Tetrahedron

Oxidation of acyclic alkenes and allyl and benzyl ethers with DIB/t-BuOOH/Mg (OAc) 2

T Sastraruji, SG Pyne, AT Ung

Index: Sastraruji, Thanapat; Pyne, Stephen G.; Ung, Alison T. Tetrahedron, 2012 , vol. 68, # 2 p. 598 - 602

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Citation Number: 2

Abstract

Oxidation of (11Z)-1′, 2′-didehydrostemofoline with DIB/TBHP/Mg (OAc) 2· 4H2O resulted in oxidative cleavage of the C-11–C-12 double bond instead of the desired allylic oxidation of the 1-butenyl side chain. Stemofoline gave a similar result. The oxidation of more simple terminal alkenes was regioselective and gave vinyl ketones while allyl and benzyl ethers gave acrylate and benzoate esters, respectively. Allyl and benzyl ethers could be ...