and the resulting solution was neutralized with 4N hydrochloric acid. The neutralized solution was extracted with ethyl acetate and the extract was washed with water and then with a saturated sodium chloride aqueous solution. The obtained solution was dried with anhydrous magnesium sulfate and then, the solvent was completely removed under reduced pressure to obtain 29.0 g of crude phenylacetic acid (72). This crude phenyacetic acid was recrystallized from ethyl acetate-hexane to obtain 23.0 g of phenylacetic acid (72). The yield was 87percent in two steps. Patent; Nippon Suisan Kaisha, Ltd.; US6602898; (2003); (B1) English View in Reaxys 28.86 g (91%)

1 : Synthesis of Phenylacetic Acid (46) Synthesis of Phenylacetic Acid (46) To 30.07 g (F.W. 331.46, 90.8 mmol) of nitrile compound (45) were added 75 mL of ethanol and 75 mL of a 6N sodium hydroxide aqueous solution [18.06 g (F.W. 40.00, 450 mmol) of sodium hydroxide] and stirred at 110° C. overnight. To the reaction solution was added ice and the resulting solution was made pH 2 with concentrated hydrochloric acid. The reaction solution thus obtained was extracted with ethyl acetate and the extract was washed with water and then with a saturated sodium chloride aqueous solution. After drying with anhydrous magnesium sulfate, the solvent was completely removed under reduced pressure and the residue was crystallized from benzene-hexane to obtain 28.86 g (91percent) of phenylacetic acid (46). (TLC; ethyl acetate:hexane=1:2 or 1:1). MS (EI): 350, 273; NMR (CDCl3): 2.49 (3H, s, CH3), 3.70 (6H, s, CH3), 3.84 (1H, s, CH2), 6.25 (3H, m, Ar-H), 7.15 (1H, dd, J=8.5, 2.3 Hz, Ar-H), 7.21 (1H, d, J=2.3 Hz, Ar-H), 7.42 (1H, d, J=8.5 Hz, Ar-H), 12.91 (1H, s, OH). Patent; Nippon Suisan Kaisha, Ltd.; US6602898; (2003); (B1) English View in Reaxys

1.36 g (66%)

R.6 : Synthesis of Phenylacetic Acid (36) Synthesis of Phenylacetic Acid (36) To 1.93 g (F.W. 303.745, 6.35 mmol) of nitrile compound (35) were added 4.56 mL of ethanol and 4.56 mL [1.13 g (F.W. 40.00, 28.3 mmol) of sodium hydroxide] of a 6N sodium hydroxide and stirred at 110° C. overnight. To the reaction solution was added ice and the resulting solution was made pH 2 with concentrated hydrochloric acid. The reaction solution thus obtained was extracted with ethyl acetate and the extract was washed with water and then with a saturated sodium chloride aqueous solution. After drying with anhydrous magnesium sulfate, the solvent was completely removed under reduced pressure and the residue was crystallized from benzene-hexane to obtain 1.36 g (66percent) of phenylacetic acid (36). (TLC; ethyl acetate: hexane=1:2 or 1:1). Patent; Nippon Suisan Kaisha, Ltd.; US6602898; (2003); (B1) English View in Reaxys I : 4-pentylaminobenzaldehyde, 4-amylbenzaldehyde. The teabags with attached trisubstituted dihydroisoquinolones were washed with DCM (2*50 mL), shaken twice in 55percent (v/v) TFA/DCM (30 mL, 30 minutes), then washed with DCM (30 mL), isopropyl alcohol (2*30 mL), DCM (2*30 mL), 5percent (v/v) DIEA/DCM (3*30 mL, 2 minutes each) and DCM (3*30 mL) and allowed to dry at room temperature. One bag was left as the Boc protected amine (R8=methyl, after reduction). A solution of phenylacetic acid (657 mg, 3.75 mmoles), HOBt (507 mg, 3.75 mmoles), and DIC (0.705 mL, 4.5 mmoles) was prepared in DMF (37.5 mL) and added to a resin packet with attached trisubstituted dihydroisoquinolone. After shaking for 16 hours, the teabag was washed with DMF (3*30 mL) and DCM (3*30 mL). Patent; Basu; Amaresh; Gahman; Timothy C.; Girten; Beverly E.; Griffith; Michael C.; Hecht; Curtis C.; Kiely; John S.; Slivka; Sandra R.; US6127381; (2000); (A1) English View in Reaxys 1.b : (b)

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(b) (+-)-Benzeneacetic acid, α-[[[2,6-bis(1-methylethyl)phenyl]amino]carbonyl] To a methanol (750 mL)/THF (100 mL) solution of the compound (33.55 g, 0.0913 tool) obtained above in step (a) was added 1N aqueous NaOH (91.3 mL, 0.0913 mol). The resulting solution was stirred overnight at room temperature. This was then concentrated in vacuo and the resulting residue was redissolved in water (500 mL). This was washed with ethyl ether (2*200 mL) and the aqueous solution acidified with 1N HCl. A white solid precipitated. This was filtered and air dried overnight to yield the title compound, mp 201°-203° C. Patent; Warner-Lambert Company; US5420339; (1995); (A1) English View in Reaxys 1.c : (b) (c) To a dichloromethane (500 mL) solution of the compound (25 g, 0.0736 mol) obtained above was added 2-tetradecanol (15.79 g, 0.0736 mol) at 0° C. under N2 with stirring. To this was added dicyclohexylcarbodiimide (16.71 g, 0.081 mol). An immediate precipitate resulted. This was allowed to warm to room temperature overnight. This solution was then filtered. After concentration in vacuo, flash chromatography (eluding with 10percent to 25percent ethyl acetate/hexane) gave 31.72 g of the title compound, Example 1, mp 94°-97° C. When in the general procedure of Example 1 only using an appropriate amount of the alcohol listed below in place of 2-tetradecanol, the products listed below in Table 2 were obtained. When in the general procedure of Example 1, only using an appropriate amount of (+-)-Benzeneacetic acid, α[[(2,4,6-trimethoxyphenyl)amino]carbonyl]-, instead of (+-)-Benzeneacetic acid, α-[[[2,6-bis(1-methylethyl)phenyl]amino]carbonyl]-, Example 17 is obtained. Patent; Warner-Lambert Company; US5420339; (1995); (A1) English View in Reaxys II. Compounds containing acid groups, such as, carboxylic acids acetic acid propionic acid ... linolic acid linolenic acid cyclohexane carboxylic acid phenylacetic acid benzoylacetic acid chlorobenzoic acid bromobenzoic acid ... Patent; Schering Aktiengesellschaft; US5501863; (1996); (A1) English View in Reaxys 5 : EXAMPLE 5 EXAMPLE 5 The procedure of Example 4 is repeated, reusing the aqueous catalyst solution separated off therein, after adjustment to pH 7, for the carbonylation of benzyl chloride. Yield: 2.38 g (87.4percent of theory) of phenylacetic acid. Patent; Hoechst Aktiengesellschaft; US5631393; (1997); (A1) English View in Reaxys I.7 : Example I-7 STR14 19.15 g (0.144 mol) of aluminum chloride are first introduced into 70 ml of benzene at 40°-50° C., and 10 g (0.048 mol) of n-butyl methanesulfonyloxyacetate are then added. The mixture is additionally stirred overnight, hydrolyzed with 10percent hydrochloric acid and worked up by the method of Examples 6 to 9.

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The crude product obtained is refluxed together with 6 g of NaOH in 15 ml of water and 50 ml of methanol for 5 hours. Further workup is carried out as in Examples 6 to 9. 5.17 g (90.3percent of theory) of phenylacetic acid are isolated. *) 1 H NMR spectra were recorded in deuterochloroform (CDCl3) with tetramethylsilane (TMS) as the internal standard. The chemical shift is given as δ value in ppm. Patent; Bayer Aktiengesellschaft; US5698735; (1997); (A1) English View in Reaxys 2.e : 1-{N-(1(H)indol-3-yl-carbonyl) (1R,2S)-2-aminocyclohexanecarbonyl}-amino-1-(phenylacetyl)amino-2phenyl-ethane and 1-{N-(1(H)indol-3-yl-carbonyl) (1S,2R)-2-aminocyclohexanecarbonyl}-amino-1-(phenylacetyl)amino-2-phenyl-ethane 2e) Diisopropylethylamine (239 ml, 1.37 mmol) was added to a mixture of phenylacetic acid (66 mg, 0.48 mmol), PyBOP (240 mg, 0.461 mmol), and the amine obtained under 2d) above (174 mg, 0.458 mmol) in tetrahydrofuran (THF) (3 ml). The resulting yellow solution was stirred at room temp. for 7 h. The THF was removed in vacuo, and the residue dissolved in ethyl acetate (100 ml). This solution was washed with 5percent NaHCO3 (25 ml), H2O, 1N HCl (3'25 ml) and brine, then dried (Na2SO4), filtered and the filtrate concentrated in vacuo. Patent; A.Menarini Industrie Farmaceutiche Riunite S.r.l.; US5760248; (1998); (A1) English View in Reaxys 20 : EXAMPLE 20 EXAMPLE 20 In the same manner as in Example 19 but using benzaldehyde (1.06 g), the reaction was carried out. The reaction mixture was subjected to gas chromatographic analysis to give the following results: conversion of benzaldehyde, 94.3percent; yield of phenylacetic acid, 87.9percent; selectivity to phenylacetic acid, 93.2percent; yield of toluene, 6.0percent. Patent; Sumitomo Chemical Co., Ltd.; US4317918; (1982); (A1) English View in Reaxys Alicyclic compounds such as: ... 4-Methylguaiacol; Methyl phenylacetate; Phenol; Phenyl acetate; Phenylacetic acid; Phenylacetic aldehyde; 2-Phenylethyl acetate; 1-Phenylethyl alcohol; ... Patent; International Flavors and Fragrances Inc.; US4092333; (1978); (A1) English View in Reaxys Aromatic compounds such as: ... 4-Methylguaiacol Methyl phenylacetate Phenol Phenyl acetate Phenylacetic acid Phenylacetic aldehyde 2-Phenylethyl acetate 1-Phenylethyl alcohol ... Patent; International Flavors and Fragrances Inc.; US4096158; (1978); (A1) English

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View in Reaxys 43.T : 2-[3-(3-Chloro-5-cyano-phenoxy)-2-fluoro4-methoxy-phenyl]-N-(2-chloro4-sulfamoyl-phenyl)-acetamide (I-190) To a solution of 56a (2.0, 5.64 mmol) in DCM (20 mL) stirred at 0° C. was added KH2PO4 (15.35 g, 112.82 mmol). To this suspension was added dropwise at 0° C. the TFPA. The reaction was stirred for 48 h. Upon consumption of starting material reaction mixture was cooled to 0° C., and diluted with brine, and quenched with aqueous 10percent sodium bisulfite. The resulting mixture was extracted with DCM and washed with brine, dried (Na2SO4), filtered and the solvent removed in vacuo to yield a yellow solid which was purified by SiO2 chromatography eluding with hexane/EtOAc (92:8) to afford 1.8 g (94percent) of 56b. step 6-To a solution of 56b (1.8 g, 5.26 mmol) in DMF (15 mL) was added Cs2CO3 (3.43,10.52 mmol) and iodomethane (0.74 g, 5.26 mmol). The reaction mixture was stirred at 85° C. for 12 h. When 56b was consumed, the reaction mixture was cooled to RT and the cured mixture extracted with EtOAc and the combined extracts washed with water and brine. The EtOAc was dried (Na2SO4), filtered and concentrated in vacuo to afford 56c as a yellow oil which was used in the next step without additional purification. step 7-A dry 100 mL round bottom was purged with nitrogen and charged with 56c (1.6 g, 4.50 mmol) and anhydrous THF (20 mL). The mixture was cooled to -20° C. and a solution of iso-PrMgCl-LiCl (5.40 ml, 5.40 mol, 2 M in THF, see step 3) was added dropwise. The reaction was stirred for 2 h at -20° C. and a solution of CuCN LiCl (0.100 mL, 0.100 mol 1 M in THF) was added and stirred continued at -20° C. To this mixture was added allyl bromide (1.08 g, 9.0 mmol) and the mixture stirred for an additional two h. The reaction was quenched by addition of aqueous NH4Cl. The mixture extracted with EtOAc and washed with water and brine. The extracts were dried (Na2SO4), filtered and the solvent was removed in vacuo to yield a yellow oil. The crude product was purified by SiO2 chromatography eluding with hexane/EtOAc (95:5) to afford I g (70percent) of 58a. step 8-To a solution of 58a (0.100 g, 0.315 mmol), EtOAc (2 mL), MeCN (2 mL) and water (3 mL) was added NaIO4 (0.437 g, 2.050 mmol) and RuCl3 (0.001 g, 0.006 mmol). When 58a was consumed, the crude mixture was filtered through a pad of CELITE.(R)., washed with EtOAc and the combined EtOAc washes were washed with brine, dried (Na2SO4) filtered and evaporated in vacuo to afford 0.090g (85percent) of 58b as a yellow solid. extracted with ethyl acetate, and washed with brine. The ethyl acetate was dried over sodium sulfate and filtered. Solvent was removed in vacuo to yield 58b as a yellow solid (0.090 g, 85percent). Patent; Roche Palo Alto LLC; US2005/239880; (2005); (A1) English View in Reaxys 13 : Compound 90 of Table 1: Benzeneacetic acid, 2-[2-[4-(6-fluorohexyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl]ethoxy]-, methyl ester EXAMPLE 13 Compound 90 of Table 1: Benzeneacetic acid, 2-[2-[4-(6-fluorohexyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2yl]ethoxy]-, methyl ester Prepared from Intermediate 7 (1.8 g, 0.006 mol) in a manner analogous to Method C. Compound 90 was obtained as a colorless oil (2.2 g, 0.005 mol). 1H (CDCl ): 7.28-6.89 (m, 8H), 4.76 (dd, 1H, J=9.5, 4.0), 4.44 (dt, 2H, J=47.3, 6.0), 4.19 (m, 2H), 3.93 (br t, 2H), 3.61 3 and 3.60 (two singlets, 5H), 2.50 (m, 3H), 2.22 (m, 1H), 1.68 (m, 4H), 1.57 (m, 4H). Patent; Burris, Thomas P.; Combs, Donald W.; Rybczynski, Philip J.; US2002/165228; (2002); (A1) English View in Reaxys Patent; Ortho-McNeil Pharmaceutical, Inc.; US6908908; (2005); (B2) English View in Reaxys 19 : Intermediate 10: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl) ethoxy]-, methyl ester EXAMPLE 19 Intermediate 10: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl) ethoxy]-, methyl ester

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Prepared from Intermediate 9 (11.16 g, 0.04 mol) in a manner analogous to Method C. Intermediate 10 was obtained as a colorless oil (9.7 g, 0.023 mol). 1H (CDCl ): 7.28-6.89 (m, 8H), 4.76 (dd, 1H, J=9.4, 4), 4.28-4.21 (m, 2H), 3.92 (t, 2H, J=7.7), 3.60 (two singlets, 5H), 3 2.49 (m, 1H), 2.23 (m, 1H), 1.66 (m, 2H), 1.34 (m, 6H), 0.89 (br t, 3H). Patent; Ortho-McNeil Pharmaceutical, Inc.; US6908908; (2005); (B2) English View in Reaxys 22 : Compound 12 of Table 1: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2yl)ethoxy]-a-oxo-, methyl ester EXAMPLE 22 Compound 12 of Table 1: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl)ethoxy]-aoxo-, methyl ester Prepared from Intermediate 9 (0.61 g, 0.0022 mol) and 2-hydroxy-α-oxo-bezeneacetic acid, methyl ester (0.4 g, 0.0022 mol). Compound 12 was obtained as a colorless oil (0.48 g, 0.0011 mol). 1H (CDCl ): 7.88 (d, 1H, J=7.4), 7.58 (t, 1H, J=6.5), 6.99 (m, 6H), 4.65 (dd, 1H, J=9.6, 3.9), 4.57 (t, 2H, J=7.4), 4.32 3 (m, 1H), 3.87 (s and m, 4H), 2.49 (m, 1H), 2.24 (m, 1H), 1.62 (m, 2H), 1.32 (m, 6H), 0.88 (br t, 3H). Patent; Ortho-McNeil Pharmaceutical, Inc.; US6908908; (2005); (B2) English View in Reaxys 36 : Compound 127 of Table 2: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazin-2-yl)ethoxy]-, methyl ester EXAMPLE 36 Compound 127 of Table 2: Benzeneacetic acid, 2-[2-(4-hexyl-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazin-2yl)ethoxy]-, methyl ester Intermediate 11 (0.26 g, 0.0006 mol) was dissolved in 10 ml THF and cooled to 0° C. Sodium hexamethyldisilazide (1.8 mL, 1.0 M) was added, then the reaction was stirred at room temperature for 30 minutes. The reaction was cooled to 0° C., iodomethane (0.07 mL, 1.2 mmol) was added, and the reaction was stirred at room temperature overnight. The reaction was diluted with water and extracted with CH2Cl2. The organics were dried (Na2SO4), filtered, and solvent was removed in vacuo. The crude mixture, DMAP (0.004 g, 0.00003 mol) and methanol (0.05 mL, 0.001 mol) were dissolved in 20 mL CH2Cl2. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 0.059 g, 0.0003 mol) was added and the reaction stirred overnight at room temperature. Solvent was removed and the product was purified by silica gel chromatography. Compound 119 was obtained as a colorless oil (0.1 g, 0.00023 mol). 1H (CDCl ): 7.3-6.9 (m, 8H), 4.3-4.1 (m, 2H), 3.92 (m, 2H), 3.66 and 3.62 (two singlets, 5H), 2.49 (m, 1H), 2.25 (m, 3 1H), 1.66 (m, 2H), 1.51 (s, 3H), 1.33 (m, 6H), 0.89 (br t, 3H). Patent; Ortho-McNeil Pharmaceutical, Inc.; US6908908; (2005); (B2) English View in Reaxys 8 : Compound 81 of Table 1: Benzeneacetic acid, 2-[2-[3,4-dihydro-4-(5-hydroxyhexyl)-3-oxo-2H-1,4-benzoxazin-2-yl]ethoxy]-, methyl ester EXAMPLE 8 Compound 81 of Table 1: Benzeneacetic acid, 2-[2-[3,4-dihydro-4-(5-hydroxyhexyl)-3-oxo-2H-1,4-benzoxazin-2yl]ethoxy]-, methyl ester A slurry of Compound 78 (0.2 g, 0.00046 mol) in 10 mL ethanol was treated with sodium borohydride (0.012 mg, 0.00031 mol), then stirred for 1 hour at room temperature. The reaction was diluted with water and extracted with ethyl acetate. The organics were dried (Na2SO4), filtered, and solvent was evaporated. Compound 81 was obtained as a colorless oil (0.052 g, 0.00012 mol). 1H (CDCl ): 7.25 (m, 2H), 6.95 (m, 6H), 4.76 (dd, 1H, J=9.4, 3.9), 4.23 (m, 2H), 3.94 (t, 2H, J=7.5), 3.80 (m, 1H), 3 3.61 and 3.60 (two singlets, 5H), 2.49 (m, 1H), 2.23 (m, 1H), 1.70 (m, 2H), 1.47 (m, 4H), 1.19 (d, 3H, J=6.0). Patent; Ortho-McNeil Pharmaceutical, Inc.; US6908908; (2005); (B2) English View in Reaxys Synthesis of Common Caps A methanol (10 mL) solution of either enantiomer of benzyl 2-(4-methylpiperazin-1-yl)-2-phenylacetate (1.0 g, 3.1 mmol) was added to a suspension of 10percent Pd/C (120 mg) in methanol (5.0 mL).

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The reaction mixture was exposed to a balloon of hydrogen, under a careful monitoring, for <50 minutes. Immediately after the completion of the reaction, the catalyst was filtered through diatomaceous earth (Celite.(R).) and the filtrate was concentrated in vacuo to provide Cap-7, contaminated with phenylacetic acid as a tan foam (867.6 mg; mass is above the theoretical yield). The product was used for the next step without further purification. 1H NMR (DMSO-d6, δ=2.5, 500 MHz) δ 7.44-7.37 (m, 2H), 7.37-7.24 (m, 3H), 3.92 (s, 1H), 2.63-2.48 (app. br s, 2H), 2.48-2.32 (m, 6H), 2.19 (s, 3H); RT=0.31 (Cond. II); >90percent homogeneity index; LC/MS: Anal. Calcd. for [M+H]+ C13H19N2O2: 235.14; found 235.15; HRMS: Anal. Calcd. for [M+H]+ C13H19N2O2: 235.1447; found 235.1440. Patent; Bristol-Myers Squibb Company; US2009/202478; (2009); (A1) English View in Reaxys Condition III A methanol (10 mL) solution of either enantiomer of benzyl 2-(4-methylpiperazin-1-yl)-2-phenylacetate (1.0 g, 3.1 mmol) was added to a suspension of 10percent Pd/C (120 mg) in methanol (5.0 mL). The reaction mixture was exposed to a balloon of hydrogen, under a careful monitoring, for <50 minutes. Immediately after the completion of the reaction, the catalyst was filtered through diatomaceous earth (Celite.(R).) and the filtrate was concentrated in vacuo to provide Cap-7, contaminated with phenylacetic acid as a tan foam (867.6 mg; mass is above the theoretical yield). The product was used for the next step without further purification. 1H NMR (DMSO-d6, δ=2.5, 500 MHz) δ 7.44-7.37 (m, 2H), 7.37-7.24 (m, 3H), 3.92 (s, 1H), 2.63-2.48 (app. br s, 2H), 2.48-2.32 (m, 6H), 2.19 (s, 3H); RT=0.31 (Cond. II); >90percent homogeneity index; LC/MS: Anal. Calcd. for [M+H]+ C13H19N2O2: 235.14; found 235.15; HRMS: Anal. Calcd. for [M+H]+ C13H19N2O2: 235.1447; found 235.1440. Patent; Bristol-Myers Squibb Company; US2009/202483; (2009); (A1) English View in Reaxys Condition III A methanol (10 mL) solution of either enantiomer of benzyl 2-(4-methylpiperazin-1-yl)-2-phenylacetate (1.0 g, 3.1 mmol) was added to a suspension of 10percent Pd/C (120 mg) in methanol (5.0 mL). The reaction mixture was exposed to a balloon of hydrogen, under a careful monitoring, for <50 minutes. Immediately after the completion of the reaction, the catalyst was filtered through diatomaceous earth (Celite.(R).) and the filtrate was concentrated in vacuo to provide Cap-7, contaminated with phenylacetic acid as a tan foam (867.6 mg; mass is above the theoretical yield). The product was used for the next step without further purification. 1H NMR (DMSO-d6, δ=2.5, 500 MHz) δ 7.44-7.37 (m, 2H), 7.37-7.24 (m, 3H), 3.92 (s, 1H), 2.63-2.48 (app. br s, 2H), 2.48-2.32 (m, 6H), 2.19 (s, 3H); RT=0.31 (Cond. II); >90percent homogeneity index; LC/MS: Anal. Calcd. for [M+H]+ C13H19N2O2: 235.14; found 235.15; HRMS: Anal. Calcd. for [M+H]+ C13H9N2O2: 235.1447; found 235.1440. Patent; Bristol-Myers Squibb Company; US2010/80772; (2010); (A1) English View in Reaxys Synthesis of Common Caps A methanol (10 mL) solution of either enantiomer of benzyl 2-(4-methylpiperazin-1-yl)-2-phenylacetate (1.0 g, 3.1 mmol) was added to a suspension of 10percent Pd/C (120 mg) in methanol (5.0 mL). The reaction mixture was exposed to a balloon of hydrogen, under a careful monitoring, for <50 minutes. Immediately after the completion of the reaction, the catalyst was filtered through diatomaceous earth (Celite.(R).) and the filtrate was concentrated in vacuo to provide Cap-7, contaminated with phenylacetic acid as a tan foam (867.6 mg; mass is above the theoretical yield). The product was used for the next step without further purification. 1H NMR (DMSO-d6, δ=2.5, 500 MHz) δ 7.44-7.37 (m, 2H), 7.37-7.24 (m, 3H), 3.92 (s, 1H) 2.63-2.48 (app. br s, 2H), 2.48-2.32 (m, 6H), 2.19 (s, 3H); RT=0.31 (Cond. II); >90percent homogeneity index; LC/MS: Anal. Calcd. for [M+H]+ C13H19N2O2: 235.14; found 235.15; HRMS: Anal. Calcd. for [M+H]+ C13H19N2O2: 235.1447; found 235.1440. Patent; Bristol-Myers Squibb Company; US2010/215616; (2010); (A1) English View in Reaxys

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O HO

HO O

Rx-ID: 25060005 View in Reaxys 831/834 Yield

Conditions & References

89.9%

2 : (B) Total yield of phenylpyruvic acid: 89.9percent Total yield of phenylacetic acid: 6.8percent Patent; Dynamit Nobel AG; US4447644; (1984); (A1) English View in Reaxys

39.8%

4 : EXAMPLE 4 EXAMPLE 4 Following the procedure according to Example 1 but using 3800 ml of tert-amyl alcohol in place of tert-butanol, a yield of 39.8percent of phenylpyruvic acid and of 12percent of phenylacetic acid was obtained. Patent; Dynamit Nobel AG; US4447644; (1984); (A1) English View in Reaxys 10 : EXAMPLE 10 EXAMPLE 10 The procedure described in Example 1 was followed, except that 22 wt. percent KOH and a carbon monoxide pressure of 20 bars were used. The total yields obtained after working up were: Phenylpyruvic acid: 50.3percent Phenylacetic acid: 35.4percent Patent; Dynamit Nobel AG; US4447644; (1984); (A1) English View in Reaxys 8 : EXAMPLE 8 EXAMPLE 8 Example 1 was repeated, 24 wt. percent NaOH and a carbon monoxide pressure of 100 bars being used. The total yield after working up was: Phenylpyruvic acid: 67.9percent Phenylacetic acid: 21.7percent Patent; Dynamit Nobel AG; US4447644; (1984); (A1) English View in Reaxys

HO O

Rx-ID: 25361819 View in Reaxys 832/834 Yield 90%

Conditions & References 4 : Fluorination of Benzeneacetic Acid Water (5 ml) was added to the residue. An exothermic reaction ensued. Excess water was evaporated off at reduced pressure; the white residue was recrystallized from hexane to give 13.8 g (90percent yield) of α-fluorobenzeneacetic acid as colorless crystals: mp 75°-77° C.; ir (KBr) 5.68μ (C=O); 19 F NMR (CDCl3) δ -181.4 ppm (d,J=48 Hz); 1 H NMR (CDCl3) δ 5.80 ppm (d,J=48 Hz, 1H), 7.43 ppm (5H) and 10.17 ppm (s, OH). Anal. Calcd. for C8 H7 FO2: C, 62.34; H, 4.58; F, 12.33; Found: C, 62.14; H, 4.47; F, 12.39. Patent; E. I. Du Pont de Nemours and Company; US4215044; (1980); (A1) English

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View in Reaxys

HO O

Rx-ID: 25059961 View in Reaxys 833/834 Yield

Conditions & References

11%

1.9 : EXAMPLES 1-9 The washing water and ether then were combined with the filtrate. The whole was acidified with HCl and extracted in ether. The ether extract was washed with a saturated solution of NaHCO3. The ether extract was then anhydrified by evaporation to dryness, thus obtaining 1.9 g of residue consisting of starting benzyl chloride. The alkaline waters were made acidic and extracted with ether. 3.8 g of phenylacetic acid (PAA) were obtained from the ether extract after evaporation. The yield was equal to 11percent, calculated on the converted benzyl chloride. Patent; Montedison S.p.A.; US4351952; (1982); (A1) English View in Reaxys

HO O

trimethylsilylated phenylacetic acid Rx-ID: 25060246 View in Reaxys 834/834

Yield

Conditions & References 4.2 : EXAMPLE 4 (2) To 50 ml of a suspension of dried dichloromethane containing 4.0 g of the phenylacetic acid obtained in (1) above and 4.9 g of trimethylsilyl chloride, 4.2 g of triethylamine was added dropwise at between 5° and 10° C. By stirring the mixture at between 15° and 20° C. for an hour, a solution of trimethylsilylated phenylacetic acid was obtained, and it was subjected to a reaction which is described below. Patent; Chugai Seiyaku Kabushiki Kaisha; US4355038; (1982); (A1) English View in Reaxys

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