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 |
|---|---|
| DOI: | https://doi.org/10.1039/c3ob40167g |
| ISSN: | 1477-0520 |
| Title of parent work (English): | Organic & biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry |
| Publisher: | Royal Society of Chemistry |
| Place of publishing: | Cambridge |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2013 |
| Publication year: | 2013 |
| Release date: | 2017/03/26 |
| Volume: | 11 |
| Issue: | 25 |
| Number of pages: | 13 |
| First page: | 4194 |
| Last Page: | 4206 |
| Funding institution: | Deutsche Forschungsgemeinschaft (DFG) [Schm 1095/6-2] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
