Acid-catalyzed cleavage of 4-halonortricyclanes. Evidence that the 2-norbornyl cation is an unsymmetrical species

NH Werstiuk, D Dhanoa…

文献索引：Werstiuk, Nick Henry; Dhanoa, Daljit; Timmins, George Canadian Journal of Chemistry, 1983 , vol. 61, p. 2403 - 2414

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被引用次数: 3

摘要

Nortrieyclanes 4 a, 4 c, 4 d, and 4 e were prepared and ring opened in D2SO4/CD3COOD. We found that the ratios of endo/exo deuterium at C (6) were 1.09±0.02, 1.30±0.03, 1.40±0.04. and 1.45±0.05 for cleavage of 4 a, 4 c, 4 d, and 4 e, respectively. The amount of 6, 2-hydride shift decreased from 14.3±1.0% in the case of nortricyclane (4 a) to 6.0±1.1%, 6.4±0.5%, and 8.1±0.7% for 4 c, 4 d, and 4 e, respectively. Although four distinct ...