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

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


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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.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1016/j.tet.2003.09.056
ISSNs: 0040-4020 (print)
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
ePrint ID: 20183
Date :
Date Event
2 February 2004Published
Date Deposited: 17 Feb 2006
Last Modified: 16 Apr 2017 22:59
Further Information:Google Scholar
URI: http://eprints.soton.ac.uk/id/eprint/20183

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