Revised mechanism and improved methodology for the Perkin condensation. Resuscitation of the mechanism involving benzal acetate and the improbability of the enolate of acetic anhydride

Chandrasekhar, Sosale and Karri, Phaneendrasai (2006) Revised mechanism and improved methodology for the Perkin condensation. Resuscitation of the mechanism involving benzal acetate and the improbability of the enolate of acetic anhydride. In: Tetrahedron Letters, 47 (13). pp. 2249-2251.

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Abstract

The Perkin condensation most likely occurs via the initial formation of a gem-diacetate from the aromatic aldehyde and acetic anhydride reactants. The key reactive nucleophile appears to be the enolate of the gem-diacetate rather than of acetic anhydride. The diacetate from PhCHO may be converted to cinnamic acid under a variety of (relatively) mild basic conditions

Item Type:	Journal Article
Publication:	Tetrahedron Letters
Publisher:	Elsavier
Additional Information:	Copyright of this article belongs to Elsavier.
Keywords:	Acetic anhydride;gem-Diacetate;Cinnamic acid;Enolate;Perkin condensation.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	08 Apr 2009 07:06
Last Modified:	19 Sep 2010 04:58
URI:	http://eprints.iisc.ac.in/id/eprint/17797

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