(PORPHINATO)IRON-CATALYZED ADDITION-REACTIONS OF THIOLS TO ALKENES VIA (SIGMA-ALKYL)IRON(II) COMPLEXES

The Markovnikov-type addition of thiols (derived from the correspondin g disulfides) to alkenes occurs in anaerobic benzene-ethanol solutions containing NaBH4 and (porphinato)iron(III) chloride (Por-Fe(III)Cl). For example, the reaction of styrene with diphenyl disulfide affords p henyl 1-phenylethyl sulfide. It has been assumed that the hydride tran sfer from BH4- to styrene yields 1-phenylethanide which is stabilized by coordinating to Por-Fe(II) and that the resulting (sigma-alkyl)iron (II) complex having a carbanion character reacts with diphenyl disulfi de to give phenyl 1-phenylethyl sulfide and the thiophenolate ion.