Ozonolysis of Allenes and Alkylidenecyclopropanes (Homoallenes)

Abstract

Allenyl methyl ether (1) and (diphenylmethylene)cyclopropane (5) were ozonized with an ozone/oxygen mixture. Formation of the observed products cannot be satisfactorily rationalized via the familiar modified Criegee mechanism. However, a single-electron transfer (SET) mechanism provides a simple rationale.