Neighbouring double bond participation in exo 5-hydroxybicyclo[2.2.2]oct-2-ene tosylate.

Abstract

The synthesis of the previously unknown exo-5-hydroxybicyclo[2.2.2]oct-2-ene is described, and its behavior under solvolysis in acetic acid is reported. The end product of the acetolysis is unrearranged and the rate is the fastest yet measured in the bicyclo[2.2.2]octane series. This result supports the theory of homoallylic resonance in the intermediate transition state for the solvolysis reaction. The construction of a preparative-scale vapour-phase chromatograph is described.