Ring expansion of 5-to 6-member zirconacycles by carbenoid insertion
Ring expansion of 5-to 6-member zirconacycles by carbenoid insertion
A wide range of carbenoids (1-lithio-1-halo species), including those with alpha-SiR3, OEt, SPh, SO2Ph, P(O)(OEt)(2), and CN substituents, insert into 5-member zirconacycles (saturated and unsaturated, mono- and bi-cyclic) to afford functionalized 6-member zirconacycles. 1-Lithio-1-haloalkenes insert to afford 6-member zirconacycles with an alkylidene substituent next to the metal. Unexpected double insertion of some carbenoids, and evidence for endocylic beta-hydride transfer processes provide additional mechanistic interest.
zirconium, carbenoid, ring expansion, multi-component, zirconacycle, insertioncarbon bond formation, metal-promoted cyclization, zirconium-mediatedsynthesis, tandem insertion, lithium chloroallylide, diethyl1, 2-epoxyalkanephosphonates, reductive cyclization, convergentsynthesis, grignard-reagents, organic-synthesis
1401-1416
Dixon, S.
943160fc-1b70-4c29-b2e3-b7785cee8a0c
Fillery, S. M.
47afbe8e-34a2-4093-88d7-4481dcedadf4
Kasatkin, A.
9c574040-4a45-46ff-8e74-e80f1bdaac22
Norton, D.
0da065d7-8760-40d3-8659-cb8e2737fe2e
Thomas, E.
f03d9d9b-5145-4066-81c7-8750faca61b2
Whitby, R. J.
45632236-ab00-4ad0-a02d-6209043e818b
2 February 2004
Dixon, S.
943160fc-1b70-4c29-b2e3-b7785cee8a0c
Fillery, S. M.
47afbe8e-34a2-4093-88d7-4481dcedadf4
Kasatkin, A.
9c574040-4a45-46ff-8e74-e80f1bdaac22
Norton, D.
0da065d7-8760-40d3-8659-cb8e2737fe2e
Thomas, E.
f03d9d9b-5145-4066-81c7-8750faca61b2
Whitby, R. J.
45632236-ab00-4ad0-a02d-6209043e818b
Dixon, S., Fillery, S. M., Kasatkin, A., Norton, D., Thomas, E. and Whitby, R. J.
(2004)
Ring expansion of 5-to 6-member zirconacycles by carbenoid insertion.
Tetrahedron, 60 (6), .
(doi:10.1016/j.tet.2003.09.056).
Abstract
A wide range of carbenoids (1-lithio-1-halo species), including those with alpha-SiR3, OEt, SPh, SO2Ph, P(O)(OEt)(2), and CN substituents, insert into 5-member zirconacycles (saturated and unsaturated, mono- and bi-cyclic) to afford functionalized 6-member zirconacycles. 1-Lithio-1-haloalkenes insert to afford 6-member zirconacycles with an alkylidene substituent next to the metal. Unexpected double insertion of some carbenoids, and evidence for endocylic beta-hydride transfer processes provide additional mechanistic interest.
This record has no associated files available for download.
More information
Published date: 2 February 2004
Keywords:
zirconium, carbenoid, ring expansion, multi-component, zirconacycle, insertioncarbon bond formation, metal-promoted cyclization, zirconium-mediatedsynthesis, tandem insertion, lithium chloroallylide, diethyl1, 2-epoxyalkanephosphonates, reductive cyclization, convergentsynthesis, grignard-reagents, organic-synthesis
Identifiers
Local EPrints ID: 20183
URI: http://eprints.soton.ac.uk/id/eprint/20183
ISSN: 0040-4020
PURE UUID: 96c7ee6d-d8af-450a-a5c9-697657465e9c
Catalogue record
Date deposited: 17 Feb 2006
Last modified: 16 Mar 2024 03:24
Export record
Altmetrics
Contributors
Author:
S. M. Fillery
Author:
A. Kasatkin
Author:
D. Norton
Author:
E. Thomas
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics
