Nuclear magnetic resonance studies. XXXI. Rearrangement and deuterium exchange through β-enolization in bicyclooctanones. An 2H nuclear magnetic resonance …

AK Cheng, JB Stothers, CT Tan

Index: Cheng,A.K. et al. Canadian Journal of Chemistry, 1977 , vol. 55, p. 447 - 453

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Citation Number: 12

Abstract

The bicyclo [2.2. 2] octan-2-one and-[3.2. 1] octan-6-one skeletons are interconvertible under strongly basic conditions. Their α, α-dimethyl derivatives in tert-Buo-/tert-BuOH at 185° C undergo very slow interconversion by β-proton abstraction. Using 2H nmr the stereoselectivity of deuterium incorporation at the β-methylene sites was established. The relative reactivities of β-methyl exchange in the [3.2. 1] system were also determined. As ...