Generation and trapping of monomeric metaphosphoric acid esters in solution: Mechanistic investigation into the fragmentation of mixed carbonic-phosphoric acid anhydrides and the chelotropic breakdown of cyclic pyrocarbonate esters

Heteroatom Chemistry

Volumn 7, Issue 6, 1996, Pages 503-514

  Banks, Malcolm R ^a   Gosney, Ian ^a   Kilgour, Derek ^a   Cadogan, J I G ^b   Hodgson, Philip K G ^c  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

^c BP EXPLORATION   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 6444242384     PISSN: 10427163     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-1071(199611)7:6<503::AID-HC12>3.0.CO;2-U     Document Type: Article

References (34)

1. F. H. Westheimer, Chem. Rev., 81, 1981, 313.
2. J. I. G. Cadogan, P. K. G. Hodgson, Phosphorus and Sulfur, 30, 1987, 3.
3. M. Regitz, G. Mass, Topics Curr. Chem., 97, 1981, 71.
4. (a) L. D. Quin, B. Pete, J. Szewczyk, A. N. Hughes, Tetrahedron Lett., 29, 1988, 2627.
5. (b) K. C. Calvo, J. D. Rozell, and F. H. Westheimer, J. Am. Chem. Soc., 105, 1983, 1693.
6. (c) S. K. Das, S. N. Balasubrahmanyam, J. Org. Chem., 48, 1983, 4232.
7. (d) F. Ramirez, F. J. Maracek, S. S. Yemul, J. Am. Chem. Soc., 104, 1982, 1345.
8. (e) C. H. Clapp, F. H. Westheimer, J. Am. Chem. Soc. 96, 1974, 6710.
9. (a) J. I. G. Cadogan, A. H. Cowley, I. Gosney, M. Pakuslski, P. M. Wright, S. Yaslak, J. Chem. Soc., Chem. Commun., 1986, 1685.
10. (b) J. I. G. Cadogan, I. Gosney, P. M. Wright, Phosphorus and Sulfur, 30, 1987, 397.
11. (a) L. Z. Avila, J. W. Frost, J. Am. Chem. Soc., 110, 1988, 7904.
12. (b) L. D. Quin, X.-P. Wu, E. Breuer, and M. Mahajna, Tetrahedron Lett., 31, 1990, 628.
13. (a) F. Ramirez, J. F. Maracek, S. S. Yemul, J. Org. Chem., 48, 1983, 1417.
14. (b) J. Symes, T. A. Modro, Can. J. Chem., 64, 1986, 1702.
15. (a) R. Bodalski, L. D. Quin, J. Org. Chem., 56, 1991, 2666.
16. (b) M. R. Banks, J. I. G. Cadogan, I. Gosney, P. K. G. Hodgson, D. Kilgour, D. R. Rodger, Phosphorus, Sulfur and Silicon, 76, 1993, 37.
17. A. C. Satterthwait, F. H. Westheimer, J. Am. Chem. Soc., 102, 1980, 4464.
18. (a) L. D. Quin, A. N. Hughes, X.-P. Wu, L. C. Dickinson, J. Chem. Soc., Chem. Commun., 1988, 555.
19. (b) L. D. Quin, X.-P. Wu, G. S. Quin, S. Jankowski, Phosphorus, Sulfur and Silicon, 76, 1993, 91.
20. (a) M. Meisel: in M. R. Regitz, O. J. Scherer (eds): Multiple Bonds and Low Coordination in Phosphorus Chemistry, Georg Thieme Verlag, Stuttgart, Chapt. E6 (1990).
21. (b) L. D. Quin, Coor. Chem. Rev., 137, 1994, 525.
22. (a) M. R. Banks, J. I. G. Cadogan, I. Gosney, P. K. G. Hodgson, A. G. C. Jack, D. R. Rodger, J. Chem. Soc., Chem. Commun., 1989, 1033.
23. (b) M. R. Banks, J. I. G. Cadogan, I. Gosney, P. K. G. Hodgson, D. R. Rodger, Phosphorus, Sulfur and Silicon, 45/50, 1990, 381.
24. (a) E. Breuer, M. Mahajna, L. D. Quin, G. S. Quin, J. Org. Chem., 56, 1991, 81.
25. (b) L. D. Quin, N. D. Sadan-ani, C. Bourdieu, X.-P. Wu, G. S. Quin, R. Bodalski, Phosphorus, Sulfur and Silicon, 49/50, 1990, 313.
26. L. D. Quin, S. Jankowski, J. Org. Chem., 59, 1994, 4402.
27. L. D. Quin, B. G. Marsi, J. Am. Chem. Soc., 107, 1985, 3389.
28. M. J. Gallagher: in J. G. Verkade, L. D. Quin (eds): Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis, VCH Publishers, Deerfield Beach, FL, pp. 308-310.
29. E. D. Laganis, B. L. Chenard, Tetrahedron Lett., 25, 1984, 5831.
30. S. M. Darling, C. W. Liao, U.S. Patent N° 2,849,553; Chem. Abstr., 52, 1958, 19112.
31. E. S. Gould: Mechanism and Structure in Organic Chemistry, Holt, Rinehart and Winston, Inc. p. 292 (1959), see also J. March; Advanced Organic Chemistry, Wiley, New York, 4th ed., p. 368.
32. E. S. Gould: Mechanism and Structure in Organic Chemistry, Holt, Rinehart and Winston, Inc. p. 292 (1959), see also J. March; Advanced Organic Chemistry, Wiley, New York, 4th ed., p. 368.
33. H. Grunze, Chem. Ber., 92, 1959, 850.
34. C. Hubert, Ch. Duschek, G. Zimmermann, M. Wahren, J. Prakt. Chem., 316, 1974, 790.