Alkene syn dihydroxylation with malonoyl peroxides

James C Griffith, Kevin M Jones, Sylvain Picon, Michael J Rawling, Benson M Kariuki, Matthew Campbell, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticlepeer-review

90 Citations (Scopus)
17 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)14409-14411
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number41
Early online date24 Sep 2010
DOIs
Publication statusPublished - 20 Oct 2010

Keywords

  • benzene
  • benzenoid compunds
  • alkene syn dihydroxylation

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