Stereochemistry of allylic oxidation with selenium dioxide. Stereospecific oxidation of gem-dimethyl olefins

H Rapoport, UT Bhalerao

Index: Bhalerao,U.T.; Rapoport,H. Journal of the American Chemical Society, 1971 , vol. 93, p. 4835 - 4840

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Citation Number: 150

Abstract

Abstract: The stereochemistry of allylic oxidation by selenium dioxide of a number of olefins has been studied. Olefins were prepared mostly by the Wittig reaction; pure stereoisomers were obtained by glpc separation from those reactions giving mixtures. Isomerization with thiophenol-azobisisobutyronitrile was employed to enrich reaction mixtures in the usually less abundant trans isomers. The sequence of reactivity toward oxidation by selenium ...