title: Alkene syn dihydroxylation with malonoyl peroxides.
abstract: Cyclopropyl malonoyl peroxide (1), which can be prepared in a single step from the commercially available diacid, is an effective reagent for the dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of 1 equiv of water at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (40-93%). With 1,2-disubstituted alkenes, the reaction proceeds with syn selectivity (3:1 to >50:1). A mechanism consistent with the experimental findings that is supported by oxygen-labeling studies is proposed.
authors.affiliation: School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff CF10 3AT, UK.
authors.forename: James C
authors.initials: JC
authors.lastname: Griffith
authors.forename: Kevin M
authors.initials: KM
authors.lastname: Jones
authors.forename: Sylvain
authors.initials: S
authors.lastname: Picon
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Rawling
authors.forename: Benson M
authors.initials: BM
authors.lastname: Kariuki
authors.forename: Matthew
authors.initials: M
authors.lastname: Campbell
authors.forename: Nicholas C O
authors.initials: NC
authors.lastname: Tomkinson
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D006900:Hydroxylation; D010545:Peroxides / Q000737:chemistry*
chemical_list: D000475:Alkenes; D010545:Peroxides