Alkene syn dihydroxylation with malonoyl peroxides
Griffith, James C and Jones, Kevin M and Picon, Sylvain and Rawling, Michael J and Kariuki, Benson M and Campbell, Matthew and Tomkinson, Nicholas C. O. (2010) Alkene syn dihydroxylation with malonoyl peroxides. Journal of the American Chemical Society, 132 (41). pp. 14409-14411. ISSN 0002-7863
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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.
| Creators(s): |
Griffith, James C, Jones, Kevin M, Picon, Sylvain, Rawling, Michael J, Kariuki, Benson M, Campbell, Matthew and Tomkinson, Nicholas C. O.  ORCID: https://orcid.org/0000-0002-5509-0133;
| Item type: | Article |
|---|---|
| ID code: | 33051 |
| Keywords: | benzene, benzenoid compunds, alkene syn dihydroxylation , Chemistry, Biochemistry, Colloid and Surface Chemistry, Chemistry(all), Catalysis |
| Subjects: | Science > Chemistry |
| Department: | Faculty of Science > Pure and Applied Chemistry |
| Depositing user: | Pure Administrator |
| Date deposited: | 30 Aug 2011 08:57 |
| Last modified: | 28 May 2020 00:37 |
| URI: | https://strathprints.strath.ac.uk/id/eprint/33051 |
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