Hyperconjugation in strained bridgehead cyclobutyl cations: an ab initio study of bicyclo[1.1.1]pent-1-yl cubyl and norcubyl cations
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 4,p. 417-419
- https://doi.org/10.1039/c39940000417
Abstract
Ab initio molecular orbital calculations (MP2/6-31G**) provide strong evidence that the bicyclo[1.1.1]pent-1-yl, cubyl and tricyclo[3.1.1.03,6]hept-6-yl (6-norcubyl) cations are principally stabilized by hyperconjugative interaction of the strained α–β and β–γ carbon–carbon bonds with the (vacant) cationic p-orbital; the degree of interaction is strongly dependent on the geometry of the charged four-membered ring in each case.Keywords
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