2-phenylbenzenethiol

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

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

Conditions: temp:375.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A volume of 1.5 ml of a tetralin solution containing 0.1 M of 2-phenylthiopheol was placed into 3 ml stainless-steel mini-bomb inside a dry-box. The mini-bomb was heated at 375° C. in an oven for a certain period of time and the content analyzed by GC/MS. Results in Table 1 below indicate desulfurization of 2-phenylthiophenol, giving biphenyl as the major product. Results in Table 1

Conditions: temp:400.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A volume of 1.5 ml of a tetralin solution containing 0.1 M of 2-phenylthiopheol was placed into 3 ml stainless-steel mini-bomb inside a dry-box. The mini-bomb was heated at 400° C. in an oven for a certain period of time and the content analyzed by GC/MS. Results in Table 1 below indicate desulfurization of 2-phenylthiophenol, giving biphenyl as the major product. Results in Table 1

Conditions: temp:400.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A volume of 1.5 ml of a tetralin solution containing 0.1 M of 2-phenylthiopheol was placed into 3 ml stainless-steel mini-bomb inside a dry-box. The mini-bomb was heated at 400° C. in an oven for a certain period of time and the content analyzed by GC/MS. Results in Table 1 below indicate desulfurization of 2-phenylthiophenol, giving biphenyl as the major product. Results in Table 1

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

Procedure: To a solution composed of 40 ml of DMF and 4.66 g (25 mmol) of 2-mercaptobiphenyl was added 1.00 g (25 mmol) of sodium hydride (60% in oil) little by little under ice cooling and stirring. Then, 13.6 g (25 mmol) of perfluorooctyl iodide was added. The temperature of the mixture was slowly elevated to room temperature, and the mixture was stirred for 2 hours. Water was addd to the reaction mixture, and the mixture was extracted with hexane. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give a brown oil. It was purified by silica gel column chromatography using hexane as an eluent to give 9.60 g (64%) of 2-(perfluorooctylthio)biphenyl as a colorless oil. The properties of the product were as shown below. was slowly elevated to room temperature the mixture was stirred for 2 hours the mixture was extracted with hexane The organic layer was washed with saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under reduced pressure to give a brown oil It was purified by silica gel column chromatography

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

Procedure: To a solution composed of 20 ml of DMF and 2.24 g (12 mmol) of 2-mercaptobiphenyl was added 481 mg (12 mmol) of sodium hydride (60% in oil) little by little under ice cooling and stirring. Then, 1.73 ml (12 mmol) of perfluoropropyl iodide was added dropwise. The temperature of the mixture was slowly elevated to room temperature, and the mixture was stirred for 2 days. The white precipitate formed in the reaction solution was removed by filtration. Water was addd to the filtrate, and the mixture was extracted with hexane. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give a brown oil. It was purified by silica gel column chromatography (ethyl acetate:hexane=1:30) to give 3.46 g (87.3%) of 2-(heptafluoropropylthio)biphenyl as a colorless oil. The properties of the product were as shown below. was slowly elevated to room temperature the mixture was stirred for 2 days The white precipitate formed in the reaction solution was removed by filtration the mixture was extracted with hexane The organic layer was washed with water dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under reduced pressure to give a brown oil It was purified by silica gel column chromatography (ethyl acetate:hexane=1:30)

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

Procedure: To a solution composed of 20 ml of DMF and 2.24 g (12 mmol) of 2-mercaptobiphenyl was added 481 mg (12 mmol) of sodium hydride (60% in oil) little by little under ice cooling and stirring. Then, 1.73 ml (12 mmol) of perfluoropropyl iodide was added dropwise. The temperature of the mixture was slowly elevated to room temperature, and the mixture was stirred for 2 days. The white precipitate formed in the reaction solution was removed by filtration. Water was addd to the filtrate, and the mixture was extracted with hexane. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give a brown oil. It was purified by silica gel column chromatography (ethyl acetate:hexane=1:30) to give 3.46 g (87.3%) of 2-(heptafluoropropylthio)biphenyl as a colorless oil. The properties of the product were as shown below. was slowly elevated to room temperature the mixture was stirred for 2 days The white precipitate formed in the reaction solution was removed by filtration the mixture was extracted with hexane The organic layer was washed with water dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under reduced pressure to give a brown oil It was purified by silica gel column chromatography (ethyl acetate:hexane=1:30)

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

Procedure: A reaction tube in a photoreaction apparatus was charged with 50 ml of dimethylformamide (DMF) and 5.59 g (30 mmol) of 2-mercaptobiphenyl, and with ice cooling and stirring, 1.2 g (30 mmol) of sodium hydride (60% in oil) was added. When foaming ceased, trifluoromethyl bromide was introduced into the reaction solution. The atmosphere within the reaction system was replaced by gaseous trifluoromethyl bromide, and while irradiating light from a high-pressure mercury lamp, about 2 equivalents of trifluoromethyl bromide was passed into the reaction system over about 2 hours. Ice water (150 ml) was added to the resulting brown reaction solution, and it was extracted with pentane. The organic layer was washed with water and then with saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The anhydrous magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give 6.71 g (87.9%) of 2-(trifluoromethylthio)biphenyl as an oil. It was purified by silica gel column chromatography. The properties of the product were as shown below. while irradiating light from a high-pressure mercury lamp was extracted with pentane The organic layer was washed with water with saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate The anhydrous magnesium sulfate was removed by filtration the filtrate was concentrated under reduced pressure

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

Conditions: temp:375.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A volume of 1.5 ml of a tetralin solution containing 0.1 M of 2-phenylthiopheol was placed into 3 ml stainless-steel mini-bomb inside a dry-box. The mini-bomb was heated at 375° C. in an oven for a certain period of time and the content analyzed by GC/MS. Results in Table 1 below indicate desulfurization of 2-phenylthiophenol, giving biphenyl as the major product. Results in Table 1

Conditions: temp:400.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A volume of 1.5 ml of a tetralin solution containing 0.1 M of 2-phenylthiopheol was placed into 3 ml stainless-steel mini-bomb inside a dry-box. The mini-bomb was heated at 400° C. in an oven for a certain period of time and the content analyzed by GC/MS. Results in Table 1 below indicate desulfurization of 2-phenylthiophenol, giving biphenyl as the major product. Results in Table 1