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), 1401-1416. (doi:10.1016/j.tet.2003.09.056).
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Description/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.
| Item Type: | Article |
|---|---|
| ISSNs: | 0040-4020 (print) |
| Related URLs: | |
| 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 |
| Subjects: | Q Science Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 20183 |
| Date Deposited: | 17 Feb 2006 |
| Last Modified: | 31 May 2011 23:32 |
| Contributors: | Dixon, S. (Author) Fillery, S. M. (Author) Kasatkin, A. (Author) Norton, D. (Author) Thomas, E. (Author) Whitby, R. J. (Author) |
| Date: | 2 February 2004 |
| Status: | Published |
| Contact Email Address: | rjw1@soton.ac.uk |
| URI: | http://eprints.soton.ac.uk/id/eprint/20183 |
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