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DOI: 10.1039/A904592I (Paper) Reference Section for: J. Chem. Soc., Dalton Trans., 1999, 3419-3430

Reactions of dithiadiphosphetane disulfides with organonitrogen compounds[hair space]†

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Mark St John Foreman, Roger J. Mortimer, Alexandra M. Z. Slawin and J. Derek Woollins

Abstract

The reactions of R1P(S)S2P(S)R1 (R1 = ferrocenyl) with a range of organic systems containing unsaturated C–N linkages have been studied. Thus treatment with dimethylcyanamide gives a 1,3,5,4-thiazaphosphorine 4-sulfide, whereas reaction with dicarbodiimides gives a thiazadiphosphetane. Furthermore reaction of diphenylurea gives a phenylthiazaphosphetane. Mechanisms for the reactions are proposed and the crystal structures of three selected examples are reported and discussed with reference to the steric effects of the reactants. These reactions provide a new entry into C–P–S–N heterocycles. Cyclic voltammetry studies on a range of ferrocenyl substituted heterocycles were also made.

References

  1. H. W. Roesky and M. Diet, Angew. Chem., Int. Ed. Engl., 1973, 12, 425 CrossRef.
  2. P. Bhattacharyya, Ph.D. Thesis, Imperial College (London University), 1995.
  3. R. W. Keyte, Ph.D. Thesis, Loughborough University, 1996.
  4. G. G. Curtis, E. Buchner and B. Buchner, US Pat., 3 286 002, 1966(Chem. Abstr., 66, 28390p) Search PubMed.
  5. H. Tolkmith, J. N. Seiber and P. B. Budde, US Pat., 3 755 348, 1973(Chem. Abstr., 79, 115731n) Search PubMed.
  6. A. A. El-Barbary and S. O. Lawesson, Indian J. Chem., Sect. B, 1984, 23, 655.
  7. K. Clausen, A. A. El-Barbary and S. O. Lawesson, Tetrahedron, 1981, 37, 1019 CrossRef CAS.
  8. L. Weber, Angew. Chem., Int. Ed. Engl., 1996, 35, 2618 CAS.
  9. W. Zeiss and A. Schmidpeter, Z. Naturforsch., Teil B, 1979, 34, 1042 Search PubMed.
  10. N. Dubau-Assibat, A. Baceiredo and G. Bertrand, J. Org. Chem., 1995, 60, 3904 CrossRef CAS.
  11. A. Schmidpeter and N. Schindler, Angew. Chem., Int. Ed. Engl., 1968, 7, 943 CrossRef CAS.
  12. N. Schindler and W. Ploger, Synthesis, 1972, 421 CrossRef CAS.
  13. N. Schindler, (on behalf of Henkel and Cie GmbH), West German Pat., 2 133 329, 1971 Search PubMed.
  14. Farbenfabriken Bayer AG, West German Pat., 1 911 329, 1969 Search PubMed.
  15. M. R. StJ. Foreman, A. M. Z. Slawin and J. D. Woollins, Chem. Commun., 1997, 1269 RSC.
  16. A. M. Z. Slawin, unpublished work.
  17. J. Emsley, The elements, Oxford University Press, Oxford, 1989 Search PubMed.
  18. H. W. Roesky and H. Zamankhan, Z. Naturforsch., Teil B, 1977, 32, 229 Search PubMed.
  19. M. Haddad, L. Lopez, J. Barrans, Y. K. Rodi and E. L. M. Essassi, Phosphorus Sulfur Relat. Elem., 1993, 80, 37 CAS.
  20. I. E. Nifant'ev, A. A. Boricenko, L. F. Manzhukova and E. E. Nifant'ev, Phosphorus Sulfur Relat. Elem., 1992, 68, 99 CAS.
  21. Search was made using the Beilstein CrossFire service.
  22. S. M. Weinreb, Acc. Chem. Res., 1985, 18, 16 CrossRef CAS.
  23. R. Shabana, M. R. Mahran and T. S. Hafez, Phosphorus Sulfur Relat. Elem., 1987, 31, 1 Search PubMed.
  24. W. Zeiss and H. Henjes, Z. Naturforsch., Teil B, 1979, 34, 1334 Search PubMed.
  25. P. Killian, personal communication.
  26. J. Hahn and T. Nataniel, Z. Anorg. Allg. Chem., 1986, 543, 7 CrossRef CAS.
  27. T. Wen, R. Bau and C. E. McKenna, J. Chem. Soc., Chem. Commun., 1991, 1223 RSC.
  28. T. M. Miller, K. J. Ahmed and M. S. Wrighton, Inorg. Chem., 1989, 28, 2347 CrossRef CAS.
  29. N. J. Long, P. R. Raithby and P. Zanello, J. Chem. Soc., Dalton Trans., 1995, 1245 RSC.
  30. W. H. Morrison, S. Krogsrud and D. H. Hendrickson, Inorg. Chem., 1973, 12, 1999.
  31. TEXSAN, Molecular Structure Corporation, The Woodlands, TX, 1998.
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