Lewis and protic acid mediated Nicholas reactions of 3-acetoxycyclohept-1-en-4-ynedicobalt hexacarbonyl: site selectivity of nucleophile incorporation

Authors

Joseph DiMartino
James R. Green, University of WindsorFollow

Document Type

Article

Publication Date

2006

Publication Title

Tetrahedron

Volume

62

Issue

7

First Page

1402

Keywords

Nicholas reaction, Cobalt–alkyne complexes, Cycloheptyne, Propargyl cations

Last Page

1409

Abstract

Nicholas reactions on the cation derived from the cyclic allylic acetate alkynedicobalt complex 1 favour the gamma-site kinetically for most nucleophiles, with increasing amounts of of-products in cases with greater nucleophilicity. Some regiocontrol in introduction of a specific nucleophilic fragment is possible by using different nucleophiles. Under conditions where reversibility is possible, the thermodynamically favoured site is exclusively gamma-. (c) 2005 Elsevier Ltd. All rights reserved.

DOI

10.1016/j.tet.2005.11.030

Comments

NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron, 62 (7), 2006 and is available here.

Recommended Citation

DiMartino, Joseph and Green, James R.. (2006). Lewis and protic acid mediated Nicholas reactions of 3-acetoxycyclohept-1-en-4-ynedicobalt hexacarbonyl: site selectivity of nucleophile incorporation. Tetrahedron, 62 (7), 1402-1409.
https://scholar.uwindsor.ca/chemistrybiochemistrypub/8