Salt effects on the Baylis-Hillman reaction

Tetrahedron

Volumn 59, Issue 27, 2003, Pages 5019-5026

  Kumar, Anil ^a   Pawar, Sanjay S ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Baylis Hillman reaction; Salt effect; Solubility

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; ANION; CATION; FORMAMIDE; LITHIUM CHLORIDE; SODIUM CHLORIDE; SOLVENT; WATER;

ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REACTION ANALYSIS; SOLUBILITY;

EID: 0038718497     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00760-9     Document Type: Article

References (33)

1. Baylis, A. B.; Hillman, M. E. D. German Patent 2,155,113, 1972; Chem. Abstr. 1972, 77, 34174q.
2. Drewes S.E., Roos G.H.P. Tetrahedron. 44:1988;4653.
3. Basavaiah D., Rao P.D., Hyma R.S. Tetrahedron. 52:1996;8001.
4. Ciganek E. Org. React. 51:1997;201.
5. Langer P. Angew. Chem. Int. Ed. 39:2000;3049.
6. For using water and salts, see: Auge J., Lubin N., Lubineau A. Tetrahedron Lett. 35:1994;7947. This report also gives references to other methods employed to speed up the Baylis-Hillman reactions.
7. For the combined use of metal catalyst and co-ligand see: Aggarwal V.K., Mereu A., Tarver G.J., McCaugue R. J. Org. Chem. 63:1998;7183.
8. For the use of more effective catalysts than DABCO, see: Aggarwal V.K., Mereu A. Chem. Commun. 1999;2311.
9. 4-diethyl ether see: Kawamura M., Kobayashi S. Tetrahedron Lett. 40:1999;1539.
10. For the use of DABCO see: Yu C., Liu B., Hu L. J. Org. Chem. 66:2001;5413.
11. For the use of catalyst see: Ameer F., Drewes S.E., Freese S., Kaye P.T. Synth. Commun. 18:1988;495.
12. For an exhaustive use of catalysts and optimum choice of 3-hydroxyquinuclidine in the Baylis-Hillman reactions, see: Aggarwal V.K., Dean D.K., Mereu A., Williams R. J. Org. Chem. 67:2002;510.
13. Breslow R. Acc. Chem. Res. 24:1991;159.
14. Garner P.P. Grieco P.A. Diels-Alder Reactions in Aqueous Media. Diels-Alder Reactions in Aqueous Media. 1998;Blackie, Glassgow. Chapter 1.
15. Kumar A. Chem. Rev. 101:2001;1. and references cited therein.
16. Breslow R., Guo T. J. Am. Chem. Soc. 110:1988;5613.
17. Pawar S.S., Phalgune U.D., Kumar A. J. Org. Chem. 64:1999;7055.
18. Debye P., McAulay J. Phys. Z. 26:1925;22.
19. Long F.A., McDevitt F.W. Chem. Rev. 52:1952;119.
20. McDevitt F.W., Long F.A. J. Am. Chem. Soc. 74:1952;1773.
21. Breslow R., Connors R.V. J. Am. Chem. Soc. 117:1995;6601.
22. Breslow R., Connors R.V., Zhu Z. Pure Appl. Chem. 68:1996;1527.
23. Kumar A., Phalgune U.D., Pawar S.S. J. Phys. Org. Chem. 14:2001;577.
24. Grieco P.A., Nunes J.J., Gaul M.D. J. Am. Chem. Soc. 112:1990;4595.
25. Kumar A., Pawar S.S. J. Org. Chem. 66:2001;7646. and references cited therein.
26. Rizzo C.J. J. Org. Chem. 57:1992;6382.
27. Hofmeister F. Ach. Exptl. Pathol. Pharmakol. 24:1888;247.
28. For details see: Collins K.D., Washabaugh M.W. Q. Rev. Biophys. 18:1985;323.
29. Marcus Y. Ion Solvation. 1986;Wiley/Interscience, New York.
30. Kumar A. Can. J. Chem. Engng. 71:1993;948.
31. Kumar A. J. Phys. Chem. B. 104:2000;9505.
32. Kumar A., Phalgune U.D., Pawar S.S. J. Phys. Org. Chem. 15:2002;131.
33. Schumacher J.C. ACS Monographs Series. ACS Monographs Series. 1960;American Chemical Society, Washington DC.