P-Toluenesulfonic acid-Celite as a reagent for synthesis of esters of alkylphosphonic acids under solvent-free conditions

Journal of Chemical Research

Volumn , Issue 6, 2007, Pages 328-331

  Gupta, Arvind K ^a   Kumar, Rajesh ^a   Dubey, Devendra K ^a   Kaushik, M P ^a  

^a DEFENCE RESEARCH AND DEVELOPMENT ESTABLISHMENT   (India)

Author keywords

Chemical warfare agents; Chemical weapons convention (CWC); P toluenesulfonic acid; Phosphate; Phosphonate

Indexed keywords

EID: 34547755541     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823407X218066     Document Type: Article

References (62)

1. R. Hildebrand, The Role of Phosphonates in Living Systems; CRC Press: Boca Raton, 1983.
2. (a) E.S. Papazoglou, In Handbook of Building Materials for Fire Protection vol. 88, pp. 1-4 C.A. Harper, Ed: McGraw-Hill: New York. 2004;
3. (b) E.D. Weil, Phosphorus Flame Retardents. In Kirk-Othmer Encyclopedia of Chemical Technology, vol. 10 4th edn.; John Wiley: New York, 1993, pp. 976-998.
4. (a) C. Fest and K.J. Schmidt, The Chemistry of Organophosphorus Pesticides, Springer- Verlag, Berlin, 1982;
5. (b) P. Hinkle and R.Y. McCarty, Scient Am. 1978, 104, 238.
6. (a) M. Eto, Organophosphorus Pesticides: Organic and Biological Chemistry, CRC Press Inc. USA, 1974, 18;
7. (b) J.R. Van Wazer, Phosphorus and its Compounds, Vol. II, Interscience Publishers, Inc. New York. 1961;
8. (c) F.M. Ashton and A.S. Crafts, Mode of Action of Herbicides, Wiley Interscience, New York, 1973.
9. (a) G.M. Kosolapoff, Organic Phosphorus Compounds Vol. 6, Wiley-Interscience, New York, 1950, 503;
10. (b) P. Kafarski and B. Lejczak, Phosphorus. Sulfur Silicon Relat. Elem. 1991, 63, 193;
11. (c) E. Shi and C. Pei, Synthesis, 2004, 2995.
12. (a) J.P. Krise and V.J. Stella, Adv. Drug Delivery Rev., 1996, 19, 287;
13. (b) R. Engel, Chem. Rev. 1977, 77, 349;
14. (c) A. Whitehead, J.D. Moore and RR. Hanson, Tetrahedron Lett., 2003, 44, 4275.
15. B. Maryanoff and A. Ritz, Chem. Rev., 1989, 89, 863.
16. C.A. Verbicky and C.K. Zencher, J.Org. Chem., 2000, 65, 5615.
17. (a) E.W.J. Hooijschuur. A.G. Hulst, A.L.de Jong, L.P. de Reuver, S.H. van Krimpen, B.L.M. van Baar, E.R.J. Wils, CE. Kientz and U.A. Th. Brinkman, Trends Anal. Chem., 2002, 21, 116;
18. (b) M. Mesilaakso and E.L. Tolppa, Anal. Chem., 1996, 66, 2313;
19. (c) R.M. Black and R.W. Read, J. Chromatogr. A. 1997, 759, 79;
20. (d) M. Mesilaakso in Chemical Weapons Chemical Analysis, (ed.), Encyclopedia of Analytical Chemistry, Wiley, New York, 2005;
21. (e) R.M. Black and J.M. Harrison, The Chemistry of Organophosphorus Chemical Warfare Agents, in The Chemistry of Organophosphorus Compounds, F.R. Hartley, Ed., John Wiley & Sons, Chichester, 1996, 781.
22. (a) W. Krutysch and R.F. Trap, A Commentary on CWC, Martinnus Nijhott, The Netherlands, 1994;
23. (b) Convention on Prohibition of the Development, Production, Stockpiling and use of Chemical Warfare and on their Destruction, US control and Disarmament Agency, Washington D.C, 1993;
24. (c) S. Mogl, In Chemical Weapons Convention Chemicals Analysis: Sample Collection, Preparation and Analytical Methods, M. Mesilaakso (ed.), John Wiley & Sons Ltd, England, 2005, vol. 2, 8.
25. (a) A.K. Bhattacharya and G. Thyagarajan, Chem. Rev., 1981, 81, 415;
26. (b) A Michaelis and R. Kaehne, Ber. Dtsch. Chem. Ges., 1898, 31, 1048;
27. (c) B.A. Arbusov, Pure Appl. Chem., 1964, 9, 315;
28. (d) R.G. Harvey and E.R. Sombre, The Michaelis-Arbuzov and Related Rections in Topics in Phosphorus Chemistry, Vol. 1, Interscience, New York, 1964, p.57.
29. (a) Methoden der Organischen Chemie (Houben-Weyl), E. Muller, Ed., George Thieme Verlag, Stuttgart, 1964; XII/I, 433;
30. (b) A. Michaelis and T. Becker, Chem. Ber., 1897, 30, 1003;
31. (c) Q. Yao and S. Levchik, Tetrahedron Lett., 2006, 47, 277;
32. (d) S. Samanta and N.K. Roy, Indian. J. Chem., 1998, 37B, 564.
33. K.C. Nicolaou, Z.Yang, M. Ouellette, G.O. Shi, P. Gaertner, J.L. Gunzner, C. Agrios, R. Huber, R. Chadha and D.H. Huang, J. Am. Chem. Soc., 1997, 119, 8105;
34. (b) E.A. Dennis and F.H. Westheimer, J. Am. Chem. Soc, 1966, 88, 3432;
35. (c) A.C. Poshkus and J.E. Herweh, J. Am. Chem. Soc., 1962, 84, 555;
36. (d) J. Acharya, P.D. Shakya, D. Pardasani, M. Palit, D.K. Dubey and A.K. Gupta, J. Chem. Res., 2005, 3, 194.
37. Q.Yao and S. Levchik, Tetrahedron Lett., 2006, 47, 277;
38. (b) M. Sathe, A.K. Gupta and M.P. Kaushik, Tetrahedron Lett., 2006, 47, 3107.
39. (a) M. Kabachnik (ed.) Reactions and Methods of Organic Compound Investigation Vol.13. Goskhimizdat, Moscow, 1953, 427;
40. (b) L.D.A. Quin, Guide to Organophosphorus Chemistry; John Wiley and Sons, 2000.
41. (a) G.M. Kosolapoff, J. Am. Chem. Soc., 1945, 67, 1180;
42. (b) M.R.M.D. Charandabi, M.L. Ettel, M.P. Kaushik, J.H. Huffman and K.W. Morse, Phosphorus, Sulfur Silicon Relat. Elem., 1989, 44, 233 and refs therein.
43. (a) A.P. Wight and M.E. Davis, Chem. Rev., 2002, 102, 3589;
44. (b) A. Fadel, R. Yefash and J. Saluan, Synthesis, 1987, 37;
45. (c) G. Rosini, R. Falarini, E. Marotta and R. Righi, J. Org. Chem., 1990, 55, 781;
46. (d) M. Kodomari, T. Sakamoto and S. Yoshitomi, J. Chem. Soc., Chem. Commun., 1990, 701;
47. (e) P.J. Kropp, K.A. Daus, S.D. Crawford, M.W. Tubergren, K.D. Kepler, S.L. Craig and V.P Wilson, J. Am. Chem. Soc., 1990, 112, 7433;
48. (f) G. Hondrogiannis, R.M. Pagni, G.W. Kabalka, P. Anisoki and R Kurt, Tetrahedron Lett., 1990, 31, 5433;
49. (g) H.K. Patney, Tetrahedron Lett., 1991, 32, 2259;
50. (h) G. Schotter, Chem. Mater., 2001, 13, 3422.
51. (a) Solvent-Free Organic Synthesis, K. Tanaka, Wiley-VCH, Weinheim, 2003;
52. (b) R.J. Gedye, K. Westaway, H. Ali, L. Baldisera, L. Laberge and J. Rousell, Tetrahedron Lett., 1986, 27, 279.
53. (a) R.J. Giguere, T.L. Bray, S.M. Duncan and G. Majetich, Tetrahedron Lett., 1986, 27, 4945;
54. (b) A. Abramovitch, Org. Prep. Proc Int., 1991, 23, 685;
55. (c) D.M.P. Mingos and D.R. Baghurst, Chem. Soc. Rev., 1991, 20, 1;
56. (d) S. Caddick, Tetrahedron. 1995, 51, 10403.
57. A. Loupy, A. Petit, M. Ramdiani, C. Yvanaeff, M. Majdoub, B. Labiad, and D. Villemin, Can. J. Chem., 1993, 71, 90;
58. (b) A. Baezza, C. Najera, R. Gracia and J.M. Sansano, Synthesis, 2005, 2787.
59. H.M. Ali and M.G. Gomes, Synthesis, 2005, 1326.
60. (a) M. Nivsarker, A.K.Gupta and M.P. Kaushik, Tetrahedron Lett., 2004, 45, 6863;
61. (b) J. Acharya, A.K. Gupta and M.P. Kaushik, Tetrahedron Lett., 2005, 46, 5293.
62. Organisation for the Prohibition of Chemical Weapons (OPCW) Central Analytical database (e-OCAD) v, 5 April 2004.