Tandem insertion of halocarbenoids and lithium acetylides into zirconacycles: A novel rearrangement to zirconium alkenylidenates by β-addition to an alkynyl zirconocene
Stec, Jozef, Thomas, Emma, Dixon, Sally and Whitby, Richard J. (2011) Tandem insertion of halocarbenoids and lithium acetylides into zirconacycles: A novel rearrangement to zirconium alkenylidenates by β-addition to an alkynyl zirconocene. Chemistry - A European Journal, (17), 4896-4904. (doi:10.1002/chem.201002962).
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Description/Abstract
Tandem insertion of 1,1-dihalo-1-lithio species (halocarbenoids) and lithium alkynides into zirconacyclopentenes and zirconcyclopentanes affords carbocyclic products in high yields via an unusual rearrangement which probably involves addition of an organolithium species to the β-position of a zirconium-alkyne complex to give an alkenylidene-zirconate species. A wide variety of cyclopentanoid organic structures are rapidly assembled in good yield using this multi-component coupling. The main side reaction, which becomes exclusive in some cases, is β-hydride elimination of an intermediate cyclopentyl- or cyclopentenyl-zirconocene.
| Item Type: | Article |
|---|---|
| ISSNs: | 0947-6539 (print) 1521-3765 (electronic) |
| Keywords: | carbenoids, carbocycles, metallacycles, rearrangement, zirconium |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 178465 |
| Date Deposited: | 24 Mar 2011 15:42 |
| Last Modified: | 25 Apr 2012 13:01 |
| Contributors: | Stec, Jozef (Author) Thomas, Emma (Author) Dixon, Sally (Author) Whitby, Richard J. (Author) |
| Date: | 2011 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/178465 |
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