Efficient electrosynthesis of α-chloro-α,β-unsaturated carboxylic and phosphonic esters using magnesium electrochemical activation

Synthesis

Volumn , Issue 6, 1999, Pages 981-984

  Goumain, Sophic ^a   Jubault, Philippe ^a   Feasson, Christian ^a   Collignon, Noël ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

Electrosynthesis; Horner Wadsworth Emmons olefination; Magnesium electrochemical activation; chloro , unsaturated phosphonic esters; chloro , unsaturated carboxylic esters

Indexed keywords

MAGNESIUM; PHOSPHONIC ACID ESTER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; SYNTHESIS;

EID: 0032996299     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3501     Document Type: Article

References (24)

1. Engel, R. In Handbook of Organophosphorus Chemistry; Engel, R. Ed.; Marcel Dekker, Inc.: New York, 1992; p 559.
2. a) Wadsworth, W. S. Org. React. 1997, 25, 73.
3. b) Walker, B. J. In Organophosphorus Reagents in Organic Synthesis; Cadogan, J. I. G. Ed.; Academic Press: London, 1979; p 155.
4. a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
5. b) Kelly, S. E. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991; p 755.
6. Le Menn, J.-C.; Sarrazin, J.; Tallec, A. Can. J. Chem. 1989, 67, 1332, and ref. cited therein.
7. a) Jubault, P.; Feasson, C.; Collignon, N. Tetrahedron Lett. 1995, 36, 7073.
8. b) Tetrahedron Lett. 1996, 37, 3679.
9. Jubault, P.; Goumain, S.; Feasson, C.; Collignon, N. Tetrahedron, accepted for publication.
10. McKenna, C. E.; Khawli, L. A. J. Org. Chem. 1986, 51, 5467.
11. 6) = 43.5 and 43.15 for 1′ and at 47.75 and 47.5 for 2′. The presence of two peaks in each case is in agreement with the existence of such stabilized carbanions as slowly interconverting species, see for example: a) Bottin-Strzalko, T.; Corset, J.; Froment, F.; Pouet, M.-J.; Seyden-Penne, J.; Simonin, M.-P. J. Org. Chem. 1980, 45, 1270.
12. b) Bottin-Strzalko, T.; Corset, J.; Froment, F.; Pouet, M.-J.; Seyden-Penne, J.; Simonin, M.-P. Phosphorus and Sulfur 1985, 22, 217.
13. Jubault, P.; Feasson, C.; Collignon, N. Bull. Soc. Chim. Fr. 1995, 132, 850.
14. Carbanions 1′ and 2′ thus electrogenerated are very stable anionic species, which can be kept for 24 h at r.t., under an inert atmosphere, without any loss of their reactivity.
15. Patois, C.; Savignac, P. Synlett 1991, 517.
16. Villieras, J.; Perriot, P.; Normant, J. F. Synthesis 1978, 31. It sould be noted that using more sophisticated substitution pattern of the phosphorus atom led to sustantial increase in (E)-stereoselectivity of 3: see Ref. 10.
17. a) Seyferth, D.; Marmor, R. S. J. Organometal. Chem. 1973, 59, 237.
18. b) Teulade, M. P.; Savignac, P.; Elia Aboujaoude, E.; Lietgé, S.; Collignon, N. J. Organometal. Chem. 1986, 304, 283.
19. Lowen, G. T.; Almond, M. R. J. Org. Chem. 1994, 59, 4548.
20. Perlikowska, W.; Mphahele, M. J.; Modro, T. A. J. Chem. Soc., Perkin Trans. 2, 1997, 967.
21. HP coupling constant of the olefinic proton [-40 Hz for (Z)-4 and - 13 Hz for (E)-4]. See for example Refs 12b and 12d.
22. 3) = - 60.8 [(Z)-isomer]; - 61.5 [(E)-isomer].
23. 1H} NMR spectrum of 4g was in agreement with a cis P-C=C-C arrangement [(Z)-isomer]; see for example: Quin, L. D. In Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis; Verkade, J. G.; Quin, L. D. Eds.; VCH: Deerfield Beach, 1987; p 401.
24. Teulade, M.-P.; Savignac, P. J. Organometal. Chem. 1988, 338, 295.