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New Approaches to the Cannizzaro and Tishchenko Reactions

Chandrasekhar, Sosale and Srimannarayana, Malempati (2009) New Approaches to the Cannizzaro and Tishchenko Reactions. In: Synthetic Communications, 39 (24). pp. 4473-4478.

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It is demonstrated that the titled reactions are best carried out at high concentrations, as indicated by mechanistic considerations: the observed high reaction orders and the possibility that the Cannizzaro reaction is driven by the hydrophobic effect, which effects proximity between the two molecules of the aldehyde reactant. The present studies have led to improved conditions, simplified workup, and excellent yields of products. The Tishchenko reaction converted benzaldehyde to benzyl benzoate with catalytic NaOMe/tetrahydrafuran in good yield, which is apparently unprecedented for this product of high commercial value.

Item Type: Journal Article
Publication: Synthetic Communications
Publisher: Taylor & Francis
Additional Information: Copyright for this article belongs to Taylor & Francis.
Keywords: Benzaldehyde; Cannizzaro; hydrophobic; oxidation; reduction; Tishchenko
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 05 Jan 2010 11:34
Last Modified: 19 Sep 2010 05:54
URI: http://eprints.iisc.ac.in/id/eprint/25326

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