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The regiochemistry of carbenoid insertion into zirconacycles

The regiochemistry of carbenoid insertion into zirconacycles
The regiochemistry of carbenoid insertion into zirconacycles
The regioselectivity of insertion of lithium chloroallylides (allyl carbenoids) into a wide variety of unsymmetrical zirconacycles has been determined. In all but one case a single regioisomer was obtained. A combination of steric and electronic effects is needed to explain the results and imply that the carbenoid is acting predominantly as an electrophilic species. The first carbenoid insertion into a zirconacyclopentadiene is noted.
zirconium, zirconacycle, carbenoid, insertion reactions metal-promoted cyclization, bond formation reaction, tandem insertion, lithium chloroallylide, zirconium chemistry, metallacycle transfer, organic-synthesis, zirconacyclopentadienes, zirconocene, complexes
0040-4020
2113-2129
Gordon, G. J.
f0cb2ca5-7610-44a7-81fd-53b9b11db9a3
Luker, T.
2565ab76-a12f-43e6-b1b3-895288e76004
Tuckett, M. W.
b7466e23-b871-468f-96e8-37ac60c46692
Whitby, R. J.
3b6b79e2-863d-4d31-a4f6-ebe786aabd79
Gordon, G. J.
f0cb2ca5-7610-44a7-81fd-53b9b11db9a3
Luker, T.
2565ab76-a12f-43e6-b1b3-895288e76004
Tuckett, M. W.
b7466e23-b871-468f-96e8-37ac60c46692
Whitby, R. J.
3b6b79e2-863d-4d31-a4f6-ebe786aabd79

Gordon, G. J., Luker, T., Tuckett, M. W. and Whitby, R. J. (2000) The regiochemistry of carbenoid insertion into zirconacycles. Tetrahedron, 56 (15), 2113-2129. (doi:10.1016/S0040-4020(99)01094-7).

Record type: Article

Abstract

The regioselectivity of insertion of lithium chloroallylides (allyl carbenoids) into a wide variety of unsymmetrical zirconacycles has been determined. In all but one case a single regioisomer was obtained. A combination of steric and electronic effects is needed to explain the results and imply that the carbenoid is acting predominantly as an electrophilic species. The first carbenoid insertion into a zirconacyclopentadiene is noted.

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More information

Published date: 7 April 2000
Keywords: zirconium, zirconacycle, carbenoid, insertion reactions metal-promoted cyclization, bond formation reaction, tandem insertion, lithium chloroallylide, zirconium chemistry, metallacycle transfer, organic-synthesis, zirconacyclopentadienes, zirconocene, complexes

Identifiers

Local EPrints ID: 18923
URI: http://eprints.soton.ac.uk/id/eprint/18923
ISSN: 0040-4020
PURE UUID: 2558e5d4-a62c-4904-b894-30255ccf9981

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Date deposited: 16 Dec 2005
Last modified: 15 Mar 2024 06:09

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Contributors

Author: G. J. Gordon
Author: T. Luker
Author: M. W. Tuckett
Author: R. J. Whitby

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