Abstract
The reaction of ethynylferrocene with arenesulphenyl chlorides [ArSCl; Ar = Ph, p-ClC6H4, p-MeC6H4, p-MeOC6H4, p-NO2C6H4, or 2,4-(NO2)2C6H3] follows an unusual pathway; the main outcome is substitution of the acetylenic proton, rather than electrophilic addition to the triple bond. The following compounds were isolated and identified: FcCCSAr, FcCClCHSAr, and FcCClCH2 or FcCOCH3(Fc = ferrocenyl), depending on the reaction conditions. A mechanistic scheme is proposed.
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