Convenient direct syntheses of novel fused-ring CB4N5 systems by nitrile hydroboration[hair space]

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Robert Coult, Mark A. Fox, Brian Rand, Kenneth Wade and Aidan V. K. Westwood


Abstract

Reactions between B2H6 or BH3·thf (thf = tetrahydrofuran) and nitriles RC[triple bond, length half m-dash]N (R = Me, Et, But or CH2F), previously known to generate borazines (RCH2NBH)3 have been found to generate also 25–37% yields of novel carboraza bicyclic systems related to dihydronaphthalene, H3B4N5(RCH2)4CHR, thus affording for the first time a direct route from commercially available acyclic reagents into mixed carbon–boron–nitrogen heterocyclic chemistry.


References

  1. J. R. Jennings and K. Wade, J. Chem. Soc. A, 1968, 1946 RSC.
  2. A. Grace and P. Powell, J. Chem. Soc. A, 1966, 673 RSC.
  3. R. M. Silverstein, G. C. Bassler and T. C. Morrill, Spectrometric Identification of Organic Compounds, Wiley, New York, 4th edn., 1981, p. 207 Search PubMed.
  4. W. Kutzelnigg, Isr. J. Chem., 1980, 19, 193 CAS; M. Schindler and W. Kutzelnigg, J. Chem. Phys., 1982, 76, 1919 CrossRef CAS; W. Kutzelnigg, M. Schindler and U. Fleischer, in NMR Basic Principles and Progress, Springer-Verlag, Berlin, 1990, vol. 23, p. 165 Search PubMed.
  5. A. A. Granovsky, PC version 4.0 of GAMESS, Moscow State University, Russia, 1997; M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. J. Su and T. L. Windus, GAMESS, Iowa State University, IA, 1997; M. Dupuis and J. A. Montgomery, J. Comput. Chem., 1993, 14, 1347 Search PubMed.
  6. M. Buhl and P. v. R. Schleyer, J. Am. Chem. Soc., 1992, 114, 477 CrossRef.
  7. For the many examples of the application of the ab initio/IGLO/ NMR method to boron compounds see refs. in M. Diaz, J. Jaballas, J. Arias, H. Lee and T. Onak, J. Am. Chem. Soc., 1996, 118, 4405 Search PubMed.
  8. U. Meier, C. van Wüllen and M. Schindler, J. Comput. Chem., 1992, 13, 551 CrossRef CAS; S. Huzinaga, Approximate Wave Functions, University of Alberta, Edmonton, 1971 Search PubMed.
  9. H. J. Emeleus and K. Wade, J. Chem. Soc., 1960, 2614 RSC.
  10. M. F. Hawthorne, Tetrahedron, 1962, 17, 117 CrossRef CAS; J. E. Lloyd and K. Wade, J. Chem. Soc., 1964, 1649 RSC; J. R. Jennings, R. Snaith, M. M. Mahmoud, S. C. Wallwork, S. J. Bryan, J. Halfpenny, E. A. Petch and K. Wade, J. Organomet. Chem., 1983, 249, C1 CrossRef CAS.
  11. M. Yalpani, R. Koster and R. Boese, Chem. Ber., 1992, 125, 15 CAS.
  12. G. Hesse, H. Witte and H. Haussleitner, Angew. Chem., Int. Ed. Engl., 1966, 5, 723 CrossRef CAS.
  13. J. H. Morris, in Comprehensive Organometallic Chemistry, eds. G. Wilkinson, E. W. Abel and F. G. A. Stone, Pergamon, Oxford, 1982, vol. 1, p. 311 Search PubMed; C. E. Housecroft, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon-Elsevier, Oxford, 1995, vol. 1, p. 129 Search PubMed.
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