The Markovnikov-type addition of thiols (derived from the corresponding disulfides) to alkenes occurs in anaerobic benzene-ethanol solutions containing NaBH 4 and (porphinato)iron(III) chloride (Por-FeIIICl). For example, the reaction of styrene with diphenyl disulfide affords phenyl 1-phenylethyl sulfide. It has been assumed that the hydride transfer from BH4- to styrene yields 1-phenylethanide which is stabilized by coordinating to Por-FeII and that the resulting (σ-alkyl)iron(II) complex having a carbanion character reacts with diphenyl disulfide to give phenyl 1-phenylethyl sulfide and the thiophenolate ion.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry