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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 20
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Original Articles

Isomerization of Hetaryl Analogues of α‐Benzoins in Basic Media

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Pages 3727-3735 | Received 19 Jan 2004, Published online: 19 Apr 2010
 

Abstract

The α → β isomerization of hetaryl analogues of benzoins occurring in basic media on heating is a convenient preparative way to obtain hydroxymethylcarbonyl‐substituted derivatives of π‐excessive heterocycles. The reaction is favored by increased catalyst basicity, solvent polarity, and the electron‐donor ability of a hetaryl residue. At room temperature, oxidation to hetaryl analogues of benzil becomes dominating.

Acknowledgments

We are pleased to acknowledge the financial support provided by the Ministry of Education and Science of Ukraine (Grant No. 0101U001529).

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