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Cyclopropyl carbenoid insertion into alkenylzirconocenes: a convergent synthesis of alkenylcyclopropanes and alkylidenecyclopropanes

Cyclopropyl carbenoid insertion into alkenylzirconocenes: a convergent synthesis of alkenylcyclopropanes and alkylidenecyclopropanes
Cyclopropyl carbenoid insertion into alkenylzirconocenes: a convergent synthesis of alkenylcyclopropanes and alkylidenecyclopropanes
The insertion of cyclopropyl carbenoids into alkenylzirconocenes, derived by hydrozirconation of terminal alkynes, affords allylzirconium species which react with protons and isonitriles to afford alkenylcyclopropanes, and with aldehydes to afford alkylidene cyclopropanes. The addition of lithium carbenoid to zirconium occurs with the inversion of the organolithium centre.
zirconium, cyclopropyl, carbenoids, organolithium
0040-4039
9181-9185
Thomas, Emma
69f1cb1a-8550-4194-9904-67f6d9535ff1
Kasatkin, Alexander N.
d41e686c-6e57-4199-af61-69117ded36a6
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b
Thomas, Emma
69f1cb1a-8550-4194-9904-67f6d9535ff1
Kasatkin, Alexander N.
d41e686c-6e57-4199-af61-69117ded36a6
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b

Thomas, Emma, Kasatkin, Alexander N. and Whitby, Richard J. (2006) Cyclopropyl carbenoid insertion into alkenylzirconocenes: a convergent synthesis of alkenylcyclopropanes and alkylidenecyclopropanes. Tetrahedron Letters, 47 (52), 9181-9185. (doi:10.1016/j.tetlet.2006.10.132).

Record type: Article

Abstract

The insertion of cyclopropyl carbenoids into alkenylzirconocenes, derived by hydrozirconation of terminal alkynes, affords allylzirconium species which react with protons and isonitriles to afford alkenylcyclopropanes, and with aldehydes to afford alkylidene cyclopropanes. The addition of lithium carbenoid to zirconium occurs with the inversion of the organolithium centre.

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Published date: 2006
Keywords: zirconium, cyclopropyl, carbenoids, organolithium
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Identifiers

Local EPrints ID: 44087
URI: http://eprints.soton.ac.uk/id/eprint/44087
DOI: doi:10.1016/j.tetlet.2006.10.132
ISSN: 0040-4039
PURE UUID: 1da12b44-ceb1-4121-b4f3-30d31d8bdcb5
ORCID for Richard J. Whitby: ORCID iD orcid.org/0000-0002-9891-5502

Catalogue record

Date deposited: 13 Feb 2007
Last modified: 16 Mar 2024 02:33

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Contributors

Author: Emma Thomas
Author: Alexander N. Kasatkin
Author: Richard J. Whitby ORCID iD

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