Acid catalysed isomerisations in the hexyne-hexadiene system

Abstract

Acid catalysed isomerisations in the hexyne-hexadiene system (1-hexyne, 2-hexyne, 3-hexyne, 1,2-hexadiene and 2,3-hexadiene) have been studied. Isomerisation, in solutions of tetrafluoroboric acid in sulpholane, occurs rapidly and all evidence favours a hexyne-hexadiene-hexyne pathway, with carbonium ion intermediates. No conjugated dienes were detected in products of isomerisation. Equilibration of the isomers could not be achieved due to irreversible addition reactions which produced 2,2 and 3,3-difluorohexane.