1-phenylprop-2-yn-1-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6.23 g (0.039 mole) of diazooxindole and 6.6 g (0.051 mole or 1.3 equiv) of the phenylethynyl ketone prepared as in part A above (dried on a porous plate before being weighed out) are suspended in benzene (275 ml) and the mixture is refluxed under N2 for 19 hours. The reaction mixture is cooled and the precipitates that form are filtered off, washed well with anhydrous ether (150 ml) and dried in a vacuum oven at ~70° for 1-1/2 hours. Yield: 10.3 g, m.p. 308°-311°. Additional product of 400 mg is obtained on refluxing the filtrate for another 24 hours. Total crude yield: 94.4%. dried on a porous plate the mixture is refluxed under N2 for 19 hours The reaction mixture is cooled the precipitates that form are filtered off washed well with anhydrous ether (150 ml) dried in a vacuum oven at ~70° for 1-1/2 hours Additional product of 400 mg is obtained on refluxing the filtrate for another 24 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6.23 g (0.039 mole) of diazooxindole and 6.6 g (0.051 mole or 1.3 equiv) of the phenylethynyl ketone prepared as in part A above (dried on a porous plate before being weighed out) are suspended in benzene (275 ml) and the mixture is refluxed under N2 for 19 hours. The reaction mixture is cooled and the precipitates that form are filtered off, washed well with anhydrous ether (150 ml) and dried in a vacuum oven at ~70° for 1-1/2 hours. Yield: 10.3 g, m.p. 308°-311°. Additional product of 400 mg is obtained on refluxing the filtrate for another 24 hours. Total crude yield: 94.4%. dried on a porous plate the mixture is refluxed under N2 for 19 hours The reaction mixture is cooled the precipitates that form are filtered off washed well with anhydrous ether (150 ml) dried in a vacuum oven at ~70° for 1-1/2 hours Additional product of 400 mg is obtained on refluxing the filtrate for another 24 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1-phenyl-2-propyne-1-ol (34.2 g) in 50 ml acetone is cooled down to 0°, stirred under N2 and treated dropwise, over a period of 3 hours with a solution of chromium trioxide (17.5 g) in water (50 ml) and concentrated sulfuric acid (14.8 ml), keeping the temperature below 5° at all times. After the addition is complete, the mixture is stirred for another hour at 5°. The reaction mixture is then diluted with water (100 ml) and extracted with two 250-ml portions of ether. The organic extracts are combined, dried over anhydrous sodium sulfate, filtered and stripped to give a yellow product. A small amount dried on a porous plate gives a m.p. of 45°-47°. the temperature below 5° After the addition the mixture is stirred for another hour at 5° extracted with two 250-ml portions of ether dried over anhydrous sodium sulfate filtered to give a yellow product A small amount dried on a porous plate gives a m.p. of 45°-47°

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6.23 g (0.039 mole) of diazooxindole and 6.6 g (0.051 mole or 1.3 equiv) of the phenylethynyl ketone prepared as in part A above (dried on a porous plate before being weighed out) are suspended in benzene (275 ml) and the mixture is refluxed under N2 for 19 hours. The reaction mixture is cooled and the precipitates that form are filtered off, washed well with anhydrous ether (150 ml) and dried in a vacuum oven at ~70° for 11/2 hours. Yield: 10.3 g, m.p. 308°-311°. Additional product of 400 mg is obtained on refluxing the filtrate for another 24 hours. Total crude yield: 94.4%. dried on a porous plate the mixture is refluxed under N2 for 19 hours The reaction mixture is cooled the precipitates that form are filtered off washed well with anhydrous ether (150 ml) dried in a vacuum oven at ~70° for 11/2 hours Additional product of 400 mg is obtained on refluxing the filtrate for another 24 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1-phenyl-2-propyne-1-ol (34.2 g) in 50 ml acetone is cooled down to 0°, stirred under N2 and treated dropwise, over a period of 3 hours with a solution of chromium trioxide (17.5 g) in water (50 ml) and concentrated sulfuric acid (14.8 ml), keeping the temperature below 5° at all times. After the addition is complete, the mixture is stirred for another hour at 5°. The reaction mixture is then diluted with water (100 ml) and extracted with two 250-ml portions of ether. The organic extracts are combined, dried over anhydrous sodium sulfate, filtered and stripped to give a yellow product. A small amount dried on a porous plate gives a m.p. of 45°-47°. the temperature below 5° After the addition the mixture is stirred for another hour at 5° extracted with two 250-ml portions of ether dried over anhydrous sodium sulfate filtered to give a yellow product A small amount dried on a porous plate gives a m.p. of 45°-47°

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6.23 g (0.039 mole) of diazooxindole and 6.6 g (0.051 mole or 1.3 equiv) of the phenylethynyl ketone prepared as in part A above (dried on a porous plate before being weighed out) are suspended in benzene (275 ml) and the mixture is refluxed under N2 for 19 hours. The reaction mixture is cooled and the precipitates that form are filtered off, washed well with anhydrous ether (150 ml) and dried in a vacuum oven at ~70° for 11/2 hours. Yield: 10.3 g, m.p. 308°-311°. Additional product of 400 mg is obtained on refluxing the filtrate for another 24 hours. Total crude yield: 94.4%. dried on a porous plate the mixture is refluxed under N2 for 19 hours The reaction mixture is cooled the precipitates that form are filtered off washed well with anhydrous ether (150 ml) dried in a vacuum oven at ~70° for 11/2 hours Additional product of 400 mg is obtained on refluxing the filtrate for another 24 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1-phenyl-2-propyne-1-ol (34.2 g) in 50 ml acetone is cooled down to 0°, stirred under N2 and treated dropwise, over a period of 3 hours with a solution of chromium trioxide (17.5 g) in water (50 ml) and concentrated sulfuric acid (14.8 ml), keeping the temperature below 5° at all times. After the addition is complete, the mixture is stirred for another hour at 5°. The reaction mixture is then diluted with water (100 ml) and extracted with two 250-ml portions of ether. The organic extracts are combined, dried over anhydrous sodium sulfate, filtered and stripped to give a yellow product. A small amount dried on a porous plate gives a m.p. of 45°-47°. the temperature below 5° After the addition the mixture is stirred for another hour at 5° extracted with two 250-ml portions of ether dried over anhydrous sodium sulfate filtered to give a yellow product A small amount dried on a porous plate gives a m.p. of 45°-47°

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6.23 g (0.039 mole) of diazooxindole and 6.6 g (0.051 mole or 1.3 equiv) of the phenylethynyl ketone prepared as in part A above (dried on a porous plate before being weighed out) are suspended in benzene (275 ml) and the mixture is refluxed under N2 for 19 hours. The reaction mixture is cooled and the precipitates that form are filtered off, washed well with anhydrous ether (150 ml) and dried in a vacuum oven at ~70° for 1-1/2 hours. Yield: 10.3 g, m.p. 308°-311°. Additional product of 400 mg is obtained on refluxing the filtrate for another 24 hours. Total crude yield: 94.4%. dried on a porous plate the mixture is refluxed under N2 for 19 hours The reaction mixture is cooled the precipitates that form are filtered off washed well with anhydrous ether (150 ml) dried in a vacuum oven at ~70° for 1-1/2 hours Additional product of 400 mg is obtained on refluxing the filtrate for another 24 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1-phenyl-2-propyne-1-ol (34.2 g) in 50 ml acetone is cooled down to 0°, stirred under N2 and treated dropwise, over a period of 3 hours with a solution of chromium trioxide (17.5 g) in water (50 ml) and concentrated sulfuric acid (14.8 ml), keeping the temperature below 5° at all times. After the addition is complete, the mixture is stirred for another hour at 5°. The reaction mixture is then diluted with water (100 ml) and extracted with two 250-ml portions of ether. The organic extracts are combined, dried over anhydrous sodium sulfate, filtered and stripped to give a yellow product. A small amount dried on a porous plate gives a m.p. of 45°-47°. the temperature below 5° After the addition the mixture is stirred for another hour at 5° extracted with two 250-ml portions of ether dried over anhydrous sodium sulfate filtered to give a yellow product A small amount dried on a porous plate gives a m.p. of 45°-47°