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

doi:10.1021/ja1066674

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

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	14409-14411
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	132
Issue number	41
Early online date	24 Sep 2010
DOIs	https://doi.org/10.1021/ja1066674
Publication status	Published - 20 Oct 2010

Keywords

benzene
benzenoid compunds
alkene syn dihydroxylation

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10.1021/ja1066674

90 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 journal › Literature review › peer-review

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45 Citations (Scopus)

258 Downloads (Pure)

Cite this

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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.",

keywords = "benzene, benzenoid compunds, alkene syn dihydroxylation ",

author = "Griffith, {James C} and Jones, {Kevin M} and Sylvain Picon and Rawling, {Michael J} and Kariuki, {Benson M} and Matthew Campbell and Tomkinson, {Nicholas C. O.}",

year = "2010",

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language = "English",

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journal = "Journal of the American Chemical Society",

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TY - JOUR

T1 - Alkene syn dihydroxylation with malonoyl peroxides

AU - Griffith, James C

AU - Jones, Kevin M

AU - Picon, Sylvain

AU - Rawling, Michael J

AU - Kariuki, Benson M

AU - Campbell, Matthew

AU - Tomkinson, Nicholas C. O.

PY - 2010/10/20

Y1 - 2010/10/20

N2 - 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.

AB - 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.

KW - benzene

KW - benzenoid compunds

KW - alkene syn dihydroxylation

U2 - 10.1021/ja1066674

DO - 10.1021/ja1066674

M3 - Article

VL - 132

SP - 14409

EP - 14411

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 41

ER -

Alkene syn dihydroxylation with malonoyl peroxides

Abstract

Keywords

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Research output

Metal-free syn-dioxygenation of alkenes

Cite this