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Communication

Prevention of Undesirable Isomerization during Olefin Metathesis

Supporting Info

Soon Hyeok Hong,^† Daniel P. Sanders,^† Choon Woo Lee,^‡ and Robert H. Grubbs*^†

Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, and Materia, Inc., Pasadena, California 91107

J. Am. Chem. Soc., 2005, 127 (49), pp 17160–17161

DOI: 10.1021/ja052939w

Publication Date (Web): November 15, 2005

†

California Institute of Technology.

‡

Materia, Inc.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, rhg@caltech.edu

Abstract

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.

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Published In Issue December 14, 2005
Received May 4, 2005

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Communication

Prevention of Undesirable Isomerization during Olefin Metathesis

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Synthesis and Activity of a New Generation of Ruthenium-Based Olefin Metathesis Catalysts Coordinated with 1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene Ligands

Enantiospecific Total Syntheses of Kapakahines B and F

Total Synthesis of (−)-Acutumine

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