Tandem insertion of halocarbenoids and lithium acetylides into zirconacycles: A novel rearrangement to zirconium alkenylidenates by ?-addition to an alkynyl zirconocene
Tandem insertion of halocarbenoids and lithium acetylides into zirconacycles: A novel rearrangement to zirconium alkenylidenates by ?-addition to an alkynyl zirconocene
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 ?-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 ?-hydride elimination of an intermediate cyclopentyl- or cyclopentenyl-zirconocene.
carbenoids, carbocycles, metallacycles, rearrangement, zirconium
4896-4904
Stec, Jozef
c8ef34c5-6d89-453b-a8aa-86d7b54864c4
Thomas, Emma
69f1cb1a-8550-4194-9904-67f6d9535ff1
Dixon, Sally
943160fc-1b70-4c29-b2e3-b7785cee8a0c
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b
2011
Stec, Jozef
c8ef34c5-6d89-453b-a8aa-86d7b54864c4
Thomas, Emma
69f1cb1a-8550-4194-9904-67f6d9535ff1
Dixon, Sally
943160fc-1b70-4c29-b2e3-b7785cee8a0c
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b
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 ?-addition to an alkynyl zirconocene.
Chemistry - A European Journal, 17 (17), .
(doi:10.1002/chem.201002962).
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 ?-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 ?-hydride elimination of an intermediate cyclopentyl- or cyclopentenyl-zirconocene.
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Published date: 2011
Keywords:
carbenoids, carbocycles, metallacycles, rearrangement, zirconium
Organisations:
Chemistry
Identifiers
Local EPrints ID: 178465
URI: http://eprints.soton.ac.uk/id/eprint/178465
ISSN: 0947-6539
PURE UUID: 9a594f7a-d28b-4e05-9b46-547d91daf4b0
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Date deposited: 24 Mar 2011 15:42
Last modified: 15 Mar 2024 02:34
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Author:
Jozef Stec
Author:
Emma Thomas
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