Reactivity of phosphonium diylids with esters and amides

Article abstract of DOI:10.1016/0022-328X(88)83132-2

The phosphonium diylid (C6H5)2P(CH2)(CH2Li) reacts readily with various esters and amides to give acylated phosphonium salts and Wittig products.In the case of N,N-dimethylbenzamide the reaction can be directed mainly to the Wittig products by protonation.Depending on the nature of the carbonyl group, unexpected reactions, such as conjugate additions to α,β-unsaturated compounds or enolization of α-hydrogenated amides, can also take place.