Carbodiphosphorane mediated synthesis of a triflyloxyphosphonium dication and its reactivity towards nucleophiles

Abstract

A carbodiphosphorane ((Ph₃P)₂C) mediated synthesis of the first triflyloxyphosphonium dication (1²⁺) bearing two electrophilic sites is presented. Depending on the nucleophile, 1²⁺ reacts selectively either at the sulfur atom of the triflyloxy moiety or at the directly attached phosphorus atom. In substitution reactions at the phosphorus atom the triflyloxy moiety serves as a leaving group and enables the synthesis of rare examples of pseudo-halophosphonium dications.