Synthesis of (E,Z)-α-,(Z,Z)-α-, and (Z)-β-farnesene

Abstract

The three farnesenes (E,Z)-or-, (Z,Z)-or-, and (2)-P- were synthesized from (cis) (2)-nerolidol by dehydration with phosphoryl chloride in pyridine. The i.r., u.v., N.M.R., and mass spectra of the six possible α- and β-farnesenes are compared as well as their behaviour on g.1.c. on several liquid phases. The α-farnesene which predominates in apples was confirmed as being (E,E)-α-farnesene and the minor isomer, previously thought to be (E,Z)-α-farnesene, was shown to be (Z,E)-α- farnesene.