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Synthesis 2011(1): 154-160  
DOI: 10.1055/s-0030-1258324
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Reactivity of β,γ-Dihalogenated Unsaturated Acids: Application to the Synthesis of 4-Substituted 5H-Furan-2-ones

S. Lamandé-Langlea, S. Inack Ngib, E. Anselmib, H. Allouchib, A. Duchêneb, M. Abarbrib, J. Thibonnet*b
a Laboratoire Groupe SUCRES, Unité Mixte 7565 CNRS, Université Henri Poincaré-Nancy 1, B.P. 239, 54506 Nancy-Vandoeuvre, France
b Laboratoire de Physicochimie des Matériaux et des Biomolécules, EA 4244, Faculté des Sciences et Techniques de Tours, Parc de Grandmont, 37200 Tours, France
Fax: +33(2)47367073; e-Mail: jerome.thibonnet@univ-tours.fr;
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Publication History

Received 14 September 2010
Publication Date:
15 November 2010 (online)

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Abstract

β,γ-Dihalogenated unsaturated acids were prepared regio­- and stereoselectively from allenic acid, and some aspects of their reactivities were studied.

Key words

α,β-unsaturated acids - halogenation - carboxylic acids - cross-coupling - organometallic reagents

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14

Crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Center under CCDC Nos. 702136 (compound 2d), 745342 (compound 2c), 745343 (compound 2a), and 785338 (compound 2b). Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk or www.http://www.ccdc.cam.ac.uk].