Selenium dioxide oxidation of endocyclic olefins. Evidence for a dissociation-recombination pathway

MA Warpehoski, B Chabaud…

Index: Warpehoski, M. A.; Chabaud, B.; Sharpless, K. B. Journal of Organic Chemistry, 1982 , vol. 47, # 15 p. 2897 - 2900

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Citation Number: 53

Abstract

The selenium-catalyzed oxidation of some simple alicyclic olefins with tert-butyl hydroperoxide produced, in addition to the expected allylic alcohols, allylic tert-butyl peroxides and allylic tert-butyl ethers. Unlike the peroxides, the ether products were not inhibited by hydroquinone, and their relative amounts increased with decreasing ring size. Analogous products were detected in minor amounts in the selenium dioxide-tert-butyl ...