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 journalArticle

80 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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  • Research Output

    • 80 Citations
    • 1 Literature review

    Metal-free syn-dioxygenation of alkenes

    Rawling, M. & Tomkinson, N., 2013, In : Organic and Biomolecular Chemistry. 11, 9, p. 1434-1440 7 p.

    Research output: Contribution to journalLiterature review

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  • 37 Citations (Scopus)
    204 Downloads (Pure)

    Cite this

    Griffith, J. C., Jones, K. M., Picon, S., Rawling, M. J., Kariuki, B. M., Campbell, M., & Tomkinson, N. C. O. (2010). Alkene syn dihydroxylation with malonoyl peroxides. Journal of the American Chemical Society, 132(41), 14409-14411. https://doi.org/10.1021/ja1066674