Prevention of Undesirable Isomerization during Olefin Metathesis

1,4-Benzoquinones have been found to prevent olefin isomerization of a number of allylic ethers and long-chain aliphatic alkenes during ruthenium-catalyzed olefin metathesis reactions. Electron-deficient benzoquinones are the most effective additives for the prevention of olefin migration. This mild...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-12, Vol.127 (49), p.17160-17161
Main Authors: Hong, Soon Hyeok, Sanders, Daniel P, Lee, Choon Woo, Grubbs, Robert H
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Organic chemistry
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Summary:1,4-Benzoquinones have been found to prevent olefin isomerization of a number of allylic ethers and long-chain aliphatic alkenes during ruthenium-catalyzed olefin metathesis reactions. Electron-deficient benzoquinones are the most effective additives for the prevention of olefin migration. This mild, inexpensive, and effective method to block olefin isomerization increases the synthetic utility of olefin metathesis via improvement of overall product yield and purity.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja052939w