Phosphate esters. Part II. The formation of monoterpene hydrocarbons from geranyl and neryl diphenyl phosphates

Abstract

The spontaneous decomposition of geranyl and neryl diphenyl phosphates in an inert solvent is shown to give a complex mixture of acyclic and cyclic terpene hydrocarbons. The constituents of the mixture have been identified, and possible mechanisms for their formation are discussed.

Terpene hydrocarbons are also formed when the two diphenyl phosphate esters are reduced with sodium borohydride. Reaction between allylic diphenyl phosphates and aryl Grignard reagents gives allylbenzenes in high yield.