Phosphate esters. Part 3. Formation of sesquiterpene hydrocarbons from cis,trans- and trans,trans-farnesyl diphenyl phosphates

Abstract

Decomposition of cis,trans- and trans,trans-farnesyl diphenyl phosphates gives mixtures of both acyclic and cyclic sesquiterpene hydrocarbons consisting of β-farnesene, cis-and trans-α-farnesenes, and cis-α- and trans-α-, β-, and γ-bisabolenes, together with small quantities of trans-nerolidol and bisabolol. The proportion of the cyclic hydrocarbons was greater from the cis,trans-farnesyl diphenyl phosphate. Solvolysis of geranyl chloride gives linaloöl and geraniol but no cyclic products. The mechanisms of these reactions are discussed.