Diphenyl disulfide → 2-(p-Isopropylphenyl)-5-(phenylthio)thiophene

Participants

Reaction Steps

Into 150 ml of reagent carbon tetrachloride were added 29 g (0.143 mole) 2-(p-isopropylphenyl)thiophene, 17 ml (21 g, 0.145 mole) of benzenesulfenyl chloride and 0.05 g of iron powder. At the end of four days a vapor phase chromatogram of the reaction mixture showed the presence of diphenyl disulfide, unreacted 2-(p-isopropylphenyl)thiophene and the desired product. An additional 4 ml (5 g, 0.035 mole) of benzenesulfenyl chloride and 0.05 g of iron powder was added and the mixture allowed to stand another four days at room temperature. Evaporation of the carbon tetrachloride gave a residue which was twice recrystallized from 250-ml portions of petroleum ether. There was obtained 16 g (36%) of 2-(p-isopropylphenyl)-5-(phenylthio)thiophene, m.p. 61°-63° C.

Provenance & Evidence