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 - Tập 149 Số 1-2 - Trang 153-160 - 1999
Rajender S. Varma1, Kannan P. Naicker1, Dalip Kumar1
1Department of Chemistry and Texas Research Institute for Environmental Studies (TRIES), Sam Houston State University, Huntsville, TX 77341-2117, USA

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Tài liệu tham khảo

S. Patai (Ed.), The Chemistry of the Azido Group, Interscience, London, 1971.

P. Molina, P.M. Fresenda, P. Almendros, Synthesis (1993) 54.

Patonay, 1988, J. Heterocyclic Chem., 25, 343, 10.1002/jhet.5570250158

Boyer, 1954, Chem. Rev., 54, 1, 10.1021/cr60167a001

Hassner, 1986, Angew. Chem., Int. Ed. Engl., 25, 478, 10.1002/anie.198604781

S.G. Alvarez, M.T. Alvarez, Synthesis (1997) 413.

Shalev, 1996, J. Org. Chem., 61, 1689, 10.1021/jo950273q

Abu-Orabi, 1989, J. Heterocyclic Chem., 26, 1461, 10.1002/jhet.5570260541

Harris, 1978, J. Am. Chem. Soc., 100, 8147, 10.1021/ja00494a021

Buckley, 1996, J. Org. Chem., 61, 7360, 10.1021/jo960729j

Murahashi, 1989, J. Org. Chem., 54, 3292, 10.1021/jo00275a011

E.J. Corey, K.C. Nicolaou, R.D. Balanson, Y. Machida, Synthesis (1975) 590.

Magnus, 1992, Tetrahedron Lett., 33, 2777, 10.1016/S0040-4039(00)78855-1

Trahanovsky, 1971, J. Am. Chem. Soc., 93, 5256, 10.1021/ja00749a050

Sant, 1987, Tetrahedron Lett., 28, 6019, 10.1016/S0040-4039(00)96852-7

Patonay, 1995, J. Org. Chem., 60, 2368, 10.1021/jo00113a015

Takeuchi, 1989, J. Org. Chem., 54, 431, 10.1021/jo00263a033

Patonay, 1994, J. Org. Chem., 59, 2902, 10.1021/jo00089a043

Marsh, 1972, J. Org. Chem., 37, 2966, 10.1021/jo00984a012

Priebe, 1984, Acta Chem. Scand. Ser. B, 38, 895, 10.3891/acta.chem.scand.38b-0895

P.A.S. Smith, In Derivatives of Hydrazine and Other Hydronitrogens Having N–N Bonds, Benjamin/Cummings, Reading, MA, 1983, p. 263.

Varma, 1998, Tetrahedron Lett., 39, 2915, 10.1016/S0040-4039(98)00416-X

Varma, 1998, Catal. Lett., 53, 225, 10.1023/A:1019042930634

P. Kannan, PhD Dissertation, Utility of Clay Microenvironment in Organic Reactions, Madurai Kamaraj University, Madurai, India, 1997.

Regen, 1975, J. Am. Chem. Soc., 97, 5956, 10.1021/ja00853a074

Li, 1993, Chem. Rev., 93, 2023, 10.1021/cr00022a004

Li, 1996, Tetrahedron, 52, 5643, 10.1016/0040-4020(95)01056-4

Caddick, 1995, Tetrahedron, 51, 10403, 10.1016/0040-4020(95)00662-R

A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault, D. Mathe, Synthesis (1998) 1213.

R.S. Varma, Green Chemistry (1999) 43.

R.S. Varma, Clean Products and Processes (1999) in press.

Mason, 1997, Chem. Soc. Rev., 26, 443, 10.1039/cs9972600443

G.J. Price (Ed.), Current Trends in Sonochemistry, Royal Society of Chemistry, Cambridge, 1993.

Luzzio, 1993, J. Org. Chem., 58, 512, 10.1021/jo00054a043

Luche, 1997, Ultrasonics Sonochem., 4, 211, 10.1016/S1350-4177(97)00008-4

J.L. Luche, P. Cintas, in: A. Fürstner (Ed.), Active Metals, VCH, Weinheim, 1995, p. 133.

K.S. Suslick, D. Docktycz, in: T.J. Mason (Ed.), Advances in Sonochemistry, JAI Press, London, 1 (1990) 197.

A. Loupy, J.L. Luche, in: Y. Sasson, R. Neumann (Eds.), Handbook of Phase Transfer Catalysis, Blackie Academic and Professional, London, 1997, p. 369.

J.L. Luche, in: T.J. Mason (Ed.), Advances in Sonochemistry, JAI Press, London, 3, 1993, p. 85.

T. Ando, T. Kawate, J. Ichihara, T. Hanafusa, Chem. Lett. (1984) 725.

Jurczak, 1988, Tetrahedron Lett., 29, 959, 10.1016/S0040-4039(00)82493-4

Priebe, 1987, Acta Chem. Scand. Ser. B, 41, 640, 10.3891/acta.chem.scand.41b-0640

T. Ando, R. Kimura, in: T.J. Mason (Ed.), Advances in Sonochemistry, JAI Press, London, 2, 1991, p. 211.

Koser, 1982, J. Org. Chem., 47, 2487, 10.1021/jo00133a053