N,N-Dichloro poly(styrene-co-divinyl benzene) sulfonamide polymeric beads: an efficient and recyclable reagent for the synthesis of dialkyl chlorophosphates from dialkylphosphites at room temperature

Tetrahedron Letters

Volumn 49, Issue 47, 2008, Pages 6704-6706

  Gupta, Hemendra K ^a   Mazumder, Avik ^a   Garg, Prabhat ^a   Gutch, Pranav K ^a   Dubey, Devendra K ^a  

^a DEFENCE RESEARCH AND DEVELOPMENT ESTABLISHMENT   (India)

Author keywords

Dialkyl chlorophosphate; Dialkylphosphite; Polymer supported synthesis

Indexed keywords

N,N DICHLORO POLY(STYRENE CO DIVINYL BENZENE)SULFONAMIDE; PHOSPHATE; PHOSPHITE; POLYMER; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; DISTILLATION; MASS FRAGMENTOGRAPHY; ROOM TEMPERATURE; SYNTHESIS;

EID: 53149123253     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.044     Document Type: Article

References (56)

1. Eto M. Organophosphorous Pesticides, Organic and Biological Chemistry (1974), CRC Press, USA
2. Van Wazer John R. Phosphorous and its Compounds Vol. II (1961), Interscience, New York
3. Engel R. Chem. Rev. 77 (1977) 349
4. Corbridge D.E.C. Studies in Inorganic Chemistry 10, Phosphorous, an Outline of its Chemistry, Biochemistry and Technology. 4th ed. (1990), Elsevier Science, New York
5. Welber M. Protein Phosphorylation (1979), Pion, London
6. Ramirez F., and Marecrk J.F. Chem. Res. 11 (1978) 239
7. Lipman F. Wandering of a Biochemist (1971), Wiley, New York
8. Hinkle P., and McCarty R.E. Sci. Am. 238 (1978) 104
9. Clayton R.K. Photosynthesis: Physical, Mechanism and Chemical Patterns (1980), Cambridge University Press
10. Kosolapaff G.M. Organic Phosphorous Compounds Vol. 6 (1950), Wiley-Interscience, New York p 503
11. Di Novi M., Trainor D.A., and Nakanishi K. Tetrahedron Lett. 24 (1993) 855
12. Audrieth L.E., and Smith W.C. J. Org. Chem. 18 (1953) 1288
13. Nilsson J., and Stawinski J. Chem. Commun. (2004) 2566
14. Atherton F.R., Openshaw H.T., and Todd A.R. J. Org. Chem. 10 (1945) 660
15. Eakin R.E. J. Am. Chem. Soc. 77 (1955) 1806
16. Froehler B.C. Tetrahedron Lett. 27 (1986) 5575
17. Kers I., Stawinski J., Girardet J.L., Imbach J.L., Perigaud C., Gossclin G., and Aubertin A.M. Nucleocides Nucleotides 18 (1999) 2317
18. Goodchild J. In: Cohen J.S. (Ed). Oligonucleocides-Antisense Inhibitors of Gene Expression Vol. 12 (1989), Macmillan Press Ltd 53
19. Shi E., and Pei C. Synthesis (2004) 2995
20. Larson E., and Lining B. Tetrahedron Lett. 35 (1994) 2737
21. Xiao Q., Sun J., Sun Q., Ju J., and Zhao Y.X. Synthesis (2003) 107
22. Zamyatina A.Y., Bushnev A.S., and Shvets V.I. Bioorg. Khim. 20 (1994) 1253
23. Whitehead A., Moore J.D., and Hanson P.R. Tetrahedron Lett. 44 (2003) 4275
24. Nicolaou K.C., Yang Y., 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
25. Yarovenko V.N., Shirokov A.V., Zavarzin I.V., Krupinova O.N., Ignatenko A.V., and Krayushkin M.M. Synthesis (2004) 17
26. Ding Y., and Hu J. J. Chem. Soc., Perkin Trans. 1 (2000) 1651
27. McCombie H., Saunders B.C., and Stacey G.J. J. Chem. Soc. (1945) 380
28. Hardy, E. E.; Kosolapoff, G. M. U.S. Patent 2,409,039, 1946; Chem. Abstr. 1947, 41, 1233.
29. Grosse-Ruyken H., and Uhlig K.J. Prakt. Chem. 18 (1962) 287
30. Dennis E.A., and Westheimer F.H. J. Am. Chem. Soc. 88 (1966) 3432
31. Atherton, F. R.; Bergel, F.; Cohen, A.; Haworth, J. H.; Openshaw, H. T.; Todd, A. R. U.S. Patent 2,490, 1949; Chem. Abstr. 1950, 44, 3525a.
32. Miyano M., and Funahashi S. J. Am. Chem. Soc. 7 (1955) 3522
33. Walsh E.N. J. Am. Chem. Soc. 81 (1959) 3023
34. deRose A.M., and Toet H.J. Rec. Trav. Chim. 77 (1958) 946
35. Steinberg G.M. J. Org. Chem. 15 (1950) 637
36. Atherton F.R., Openshaw H.T., and Todd A.R. J. Chem. Soc. 36 (1945) 4237
37. Kabachnik M.I., and Rossiiskaya M.P.A. Nau. Otdel. Khim. (1958) 1398 Chem. Abstr. 1959, 53, 6988e
38. Pudovik A.N., and Platonova R.N. Obshch. Khim. 29 (1959) 505 Chem. Abstr. 1960, 54, 254f
39. Fiszer B., and Michalski J. Roczniki Chem. 26 (1952) 688 Chem. Abstr. 1955, 49, 2306c
40. Atherton F.R., Howard H.T., and Todd A.R. J. Chem. Soc. (1948) 1106
41. Ettel V., and Zbirovsky M. Chem. Listy 50 (1956) 1261 Chem. Abstr. 1956, 50, 16025f
42. Poshkus A.C., and Herweh J.E. J. Am. Chem. Soc. 84 (1962) 555
43. Stein S.S., and Koshland D.E. Arch. Biochem. Biophys. 39 (1952) 229
44. Kamai G. Dokl. Akad. Nauk. SSSR 79 (1951) 795 Chem. Abstr. 1952, 46, 6081f
45. Chawalinski S., and Rypinska W. Roczniki Chem. 31 (1957) 539 Chem. Abstr. 958, 52, 5284a
46. Kamai G. Otdel Khim. Nauk (1952) 923 Chem. Abstr. 1953, 47, 10461a
47. Ettel V., and Zbirovsky M. Chem. Listy 50 (1956) 1265 Chem. Abstr. 1956, 50, 16025h
48. Smith T.D. J. Chem. Soc. (1962) 1122
49. Kosolapaff G.M. Organic Phosphorus Compounds Vol. 6 (1950), Wiley-Interscience, John Wiley & Sons, New York p 502
50. Mark V. U.S. Patent 328 3 (1967) 472 [Chem. Abstr. 1967, 67, 118098]
51. Goldwhite M., and Saunders B.C. J. Chem. Soc. (1955) 3564
52. Tichy V., and Truchlik S. Chem. Zvesti 12 (1958) 345
53. Gutch P.K., Srivastava R.K., and Dubey D.K. J. Appl. Polym. Sci. 105 (2007) 2203
54. Vijayraghvan R., Kumar P., Dubey D.K., and Singh R. Biomed. Environ. Sci. 15 (2002) 25
55. 31 The reaction was monitored by GC-MS. After complete consumption of the dialkylphosphite, the mixture was decanted and the pure product was obtained by vacuum distillation after removing the solvent by distillation.
56. Kolthoff I.M., Sandell E.B., Meehan E.J., and Bruckenstein S. Quantitative Chemical Analysis. 4th ed. (1969), Macmillan, New York