Novel efficient aromatic arylthiolation by disulfide radical cations generated by oxidation of diaryl disulfides

H Takeuchi, T Hiyama, N Kamai, H Ōya

Index: Takeuchi, Hiroshi; Hiyama, Takehiro; Kamai, Noriyoshi; Oya, Hiromi Journal of the Chemical Society. Perkin Transactions 2, 1997 , # 11 p. 2301 - 2305

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Abstract

The disulfide radical cation was generated by oxidation of diphenyl disulfide using H2SO4 in CF3CO2H or SbCl5 in CH2Cl2, and allowed to react with benzene, toluene, ethylbenzene, chlorobenzene, anisole and alkyl phenyl sulfides to give efficiently para-substituted diphenyl sulfides along with a small amount of the ortho-isomers. The intermediacy of the radical cation in this aromatic phenylthiolation is consistent with the evidence derived from a ...