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Cross metathesis of allyl alcohols

  • Under standard conditions the cross metathesis of allyl alcohols and methyl acrylate is accompanied by the formation of ketones, resulting from uncontrolled and undesired double bond isomerization. By conducting the CM in the presence of phenol, the catalyst loading and the reaction time required for quantiative conversion can be reduced, and isomerization can be suppressed. On the other hand, consecutive isomerization can be deliberately promoted by evaporating excess methyl acrylate after completing cross metathesis and by adding a base or silane as chemical triggers.

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Metadaten
Author details:Bernd SchmidtORCiDGND, Sylvia Hauke
URN:urn:nbn:de:kobv:517-opus4-95037
Subtitle (English):how to suppress and how to promote double bond isomerization
Publication series (Volume number):Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe (241)
Publication type:Postprint
Language:English
Date of first publication:2013/05/01
Publication year:2013
Publishing institution:Universität Potsdam
Release date:2016/09/06
Tag:alkynol cycloisomerization; carbohydrate-based oxepines; carbonyl-compounds; catalyzed redox isomerization; de-novo synthesis; diels-alder reaction; in-situ; olefin-metathesis; ring-closing metathesis; ruthenium carbene
First page:4194
Last Page:4206
Source:Org. Biomol. Chem. (2013) Nr. 11, S. 4194-4206. - DOI: 10.1039/C3OB40167G
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
DDC classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Peer review:Referiert
Publishing method:Open Access
License (German):License LogoKeine öffentliche Lizenz: Unter Urheberrechtsschutz
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