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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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Author:Bernd SchmidtORCiDGND, Sylvia Hauke
Subtitle (English):how to suppress and how to promote double bond isomerization
Series (Serial Number):Postprints der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe (241)
Document Type:Postprint
Date of first Publication:2013/05/01
Year of Completion: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
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Peer Review:Referiert
Publication Way:Open Access
Licence (German):License LogoKeine Nutzungslizenz vergeben - es gilt das deutsche Urheberrecht