Abstract: Buffered acetolysis of exo-bicyclo [3.1. 0] hex-2-en-6-yl triflate (8) and exo-bicyclo [4.1. O] hept-2-en-7-yl triflate (5) suggests an olefin-assisted ionization in the former and competing" normal" and olefin-assisted ionization in the latter. Proposed intermediates are the bicyclo [2. ll] hex-2-en-5-yl cation (21) in the ionization of 8 and the 7-norbornenyl cation (17) along with partially opened allylic cation 14 in the acetolysis of 5. A solvent study ...
