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Electron-transfer-induced reductive cleavage of chlorinated aryloxyalkanoic acids

Azzena, Ugo Gavino and Pittalis, Mario (2011) Electron-transfer-induced reductive cleavage of chlorinated aryloxyalkanoic acids. Tetrahedron, Vol. 67 (19), p. 3360-3362. ISSN 0040-4020. Article.

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DOI: 10.1016/j.tet.2011.03.057


We investigated the degradation of chlorinated herbicides, with an aryloxyalkanoic acid skeleton, under reductive electron transfer reaction conditions. Although Li and Na metals proved useless, activated forms of these metals, either their soluble naphthalene radical anions or 1,2-diarylethane dianions, promoted the degradation of the starting materials to various extents. Indeed, lithium naphthalenide promoted both extensive dehalogenation and dealkylation of chlorinated aryloxyalkanoic acids, with formation of the corresponding phenols as the main reaction products. In contrast, the employment of 1,2-diphenyl-1,2-disodioethane as a reducing agent led, in most examples, to the chemoselective recovery of the corresponding dechlorinated acids.

Item Type:Article
ID Code:6213
Uncontrolled Keywords:Aryloxyalkanoic acid, chlorinated herbicide, electron transfer, hydrodealkylation, hydrodehalogenation, reduction
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
Publisher:Pergamon / Elsevier
Copyright Holders:© 2011 Elsevier Ltd.
Deposited On:04 Jul 2011 17:05

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