Allylic oxidations by peroxy esters catalyzed by copper salts. The potential for stereoselective syntheses

ALJ Beckwith, AA Zavitsas

Index: Beckwith,A.J.; Zavitsas,A.A. Journal of the American Chemical Society, 1986 , vol. 108, p. 8230

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Citation Number: 94

Abstract

Abstract: The mechanism of the title reaction has been investigated. 1-Butene, cis-2-butene, and trans-2-butene with tert-butyl peroxyacetate and cuprous or cupric salts give 3- acetoxybut-I-ene (90% of ester) and trans-acetoxybut-2-ene (10%); cis-and trans-2-pentene give trans-4-acetoxypent-2-ene as the major product. It is concluded that the following steps are involved: formation of an allylic radical, reaction of the radical with Cu (I1) carboxylate ...