Reactions of the oxirane group

Epoxidized oils and esters have been used commercially for about two decades; their consumption is now of the order of 100 million lb./year, mainly as stabilizer‐plasticizers for vinyl chloride polymers. Yet in spite of their low price and ready availability, chemical derivatives of these substances have not achieved similar commercialization. It has long been known that the oxirane group is highly reactive and undergoes a wide variety of ring‐opening reactions with a broad range of electrophiles and nucleophiles. During the past ten years, in particular, new and interesting reactions of the oxirane group have been described that provide new routes to other heterocyclic ring systems and functional groups. After a brief background survey, recently published and unpublished reactions from the author’s laboratory, as well as reactions published by other groups, are described.