| Abstract: | Further evidence is presented that the 2-norbornyl cation is stabilized primarily by C(2)–C(6) bridging, and that C(2)–C(7) bridging leads to prohibitive strain. Thus, a comparison of the heats of hydrogenation of nortricyclene 17 and bicyclo3. 2. 0. 0.2,7]heptane 18 indicates that the strain energy of the latter is ca. 21.5 kcal/mol higher that that of 17 . Furthermore, 6-exo-2-oxabicyclo2. 2. 1]heptyl sulfonates 8 ionize with strong O(2) participation to the bridged oxonium ion 12. In contrast, 2-endo-7-oxabicyclo2.2.1]heptyl sulfonates 11 ionize without O(7) participation to form the unbridged carbenium ion 15 . |
