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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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
Publication:	ORGANIC & BIOMOLECULAR CHEMISTRY
Publisher:	ROYAL SOC CHEMISTRY
Additional Information:	copyright for this article belongs to RSC
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
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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