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.
| Author details: | Bernd SchmidtORCiDGND, Sylvia Hauke |
|---|---|
| URL: | http://pubs.rsc.org/en/content/articlepdf/2013/ob/c3ob40167g |
| DOI: | https://doi.org/10.1039/c3ob40167g |
| ISSN: | 1477-0520 |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2014 |
| Publication year: | 2014 |
| Release date: | 2017/03/25 |
| Source: | Organic and biomolecular chemistry. - ISSN 1477-0520. - 11 (2014) 25, S. 4194 - 4206 |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
