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Et₂Zn-Mediated Rearrangement of Bromohydrins

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Lezhen Li^‡, Peijie Cai^‡, Qingxiang Guo^‡ and Song Xue ^†

Department of Applied Chemistry, Tianjin University of Technology, Tianjin, 300191, China, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China

J. Org. Chem., 2008, 73 (9), pp 3516–3522

DOI: 10.1021/jo800231s

Publication Date (Web): April 2, 2008

, †

Tianjin University of Technology.

, ‡

University of Science and Technology of China.

Section:

General Organic Chemistry

Abstract

A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et₂Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et₂Zn to form a zinc complex in CH₂Cl₂ at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Et₂Zn-Mediated Rearrangement of Bromohydrins
Lezhen Li, Peijie Cai, Qingxiang Guo and Song Xue
The Journal of Organic Chemistry2008 73 (9), 3516-3522
- Et₂Zn-Mediated Rearrangement of Bromohydrins
  Lezhen Li, Peijie Cai, Qingxiang Guo and Song Xue
  The Journal of Organic Chemistry2008 73 (9), 3516-3522
  A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH2Cl2 at room ...
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History

Published In Issue May 02, 2008
Article ASAPApril 02, 2008
Received: January 29, 2008

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Et₂Zn-Mediated Rearrangement of Bromohydrins

Abstract

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Et₂Zn-Mediated Rearrangement of Bromohydrins