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Ring expansion of 5-to 6-member zirconacycles by carbenoid insertion

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
0040-4020
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
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), 1401-1416. (doi:10.1016/j.tet.2003.09.056).

Record type: Article

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.

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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
ORCID for S. Dixon: ORCID iD orcid.org/0000-0003-2219-3635
ORCID for R. J. Whitby: ORCID iD orcid.org/0000-0002-9891-5502

Catalogue record

Date deposited: 17 Feb 2006
Last modified: 07 Aug 2019 00:55

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Contributors

Author: S. Dixon ORCID iD
Author: S. M. Fillery
Author: A. Kasatkin
Author: D. Norton
Author: E. Thomas
Author: R. J. Whitby ORCID iD

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