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

A wide range of carbenoids (1-lithio-1-halo species), including those with α-SiR 3, OEt, SPh, SO 2Ph, 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 t...

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Bibliographic Details
Published in:Tetrahedron 2004-02, Vol.60 (6), p.1401-1416
Main Authors: Dixon, Sally, Fillery, Shaun M., Kasatkin, Aleksandra, Norton, David, Thomas, Emma, Whitby, Richard J.
Format: Article
Language:English
Subjects:
Carbenoid
Insertion
Multi-component
Ring expansion
Zirconacycle
Zirconium
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Summary:A wide range of carbenoids (1-lithio-1-halo species), including those with α-SiR 3, OEt, SPh, SO 2Ph, 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 β-hydride transfer processes provide additional mechanistic interest. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2003.09.056