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DOI: 10.1039/A702843A (Paper) Reference Section for: Chem. Commun., 1997, 1799-1800

Synthesis of the first amine–dicarboxyboranes and their derivatives

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Zoltán Berente and Béla Györi

Abstract

The first amine–dicarboxyboranes and their dimethyl esters are synthesized from amine–dicyanoboranes via [amine–bis(ethylnitrilium)hydroboron(2+)] tetrafluoroborates, [amine–bis(C-hydroxy-N-ethyliminium)hydroboron(2 )] cations and amine–bis(N-ethylcarbamoyl)boranes; C-methoxy-N-ethyliminium groups adjacent to boron undergo unusual hydrolysis.

References

  1. B. F. Spielvogel, L. Wojnowich, M. K. Das, A. T. McPhail and K. D. Hargrave, J. Am. Chem. Soc., 1976, 98, 5702 CrossRef CAS.
  2. See for example: I. H. Hall, C. O. Starnes, A. T. McPhail, P. Wisian-Neilson, M. K. Das and L. Wojnowich, J. Pharm. Sci., 1979, 68, 685 Search PubMed; A. Sood, C. K. Sood, B. F. Spielvogel and I. H. Hall, Eur. J. Med. Chem., 1990, 25, 301 CAS; M. E. Murphy, R. P. Shrewsbury, A. Sood, B. F. Spielvogel and I. H. Hall, Met.-Based Drugs, 1995, 2, 257 CrossRef CAS; S. Y. Chen, B. S. Burnham, B. F. Spielvogel, A. Sood, S. D. Wyrick and I. H. Hall, Appl. Organomet. Chem., 1996, 10, 279 Search PubMed.
  3. See for example: C. K. Sood, A. Sood, B. F. Spielvogel, J. A. Yousef, B. Burnham and I. H. Hall, J. Pharm. Sci., 1991, 80, 1133 Search PubMed; S. Karthikeyan, A. Sood, J. Tomasz, B. F. Spielvogel and I. H. Hall, Amino Acids, 1995, 8, 323 CAS.
  4. K. G. Rajendran, S. Y. Chen, A. Sood, B. F. Spielvogel and I. H. Hall, Biomed. Pharmacother., 1995, 49, 131 CrossRef CAS; K. G. Rajendran, A. Sood, B. F. Spielvogel, I. H. Hall, V. M. Norwood, III and K. W. Morse, Appl. Organomet. Chem., 1995, 9, 111 CrossRef CAS.
  5. See for example: I. H. Hall, K. G. Rajendran, S. Y. Chen, O. T. Wong, A. Sood and B. F. Spielvogel, Arch. Pharm. (Weinheim), 1995, 328, 39 Search PubMed.
  6. See for example: I. H. Hall, B. F. Spielvogel, A. Sood, K. W. Morse, V. M. Norwood, III and O. T. Wong, Met.-Based Drugs, 1994, 1, 329 Search PubMed.
  7. C. Morin, Tetrahedron, 1994, 50, 12 521 CrossRef CAS and references therein.
  8. I. Langmuir, J. Am. Chem. Soc., 1919, 41, 1543 CrossRef CAS.
  9. K. H. Scheller, R. B. Martin, B. F. Spielvogel and A. T. McPhail, Inorg. Chim. Acta, 1982, 57, 227 CrossRef CAS; V. M. Norwood, III and K. W. Morse, Inorg. Chem., 1986, 25, 3690 CrossRef.
  10. B. Györi, Z. Kovács and Z. Berente, in preparation.
  11. B. Györi, Z. Kovács, J. Emri and Z. Berente, J. Organomet. Chem., 1994, 484, 225 CrossRef.
  12. B. C. Challis and J. A. Challis, in Comprehensive Organic Chemistry, ed. D. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979, vol. 2, p. 995 Search PubMed.
  13. B. Györi, J. Emri and I. Fehér, J. Organomet. Chem., 1983, 255, 17 CrossRef CAS.
  14. B. C. Challis and J. A. Challis, in Comprehensive Organic Chemistry, ed. D. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979, vol. 2, p. 1007 Search PubMed.
  15. A. Sood and B. F. Spielvogel, Main Group Met. Chem., 1989, 12, 143 Search PubMed; C. H. Sutton, M. W. Baize and L. J. Todd, Inorg. Chem., 1992, 31, 4911 CrossRef CAS; 1994, 33, 4221.
  16. B. Györi, Z. Berente, J. Emri and I. Lázár, Synthesis, 1995, 191 CrossRef CAS.
  17. D. G. Neilson, in The Chemistry of Amidines and Imidates, ed. S. Patai, Wiley, London, 1975, p. 422 Search PubMed.
  18. M. Mittakanti and K. W. Morse, Inorg. Chem., 1990, 29, 554 CrossRef CAS.
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