28444-00-0Relevant academic research and scientific papers
Novel efficient aromatic arylthiolation by disulfide radical cations generated by oxidation of diaryl disulfides
Takeuchi, Hiroshi,Hiyama, Takehiro,Kamai, Noriyoshi,Oya, Hiromi
, p. 2301 - 2305 (2007/10/03)
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 Hammett plot with ρ = -7.0 (using SbCl5 in CH2Cl2), from effects of oxidants, counter-anions and solvents and from electronic absorptions (540 and 650 nm). Using di-4-anisyl, di-4-tolyl and di-4-chlorophenyl disulfides instead of diphenyl disulfide, the aromatic arylthiolation similarly occurs via radical cations from their disulfides.
