2, 4-Methano-2, 4-dehydroadamantane. A [3.1. 1] propellane

K Mlinaric-Majerski, Z Majerski

Index: Mlinaric-Majerski,K.; Majerski,Z. Journal of the American Chemical Society, 1980 , vol. 102, p. 1418

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Citation Number: 26

Abstract

In this case one now anticipates, and finds, an isotope discrimination. Again, using the formalism of the perepoxide for purposes of discussion, one sees that, in 7, the system has a choice of abstracting D from the chiral center or reacting with methyl CH bonds and, in 8, a choice of-H or the methyl CH. We find an isotope effect of 1.2. This is exactly half the effect (1.4) found for the system 9, which is ideally suited for 1 a 2 cis competition on both top ...