Trichloroisocyanuric acid: An efficient reagent for the synthesis of dialkyl chlorophosphates from dialkyl phosphites

Tetrahedron Letters

Volumn 46, Issue 32, 2005, Pages 5293-5295

  Acharya, J ^a   Gupta, A K ^a   Shakya, P D ^a   Kaushik, M P ^a  

^a Process Technology Development Division   (India)

Author keywords

Cyanuric acid; Dialkyl chlorophosphate; Dialkyl phosphite; Trichloroisocyanuric acid

Indexed keywords

CYANURIC ACID; PHOSPHATE; PHOSPHITE; REAGENT; SYMCLOSENE; UNCLASSIFIED DRUG;

ARTICLE; SYNTHESIS; TECHNIQUE;

EID: 22044455862     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.024     Document Type: Article

References (38)

1. P. Hinkle, and R.Y. McCarty Sci. Am. 104 1978 238
2. M. Eto Organophosphorus Pesticides: Organic and Biological Chemistry 1974 CRC Press USA pp 18-19
3. R. Van Wazer John Phosphorus and its Compounds Vol. II 1961 Interscience New York
4. R. Engel Chem. Rev. 77 1977 349
5. Corbridge, D. E. C. Studies in Inorganic Chemistry 10, Phosphorus, An outline of its Chemistry, Biochemistry, and Technology, 4th ed., Elsevier Science Publishing Company: New York.
6. G.M. Kosolapoff Organic Phosphorus Compounds Vol. 6 1950 Wiley-Interscience New York p 503
7. M. Di Novi, D.A. Trainor, and K. Nakanishi Tetrahedron Lett. 24 1983 855
8. L.E. Audrieth, and W.C. Smith J. Org. Chem. 18 1953 1288
9. J. Nilsson, and J. Stawinski Chem. Commun. 2004 2566
10. F.R. Atherton, H.T. Openshaw, and A.R. Todd J. Org. Chem. 10 1945 660
11. B.C. Froehler Tetrahedron Lett. 27 1986 5575
12. E. Shi, and C. Pei Synthesis 2004 2995
13. E. Larson, and B. Lining Tetrahedron Lett. 35 1994 2737
14. Q. Xiao, J. Sun, Q. Sun, Y. Ju, Y-f Zhao, and Y-x Cui Synthesis 2003 107
15. A.Y. Zamyatina, A.S. Bushnev, and V.I. Shvets Bioorg. Khim. 20 1994 1253
16. A. Whitehead, J.D. Moore, and P.R. Hanson Tetrahedron Lett. 44 2003 4275
17. V.N. Yarovenko, A.V. Shirokov, I.V. Zavarzin, O.N. Krupinova, A.V. Ignatenko, and M.M. Krayushkin Synthesis 2004 17
18. Y. Ding, and J. Hu J. Chem. Soc., Perkin Trans. 1 2000 1651
19. 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. 119 1997 8105
20. H. McCombie, B.C. Saunders, and G.J. Stacey J. Chem. Soc. 1945 380
21. Hardy, E. E.; Kosolapoff, G. M. U.S. Patent 2,409,039, 1946; [Chem. Abstr. 1947, 41, 1233].
22. H. Grosse-Ruyken, and K. Uhlig J. Prakt. Chem. 18 1962 287
23. E.A. Dennis, and F.H. Westheimer J. Am. Chem. Soc. 88 1966 3432
24. E.N. Walsh J. Am. Chem. Soc. 81 1959 3023
25. G.M. Steinberg J. Org. Chem. 15 1950 637
26. F.R. Atherton, H.T. Openshaw, and A.R. Todd J. Chem. Soc. 36 1945 4237
27. M.I. Kabachnik, and M.P.A. Rossiiskaya Nauk SSSR, Izv. Akad.; Nauk, Otdel Khim. 1958 1398 [Chem. Abstr. 1959; 53, 6988e]
28. B. Fiszer, and J. Michalski Roczniki Chem. 26 1952 688 [Chem. Abstr. 1955; 49, 2306c]
29. F.R. Atherton, H.T. Howard, and A.R. Todd J. Chem. Soc. 1948 1106
30. V. Ettel, and M. Zbirovsky Chem. Listy. 50 1956 1261 [Chem. Abstr. 1956; 50, 16025f]
31. A.C. Poshkus, and J.E. Herweh J. Am. Chem. Soc. 84 1962 555
32. S.S. Stein, and D.E. Koshland Arch. Biochem. Biophys. 39 1952 229
33. S. Chawalinski, and W. Rypinska Roczniki Chem. 31 1957 539 [Chem. Abstr. 1958; 52, 5284a]
34. T.D. Smith J. Chem. Soc. 1962 1122
35. G.M. Kosolapaff Organic Phosphorus Compounds Vol. 6 1950 Wiley-Interscience New York p 502
36. M. Goldwhite, and B.C. Saunders J. Chem. Soc. 1955 3564
37. V. Tichy, and S. Truchlik Chem. Zvesti. 12 1958 345 [Chem. Abstr. 1958; 52, 18258a]
38. 31P NMR. After 10 min, cyanuric acid precipitated indicating completion of the reaction. It was then further stirred for 5 min and filtered to remove the precipitate followed by removal of solvent and distillation under vacuum to afford the pure product.