Elsevier

Tetrahedron Letters

Volume 38, Issue 34, 25 August 1997, Pages 6103-6106
Tetrahedron Letters

Regio- and stereoselective copper-induced isomerization of 2-alkenyl 2-lithiophenyl ethers to 2-(2-alkenyl)phenols

https://doi.org/10.1016/S0040-4039(97)01379-8Get rights and content

Abstract

N-Allyl-N-(2-lithioallyl)aniline undergoes intramolecular carbometallation via 5-exo addition on treatment with CuCN, 2-Alkenyl 2-bromophenyl ethers rearrange to 2-(2-alkenyl)phenols by bromine-lithium exchange and further transmetallation with CuCN.

2-Alkenyl 2-lithiophenyl ethers rearrange to 2-(2-alkenyl)phenols in regio- and stereoselective way in the presence of copper(I) cyanide.

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