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Cross metathesis of allyl alcohols how to suppress and how to promote double bond isomerization

  • 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
ISSN:1477-0520 (print)
Parent Title (English):Organic & biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry
Publisher:Royal Society of Chemistry
Place of publication:Cambridge
Document Type:Article
Year of first Publication:2013
Year of Completion:2013
Release Date:2017/03/26
First Page:4194
Last Page:4206
Funder:Deutsche Forschungsgemeinschaft (DFG) [Schm 1095/6-2]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert