Issue 4, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

The synthesis of 2-arylmethyl-6-hydroxybenzenecarbonitriles from the base-mediated aryne reaction of bromophenols with arylacetonitriles

Sagun Tandel,a   Hongming Zhang,a   Nabil Qadri,a   George P. Forda  and  Edward R. Biehl*a  

* Corresponding authors

a Department of Chemistry, Southern Methodist University, Dallas, USA
E-mail: ebiehl@post.smu.edu

Abstract

A facile one-step synthesis of 2-arylmethyl-6-hydroxybenzenecarbonitriles from readily available arylacetonitriles is described. The substitution pattern was verified by X-ray diffractometric analysis of 2-benzyl-6-hydroxybenzonitrile. An explanation of the addition to and reactivity of the 2,3-didehydrophenoxide intermediate, which is supported by DFT calculations, is presented.

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Article information

DOI
https://doi.org/10.1039/A907980G
Article type
Paper
Submitted
04 Oct 1999
Accepted
23 Dec 1999
First published
09 Feb 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 587-589

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The synthesis of 2-arylmethyl-6-hydroxybenzenecarbonitriles from the base-mediated aryne reaction of bromophenols with arylacetonitriles

S. Tandel, H. Zhang, N. Qadri, G. P. Ford and E. R. Biehl, J. Chem. Soc., Perkin Trans. 1, 2000, 587 DOI: 10.1039/A907980G

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