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Haller–Bauer Reaction Revisited: Synthetic Applications of a Versatile C–C Bond Scission Reaction

Mehta, Goverdhan and Venkateswaran, RV (2000) Haller–Bauer Reaction Revisited: Synthetic Applications of a Versatile C–C Bond Scission Reaction. In: Tetrahedron, 56 (11). pp. 1399-1422.

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Abstract

The base-induced cleavage of non-enolisable ketones leading to a carboxylic acid derivative and a neutral fragment in which the carbonyl group is replaced by a hydrogen, is referred to as the Haller–Bauer (HB) reaction (Eq. (1)) This C–C bond cleavage reaction was first discovered by Semmler1 in 1906, during his classical studies on the degradation of the monoterpene fenchone, which on treatment with sodamide furnished a cyclopentanecarboxylic acid amide (Eq. (2)). Haller and Bauer followed up on this novel observation and explored its generality employing a variety of relatively simple aliphatic and aromatic ketones.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 24 Sep 2008 10:20
Last Modified: 19 Sep 2010 04:49
URI: http://eprints.iisc.ernet.in/id/eprint/15846

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