Journal of Organic Chemistry p. 3066 - 3073 (1988)
Update date:2022-07-30
Topics:
Bentley, T. William
Goer, Bernhard
Kirmse, Wolfgang
The objective of this work was to explore the effect of ring strain on ? delocalization of carbocations.The 6-tricyclo<3.3.0.02,7>octyl cation (3) incorporates 2-norbornyl and 2-bicyclo<2.1.1>hexyl structures in a highly strained molecular framework.Solvolyses of the epimeric brosylates 22 and 23, as well as nitrous acid deaminations of the analogues amines, 24 and 21, served to generate 3.The exo:endo rate ratios of the brosylates and the exo:endo product ratios of the tricyclo<3.3.0.02,7>octan-6-ols (19, 20) are close to unity.Product distributions and kinetic data suggest a weak ka contribution at least for the endo brosylate 23.Several nondegenerate rearrangements of 3 were elucidated: Migration of C-2 from C-7 to C-6 (3
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