The Journal of organic chemistry

Metal-free dihydroxylation of alkenes using cyclobutane malonoyl peroxide

KM Jones, NCO Tomkinson

Index: Jones, Kevin M.; Tomkinson, Nicholas C. O. Journal of Organic Chemistry, 2012 , vol. 77, # 2 p. 921 - 928

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Citation Number: 30

Abstract

Cyclobutane malonoyl peroxide (7), prepared in a single step from the commercially available diacid 6, is an effective reagent for the dihydroxylation of alkenes. Reaction of a chloroform solution of 7 with an alkene in the presence of 1 equiv of water at 40° C followed by alkaline hydrolysis leads to the corresponding diol (30–84%). With 1, 2-disubstituted alkenes, the reaction proceeds with syn-selectivity (3: 1→ 50: 1). A mechanism consistent ...