An efficient method for the esterification of phosphonic and phosphoric acids using silica chloride

Tetrahedron Letters

Volumn 47, Issue 18, 2006, Pages 3107-3109

  Sathe, Manisha ^a   Gupta, Arvind K ^a   Kaushik, M P ^a  

^a Process Technology Development Division   (India)

Author keywords

CWA; CWC; Dialkyl phosphite; Heterogeneous catalyst; Phosphate; Phosphonate; Silica chloride; Trialkyl phosphite

Indexed keywords

CHLORINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORIC ACID DERIVATIVE; SILICA CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; ESTERIFICATION; QUANTITATIVE ANALYSIS; QUANTUM YIELD;

EID: 33646026731     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.159     Document Type: Article

References (36)

1. Hinkle P., and McCarty R.Y. Sci. Am. 104 (1978) 238
2. Eto M. Organophosphorus Pesticides: Organic and Biological Chemistry (1974), CRC Press, USA p 18
3. Van Wazer John R. Phosphorus and its Compounds Vol. II (1961), Interscience, New York
4. Engel R. Chem. Rev. 77 (1977) 349
5. Kosolapoff G.M. Organic Phosphorus Compounds Vol. 6 (1950), Wiley-Interscience, New York p 503
6. Kafarski P., and Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem. 63 (1991) 193
7. Shi E., and Pei C. Synthesis (2004) 2995
8. Krise J.P., and Stella V.J. Adv. Drug Delivery Rev. 19 (1996) 287
9. Hildebrand R. The Role of Phosphonates in Living Systems (1983), CRC Press, Boca Raton
10. Engel R. Chem. Rev. 77 (1977) 349
11. Whitehead A., Moore J.D., and Hanson P.R. Tetrahedron Lett. 44 (2003) 4275
12. Hooijschuur E.W.J. Trends Anal. Chem. 21 (2002) 116
13. Mesilaakso M., and Tolppa E.L. Anal. Chem. 66 (1996) 2313
14. Black R.M., and Read R.W. J. Chromatogr., A 759 (1997) 79
15. In: Mesilaakso M. (Ed). Chemical Weapons Chemical Analysis. Encyclopedia of Analytical Chemistry (2000), Wiley, New York
16. Krutysch W., and Trap R.F. A Commentary on CWC (1994), Martinus Nijhott, The Netherlands
17. Convention of Prohibition of the Development, Production, Stockpiling and Use of Chemical Warfare and on Their Destruction (1993), US Control and Disarmament Agency, Washington, DC
18. Bhattacharya A.K., and Thyagarajan G. Chem. Rev. 81 (1981) 415
19. Michaelis A., and Kaehne R. Ber. Dtsch. Chem. Ges. 31 (1898) 1048
20. Arbusov B.A. Pure Appl. Chem. 9 (1964) 315
21. In: Muller E. (Ed). Methoden der Organischen Chemie (Houben-Weyl) Vol. XII/I (1964), George Thieme, Stuttgart 433
22. Michaelis A., and Becker T. Chem. Ber. 30 (1897) 1003
23. Nicolaou K.C., Yang Z., Ouellette M., Shi G.O., Gaertner P., Gunzner J.L., Agrios C., Huber R., Chadha R., and Huang D.H. J. Am. Chem. Soc. 119 (1997) 8105
24. Dennis E.A., and Westheimer F.H. J. Am. Chem. Soc. 88 (1966) 3432
25. Poshkus A.C., and Herweh J.E. J. Am. Chem. Soc. 84 (1962) 555
26. In: Kabachnik M. (Ed). Reactions and Methods of Organic Compound Investigation Vol. 13 (1953), Goskhimizdat, Moscow 427
27. Grapov A.F. Reakts. Metody Issled. Org. Soedin. 15 (1966) 41
28. Kosolapoff G.M. J. Am. Chem. Soc. 67 (1945) 1180
29. McKillop A., and Young D.W. Synthesis (1979) 401
30. Cornelis A., and Laszlo P. Synthesis (1985) 909
31. Tal D.M., Keinan E., and Mazur Y. Tetrahedron 37 (1981) 4327
32. Onofrio F.D., and Scettri A. Synthesis (1985) 1159
33. Kamitori Y., Hojo M., Masuda R., Kimura T., and Yoshida T. J. Org. Chem. 51 (1986) 1427
34. 31P NMR data of the synthesized compounds were matched with the spectral library available in the latest official database of the Organization for the Prohibition of Chemical Weapons (e-OCAD).
35. Organization for the Prohibition of Chemical Weapons (OPCW) Central Analytical database (e-OCAD) v, 5 April 2004.
36. 2-Cl could be stored in sealed vessels for 6 months without any critical decline in activity.