Coupling constants 1J(15N,31P) as a probe for the conformational equilibria of 2-amino-substituted 1,3,2λ5-oxazaphosphinan-2-ones[hair space]

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Tapio Viljanen, Karel D. Klika, Ferenc Fülöp and Kalevi Pihlaja


Abstract

The 15N NMR spectra of both P(2) diastereomers of the trans-fused 2-bis(2-chloroethyl)amino-3,4,4a,5,6,7,8,8a-octahydro-1,3,2λ5-benzoxazaphosphinin-2-ones and their 3-methyl and 3-benzyl derivatives have been measured. Depending on the P(2) configuration, the coupling constants 1J(15N,31P) vary markedly. The applicability of the coupling between exocyclic nitrogen and phosphorus for determination of the heteroring conformation is discussed.


References

  1. W. J. Stec, Z. Naturforsch., Teil B, 1974, 29, 109 Search PubMed.
  2. W. J. Stec, R. Kinas and A. Okruszek, Z. Naturforsch., Teil B, 1975, 31, 393 Search PubMed.
  3. J. Baraniak, R. W. Kinas, K. Lesiak and W. J. Stec, J. Chem. Soc., Chem. Commun., 1979, 940 RSC.
  4. W. J. Stec and W. S. Zielinski, Tetrahedron Lett., 1980, 21, 1361 CrossRef CAS.
  5. G. Gompler, R. W. Kinas and W. J. Stec, Z. Naturforsch., Teil B, 1983, 38, 815 Search PubMed.
  6. J. G. Verkade and J. A. Mosbo, in Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis, ed. J. G. Verkade and L. D. Quin, VCH, Deerfield Beach, FL, 1987, p. 449 and references cited therein Search PubMed.
  7. D. Gudat, M. Link and G. Schröder, Magn. Reson. Chem., 1995, 33, 59 CAS.
  8. A. M. Modro, T. A. Modro, P. Bernatowicz, W. Schilf and L. Stefaniak, Magn. Reson. Chem., 1997, 35, 774 CrossRef CAS.
  9. J.-C. Yang, D. O. Shah, N. U. M. Rao, W. A. Freeman, G. Sosnovsky and D. G. Gorenstein, Tetrahedron, 1988, 44, 6305 CrossRef CAS.
  10. Unpublished result from our laboratory.
  11. W. G. Bentrude, W. N. Setzer, A. A. Kergaye, V. Ethridge, M. R. Saadein and A. M. Arif, Phosphorus, Sulfur Silicon Relat. Elem., 1991, 57, 37 CAS.
  12. D. G. Jones, H. Thönnesen, A. Fischer, I. Neda, K. Schmutzler, J. Engel, B. Kutscher and V. Niemeyer, Acta Crystallogr., Sect. C, 1996, 52, 2359 CrossRef.
  13. R. R. Holmes, R. O. Day, W. N. Setzer, A. E. Sopchik and W. G. Bentrude, J. Am. Chem. Soc., 1984, 106, 2353 CrossRef CAS.
  14. G. M. Newton, N. Pantaleo, W. G. Bentrude and S. Chandrasekaran, Tetrahedron Lett., 1982, 23, 1527 CrossRef.
  15. W. G. Bentrude, R. O. Day, J. M. Holmes, G. S. Quin, W. N. Setzer, A. E. Sopchik and R. R. Holmes, J. Am. Chem. Soc., 1984, 106, 106 CrossRef CAS.
  16. G. S. Bajwa, W. G. Bentrude, N. S. Pantaleo, M. G. Newton and J. H. Hargis, J. Am. Chem. Soc., 1979, 101, 1602 CrossRef CAS.
  17. W. G. Bentrude, W. N. Setzer, M. G. Newton, E. J. Meehan, E. Ramli, M. Khan and S. Ealick, Phosphorus, Sulfur Silicon Relat. Elem., 1991, 57, 25 CAS.
  18. U. Salzner, J. Org. Chem., 1995, 60, 986 CrossRef CAS and references cited therein.
  19. T. Viljanen, P. Tähtinen, K. Pihlaja and F. Fülöp, J. Org. Chem., 1998, 63, 618 CrossRef CAS.
  20. See for example: W. G. Bentrude, W. N. Setzer, M. Khan, A. E. Sopchik and E. Ramli, J. Org. Chem., 1991, 56, 6127 Search PubMed.
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