Solvolytic rearrangements of bicyclo[3,2,0]hept-6-en-2-yl and bicyclo-[3,2,0]hept-2-yl derivatives

Abstract

The major products from acetolysis of the toluene-p-sulphonates of exo- and endo-1,4,4-trimethyl- and 4,4,6-trimethylbicyclo[3,2,0]hept-6-en-2-ol, and the corresponding saturated alcohols, in buffered acetic acid have been determined. Rearranged materials with the norbornyl skeleton predominate. The possible bearing of the structure and sterochemistry of the products on the nature of the cationic intermediates involved is discussed.