The major products from acetolysis of the toluene-p-sulphonates of exo-and endo-l.4.4-trimethyl-and 4.4.6trimethylbicyclo[3,2,0] hept-6-en-2-01, 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 stereochemistry of the products on the nature of the cationic intermediates involved is discussed.STuDrEs on rigid bicyclic molecules which possess a potential carbonium ion centre homoallylic to a double bond, e.g., exo-and endo-norborn-5-en-2-yl derivatives,2 and synand anti-norborn-2-en-7-yl derivatives J3 have led to particularly interesting results contributing to carbonium ion theory in general. A potentially instructive system, related to the norborn-2-en-7-yl cation by Wagner-Meenvein rearrangement, is that of the bicyclo[3,2,O]hept-6-en-2-yl cation (I), We have therefore investigated the reactions of some progenitors of this formal cation.
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