Selective Synthesis of Dihalo-Substituted Unsaturated Carboxylic Acids and Derivatives

Sandrine Langle; Samuel Inack Ngi; Elsa Anselmi; Mohamed Abarbri; Jérôme Thibonnet; Alain Duchêne

doi:10.1055/s-2007-966043

PAPER

Selective Synthesis of Dihalo-Substituted Unsaturated Carboxylic Acids and Derivatives

Sandrine Langle^a, Samuel Inack Ngi^b, Elsa Anselmi^b, Mohamed Abarbri^b, Jérôme Thibonnet^b, Alain Duchêne*^b
^a Laboratoire Groupe SUCRES, Unité Mixte 7565 CNRS, Université Henri Poincaré-Nancy 1, B.P. 239, 54506 Nancy-Vandoeuvre, France
^b Laboratoire de Synthèse et Physicochimie Organique et Thérapeutique, Faculté des Sciences et Techniques de Tours, Parc de Granmont, 37200 Tours, France
Fax: +33(2)47367073; e-Mail: alain.duchene@univ-tours.fr;

Abstract

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Abstract

A selective one-pot procedure was developed for the production of E-dihalo-substituted α,β-unsaturated alkenoic acids and derivatives from the corresponding α,β-unsaturated alkynoic acids.

Key words

α,β-unsaturated acids - carboxylic acids - α,β-dihalo-substituted acrylic acids - halogenation - addition reactions

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References

1a Larson S. Luidhardt T. Kabalka GW. Pagni RM. Tetrahedron Lett. 1988, 29: 35

1b Pagni RM. Kabalka GW. Boothe R. Gaetano K. Stewart LJ. Conaway R. Dial C. Gray D. Larson S. Luidhardt T. J. Org. Chem. 1988, 53: 4477

1c Hondrogiannis G. Lee LC. Kabalka GW. Pagni RM. Tetrahedron Lett. 1989, 30: 2069

2a Hollins RA. Campos MPA. J. Org. Chem. 1979, 44: 3931

2b Heasley VL. Shellhamer DF. Heasley LE. Yaeger DB. Heasley GE. J. Org. Chem. 1980, 45: 4649

2c Duan J. Dolbier WR. Chen QY. J. Org. Chem. 1998, 63: 9486

2d Armengol M. Joule J. J. Chem. Soc., Perkin Trans. 1 2001, 978

2e Manickam G. Siddappa U. Li Y. Tetrahedron Lett. 2006, 47: 5867

3a Lemay A. Vulic K. Ogilvie W. J. Org. Chem. 2006, 71: 3615

3b Berthelot J. Fournier M. Can. J. Chem. 1986, 64: 603

4a Rossi R. Bellina F. Carpita A. Gori R. Gazz. Chim. Ital. 1995, 125: 381

4b Rossi R. Bellina F. Carpita A. Mazzarella F. Tetrahedron 1996, 52: 4095

4c Rossi R. Bellina F. Mannina L. Tetrahedron Lett. 1998, 39: 3017

5a Henaff N. Stewart SK. Whiting A. Tetrahedron Lett. 1997, 38: 4525

5b Henaff N. Whiting A. J. Chem. Soc., Perkin Trans. 1 2000, 395

5c Bellina F. Colzi F. Mannina L. Rossi R. Viel S. J. Org. Chem. 2003, 68: 10175

6a Andersson K. Chem. Scr. 1972, 2: 113

6b Andersson K. Chem. Scr. 1972, 2: 117

7 Castro CE. Gaughan EJ. Owsley DC. J. Org. Chem. 1965, 30: 587

8 Otwinowsky Z. Minor W. In Methods in Enzymology: Macromolecular Crystallography Part A, Vol. 276: Carter CW. Sweet RM. Academic Press; New York: 1997. p.307-326

9 Blessing RH. J. Appl. Crystallogr. 1997, 30: 421

10 Altamore A. Cascarano G. Giacovazzo C. Guagliardi A. Burla MC. Polidori G. Camalli M. J. Appl. Crystallogr. 1994, 27: 435

11 Sheldrick GM. Acta Crystallogr., Sect. A 1990, 46: 467

12 Sheldrick GM. SHELXL-97, Program for the Refinement of Crystal Structures University of Göttingen; Göttingen, Germany: 1997.