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Gold-Catalyzed Rearrangement of (Silylcyclopropenyl)methyl Ethers into (Silylmethylene)cyclopropanes
| Content Provider | Scilit |
|---|---|
| Author | Hiault, Florence Archambeau, Alexis Miege, Frédéric Meyer, Christophe Cossy, Janine |
| Copyright Year | 2016 |
| Description | Methoxymethyl ethers derived from 2-(dimethylphenylsilyl)cycloprop-1-enyl carbinols undergo gold-catalyzed rearrangement leading to [(Z)-(dimethylphenylsilyl)methylene]cyclopropanes in moderate to high yields with methyl formate as a byproduct. This transformation proceeds by initial regioselective ring opening of the three-membered ring leading to an α-silyl vinyl gold carbenoid. This latter organogold species evolves by 1,5-hydride transfer, which triggers subsequent rearrangement involving loss of methyl formate, 2π-electrocyclization of the resulting allylic cation, and elimination of the metal to regenerate the catalyst. |
| Related Links | http://pdfs.semanticscholar.org/8450/ea0eff26d7fcd75895357483a18c4266d53e.pdf http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0035-1561486.pdf |
| Ending Page | 3174 |
| Page Count | 10 |
| Starting Page | 3165 |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/s-0035-1561486 |
| Journal | Synthesis |
| Issue Number | 19 |
| Volume Number | 48 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2016-07-27 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
