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Synthesis of substituted nitroolefins: a copper catalyzed nitrodecarboxylation of unsaturated carboxylic acids

Rokade, Balaji V and Prabhu, Kandikere Ramaiah (2013) Synthesis of substituted nitroolefins: a copper catalyzed nitrodecarboxylation of unsaturated carboxylic acids. In: ORGANIC & BIOMOLECULAR CHEMISTRY, 11 (39). pp. 6713-6716.

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Official URL: http://dx.doi.org/10.1039/c3ob41408f

Abstract

A novel, mild and convenient method for the nitrodecarboxylation of substituted cinnamic acid derivatives to their nitroolefins is achieved using a catalytic amount of CuCl (10 mol%) and tert-butyl nitrite (2 equiv.) as a nitrating agent in the presence of air. This reaction provides a useful method for the synthesis of beta,beta-disubstituted nitroolefin derivatives, which are generally difficult to access from other conventional methods. Additionally, this reaction is selective as the E-isomer of the acid derivatives furnishes the corresponding E-nitroolefins. One more salient feature of the method is, unlike other methods, no metal nitrates or HNO3 are employed for the transformation.

Item Type: Journal Article
Additional Information: copyright for this article belongs to RSC
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 01 Nov 2013 09:46
Last Modified: 01 Nov 2013 09:46
URI: http://eprints.iisc.ac.in/id/eprint/47632

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