INVOLVEMENT OF OXYGENATED FUNCTIONS IN ACETOLYSIS OF 7-OXYGENATED NORBORNYL TOSYLATES

Acetolyses of exo- and endo-2-tosyloxybicyclo[2.2.1]heptan-7-one ethylene glycol ketal have been studied. Whereas the exo-tosylate gave exo-acetate as the major product, the predominant reaction path followed by the endo isomer was one of ring cleavage to yield substituted cyclohexenes. The exo-tosylate solvolyzed eleven times faster than the endo isomer. Although the rates of solvolysis were similar to endo-2-tosyloxybicyclo[2.2.1]heptane, the dramatic change in product ratios showed that more than one mechanism was involved. © 1969, American Chemical Society. All rights reserved.