1-phenylprop-2-enylbenzene

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A flask was charged with 3,3-diphenylpropene (5.1 g, 26.3 mmol) in 100 ml CH2Cl2. It was followed by portionwise addition of mCPBA (9.1 g, 70% purity, 52.6 mmol) at 0° C. The mixture was stirred at room temperature for 24 h and the reaction was then quenched with 30 ml 1M Na2SO3. The aqueous layer was extracted with CH2Cl2 (2×100 ml). The combined organic phases were washed in turn with saturated NaHCO3, brine, and then dried over anhydrous Na2SO4. Purification by flash chromatography (Hexane/ether=9:1) gave pure 2-benzhydryl-oxirane, 4.7 g (85%). the reaction was then quenched with 30 ml 1M Na2SO3 The aqueous layer was extracted with CH2Cl2 (2×100 ml) The combined organic phases were washed in turn with saturated NaHCO3, brine dried over anhydrous Na2SO4 Purification by flash chromatography (Hexane/ether=9:1)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyltriphenylphosphonium bromide (4 g, 11.12 mmol) was added over a 15-min period to a mixture of butyllithium (7.3 ml of 1.6 M solution in THF, 11.76 mmol) and dry THF (50 ml) with stirring and under nitrogen atmosphere at 0° C. The reaction mixture was stirred for 2 h at room temperature and the mixture was then recooled to −78° C. A solution of diphenylacetaldehyde (2.2 g, 11.12 mmol) in dry THF (10 ml) was added to the above mixture over a 15-min period. The reaction mixture was stirred for 24 h at room temperature, followed by addition of ethyl ether (200 ml), and the reaction mixture was then filtered. The ether extracts were washed with water (3×50 ml), brine (100 ml) and dried over anhydrous sodium sulfate. The crude material was purified by flash chromatography on silical gel (Hexane:Ethyl ether=9:1) to give pure 3,3-diphenylpropene 460 mg (46%). The reaction mixture was stirred for 2 h at room temperature was then recooled to −78° C The reaction mixture was stirred for 24 h at room temperature the reaction mixture was then filtered The ether extracts were washed with water (3×50 ml), brine (100 ml) dried over anhydrous sodium sulfate The crude material was purified by flash chromatography on silical gel (Hexane:Ethyl ether=9:1)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyltriphenylphosphonium bromide (4 g, 11.12 mmol) was added over a 15-min period to a mixture of butyllithium (7.3 ml of 1.6 M solution in THF, 11.76 mmol) and dry THF (50 ml) with stirring and under nitrogen atmosphere at 0° C. The reaction mixture was stirred for 2 h at room temperature and the mixture was then recooled to −78° C. A solution of diphenylacetaldehyde (2.2 g, 11.12 mmol) in dry THF (10 ml) was added to the above mixture over a 15-min period. The reaction mixture was stirred for 24 h at room temperature, followed by addition of ethyl ether (200 ml), and the reaction mixture was then filtered. The ether extracts were washed with water (3×50 ml), brine (100 ml) and dried over anhydrous sodium sulfate. The crude material was purified by flash chromatography on silical gel (Hexane:Ethyl ether=9:1) to give pure 3,3-diphenylpropene 460 mg (46%). The reaction mixture was stirred for 2 h at room temperature was then recooled to −78° C The reaction mixture was stirred for 24 h at room temperature the reaction mixture was then filtered The ether extracts were washed with water (3×50 ml), brine (100 ml) dried over anhydrous sodium sulfate The crude material was purified by flash chromatography on silical gel (Hexane:Ethyl ether=9:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A flask was charged with 3,3-diphenylpropene (5.1 g, 26.3 mmol) in 100 ml CH2Cl2. It was followed by portionwise addition of mCPBA (9.1 g, 70% purity, 52.6 mmol) at 0° C. The mixture was stirred at room temperature for 24 h and the reaction was then quenched with 30 ml 1M Na2SO3. The aqueous layer was extracted with CH2Cl2 (2×100 ml). The combined organic phases were washed in turn with saturated NaHCO3, brine, and then dried over anhydrous Na2SO4. Purification by flash chromatography (Hexane/ether=9:1) gave pure 2-benzhydryl-oxirane, 4.7 g (85%). the reaction was then quenched with 30 ml 1M Na2SO3 The aqueous layer was extracted with CH2Cl2 (2×100 ml) The combined organic phases were washed in turn with saturated NaHCO3, brine dried over anhydrous Na2SO4 Purification by flash chromatography (Hexane/ether=9:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A flask was charged with 3,3-diphenylpropene (5.1 g, 26.3 mmol) in 100 ml CH2Cl2. It was followed by portionwise addition of mCPBA (9.1 g, 70% purity, 52.6 mmol) at 0° C. The mixture was stirred at room temperature for 24 h and the reaction was then quenched with 30 ml 1M Na2SO3. The aqueous layer was extracted with CH2Cl2 (2×100 ml). The combined organic phases were washed in turn with saturated NaHCO3, brine, and then dried over anhydrous Na2SO4. Purification by flash chromatography (Hexane/ether=9:1) gave pure 2-benzhydryl-oxirane, 4.7 g (85%). the reaction was then quenched with 30 ml 1M Na2SO3 The aqueous layer was extracted with CH2Cl2 (2×100 ml) The combined organic phases were washed in turn with saturated NaHCO3, brine dried over anhydrous Na2SO4 Purification by flash chromatography (Hexane/ether=9:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyltriphenylphosphonium bromide (4 g, 11.12 mmol) was added over a 15-min period to a mixture of butyllithium (7.3 ml of 1.6 M solution in THF, 11.76 mmol) and dry THF (50 ml) with stirring and under nitrogen atmosphere at <ALOKE, Temp.>° C. The reaction mixture was stirred for 2 h at room temperature and the mixture was then recooled to −78° C. A solution of diphenylacetaldehyde (2.2 g, 11.12 mmol) in dry THF(10 ml) was added to the above mixture over a 15-min period. The reaction mixture was stirred for 24 h at room temperature, followed by addition of ethyl ether (200 ml), and the reaction mixture was then filtered. The ether extracts were washed with water (3×50 ml), brine (100 ml) and dried over anhydrous sodium sulfate. The crude material was purified by flash chromatography on silical gel (Hexane:Ethyl ether=9:1) to give pure 3,3-diphenylpropene 460 mg (46%). The reaction mixture was stirred for 2 h at room temperature was then recooled to −78° C The reaction mixture was stirred for 24 h at room temperature the reaction mixture was then filtered The ether extracts were washed with water (3×50 ml), brine (100 ml) dried over anhydrous sodium sulfate The crude material was purified by flash chromatography on silical gel (Hexane:Ethyl ether=9:1)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A flask was charged with 3,3-diphenylpropene (5.1 g, 26.3 mmol) in 100 ml CH2Cl2. It was followed by portionwise addition of mCPBA (9.1 g, 70% purity, 52.6 mmol) at 0° C. The mixture was stirred at room temperature for 24 h and the reaction was then quenched with 30 ml 1M Na2SO3. The aqueous layer was extracted with CH2Cl2 (2×100 ml). The combined organic phases were washed in turn with saturated NaHCO3, brine, and then dried over anhydrous Na2SO4. Purification by flash chromatography (Hexane/ether=9:1) gave pure 2-benzhydryl-oxirane, 4.7 g (85%). the reaction was then quenched with 30 ml 1M Na2SO3 The aqueous layer was extracted with CH2Cl2 (2×100 ml) The combined organic phases were washed in turn with saturated NaHCO3, brine dried over anhydrous Na2SO4 Purification by flash chromatography (Hexane/ether=9:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyltriphenylphosphonium bromide (4 g, 11.12 mmol) was added over a 15-min period to a mixture of butyllithium (7.3 ml of 1.6 M solution in THF, 11.76 mmol) and dry THF (50 ml) with stirring and under nitrogen atmosphere. The reaction mixture was stirred for 2 h at room temperature and the mixture was then recooled to −78° C. A solution of diphenylacetaldehyde (2.2 g, 11.12 mmol) in dry THF (10 ml) was added to the above mixture over a 15-min period. The reaction mixture was stirred for 24 h at room temperature, followed by addition of ethyl ether (200 ml), and the reaction mixture was then filtered. The ether extracts were washed with water (3×50 ml), brine (100 ml) and dried over anhydrous sodium sulfate. The crude material was purified by flash chromatography on silical gel (Hexane:Ethyl ether=9:1) to give pure 3,3-diphenylpropene 460 mg (46%). The reaction mixture was stirred for 2 h at room temperature was then recooled to −78° C The reaction mixture was stirred for 24 h at room temperature the reaction mixture was then filtered The ether extracts were washed with water (3×50 ml), brine (100 ml) dried over anhydrous sodium sulfate The crude material was purified by flash chromatography on silical gel (Hexane:Ethyl ether=9:1)