Preparation and properties of some stable arsonium ylides

Stable crystalline arsonium ylides have been prepared by thermal decomposition of diazo compounds in the presence of triphenylarsine, and by condensation reactions of reactive methylene compounds with triphenylarsine oxide. The spectra of these ylides, and their reactions with benzaldehydes are discussed. Like other stabilised arsonium ylides they give alkenes rather than epoxides in Wittig reactions. They are generally more polar than their phosphonium analogues and also are more reactive in the Wittig reaction. With diphenylcyclopropenone some more reactive arsonium ylides form α-pyrones.