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.
J. K. Groves and N. Jones, J. Chem. Soc. C, 1969, 1718 DOI: 10.1039/J39690001718
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