3. 2-Allylcyclohexan-1-one by Asch

Reaxys

PubChem

eMolecules

Reactions (111)

Yield

Substances (4)

Citations (112)

Conditions

References

Synthesize Find similar

Rx-ID: 554673 Find similar reactions

Synthesize Find similar

87%

Stage #1: cyclohexanone With lithium diisopropyl amide in tetrahydrofuran

T=-78°C; 0.333333 h; Inert atmosphere; Stage #2: allyl bromide in tetrahydrofuran

T=-78 - 20°C; 0.5 h; Inert atmosphere;

Zheng, Shuyan; Zhang, Jinghua; Shen, Zhengwu

Advanced Synthesis and Catalysis, 2015 , vol. 357, # 13 p. 2803 - 2808 Title/Abstract Full Text View citing articles Show Details

79%

Stage #1: cyclohexanone With tris(dimethylamino)phosphine oxide; n-butyllithium in tetrahydrofuran; hexane

T=-78°C; Stage #2: allyl bromide T=-40 - 20°C;

Juma, Benard; Adeel, Muhammad; Villinger, Alexander; Reinke, Helmut; Spannenberg, Anke; Fischer, Christine; Langer, Peter

Advanced Synthesis and Catalysis, 2009 , vol. 351, # 7-8 p. 1073 - 1079 Title/Abstract Full Text View citing articles Show Details

53%

Stage #1: cyclohexanone With potassium tert-butylate in diethyl ether

T=20°C; Inert atmosphere; Stage #2: allyl bromide in diethyl ether

0.5 h;

Portela-Cubillo, Fernando; Lymer, James; Scanlan, Eoin M.; Scott, Jackie S.; Walton, John C.

Tetrahedron, 2008 , vol. 64, # 52 p. 11908 - 11916 Title/Abstract Full Text View citing articles Show Details

23%

Stage #1: cyclohexanone With lithium diisopropyl amide in tetrahydrofuran

T=-78°C; 0.75 h; Stage #2: allyl bromide in tetrahydrofuran

T=-78 - 20°C; 16 h;

Pryde, David C.; Maw, Graham N.; Planken, Simon; Platts, Michelle Y.; Sanderson, Vivienne; Corless, Martin; Stobie, Alan; Barber, Christopher G.; Russell, Rachel; Foster, Laura; Barker, Laura; Wayman, Christopher; Van Der Graaf, Piet; Stacey, Peter; Morren, Debbie; Kohl, Christopher; Beaumont, Kevin; Coggon, Sara; Tute, Michael

Journal of Medicinal Chemistry, 2006 , vol. 49, # 14 p. 4409 - 4424 Title/Abstract Full Text View citing articles Show Details

With potassium tert-butylate; benzene

Mousseron et al.

Bulletin de la Societe Chimique de France, 1957 , p. 346,352 Full Text Show Details

Stage #1: cyclohexanone With N,N-Dimethylhydrazine

Inert atmosphere; Stage #2: allyl bromide With n-butyllithium

Inert atmosphere;

Moreau, Xavier; Goddard, Jean-Philippe; Bernard, Matthieu; Lemiere, Gilles; Lopez-Romero, Juan Manuel; Mainetti, Emily; Marion, Nicolas; Mouries, Virginie; Thorimbert, Serge; Fensterbank, Louis; Malacria, Max

Advanced Synthesis and Catalysis, 2008 , vol. 350, # 1 p. 43 - 48 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 2342705 Find similar reactions

Synthesize Find similar

93%

Stage #1: allyl alcohol With 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 0.166667 h; Inert atmosphere; Stage #2: cyclohexanone With pyrrolidine in methanol

8 h; Inert atmosphere;

Huo, Xiaohong; Yang, Guoqiang; Liu, Delong; Liu, Yangang; Gridnev, Ilya D.; Zhang, Wanbin

Angewandte Chemie - International Edition, 2014 , vol. 53, # 26 p. 6776 - 6780 Angew. Chem., 2014 , vol. 126, # 26 p. 6894 - 6898,5 Title/Abstract Full Text View citing articles Show Details

91%

With bis(η3-allyl-μ-chloropalladium(II)); 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; DL-proline in dimethyl sulfoxide

Usui, Ippei; Schmidt, Stefan; Breit, Bernhard

Organic Letters, 2009 , vol. 11, # 6 p. 1453 - 1456 Title/Abstract Full Text View citing articles Show Details

T=70°C; 20 h; Inert atmosphere;

83%

With toluene-4-sulfonic acid; 2,2-dimethoxy-propane

T=150°C;

Carita, Adriana; Burtoloso, Antonio C.B.

Tetrahedron Letters, 2010 , vol. 51, # 4 p. 686 - 688 Title/Abstract Full Text View citing articles Show Details

Hide Details 72%

With 2,2-dimethoxy-propane; toluene-4-sulfonic acid in toluene

reflux with a microdistillation column; Hide Experimental Procedure

Givaudan SA

Patent: US2010/292128 A1, 2010 ; Location in patent: Page/Page column 26 ; Title/Abstract Full Text Show Details

34.a: a) Spiro[4.5]dec-2-en-6-oneA solution of cyclohexanone (98.1 g, 1 mol), allyl alcohol (127.8 g, 2.2 mol), dimethoxypropane (114.6 g, 1.1 mol), and PTSA.H2O (0.1 g, 0.5 mmol) in toluene (0.51) was heated at reflux in a flask equipped with a microdistillation column (30.x.2.5 cm, filled with Raschig rings). After collecting the fractions distilling at 25-60° C. and 60-110° C., the residue (120 g) was distilled using a 10 cm-Vigreux-column (0.07-0.06 mbar, head temperature: 57° C.) giving 2-allylcyclohexanone (99.1 g, 72percent).13C-NMR (100 MHz, CDCl3): 5212.14 (s), 136.38 (d), 116.05 (t), 50.14 (d), 41.93 (t), 33.69 (t), 39.29 (t), 27.85 (t), 24.87

(t).MS (EI): 138 (36), 123 (21), 110 (18), 109 (52), 97 (19), 96 (12), 95 (59), 94 (74), 81 (48), 79 (74), 67 (100), 55 (61), 54 (61), 53 (35), 41 (86), 39 (57).A solution of 2-allylcyclohexanone (50 g, 0.36 mol), allyl alcohol (46.2 g, 0.8 mol), dimethoxypropane (41.4 g, 0.4 mol), and PTSA.H2O (35 mg, 0.18 mmol) in toluene (0.25 l) was heated at reflux in a flask equipped with a microdistillation column (30.x.2.5 cm, filled with Raschig rings). After collecting the fractions distilling at 25-60° C. and 60-110° C., the residue (58 g) was distilled using a 10 cm-Vigreux-column giving a 28:72 mixture of 2-allylcyclohexanone/diallylcyclohexanones (36.85 g, 0.06 mbar, head temperature: 60° C.) and 6,6-diallylcyclohexanone (6.74 g, 10percent, contaminated with 20percent 2,6-diallycyclohexanone, 0.06 mbar, head temperature: 60° C.). The first fraction was redistilled using a microdistillation column (20.x.1.0 cm, filled with 3.x.3 mm rolled wire netting) giving additional 6,6diallylcyclohexanone (22.56 g, 35percent, contaminated with 20percent 2,6-diallycyclohexanone, 0.07 mbar, head temperature: 61-70° C.).6,6-Diallylcyclohexanone13C-NMR (100 MHz, CDCl3): δ214.01 (s), 133.62 (d, 2C), 118.00 (t, 2C), 51.44 (s), 39.28 (t), 39.24 (t, 2C), 35.93 (t), 27.02 (t), 20.77 (t).MS (EI): 178 (8), 163 (3), 150 (4), 149 (8), 137 (49), 135 (43), 123 (13), 119 (16), 109 (16), 98 (11), 95 (24), 93 (46), 91 (39), 81 (31), 79 (60), 77 (28), 67 (100), 55 (55), 53 (29), 41 (69), 39 (41).2,6-Diallylcyclohexanone13C-NMR (100 MHz, CDCl3): δ214.64 (s), 135.89 (d, 2C), 116.44 (t, 2C), 48.43 (d, 2C), 34.54 (t, 2C), 32.08 (t, 2C), 20.31 (t).A

solution of a 80:20 mixture of 6,6- and 2,6-diallylcyclohexanone (22.0 g, 0.123 mol) in 1,2-dichloroethane (300 ml) was treated with PhCHRu(PCy3)2Cl2 (10.2 g, 12.3 mmol).The resulting mixture was stirred at 60° C. for 24 h and concentrated. Ball-to-ball distillation (25-140° C., 0.1 mbar) of the residue (30.68 g) followed by FC (800 g SiO2, hexane/MTBE 30:1) of the volatile fraction (14.9 g) gave spiro[4.5]dec-2-en-6-one (14.1 g, 95percent).13C-NMR (100 MHz, CDCl3): δ213.06 (s), 127.81 (d, 2C), 55.73 (s, C(5)), 41.72 (t, 2C), 40.12 (t), 39.48 (t), 27.19 (t), 22.26 (t).MS (EI): 150 (96), 135 (41), 121 (33), 108 (34), 107 (48), 106 (49), 93 (81), 91 (43), 80 (63), 79 (100), 77 (58), 67 (25), 66 (37), 65 (29), 55 (38), 41 (29), 39 (45).

55%

Stage #1: With 2,2-dimethoxy-propane; benzenesulfonic Acid

T=70 - 150°C; Stage #2: With sodium hydroxide in water

PHARMACIA CORPORATION

Patent: WO2004/12726 A2, 2004 ; Location in patent: Page/Page column 113-114 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

X.1: To a 22L round bottom flask equipped with overhead stirrer, half moon shape paddle, heating mantle, thermocouple, and a silver vacuum jackeed distillation column (5 plates) was charged cyclohexanone (4500.0 g, 45. 85 mol), acetone dimethyl acetal (5252.6 g, 50.43 mol), allyl alcohol (6390.87 g, 110.04 mol) and p- toluene sulfonic acid (PTSA) (0.256 g, 0.001 mol). After the stirring was started (137 rpm) the pot was heated slowly with the initial set point being [70 XB0;C.] Heating was increased step wise to a final pot temperature of 150 [XB0;C.] The decision to increase the reactor set point was made based on distillation rate. If the rate of distillate slowed or stopped, additional heat was applied. The additional heating to 150 [XB0;C] allowed the Claisen rearrangement to occur. After the pot temperature was raised to 150 [XB0;C] and no distillate was observed, the heating mantle was lowered and the reaction mixture allowed to cool to 130 [XB0;C.] The PTSA was then neutralized with 3 drops of 2.5 N [NAOH.] The vacuum stripping was then started with the heating mantle lowered away from the flask. Evaporative cooling was used to lower the pot temperature, and the pressure was gradually lowered to 40 mm Hg. When the pot temperature had decreased to-100 °C, the heating mantle was raised back into the proper position for heating. Unreacted cyclohexanone and low boiling impurities were distilled off. The pot temperature was slowly raised (the maximum temperature deferential between the pot and vapor [WAS-12 OC).] The product was isolated at 109-112 [XB0;C] [COMMAT; ] 40 mm Hg. Typical yields were 40-45percent. Fractions which were <95percent by area (GC) were combined and redistilled to afford the title product in a total yield of 55percent. [H NMR (CDOS, 8] ppm): 5.8-5. 6 (m, 1H), 4.8-5. 0 (m, 2H), 2.5-2. 4 (m, [1H),] 2.3-2. 1 (m, 3H), 2.1-1. 2 (m, 7H). [13C] NMR [(CDCI3,] 5 ppm): 212.53, 136.62, 116.32, 50.39, 42. 18, 33.91, 33.52, 28.09, 25.10. [GC/MS M/Z = 138.] 55%

With 2,2-dimethoxy-propane; toluene-4-sulfonic acid

T=70 - 150°C; Neat (no solvent); Hide Experimental Procedure

PHARMACIA CORPORATION

Patent: WO2005/25620 A2, 2005 ; Location in patent: Page/Page column 113-114 ; Title/Abstract Full Text Show Details

X.Ex-X-1: To a 22L round bottom flask equipped with overhead stirrer, half moon shape paddle, heating mantle, thermocouple, and a silver vacuum jacketed distillation column (5 plates) was charged cyclohexanone (4500.0 g, 45.85 mol), acetone dimethyl acetal (5252.6 g, 50.43 mol), allyl alcohol (6390. 87 g, 110.04 mol) and p-toluene SULFONIC acid (PTSA) (0.256 g, 0.001 mol). After the stirring was started (137 rpm) the pot was heated slowly with the initial set point being 70°C. Heating was increased step wise to a final pot temperature of 150°C. The decision to increase the reactor set point was made based on distillation rate. If the rate of distillate slowed or stopped, additional heat was applied. The additional heating to 150°C allowed the Claisen rearrangement to occur. After the pot temperature was raised to 150°C and no distillate was observed, the heating mantle was lowered and the reaction mixture allowed to cool to 130°C. The PTSA was then neutralized with 3 drops of 2.5 N NaOH. The vacuum stripping was then started with the heating mantle lowered away from the flask. Evaporative cooling was used to lower the pot temperature, and the pressure was gradually lowered to 40 mm Hg. When the pot temperature had decreased TO-100 OC, the heating mantle was raised back into the proper position for heating. Unreacted cyclohexanone and low boiling impurities were distilled off. The temperature was slowly raised (the maximum temperature deferential between the pot and vapor WAS-12 °C). The product was isolated at 109-112 °C #x0;COMMAT; 40 mm Hg. Typical yields were 40-45percent. Fractions which were <95percent by area (GC) were combined and redistilled to afford the title product in a total yield of 55percent.#x0;H NMR (CDC13, 8 ppm): 5.8-5. 6 (m, 1H), 4.8-5. 0 (m, 2H), 2.5-2. 4 (m, 1H), 2.3-2. 1 (m, 3H), 2.1- 1.2 (m, 7H). 13C NMR (CDC13, 5 ppm): 212.53, 136.62, 116.32, 50.39, 42.18, 33.91, 33.52, 28.09, 25.10. GC/MSM/Z=138. 52.8%

With toluene-4-sulfonic acid; 2,2-dimethoxy-propane in water; benzene

T=130 - 190°C; Hide Experimental Procedure

IRONWOOD PHARMACEUTICALS, INC.; ROHDE, Jason; PENG, Bo; NAKAI, Takashi; SPROTT, Kevin; MERMERIAN, Ara; SCHAIRER, Wayne, C.

Patent: WO2011/100359 A1, 2011 ; Location in patent: Page/Page column 72-73 ; Title/Abstract Full Text Show Details

3.1.1:

Example 3: cycloalkylpyrrolesGeneral Scheme 3: preparation of cvclohexyl pyrroleStep l Step 2palladium(ll) chloridePreparation of intermediate iii:CO-Step 1:[00262] In a 250 ml round bottom flask equipped with a short-path distillation flask, the mixture of cyclohexanone (15.84 mL, 153 mmol), allyl alcohol (31.2 mL, 459 mmol), 2,2-dimethoxypropane (37.5 mL, 306 mmol), 4-methylbenzenesulfonic acid hydrate (0.029 g, 0.153 mmol), and benzene (102 mL) was heated at 130 °C. An azetropic mixture of benzene, methanol, and acetone was removed. After the distillation had completed, the mixture was heated at 190 °C. The mixture was stirred for an additional 30 min. It was then additionally purified by vacuum distillation (40 °C, 1 torr) to give 2-allylcyclohexanone (1 1.16 g, 81 mmol, 52.8 percent yield) as a clear oil. IH NMR (CDCl3/400 MHz) δ 5.78-5.76 (m, IH), 5.04- 4.98 (m, 2H), 2.55-2.52 (m, IH), 2.38-2.24 (m, 3H), 2.15-1.96 (m, 3H), 1.87-1.85 (m, IH), 1.69-1.63 (m, 3H ), 1.38-1.34 (m, IH). 5.5%

With toluene-4-sulfonic acid in toluene

28 h; Heating;

Wu; Kover

Synthetic Communications, 1993 , vol. 23, # 3 p. 395 - 403 Title/Abstract Full Text View citing articles Show Details

With hydrogen cation

Heating;

Boivin, Jean; Fouquet, Eric; Zard, Samir Z.

Tetrahedron Letters, 1990 , vol. 31, # 1 p. 85 - 88 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 37511276 Find similar reactions

91%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 9 h; Inert atmosphere; regioselective reaction;

Synthesize Find similar

Huo, Xiaohong; Quan, Mao; Yang, Guoqiang; Zhao, Xiaohu; Liu, Delong; Liu, Yangang; Zhang, Wanbin

Organic Letters, 2014 , vol. 16, # 6 p. 1570 - 1573

Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 37511277 Find similar reactions

93%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 24 h; Inert atmosphere; regioselective reaction;

Synthesize Find similar

Huo, Xiaohong; Quan, Mao; Yang, Guoqiang; Zhao, Xiaohu; Liu, Delong; Liu, Yangang; Zhang, Wanbin

Organic Letters, 2014 , vol. 16, # 6 p. 1570 - 1573 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 37511278 Find similar reactions

92%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 2 h; Inert atmosphere; regioselective reaction;

Synthesize Find similar

Huo, Xiaohong; Quan, Mao; Yang, Guoqiang; Zhao, Xiaohu; Liu, Delong; Liu, Yangang; Zhang, Wanbin

Organic Letters, 2014 , vol. 16, # 6 p. 1570 - 1573 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 37511279 Find similar reactions

95%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 4 h; Inert atmosphere; SolventTemperatureTimeReagent/catalyst; regioselective reaction;

Synthesize Find similar

Huo, Xiaohong; Quan, Mao; Yang, Guoqiang; Zhao, Xiaohu; Liu, Delong; Liu, Yangang; Zhang, Wanbin

Organic Letters, 2014 , vol. 16, # 6 p. 1570 - 1573 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 37511355 Find similar reactions

93%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 4 h; Inert atmosphere; regioselective reaction;

Synthesize Find similar

Huo, Xiaohong; Quan, Mao; Yang, Guoqiang; Zhao, Xiaohu; Liu, Delong; Liu, Yangang; Zhang, Wanbin

Organic Letters, 2014 , vol. 16, # 6 p. 1570 - 1573 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 37511356 Find similar reactions

92%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 6 h; Inert atmosphere; regioselective reaction;

Synthesize Find similar

Huo, Xiaohong; Quan, Mao; Yang, Guoqiang; Zhao, Xiaohu; Liu, Delong; Liu, Yangang; Zhang, Wanbin

Organic Letters, 2014 , vol. 16, # 6 p. 1570 - 1573 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 37511357 Find similar reactions

91%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 4 h; Inert atmosphere; regioselective reaction;

Synthesize Find similar

Huo, Xiaohong; Quan, Mao; Yang, Guoqiang; Zhao, Xiaohu; Liu, Delong; Liu, Yangang; Zhang, Wanbin

Organic Letters, 2014 , vol. 16, # 6 p. 1570 - 1573 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 32179859 Find similar reactions

96%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=40°C; 1 h; Inert atmosphere;

Synthesize Find similar

Zhao, Xiaohu; Liu, Delong; Guo, Hui; Liu, Yangang; Zhang, Wanbin

Journal of the American Chemical Society, 2011 , vol. 133, # 48 p. 19354 - 19357 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 32179867 Find similar reactions

92%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 8 h; Inert atmosphere;

Synthesize Find similar

Zhao, Xiaohu; Liu, Delong; Guo, Hui; Liu, Yangang; Zhang, Wanbin

Journal of the American Chemical Society, 2011 , vol. 133, # 48 p. 19354 - 19357 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 32179868 Find similar reactions

91%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 8 h; Inert atmosphere;

Synthesize Find similar

Zhao, Xiaohu; Liu, Delong; Guo, Hui; Liu, Yangang; Zhang, Wanbin

Journal of the American Chemical Society, 2011 , vol. 133, # 48 p. 19354 - 19357 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 32179869 Find similar reactions

92%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 4 h; Inert atmosphere;

Synthesize Find similar

Zhao, Xiaohu; Liu, Delong; Guo, Hui; Liu, Yangang; Zhang, Wanbin

Journal of the American Chemical Society, 2011 , vol. 133, # 48 p. 19354 - 19357 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 32179871 Find similar reactions

93%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 12 h; Inert atmosphere;

Synthesize Find similar

Zhao, Xiaohu; Liu, Delong; Guo, Hui; Liu, Yangang; Zhang, Wanbin

Journal of the American Chemical Society, 2011 , vol. 133, # 48 p. 19354 - 19357 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 32179872 Find similar reactions

83%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 12 h; Inert atmosphere;

Synthesize Find similar

Zhao, Xiaohu; Liu, Delong; Guo, Hui; Liu, Yangang; Zhang, Wanbin

Journal of the American Chemical Society, 2011 , vol. 133, # 48 p. 19354 - 19357 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 32179874 Find similar reactions

88%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 12 h; Inert atmosphere;

Synthesize Find similar

Zhao, Xiaohu; Liu, Delong; Guo, Hui; Liu, Yangang; Zhang, Wanbin

Journal of the American Chemical Society, 2011 , vol. 133, # 48 p. 19354 - 19357 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 32179881 Find similar reactions

90%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 12 h; Inert atmosphere;

Synthesize Find similar

Zhao, Xiaohu; Liu, Delong; Guo, Hui; Liu, Yangang; Zhang, Wanbin

Journal of the American Chemical Society, 2011 , vol. 133, # 48 p. 19354 - 19357 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 32179883 Find similar reactions

94%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 4 h; Inert atmosphere;

Synthesize Find similar

Zhao, Xiaohu; Liu, Delong; Guo, Hui; Liu, Yangang; Zhang, Wanbin

Journal of the American Chemical Society, 2011 , vol. 133, # 48 p. 19354 - 19357 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 32179884 Find similar reactions

78%

Synthesize Find similar

With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) in methanol

T=20°C; 12 h; Inert atmosphere;

Zhao, Xiaohu; Liu, Delong; Guo, Hui; Liu, Yangang; Zhang, Wanbin

Journal of the American Chemical Society, 2011 , vol. 133, # 48 p. 19354 - 19357 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 10411194 Find similar reactions

95%

Synthesize Find similar

With pyrrolidine; tetrakis(triphenylphosphine) palladium(0) in dimethyl sulfoxide

T=20°C; 16 h;

Ibrahem, Ismail; Cordova, Armando

Angewandte Chemie - International Edition, 2006 , vol. 45, # 12 p. 1952 - 1956 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 9085041 Find similar reactions

76%

Synthesize Find similar

With copper(l) iodide in N,N-dimethyl-formamide

T=40°C; 24 h;

Yasuda, Makoto; Tsuji, Shoki; Shigeyoshi, Yusuke; Baba, Akio

Journal of the American Chemical Society, 2002 , vol. 124, # 25 p. 7440 - 7447 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 24009313 Find similar reactions

Hansen JR., Donald W.; Webber, R. Keith; Hallinan, E. Ann; Toth, Mihaly V.; Pitzele, Barnett S.; Awasthi, Alok K.; Moormann, Alan E.; Metz, Suzanne; Snyder, Jeffery S.; Moore, William M.; Scholten, Jeffrey A.

Patent: US2001/44539 A1, 2001 ;

A: 158.4 g (71.6%)

Title/Abstract Full Text Show Details

6:6,7,8,9-tetrahydro-5-(2-propenyl)-3H,5H-[1,2,4]oxadiazolo[4,3-a]azepin-3-one

EXAMPLE 6 6,7,8,9-tetrahydro-5-(2-propenyl)-3H,5H-[1,2,4]oxadiazolo[4,3-a]azepin-3-one EX-6a) A suspension of potassium t-butoxide (200 g, 1.78 mol) in toluene which was cooled to 0° C. in an ice bath under N2 was treated with cyclohexanone (157 g, 1.60 mol). To the reaction mixture was slowly added allyl bromide (194 g, 1.60 mol) over a 2 hour period. The reaction was warmed to room temperature over 5 hours. The reaction was then poured into EtOAc (400 mL) and washed once with 10percent potassium hydrogen sulfate (250 mL). The organic solution was then washed with brine (3*200 mL), dried over magnesium sulfate, and evaporated under reduced pressure. The resulting oil was then chromatographed to yield 158.4 g (71.6percent) of 2-allyl cyclohexanone as an oil. 1H NMR (CDCl3, 300 MHz) d 1.2-2.5 (m, 1OH), 2.59 (m, 1H), 5.0 (dd, 2H), 5.75 (m, 1H).

NMR (CDCl3, 75 MHz) d 25.04, 28.03, 33.46, 33.86, 42.12, 50.35, 116.3, 136.6, 212.5. A

Synthesize Find similar

A: 158.4 g (71.6%)

Rx-ID: 24009314 Find similar reactions

Patent: US2001/44539 A1, 2001 ; Title/Abstract Full Text Show Details

125:(2S,3Z)-2-amino-5-(6,7,8,9-tetrahydro-3-oxo-3H,5H-[1,2,4]oxadiazolo[4,3-a]azepin-5-yl)-3-pentenoic acid

EXAMPLE 125 (2S,3Z)-2-amino-5-(6,7,8,9-tetrahydro-3-oxo-3H,5H-[1,2,4]oxadiazolo[4,3-a]azepin-5-yl)-3-pentenoic acid Ex-125a) A suspension of potassium t-butoxide (200g, 1.78 mol) in toluene which was cooled to 0° C. in an ice bath under N2 was treated with cyclohexanone (I157g, 1.610 mol). To the reaction mixture was slowly added allyl bromide (194g, 1.60 mol) over a 2 hour period. The reaction warmed to room temperature over 5 hours. The reaction was then poured onto ethyl acetate (400 mL) and washed once with 10percent potassium hydrogen sulfate (250 mL). The organic solution was then washed with brine (3*200 mL), dried over magnesium sulfate, and evaporated under reduced pressure. The resulting oil was then chromatographed to yield the allyl cyclohexanone as an oil, 158.4 g (71.6percent). 1H NMR (CDCl , 300 MHz) d 1.2-2.5(m, 10H), 2.59 (m, 1H), 5.0(dd, 2H), 5.75(m, 1H). 3 13C

NMR (CDCl3, 75 MHz) d 25.04, 28.03, 33.46, 33.86,42.12, 50.35, 116.3, 136.6, 212.5.

Synthesize Find similar

Rx-ID: 7020441 Find similar reactions

Curphey,T.J. et al.

Journal of Organic Chemistry, 1975 , vol. 40, p. 607 - 614 Full Text View citing articles Show Details

Fortunato,J.M.; Canem,B.

Journal of Organic Chemistry, 1976 , vol. 41, # 12 p. 2194 - 2200 Full Text View citing articles Show Details

Eisch; Kaska

Journal of Organic Chemistry, 1962 , vol. 27, p. 3745,3751 Full Text Show Details

Goyal; Gupta

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1977 , vol. 15, p. 758 Full Text Show Details

Onoue et al.

Tetrahedron Letters, 1973 , p. 121,123 Full Text Show Details

Tsuji et al.

Tetrahedron Letters, 1965 , p. 4387 Full Text View citing articles Show Details

Gutsche; Bailey

Journal of Organic Chemistry, 1963 , vol. 28, p. 607,609 Full Text Show Details

Tsuji et al.

Kogyo Kagaku Zasshi, 1966 , vol. 69, p. 920,924 Full Text Show Details

Normant

Anales de Quimica (1968-1979), 1972 , vol. 68, p. 667,674 Full Text Show Details

Monson et al.

Tetrahedron Letters, 1972 , p. 929 Full Text View citing articles Show Details

Staninets et al.

Sov. Prog. Chem. (Engl. Transl.), 1973 , vol. 39, # 10 p. 1043,68 Full Text Show Details

Bercot; Horeau

Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1971 , vol. 272, p. 1509 Full Text Show Details

Negeshi; Idacavage

Tetrahedron Letters, 1979 , p. 845,847 Full Text Show Details

Dow Chem. Co.

Patent: US3114772 , 1960 ; Chem.Abstr., 1964 , vol. 60, # 7933b Full Text Show Details

Hajela; Gupta

Agra University Journal of Research, Science, 1974 , vol. 23, p. 31 Full Text Show Details

Cuvigny; Normant

Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1969 , vol. 268, p. 1380 Full Text Show Details

Marcou et al.

Bulletin de la Societe Chimique de France, 1967 , p. 2429 Full Text Show Details

Jones; Ando

Journal of the American Chemical Society, 1968 , vol. 90, p. 2200 Full Text View citing articles Show Details

G. D. Searle and Co. Patent: US5883251 A1, 1999 ; Title/Abstract Full Text Show Details

G.D. Searle and Co. Patent: US6011028 A1, 2000 ; Title/Abstract Full Text Show Details

17:2-(2-propenyl)cyclohexanone, oxime STR19

EXAMPLE 17 2-(2-propenyl)cyclohexanone, oxime STR19 A sample of 2-allylcyclohexanone (Frinton, 2.0 g, 14.5 mmol) was converted to the title compound by the method of Example 1 using 1.5 g (21.7 mmol) of hydroxylamine hydrochloride and 2.0 g (24.6 mmol) of NaOAc in a mixture of 25 mL of EtOH and 25 mL of water. The procedure produced 2.6 g of the crude title compound. G. D. Searle and Co. Patent: US5854234 A1, 1998 ; Title/Abstract Full Text Show Details

G.D. Searle and Co. Patent: US6046211 A1, 2000 ; Title/Abstract Full Text Show Details

103:2-(2-propenyl)cyclohexanone, oxime STR109

EXAMPLE 103 2-(2-propenyl)cyclohexanone, oxime STR109 A sample of 2-allylcyclohexanone (Frinton, 2.0 g, 14.5 mmol) was converted to the title compound by the method of EXAMPLE 24 using 1.5 g (21.7 mmol) of hydroxylamine hydrochloride and 2.0 g (24.6 mmol) of NaOAc in a mixture of 25 mL of EtOH and 25 mL of water. The procedure produced 2.6 g of the crude title compound.

Synthesize Find similar

Rx-ID: 4836767 Find similar reactions

66%

With lithium aluminium tetrahydride; lithium diisopropyl amide

THF, heptane, ethylbenzene, -78 deg C to room temp.; room temp., 30 min;

Lee, Shi Yong; Hong, Jong Eoun; Jang, Won Bum; Oh, Dong Young

Tetrahedron Letters, 1997 , vol. 38, # 26 p. 4567 - 4570 Title/Abstract Full Text View citing articles Show Details

66%

Stage #1: With lithium diisopropyl amide in tetrahydrofuran; n-heptane; ethylbenzene

T=-78 - 20°C; Metallation; Stage #2: With lithium aluminium tetrahydride; sulfuric acid in tetrahydrofuran; n-heptane; ethylbenzene

T=20°C; Reduction; 0.5 h;

Lee, Shi Yong; Lee, Chi-Wan; Oh, Dong Young

Journal of Organic Chemistry, 1999 , vol. 64, # 19 p. 7017 - 7022 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 89%

With copper dichloride in tetrahydrofuran

14 h;

Synthesize Find similar

Rx-ID: 5089223 Find similar reactions

Enders, Dieter; Hundertmark, Thomas; Lazny, Ryszard

Synthetic Communications, 1999 , vol. 29, # 1 p. 27 - 33 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 5199665 Find similar reactions

With pig liver esterase

Decarboxylation; Enzymatic reaction;

Diedrichs, Nicole; Westermann, Bernhard

Synlett, 1999 , # 7 p. 1127 - 1129 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 16078185 Find similar reactions

Multi-step reaction with 2 steps 1.1: NaH / tetrahydrofuran / 0 - 20 °C 1.2: 67 percent / tetrahydrofuran / 5 h / 20 °C 2.1: LDA / tetrahydrofuran; heptane; ethylbenzene / -78 - 20 °C 2.2: 66 percent / LiAlH4; aq. H2SO4 / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / 20 °C View Scheme

Lee, Shi Yong; Lee, Chi-Wan; Oh, Dong Young

Journal of Organic Chemistry, 1999 , vol. 64, # 19 p. 7017 - 7022 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 67 percent / NaH / tetrahydrofuran; hexane / 5 h / Ambient temperature 2: 66 percent / LDA; LiAlH4 / THF, heptane, ethylbenzene, -78 deg C to room temp.; room temp., 30 min View Scheme

Lee, Shi Yong; Hong, Jong Eoun; Jang, Won Bum; Oh, Dong Young

Tetrahedron Letters, 1997 , vol. 38, # 26 p. 4567 - 4570 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 4811506 Find similar reactions

Synthesize Find similar

Moriarty, Robert M.; Epa, Widanagamage R.; Prakash, Om

Journal of Chemical Research - Part S, 1997 , # 7 p. 262 - 263 Title/Abstract Full Text View citing articles Show Details

With trimethylsilyl trifluoromethanesulfonate; iodosylbenzene

Ambient temperature1.) CH2Cl2, 2.) CH2Cl2, RT, overnight; Yield given;

Synthesize Find similar

Rx-ID: 4357484 Find similar reactions

Synthesize Find similar

With N,N,N',N',N'',N''-hexamethylphosphoric triamide; 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride

multistep reaction: 1.) benzene, 4 h, reflux, 2.) benzene, 3 min, room t. and 14 h reflux; reactions of derivatives with halides, reactions under var. conditions; Product distribution;

Enholm, Eric J.; Whitley, Paul E.

Tetrahedron Letters, 1996 , vol. 37, # 5 p. 559 - 562 Title/Abstract Full Text View citing articles Show Details

With N,N,N',N',N'',N''-hexamethylphosphoric triamide; 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride

1.) benzene, 4 h, reflux, 2.) benzene, 3 min, room t. and 14 h, reflux; Yield given. Multistep reaction;

Enholm, Eric J.; Whitley, Paul E.

Tetrahedron Letters, 1996 , vol. 37, # 5 p. 559 - 562 Title/Abstract Full Text View citing articles Show Details

Yield given. Multistep reaction;

Enholm, Eric J.; Whitley, Paul E.; Xie, Yongping

Journal of Organic Chemistry, 1996 , vol. 61, # 16 p. 5384 - 5390 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 2032315 Find similar reactions

B: 50%

A: 32 % Chromat. B: 68 % Chromat.

With 9,10-anthracenedicarbonitrile; triphenylphosphine in water; N,N-dimethyl-formamide; isopropyl alcohol

Irradiation; Yields of byproduct given;

Pandey, Ganesh; Hajra, Saumen; Ghorai, Manas K.

Tetrahedron Letters, 1994 , vol. 35, # 42 p. 7837 - 7840 Title/Abstract Full Text View citing articles Show Details

With 9,10-anthracenedicarbonitrile; triphenylphosphine in water; N,N-dimethyl-formamide; isopropyl alcohol

50 h; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Pandey, Ganesh; Hajra, Saumen

Angewandte Chemie, 1994 , vol. 106, # 11 p. 1217 - 1218 Title/Abstract Full Text Show Details

With 9,10-anthracenedicarbonitrile; triphenylphosphine in water; N,N-dimethyl-formamide; isopropyl alcohol

Irradiation; Title compound not separated from byproducts;

Pandey, Ganesh; Hajra, Saumen; Ghorai, Manas K.

Tetrahedron Letters, 1994 , vol. 35, # 42 p. 7837 - 7840 Title/Abstract Full Text View citing articles Show Details

With 9,10-anthracenedicarbonitrile; triphenylphosphine in N,N-dimethyl-formamide; isopropyl alcohol

50 h; Irradiation; Product distributionQuantum yield;

Pandey, Ganesh; Hajra, Saumen

Angewandte Chemie, 1994 , vol. 106, # 11 p. 1217 - 1218 Title/Abstract Full Text Show Details

Synthesize Find similar

Rx-ID: 3857584 Find similar reactions

A: 36 % Chromat. B: 17 % Chromat.

With [VO(OEt)Cl2] in dichloromethane

T=-75°C;

Hirao, Toshikazu; Fujii, Takashi; Ohshiro, Yoshiki

Tetrahedron, 1994 , vol. 50, # 34 p. 10207 - 10214 Title/Abstract Full Text View citing articles Show Details

A: 36 % Chromat. B: 17 % Chromat.

With [VO(OEt)Cl2] in dichloromethane

T=-75°C;

Hirao, Toshikazu; Fujii, Takashi; Ohshiro, Yoshiki

Tetrahedron, 1994 , vol. 50, # 34 p. 10207 - 10214 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 7056689 Find similar reactions

A: 7% B: 80%

in tetrahydrofuran

T=-40°C; 0.166667 h; quench: glacial AcOH;

Bartoli, Giuseppe; Bosco, Marcella; Sambri, Letizia; Marcantoni, Enrico

Tetrahedron Letters, 1994 , vol. 35, # 46 p. 8651 - 8654 Title/Abstract Full Text View citing articles Show Details

A: 7% B: 80%

in tetrahydrofuran

T=-40°C; 0.166667 h; quench: glacial AcOH;

Bartoli, Giuseppe; Bosco, Marcella; Sambri, Letizia; Marcantoni, Enrico

Tetrahedron Letters, 1994 , vol. 35, # 46 p. 8651 - 8654 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 555051 Find similar reactions

With sodium amide

Behandeln mit Allyljodid;

Cornubert

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1914 , vol. 158, p. 1901 Full Text Show Details

With diethyl ether; sodium amide

nachfolgend Einw. von Allyljodid oder Allylbromid;

Cornubert

Annales de Chimie (Cachan, France), 1921 , vol. <9> 16, p. 153,168 Full Text Show Details

Multi-step reaction with 3 steps 1: p-TsOH / benzene / 24 h / Heating 2: butan-1-ol / 12 h / Heating 3: H2O / 3 h / Heating View Scheme

Ihara, Masataka; Taniguchi, Takahiko; Makita, Kei; Takano, Michiko; Ohnishi, Masaru; Taniguchi, Nobuaki; Fukumoto, Keiichiro; Kabuto, Chizuko

Journal of the American Chemical Society, 1993 , vol. 115, # 18 p. 8107 - 8115 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 1.) t-BuOK / Var. bases 2: 91 percent / PPh3 / Pd2(dba)3*CHCl3 / 1,2-dimethoxy-ethane / 0.5 h / 0 °C View Scheme

Tsuji, Jiro; Minami, Ichiro; Shimizu, Isao

Tetrahedron Letters, 1983 , vol. 24, # 17 p. 1793 - 1796 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 85 percent / TiCl4 / diethyl ether; pentane / 1 h / Ambient temperature 2: 1) methyl trifluoromethanesulfonate, 2) 1,8-bis(dimethylamino)naphthalene / 1a) -80 deg C, 1b) RT, 15 min, 2) CH3CN, RT, 2h View Scheme

Welch, John T.; Corte, Bart De; Kimpe, Norbert De

Journal of Organic Chemistry, 1990 , vol. 55, # 17 p. 4981 - 4983 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar With water

3 h; Heating; Yield given;

Synthesize Find similar

Rx-ID: 3222226 Find similar reactions

Ihara, Masataka; Taniguchi, Takahiko; Makita, Kei; Takano, Michiko; Ohnishi, Masaru; Taniguchi, Nobuaki; Fukumoto, Keiichiro; Kabuto, Chizuko

Journal of the American Chemical Society, 1993 , vol. 115, # 18 p. 8107 - 8115 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 3630417 Find similar reactions

With amberlyst-15; water; acetone

17 h; Yield given;

Molander, Gary A.; Cameron, Kimberly O.

Journal of Organic Chemistry, 1993 , vol. 58, # 22 p. 5931 - 5943 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 18732700 Find similar reactions

Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 45 min, 2.) r.t., 3 h 2: acetone, Amberlyst-15, H2O / 17 h View Scheme

Molander, Gary A.; Cameron, Kimberly O.

Journal of Organic Chemistry, 1993 , vol. 58, # 22 p. 5931 - 5943 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar Multi-step reaction with 2 steps 1: butan-1-ol / 12 h / Heating 2: H2O / 3 h / Heating View Scheme

Synthesize Find similar

Rx-ID: 18771647 Find similar reactions

Ihara, Masataka; Taniguchi, Takahiko; Makita, Kei; Takano, Michiko; Ohnishi, Masaru; Taniguchi, Nobuaki; Fukumoto, Keiichiro; Kabuto, Chizuko

Journal of the American Chemical Society, 1993 , vol. 115, # 18 p. 8107 - 8115 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 3324623 Find similar reactions

99%

Synthesize Find similar

With sodium carbonate in water

48 h;

King; Rathore; Lam; Guo; Klassen

Journal of the American Chemical Society, 1992 , vol. 114, # 8 p. 3028 - 3033 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 3324624 Find similar reactions

A: 2 % Spectr. B: 92 % Spectr.

With sodium hydroxide in water

2 h; Ambient temperaturepH 10.8; Title compound not separated from byproducts;

King; Rathore; Lam; Guo; Klassen

Journal of the American Chemical Society, 1992 , vol. 114, # 8 p. 3028 - 3033 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

With N,N,N',N'-tetra-methylnaphthalene-1,8-diamine; methyl trifluoromethanesulfonate

1a) -80 deg C, 1b) RT, 15 min, 2) CH3CN, RT, 2h; Yield given. Multistep reaction;

Rx-ID: 2059307 Find similar reactions

Welch, John T.; Corte, Bart De; Kimpe, Norbert De

Journal of Organic Chemistry, 1990 , vol. 55, # 17 p. 4981 - 4983 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 2480679 Find similar reactions

With sulfuric acid; acetic acid in water

6 h; Heating;

Matsumoto, Kazutsugu; Tsutsumi, Seiji; Ihori, Tamiko; Ohta, Hiromichi

Journal of the American Chemical Society, 1990 , vol. 112, # 26 p. 9614 - 9619 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 21750648 Find similar reactions

Multi-step reaction with 2 steps 1: K2CO3 / acetone / Heating 2: conc. H2SO4, acetic acid / H2O / 6 h / Heating View Scheme

Matsumoto, Kazutsugu; Tsutsumi, Seiji; Ihori, Tamiko; Ohta, Hiromichi

Journal of the American Chemical Society, 1990 , vol. 112, # 26 p. 9614 - 9619 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 1793866 Find similar reactions

With ethylmagnesium bromide; triphenylphosphine; bis(acetylacetonato) palladium

1.) ether, 36-40 deg C, 3 h,2.) 40 deg C, 5 h; Multistep reaction;

Dzhemilev, U. M.; Minsker, D. L.; Khalilov, L. M.; Ibragimov, A. G.

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1988 , vol. 37, # 2 p. 298 - 302 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1988 , # 2 p. 378 - 382 Title/Abstract Full Text View citing articles Show Details

With ethylmagnesium bromide; triphenylphosphine; bis(acetylacetonato) palladium

1.) ether, 36-40 deg C, 3 h,2.) 40 deg C, 5 h; Yield given. Multistep reaction. Yields of byproduct given;

Dzhemilev, U. M.; Minsker, D. L.; Khalilov, L. M.; Ibragimov, A. G.

Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 1793867 Find similar reactions

With ethylmagnesium bromide; triphenylphosphine; bis(acetylacetonato) palladium

1.) ether, 2.) 36-40 deg C, 5 h; Yield given. Multistep reaction;

Dzhemilev, U. M.; Minsker, D. L.; Khalilov, L. M.; Ibragimov, A. G.

Synthesize Find similar

Rx-ID: 1793868 Find similar reactions

With ethylmagnesium bromide; triphenylphosphine; bis(acetylacetonato) palladium

1.) ether, 2.) 36-40 deg C, 5 h; Yield given. Multistep reaction;

Dzhemilev, U. M.; Minsker, D. L.; Khalilov, L. M.; Ibragimov, A. G.

Synthesize Find similar

Synthesize Find similar Rx-ID: 1793869 Find similar reactions

Synthesize Find similar

With ethylmagnesium bromide; triphenylphosphine; bis(acetylacetonato) palladium

1.) ether, 2.) 36-40 deg C, 5 h; Yield given. Multistep reaction;

Dzhemilev, U. M.; Minsker, D. L.; Khalilov, L. M.; Ibragimov, A. G.

Synthesize Find similar

Rx-ID: 1793870 Find similar reactions

With ethylmagnesium bromide; triphenylphosphine; bis(acetylacetonato) palladium

1.) ether, 2.) 36-40 deg C, 5 h; Yield given. Multistep reaction;

Dzhemilev, U. M.; Minsker, D. L.; Khalilov, L. M.; Ibragimov, A. G.

Synthesize Find similar

Rx-ID: 1793872 Find similar reactions

With ethylmagnesium bromide; triphenylphosphine; bis(acetylacetonato) palladium

1.) ether, 2.) 36-40 deg C, 5 h; Yield given. Multistep reaction;

Dzhemilev, U. M.; Minsker, D. L.; Khalilov, L. M.; Ibragimov, A. G.

Synthesize

Find similar

Rx-ID: 1793873 Find similar reactions

Find similar

With ethylmagnesium bromide; triphenylphosphine; bis(acetylacetonato) palladium

1.) ether, 2.) 36-40 deg C, 5 h; Yield given. Multistep reaction;

Find similar

Dzhemilev, U. M.; Minsker, D. L.; Khalilov, L. M.; Ibragimov, A. G.

Synthesize Find similar

Rx-ID: 1793875 Find similar reactions

Dzhemilev, U. M.; Minsker, D. L.; Khalilov, L. M.; Ibragimov, A. G.

With ethylmagnesium bromide; triphenylphosphine; bis(acetylacetonato) palladium

1.) ether, 2.) 36-40 deg C, 5 h; Yield given. Multistep reaction;

Synthesize Find similar

Rx-ID: 1793877 Find similar reactions

With ethylmagnesium bromide; triphenylphosphine; bis(acetylacetonato) palladium

1.) ether, 2.) 36-40 deg C, 5 h; Yield given. Multistep reaction;

Dzhemilev, U. M.; Minsker, D. L.; Khalilov, L. M.; Ibragimov, A. G.

Synthesize Find similar

Rx-ID: 2126291 Find similar reactions

81%

Synthesize Find similar

Toru, Takeshi; Yamada, Yoshio; Ueno, Toshio; Maekawa, Eturo; Ueno, Yoshio

Journal of the American Chemical Society, 1988 , vol. 110, # 14 p. 4815 - 4817 Title/Abstract Full Text View citing articles Show Details

in benzene

1.5 h; Irradiation;

Synthesize Find similar

Rx-ID: 2550658 Find similar reactions

With hydrogenchloride; tetrakis(triphenylphosphine) palladium(0); trifluoroacetic acid

1.) benzene, 50 deg C, 20 h; Yield given. Multistep reaction;

Murahashi, Shun-Ichi; Makabe, Yoshiki

Tetrahedron Letters, 1985 , vol. 26, # 45 p. 5563 - 5566 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 72 percent / Pd(PPh3), CF3COOH / benzene / 20 h / 50 °C 2: 2 N HCl / benzene / 1 h / Ambient temperature View Scheme

Murahashi, Shun-Ichi; Makabe, Yoshiki; Kunita, Kazuto

Journal of Organic Chemistry, 1988 , vol. 53, # 19 p. 4489 - 4495 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar With hydrogenchloride in benzene

1 h; Ambient temperature; Yield given;

Synthesize Find similar

Rx-ID: 2825139 Find similar reactions

Murahashi, Shun-Ichi; Makabe, Yoshiki; Kunita, Kazuto

Journal of Organic Chemistry, 1988 , vol. 53, # 19 p. 4489 - 4495 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 20433820 Find similar reactions

Multi-step reaction with 3 steps 1: 36 percent / p-toluenesulphonic acid monohydrate / benzene / Heating 2: 72 percent / Pd(PPh3), CF3COOH / benzene / 20 h / 50 °C 3: 2 N HCl / benzene / 1 h / Ambient temperature View Scheme

Murahashi, Shun-Ichi; Makabe, Yoshiki; Kunita, Kazuto

Journal of Organic Chemistry, 1988 , vol. 53, # 19 p. 4489 - 4495 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 1.) lithium diisopropylamide (LDA) / 1.) THF, -70 deg C, 20 min, 2.) THF, from -70 deg C to RT 2: 1.) MeLi / 1.) ether, RT, 90 min, 2.) THF, HMPA, from -70 deg C to RT View Scheme

Denmark, Scott E.; Hammer, Robert P.; Weber, Eric J.; Habermas, Karl L.

Journal of Organic Chemistry, 1987 , vol. 52, # 1 p. 165 - 168 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 3326904 Find similar reactions

Synthesize Find similar

With methyllithium

1.) ether, RT, 90 min, 2.) THF, HMPA, from -70 deg C to RT; Yield given. Multistep reaction;

Denmark, Scott E.; Hammer, Robert P.; Weber, Eric J.; Habermas, Karl L.

Journal of Organic Chemistry, 1987 , vol. 52, # 1 p. 165 - 168 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 76%

With Et2AlSPh in dichloromethane

T=25°C; 0.5 h;

Synthesize Find similar

Rx-ID: 1117465 Find similar reactions

Takai, Kazuhiko; Mori, Ichiro; Oshima, Koichiro; Nozaki, Hitosi

Tetrahedron Letters, 1981 , vol. 22, # 40 p. 3985 - 3988 Title/Abstract Full Text View citing articles Show Details

Takai; Mori; Oshima; Nozaki

Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 2 p. 446 - 451 Title/Abstract Full Text View citing articles Show Details

Lorette,N.B.; Howard,W.L.

Journal of Organic Chemistry, 1961 , vol. 26, p. 3112 - 3115 Full Text View citing articles Show Details

(heating);

House,H.O. et al.

Journal of Organic Chemistry, 1978 , vol. 43, p. 700 - 710 Full Text View citing articles Show Details

65 % Chromat.

With dichloro bis(acetonitrile) palladium(II) in benzene

2 h; Ambient temperature;

Baan, J. L. van der; Bickelhaupt, F.

Tetrahedron Letters, 1986 , vol. 27, # 51 p. 6267 - 6270 Title/Abstract Full Text View citing articles Show Details

With dichloro bis(acetonitrile) palladium(II)

2 h; Ambient temperaturevarious solvents; Product distribution;

Baan, J. L. van der; Bickelhaupt, F.

Tetrahedron Letters, 1986 , vol. 27, # 51 p. 6267 - 6270 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 90%

Synthesize Find similar

Rx-ID: 2154754 Find similar reactions

Vankar, Padma; Rathore, Rajendra; Chandrasekaran, Srinivasan

Journal of Organic Chemistry, 1986 , vol. 51, # 15 p. 3063 - 3065 Title/Abstract Full Text View citing articles Show Details

With (cetyl)Me3N(1+)MnO4(1-) in dichloromethane T=25°C; 0.333333 h;

Synthesize Find similar

Rx-ID: 3804210 Find similar reactions

Synthesize Find similar

With tetrakis(triphenylphosphine) palladium(0) in benzene

3 h; Ambient temperatureother β-keto acids and their lithium salts; other allylic acetates; Product distributionMechanism;

93 %

(0)

Tsuda, Tetsuo; Okada, Masahiro; Nishi, Sei-ichi; Saegusa, Takeo

Journal of Organic Chemistry, 1986 , vol. 51, # 4 p. 421 - 426 Title/Abstract Full Text View citing articles Show Details

Tsuda, Tetsuo; Okada, Masahiro; Nishi, Sei-ichi; Saegusa, Takeo

Chromat.

With tetrakis(triphenylphosphine) palladium 3 h; Ambient temperature;

in benzene

Journal of Organic Chemistry, 1986 , vol. 51, # 4 p. 421 - 426 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 3971349 Find similar reactions

Synthesize Find similar

37 % Chromat.

With lt;Pd(Ph3P)3gt; in tetrahydrofuran

4 h; Heatingmonoallylation; further substrates, allylic-substituted isoureas; further catalysts, solvents, temperatures, times; effect of solvents, ligands for catalysts investigated; regio- and stereoselectivity with propiophenone investigated; Product distribution;

Inoue, Yoshio; Toyofuku, Masanori; Taguchi, Masaaki; Okada, Shin-ichi; Hashimoto, Harukichi

Bulletin of the Chemical Society of Japan, 1986 , vol. 59, # 3 p. 885 - 892 Title/Abstract Full Text Show Details

37 % Chromat.

With lt;Pd(PhP3)3gt; in tetrahydrofuran

4 h; Heating;

Inoue, Yoshio; Toyofuku, Masanori; Taguchi, Masaaki; Okada, Shin-ichi; Hashimoto, Harukichi

Bulletin of the Chemical Society of Japan, 1986 , vol. 59, # 3 p. 885 - 892 Title/Abstract Full Text Show Details

Synthesize Find similar

Rx-ID: 3971350 Find similar reactions

A: 65 % Chromat.

With Pd(0)-bis(diphenylphosphino)ethane in dimethyl sulfoxide

0.25 h; Ambient temperaturemono- and diallylation; further solvents: hexamethylphosphoric triamide, dimethylformamide; further catalysts, temperatures, times; Product distribution;

Inoue, Yoshio; Toyofuku, Masanori; Taguchi, Masaaki; Okada, Shin-ichi; Hashimoto, Harukichi

Bulletin of the Chemical Society of Japan, 1986 , vol. 59, # 3 p. 885 - 892 Title/Abstract Full Text Show Details

A: 78 % Chromat.

With lt;Pd(PhP3)gt; in dimethyl sulfoxide

4 h; Ambient temperature;

Inoue, Yoshio; Toyofuku, Masanori; Taguchi, Masaaki; Okada, Shin-ichi; Hashimoto, Harukichi

Bulletin of the Chemical Society of Japan, 1986 , vol. 59, # 3 p. 885 - 892 Title/Abstract Full Text Show Details

A: 20 % Chromat.

With lt;Pd(Me2P(CH2)2PMe2)gt; in N,N-dimethyl-formamide

0.25 h; Ambient temperature; Title compound not separated from byproducts;

Inoue, Yoshio; Toyofuku, Masanori; Taguchi, Masaaki; Okada, Shin-ichi; Hashimoto, Harukichi

Bulletin of the Chemical Society of Japan, 1986 , vol. 59, # 3 p. 885 - 892 Title/Abstract Full Text Show Details

Synthesize Find similar

Rx-ID: 2341936 Find similar reactions

2 % Chromat.

Synthesize Find similar

Minami, Ichiro; Ohashi, Yukihiro; Shimizu, Isao; Tsuji, Jiro

Tetrahedron Letters, 1985 , vol. 26, # 20 p. 2449 - 2452 Title/Abstract Full Text View citing articles Show Details

With triphenylphosphine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex in tetrahydrofuran

T=65°C; 5 h;

Synthesize Find similar

Synthesize Find similar Rx-ID: 3568260 Find similar reactions

A: 82% B: 85%

With Celite; pyridinium chlorochromate in dichloromethane

40 h; Heatinghighly selective oxidative cleavage;

Narasimmhan, Vikram; Rathore, Rajendra; Chandrasekaran, S.

Synthetic Communications, 1985 , vol. 15, # 9 p. 769 - 774 Title/Abstract Full Text Show Details

Synthesize Find similar 60%

With potassium hydroxide in methanol

5 h; Ambient temperature;

Synthesize Find similar

Rx-ID: 7020446 Find similar reactions

Ravikumar, V. T.; Sathyamoorthi, G.; Thangaraj, K.; Rajagopalan, K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985 , vol. 24, p. 959 Title/Abstract Full Text Show Details

Synthesize Find similar

Rx-ID: 374273 Find similar reactions

With toluene-4-sulfonic acid; toluene

Howard; Lorette

Org. Synth. Coll. Vol., 1973 , vol. V, p. 25 Full Text Show Details

With toluene-4-sulfonic acid in toluene

Lorette,N.B.; Howard,W.L.

Journal of Organic Chemistry, 1961 , vol. 26, p. 3112 - 3115 Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 58 percent / Et2AlI, triethylamine / CH2Cl2 / 5 h / 25 °C 2: 76 percent / Et2AlSPh / CH2Cl2 / 0.5 h / 25 °C View Scheme

Takai; Mori; Oshima; Nozaki

Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 2 p. 446 - 451 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: TsOH / (heating) 2: (heating) View Scheme

Lorette,N.B.; Howard,W.L.

Journal of Organic Chemistry, 1961 , vol. 26, p. 3112 - 3115 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 1294993 Find similar reactions

Synthesize Find similar

(i) EtMgBr, THF, (ii) /BRN= 605308/, (iii) aq. HCl; Multistep reaction;

Stork,G.; Dowd,S.R.

Journal of the American Chemical Society, 1963 , vol. 85, p. 2178 - 2180 Full Text View citing articles Show Details

(i) LiNEt2, HMPT, benzene, Et2O, (ii) /BRN= 605308/, (iii) aq. HCl; Multistep reaction;

Cuvigny,T.; Normant,H.

Organometallics in Chemical Synthesis, 1971 , vol. 1, p. 237 - 247 Full Text View citing articles Show Details

With sodium amide; sodium t-butanolate

1.) THF, 60 deg C, 5 h; 2.) -35 deg C; Yield given. Multistep reaction;

Carre, M. C.; Ndebeka, G.; Riondel, A.; Bourgasser, P.; Caubere, P.

Tetrahedron Letters, 1984 , vol. 25, # 15 p. 1551 - 1554 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 1650005 Find similar reactions

A: 82 % Chromat. B: 7 % Chromat.

With triphenylphosphine; Pd-Gr in tetrahydrofuran; N-dodecane

2 h; Heating;

Boldrini, Gian Paolo; Savoia, Diego; Tagliavini, Emilio; Trombini, Claudio; Umani-Ronchi, Achille

Journal of Organometallic Chemistry, 1984 , vol. 268, # 1 p. 97 - 106 Title/Abstract Full Text View citing articles Show Details

A: 73 % Chromat. B: 16 % Chromat.

With triphenylphosphine; Pd-Gr in tetrahydrofuran; N-dodecane

2 h; Heating;

Boldrini, Gian Paolo; Savoia, Diego; Tagliavini, Emilio; Trombini, Claudio; Umani-Ronchi, Achille

Journal of Organometallic Chemistry, 1984 , vol. 268, # 1 p. 97 - 106 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 1650013 Find similar reactions

A: 81 % Chromat. B: 7 % Chromat.

With triphenylphosphine; Pd-Gr in tetrahydrofuran; N-dodecane

8 h; Heating;

Boldrini, Gian Paolo; Savoia, Diego; Tagliavini, Emilio; Trombini, Claudio; Umani-Ronchi, Achille

Journal of Organometallic Chemistry, 1984 , vol. 268, # 1 p. 97 - 106 Title/Abstract Full Text View citing articles Show Details

A: 81 % Chromat. B: 7 % Chromat.

With triphenylphosphine; Pd-Gr in tetrahydrofuran; N-dodecane

8 h; Heating;

Boldrini, Gian Paolo; Savoia, Diego; Tagliavini, Emilio; Trombini, Claudio; Umani-Ronchi, Achille

Journal of Organometallic Chemistry, 1984 , vol. 268, # 1 p. 97 - 106 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 1941092 Find similar reactions

56%

Synthesize Find similar

With [Rh(H)(PEt3)3]; tributylphosphine in 1,4-dioxane

T=100°C; 2 h;

Tsuji, Jiro; Minami, Ichiro; Shimizu, Isao

Tetrahedron Letters, 1984 , vol. 25, # 45 p. 5157 - 5160 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 1941096 Find similar reactions

A: 9 % Chromat. B: 91 % Chromat.

With tri-n-butyltin methoxide; [Pd(1,2-bis(diphenylphosphino)ethane)(OAc)2] in acetonitrile

T=80°C; var. catalyst,; Product distribution;

Tsuji, Jiro; Minami, Ichiro; Shimizu, Isao; Kataoka, Hideaki

Chemistry Letters, 1984 , p. 1133 - 1136 Title/Abstract Full Text Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 2342560 Find similar reactions

A: 67%

Synthesize Find similar

With 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) in N,N-dimethyl-formamide

1 h; Ambient temperaturevar.: solvent(THF, CH3CN), time, temperature(0 deg C, 60 deg C), catalyst; Yields of byproduct given;

Inoue, Yoshio; Toyofuku, Masanori; Hashimoto, Harukichi

Chemistry Letters, 1984 , p. 1227 - 1228 Title/Abstract Full Text Show Details

A: 20%

Inoue, Yoshio; Toyofuku, Masanori; Hashimoto, Harukichi

Chemistry Letters, 1984 , p. 1227 - 1228 Title/Abstract Full Text Show Details

With 1,2-bis(dimethylphosphine)ethane; bis(dibenzylideneacetone)-palladium(0) in N,N-dimethyl-formamide

0.25 h; Ambient temperaturevar.: solvent(CH3CN), time, temperature(0 deg C, 60 deg C), catalyst; Yield given;

Synthesize Find similar

Synthesize Find similar Rx-ID: 2542578 Find similar reactions

A: 15 % Chromat. B: 12 % Chromat. C: 21 % Chromat.

With palladium diacetate in triethylamine

T=80°C; var. catalyst, solvent and temp;; Product distribution;

Tsuji, Jiro; Minami, Ichiro; Shimizu, Isao; Kataoka, Hideaki

Chemistry Letters, 1984 , p. 1133 - 1136 Title/Abstract Full Text Show Details

Synthesize Find similar

Rx-ID: 2544311 Find similar reactions

98%

With tetrakis(triethylphosphite)nickel(O) in tetrahydrofuran

T=65°C; 1 h;

Tsuji, Jiro; Minami, Ichiro; Shimizu, Isao

Chemistry Letters, 1984 , p. 1721 - 1724 Title/Abstract Full Text Show Details

91%

With triphenylphosphine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex in ethylene glycol dimethyl ether

T=0°C; 0.5 h;

Tsuji, Jiro; Minami, Ichiro; Shimizu, Isao

Tetrahedron Letters, 1983 , vol. 24, # 17 p. 1793 - 1796 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 2653792 Find similar reactions

85%

With hexacarbonyl molybdenum in toluene

T=110°C; 10 h;

Tsuji, Jiro; Minami, Ichiro; Shimizu, Isao

Chemistry Letters, 1984 , p. 1721 - 1724 Title/Abstract Full Text Show Details

96 % Chromat.

With tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide

0.5 h; Ambient temperature;

Tsuda, Tetsuo; Chujo, Yoshiki; Nishi, Sei-ichi; Tawara, Kunio; Saegusa, Takeo

Journal of the American Chemical Society, 1980 , vol. 102, # 20 p. 6381 - 6384 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Synthesize Find similar Rx-ID: 2653793 Find similar reactions

A: 58% B: 19%

With tetrakis(triethylphosphite)nickel(O) in tetrahydrofuran

T=65°C; 3 h;

Tsuji, Jiro; Minami, Ichiro; Shimizu, Isao

Chemistry Letters, 1984 , p. 1721 - 1724 Title/Abstract Full Text Show Details

Synthesize Find similar

Rx-ID: 3325751 Find similar reactions

87%

Synthesize Find similar

Smith,A.B.; Toder,B.H.; Richmond,R.E.

Journal of the American Chemical Society, 1984 , vol. 106, p. 4001 Full Text View citing articles Show Details

in methanol

3 h; Heating;

Synthesize Find similar

Rx-ID: 1947996 Find similar reactions

Synthesize Find similar

A: 9% B: 81% C: 5%

With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine in tetrahydrofuran

0.333333 h; Ambient temperaturealso cat. Pd(O)-P(OEt)3; reaction time and temperature; allyl β-keto-carboxylates with allylic carbonates; new method for the diallylation of ketones; Product distributionMechanism;

Shimizu, Isao; Ohashi, Yukihiro; Tsuji, Jiro

Tetrahedron Letters, 1983 , vol. 24, # 36 p. 3865 - 3868 Title/Abstract Full Text View citing articles Show Details

A: 11% B: 2% C: 79%

With palladium; triethyl phosphite in tetrahydrofuran

T=65°C; 0.5 h;

Shimizu, Isao; Ohashi, Yukihiro; Tsuji, Jiro

Tetrahedron Letters, 1983 , vol. 24, # 36 p. 3865 - 3868 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 2542692 Find similar reactions

Henderson, Douglas; Richardson, Kevan A.; Taylor, Richard J. K.; Saunders, John

Synthesis, 1983 , # 12 p. 996 - 997 Title/Abstract Full Text Show Details

T=50°C; P=0.8 Torr; Yield given;

Synthesize Find similar

Synthesize Find similar Rx-ID: 2653791 Find similar reactions

A: 15% B: 16%

With [Pd(1,2-bis(diphenylphosphino)ethane)(OAc)2] in acetonitrile

Shimizu, Isao; Minami, Ichiro; Tsuji, Jiro

Tetrahedron Letters, 1983 , vol. 24, # 17 p. 1797 - 1800

Synthesize Find similar

C: 22%

Title/Abstract Full Text View citing articles Show Details

A: 15% B: 16% C: 22%

With [Pd(1,2-bis(diphenylphosphino)ethane)(OAc)2] in acetonitrile

Shimizu, Isao; Minami, Ichiro; Tsuji, Jiro

Tetrahedron Letters, 1983 , vol. 24, # 17 p. 1797 - 1800 Title/Abstract Full Text View citing articles Show Details

A: 15% B: 16% C: 22%

With [Pd(1,2-bis(diphenylphosphino)ethane)(OAc)2] in acetonitrile

Shimizu, Isao; Minami, Ichiro; Tsuji, Jiro

Tetrahedron Letters, 1983 , vol. 24, # 17 p. 1797 - 1800 Title/Abstract Full Text View citing articles Show Details

A: 15 % Chromat. B: 16 % Chromat. C: 22 % Chromat.

With palladium diacetate; 1,2-bis-(diphenylphosphino)ethane in acetonitrile

0.333333 h; Heating;

Shimizu, Isao; Tsuji, Jiro

Journal of the American Chemical Society, 1982 , vol. 104, # 21 p. 5844 - 5846 Title/Abstract Full Text View citing articles Show Details

A: 15 % Chromat. B: 16 % Chromat. C: 22 % Chromat.

With palladium diacetate; 1,2-bis-(diphenylphosphino)ethane in acetonitrile

0.333333 h; Heating;

Shimizu, Isao; Tsuji, Jiro

Journal of the American Chemical Society, 1982 , vol. 104, # 21 p. 5844 - 5846 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 3843390 Find similar reactions

93%

Synthesize Find similar

Tsuji, Jiro; Minami, Ichiro; Shimizu, Isao

Tetrahedron Letters, 1983 , vol. 24, # 43 p. 4713 - 4714 Title/Abstract Full Text View citing articles Show Details

With Pd(0)-bis(diphenylphosphino)ethane; tri-n-butyltin methoxide in 1,4-dioxane

10 h; Heating;

Synthesize Find similar Multi-step reaction with 3 steps 1: 1.) NaH, 2.) NaI / 1.) benzene, DMF, 30 min, 2.) 1h

Synthesize Find similar

Rx-ID: 21251406 Find similar reactions

Henderson, Douglas; Richardson, Kevan A.; Taylor, Richard J. K.; Saunders, John

Synthesis, 1983 , # 12 p. 996 - 997

2: trifluoroacetic acid / 0.5 h 3: 50 °C / 0.8 Torr View Scheme

Title/Abstract Full Text Show Details

Synthesize Find similar

Rx-ID: 21254097 Find similar reactions

Multi-step reaction with 2 steps 1: trifluoroacetic acid / 0.5 h 2: 50 °C / 0.8 Torr View Scheme

Henderson, Douglas; Richardson, Kevan A.; Taylor, Richard J. K.; Saunders, John

Synthesis, 1983 , # 12 p. 996 - 997 Title/Abstract Full Text Show Details

Synthesize Find similar

Rx-ID: 1983869 Find similar reactions

Synthesize Find similar

Hirao, Toshikazu; Yamada, Naoto; Ohshiro, Yoshiki; Agawa, Toshio

Journal of Organometallic Chemistry, 1982 , vol. 236, # 3 p. 409 - 414 Title/Abstract Full Text View citing articles Show Details

With tetrakis(triphenylphosphine) palladium(0); n-butyllithium

1.) THF, hexane, -78 deg C, 2.) THF, hexane, a) -78 deg C, 1 h, b) RT, overnight; Yield given. Multistep reaction;

Synthesize Find similar

Rx-ID: 2546699 Find similar reactions

A: 44% B: 46%

With tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide

Ambient temperaturefurther solvent;

Tsuda, Tetsuo; Chujo, Yoshiki; Nishi, Sei-ichi; Tawara, Kunio; Saegusa, Takeo

Journal of the American Chemical Society, 1980 , vol. 102, # 20 p. 6381 - 6384

C: 54% D: 40%

A: 44% B: 46% C: 54% D: 40%

Title/Abstract Full Text View citing articles Show Details

Tsuda, Tetsuo; Chujo, Yoshiki; Nishi, Sei-ichi; Tawara, Kunio; Saegusa, Takeo

Journal of the American Chemical Society, 1980 , vol. 102, # 20 p. 6381 - 6384 Title/Abstract Full Text View citing articles Show Details

With tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide

Ambient temperaturefurther solvents;

Synthesize Find similar

Synthesize Find similar Rx-ID: 2553854 Find similar reactions

A: 9% B: 67 % Chromat.

Tsuda, Tetsuo; Chujo, Yoshiki; Nishi, Sei-ichi; Tawara, Kunio; Saegusa, Takeo

Journal of the American Chemical Society, 1980 , vol. 102, # 20 p. 6381 - 6384 Title/Abstract Full Text View citing articles Show Details

With tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide

2 h; Ambient temperature;

Synthesize Find similar 79%

Synthesize Find similar

Rx-ID: 7020444 Find similar reactions

With triphenylphosphine in N,N-dimethyl-formamide

Ambient temperature;

Tsuda, Tetsuo; Chujo, Yoshiki; Nishi, Sei-ichi; Tawara, Kunio; Saegusa, Takeo

Journal of the American Chemical Society, 1980 , vol. 102, # 20 p. 6381 - 6384 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 371711 Find similar reactions

With potassium hydroxide

Cope; Hofmann; Hardy

Journal of the American Chemical Society, 1941 , vol. 63, p. 1855 Full Text Show Details

With potassium hydroxide in ethanol

Araujo,H.C.; Mahajan,J.R.

Synthesis, 1978 , p. 228 - 230 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 22067605 Find similar reactions

Multi-step reaction with 2 steps 1: ethanolic sodium ethylate 2: aqueous Ba(OH)2 View Scheme

Tiffeneau; Tchoubar; Saiaslambert

Bulletin de la Societe Chimique de France, 1947 , p. 445,448 Full Text Show Details

Multi-step reaction with 2 steps 1: ethanolic sodium ethylate 2: aqueous KOH View Scheme

Cope; Hofmann; Hardy

Journal of the American Chemical Society, 1941 , vol. 63, p. 1855 Full Text Show Details

Multi-step reaction with 2 steps 1: sodium; xylene 2: aqueous Ba(OH)2 View Scheme

Grewe

Chemische Berichte, 1943 , vol. 76, p. 1072,1076 Full Text Show Details

Multi-step reaction with 2 steps 1: KOtBu / 2-methyl-propan-2-ol 2: aq. KOH / ethanol View Scheme

Araujo,H.C.; Mahajan,J.R.

Synthesis, 1978 , p. 228 - 230 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 1294544 Find similar reactions

Synthesize Find similar

(i) nBuLi, THF, hexane, (ii) /BRN= 605308/, (iii) TiCl3; Multistep reaction;

Synthesize Find similar

Kofron,W.G.; Yeh,M.-K.

Journal of Organic Chemistry, 1976 , vol. 41, # 3 p. 439 - 442 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 1295609 Find similar reactions

Synthesize Find similar

Odic,Y.; Pereyre,M.

Journal of Organometallic Chemistry, 1973 , vol. 55, p. 273 - 294 Full Text View citing articles Show Details

(i) nBu3SnOMe, Et2O, (ii) MeLi, 1,2-dimethoxy-ethane, (iii) /BRN= 605308/; Multistep reaction;

Synthesize Find similar

Rx-ID: 4384013 Find similar reactions

Synthesize Find similar

Tsuji,J.

Bulletin of the Chemical Society of Japan, 1973 , vol. 46, p. 1896 - 1897 Full Text View citing articles Show Details

(i) Pd(OAc)2, Ph3P, MeCN, (ii) aq. HCl; Multistep reaction;

Synthesize Find similar With chromium(VI) oxide in acetone

Synthesize Find similar

Rx-ID: 1078980 Find similar reactions

Crandall,J.K. et al.

Journal of Organic Chemistry, 1971 , vol. 36, p. 1428 - 1433 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 1108876 Find similar reactions

in methanol

Irradiation;

Crandall,J.K. et al.

Journal of Organic Chemistry, 1971 , vol. 36, p. 1428 - 1433 Full Text View citing articles Show Details

in diethyl ether

Irradiation;

Moon,S.; Bohm,H.

Journal of Organic Chemistry, 1971 , vol. 36, # 10 p. 1434 - 1438 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 22520471 Find similar reactions

Multi-step reaction with 2 steps 1: aq. CrO3, H2SO4 / acetone 2: diethyl ether / Irradiation View Scheme

Moon,S.; Bohm,H.

Journal of Organic Chemistry, 1971 , vol. 36, # 10 p. 1434 - 1438 Full Text View citing articles Show Details

Synthesize Find similar Multi-step reaction with 3 steps 1: Py 3: methanol / Irradiation View Scheme

Synthesize Find similar

Rx-ID: 22535976 Find similar reactions

Crandall,J.K. et al.

Journal of Organic Chemistry, 1971 , vol. 36, p. 1428 - 1433 Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: Zn-Cu, I2 / diethyl ether 2: aq. CrO3, H2SO4 / acetone 3: diethyl ether / Irradiation View Scheme

Moon,S.; Bohm,H.

Journal of Organic Chemistry, 1971 , vol. 36, # 10 p. 1434 - 1438 Full Text View citing articles Show Details

Synthesize Find similar

Multi-step reaction with 2 steps 2: methanol / Irradiation View Scheme

Rx-ID: 22544466 Find similar reactions

Crandall,J.K. et al.

Journal of Organic Chemistry, 1971 , vol. 36, p. 1428 - 1433 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 923962 Find similar reactions

Synthesize Find similar

(i) MeCN, (ii) H2O; Multistep reaction;

Stork,G. et al.

Journal of the American Chemical Society, 1963 , vol. 85, p. 207 - 222 Full Text View citing articles Show Details

(i) dicyclohexyl-ethyl-amine, CHCl3, (ii) aq. HCl; Multistep reaction;

Opitz,G. et al.

Justus Liebigs Annalen der Chemie, 1961 , vol. 649, p. 47 - 57 Full Text View citing articles Show Details

Synthesize Find similar

Rx-ID: 7020442 Find similar reactions

With water; hydrogen bromide

Christol et al.

Bulletin de la Societe Chimique de France, 1959 , p. 543,553 Full Text Show Details

With sodium hydroxide; water

Colonge; Collomb

Bulletin de la Societe Chimique de France, 1951 , p. 241 Full Text View citing articles Show Details