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Metal-free dihydroxylation of alkenes using cyclobutane malonoyl peroxide

Tomkinson, Nick and Jones, Kevin M (2012) Metal-free dihydroxylation of alkenes using cyclobutane malonoyl peroxide. Journal of Organic Chemistry, 77 (2). pp. 921-928. ISSN 0022-3263

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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 one equivalent 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 with experimental findings is proposed which is supported by deuterium and oxygen labeling studies and explains the stereoselectivity observed. Alternative reaction pathways that are dependent on the structure of the starting alkene are also described leading to the synthesis of allylic alcohols and γ-lactones.