Helvetica Chimica Acta p. 1017 - 1024 (1988)
Update date:2022-07-30
Topics:
Flury, Peter
Grob, Cyril A.
Wang, Guang Yi
Lennartz, Hans-Werner
Roth, Wolfgang R.
Further evidence is presented that the 2-norbonyl 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 bicyclo<3.2.0.02,7>heptane 18 indicates that the strain energy of the latter is ca. 21.5 kcal/mol higher than that of 17.Furthermore, 6-exo-2-oxabicyclo<2.2.1>heptyl sulfonates 8 ionize with strong O(2) participation to the bridged oxonium ion 12.In contrast, 2-endo-7-oxabicyclo<2.2.1>heptyl sulfonates 11 ionize without O(7) participation to form the unbridged carbenium ion 15.
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Doi:10.1016/S0957-4166(00)86322-3
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