Can ultrasound substitute for a phase-transfer catalyst? Triphase catalysis and sonochemical acceleration in nucleophilic substitution of alkyl halides and α-tosyloxyketones: Synthesis of alkyl azides and α-azidoketones

Journal of Molecular Catalysis A: Chemical

Volumn 149, Issue 1-2, 1999, Pages 153-160

  Varma, Rajender S ^a   Naicker, Kannan P ^a   Kumar, Dalip ^a  

^a SAM HOUSTON STATE UNIVERSITY   (United States)

Author keywords

Azidoketones; Tosyloxyketones; Alkyl azides; Alkyl halides; Montmorillonite K 10 clay; Sonochemical acceleration; Tetraalkylammonium bromides; Triphase catalyst

Indexed keywords

AZIDE; HALIDE; KETONE DERIVATIVE; SODIUM AZIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; NONHUMAN; REACTION ANALYSIS; SYNTHESIS; ULTRASOUND;

EID: 0033573119     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(99)00168-5     Document Type: Article

References (44)

1. S. Patai (Ed.), The Chemistry of the Azido Group, Interscience, London, 1971.
2. P. Molina, P.M. Fresenda, P. Almendros, Synthesis (1993) 54.
3. Patonay T., Patonay-Peli E., Litkei G., Szilagyi L., Batta G., Dinya Z. J. Heterocyclic Chem. 25:1988;343.
4. Boyer J.H., Canter F.C. Chem. Rev. 54:1954;1.
5. Hassner A., Stern M. Angew. Chem., Int. Ed. Engl. 25:1986;478.
6. S.G. Alvarez, M.T. Alvarez, Synthesis (1997) 413.
7. Shalev D.E., Chiacchiera S.M., Radkowsky A.E., Kosower E.M. J. Org. Chem. 61:1996;1689.
8. Abu-Orabi S.T., Adnan Atfah M., Jibril I., Mari'i F.M., Al-Sheikh Ali A. J. Heterocyclic Chem. 26:1989;1461.
9. Harris J.M., Mount D.L., Smith M.R., Neal W.C., Dukes M.D., Raber D.J. J. Am. Chem. Soc. 100:1978;8147.
10. Buckley N., Oppenheimer N.J. J. Org. Chem. 61:1996;7360.
11. Murahashi S.I., Taniguchi Y., Imada Y., Tanigawa Y. J. Org. Chem. 54:1989;3292.
12. E.J. Corey, K.C. Nicolaou, R.D. Balanson, Y. Machida, Synthesis (1975) 590.
13. Magnus P., Barth L. Tetrahedron Lett. 33:1992;2777.
14. Trahanovsky W.S., Robbins M.D. J. Am. Chem. Soc. 93:1971;5256.
15. Sant K.V., South M.S. Tetrahedron Lett. 28:1987;6019.
16. Patonay T., Hoffman R.V. J. Org. Chem. 60:1995;2368.
17. Takeuchi H., Yanagida S., Ozaki T., Hagiwara S., Eguchi S. J. Org. Chem. 54:1989;431.
18. Patonay T., Hoffman R.V. J. Org. Chem. 59:1994;2902.
19. Marsh F.D. J. Org. Chem. 37:1972;2966.
20. Priebe H. Acta Chem. Scand. Ser. B. 38:1984;895.
21. P.A.S. Smith, In Derivatives of Hydrazine and Other Hydronitrogens Having N-N Bonds, Benjamin/Cummings, Reading, MA, 1983, p. 263.
22. Varma R.S., Naicker K.P. Tetrahedron Lett. 39:1998;2915.
23. Varma R.S., Kumar D. Catal. Lett. 53:1998;225.
24. P. Kannan, PhD Dissertation, Utility of Clay Microenvironment in Organic Reactions, Madurai Kamaraj University, Madurai, India, 1997.
25. Regen S.L. J. Am. Chem. Soc. 97:1975;5956.
26. Li C.J. Chem. Rev. 93:1993;2023.
27. Li C.J. Tetrahedron. 52:1996;5643.
28. Caddick S. Tetrahedron. 51:1995;10403.
29. A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault, D. Mathe, Synthesis (1998) 1213.
30. R.S. Varma, Green Chemistry (1999) 43.
31. R.S. Varma, Clean Products and Processes (1999) in press.
32. Mason T.J. Chem. Soc. Rev. 26:1997;443.
33. G.J. Price (Ed.), Current Trends in Sonochemistry, Royal Society of Chemistry, Cambridge, 1993.
34. Luzzio F.A., Moore W.J. J. Org. Chem. 58:1993;512.
35. Luche J.L. Ultrasonics Sonochem. 4:1997;211.
36. J.L. Luche, P. Cintas, in: A. Fürstner (Ed.), Active Metals, VCH, Weinheim, 1995, p. 133.
37. K.S. Suslick, D. Docktycz, in: T.J. Mason (Ed.), Advances in Sonochemistry, JAI Press, London, 1 (1990) 197.
38. A. Loupy, J.L. Luche, in: Y. Sasson, R. Neumann (Eds.), Handbook of Phase Transfer Catalysis, Blackie Academic and Professional, London, 1997, p. 369.
39. J.L. Luche, in: T.J. Mason (Ed.), Advances in Sonochemistry, JAI Press, London, 3, 1993, p. 85.
40. T. Ando, T. Kawate, J. Ichihara, T. Hanafusa, Chem. Lett. (1984) 725.
41. Jurczak J., Ostaszewski R. Tetrahedron Lett. 29:1988;959.
42. Priebe H. Acta Chem. Scand. Ser. B. 41:1987;640.
43. T. Ando, R. Kimura, in: T.J. Mason (Ed.), Advances in Sonochemistry, JAI Press, London, 2, 1991, p. 211.
44. Koser G.F., Relenyi A.G., Kalos A.N., Rebrovic L., Wettach R.H. J. Org. Chem. 47:1982;2487.