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 inJournal of the American Chemical Society Vol. 127; no. 49; pp. 17160 - 17161
Main Authors Hong, Soon Hyeok, Sanders, Daniel P, Lee, Choon Woo, Grubbs, Robert H
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 14.12.2005
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Exact sciences and technology
Organic chemistry
Physical Sciences
Science & Technology
ALCOHOLS
CARBENE
CATALYZED AEROBIC OXIDATION
GRUBBS CATALYST
CROSS-METATHESIS
DEPROTECTION
Mixed catalyst
Allyl ether
Catalytic reaction
Isomerization
Metathesis
Ruthenium Complexes
Competitive reaction
Platinoid Complexes
Transition metal Complexes
Experimental study
Catalyst activity
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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.
Bibliography:ark:/67375/TPS-H0L82BNK-X
istex:9E01A8BDEF2017458AB720AC03A5C135BE16C1CC
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja052939w