Unusual C→N migration of phosphoryl group; synthesis of N′-phosphorylated amidines

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Won Bum Jang and Dong Young Oh


Abstract

Synthetically and structurally interesting N′-phosphoryl amidines were obtained by the reaction of lithiated alkyl phosphonates with N,N-dialkylcyanamide via an unprecedented migration of the phosphoryl group.


References

  1. K. Lee and D. Y. Oh, Bull. Korean Chem. Soc., 1989, 10, 613 CAS.
  2. K. Lee and D. Y. Oh, Synthesis, 1991, 213 CrossRef.
  3. K. Lee and D. Y. Oh, Bull. Korean Chem. Soc., 1991, 12, 254 CAS.
  4. W. S. Shin, K. Lee and D. Y. Oh, Tetrahedron Lett., 1995, 36, 281 CrossRef CAS.
  5. S. Patai, The Chemistry of Amidines and Imidates, Wiley, London, 1975, p. 60 Search PubMed.
  6. Some examples of phosphoryl group migration: (a) O.→C. migration, B. Dhawan and D. Redmore, J. Org. Chem., 1986, 51, 179 CrossRef; Y.-Z. An and D. F. Wiemer, J. Org. Chem., 1992, 57, 317 CrossRef CAS; (b) S.→C. migration, G. Sturtz, B. Corbel and J. P. Paugam, Tetrahedron Lett., 1976, 32, 47; S. Masson, J.-F. Saint-Clair and M. Saquet, Tetrahedron Lett., 1994, 35, 3083 CrossRef CAS; (c) C.→O. migration, F. Hammerschmidt and E. Zbiral, Chem. Ber., 1980, 113, 3891; C. E. Burgos-Lepley, S. A. Mizsak, R. A. Nugent and K. A. Johnson, J. Org. Chem., 1993, 58, 4159 CrossRef CAS; (d) S.→N. migration, C. Blonski, M. B. Gasc, A. F. Hegarty and J. J. Perie, J. Org. Chem., 1984, 106, 7523; (e) O.→O.′ migration, S. N. Mikhailov, M. Oivanen, P. Oksman and H. Lönnberg, J. Org. Chem., 1992, 57, 4122 CrossRef CAS; (f) other related phosphorus-containing functional group migration, M. J. P. Harger, Chem. Commun., 1997, 403 Search PubMed; M. J. P. Harger, J. Chem. Soc., Perkin Trans. 1, 1989, 563 RSC; C. Earnshaw, J. I. Grayson and S. Warren, J. Chem. Soc., Perkin Trans. 1., 1979, 1506 RSC.
  7. D. Leibfritz, Dissertation, Universität Tübingen, 1970.
  8. C. K. Tseng and F. M. Pallos, Spectroscopy Lett., 1972, 5, 43 CAS.
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