Aliphatic Friedel–Crafts reactions. Part IX. Acetylation of cis-cyclooctene
Abstract
The effect of catalyst on the acetylation of cis-cyclo-octene and the occurrence of a transannular hydride shift in the intermediate carbonium ion are reported. Stannic chloride as catalyst affords 1-acetylcyclo-octene, whilst boron trifluoride or zinc chloride affords 4-acetylcyclo-octene. Aluminium chloride yields 1-acetyl-4-chlorocyclo-octene or 4-acetyl-1-ethylcyclohexene according to the catalyst activity.