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DOI: 10.1039/A804191A (Paper) Reference Section for: Chem. Soc. Rev., 1999, 28, 17-23

Travelling the organometallic road: a Wittig student’s journey from lithium to magnesium and beyond

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Friedrich Bickelhaupt

Abstract

Both organomagnesium compounds (Grignard reagents) and organolithium compounds are of utmost importance in synthesis. New developments in the area of difunctional organometallic compounds will be described against a historical background in which the author’s interest gradually drifted from organolithium chemistry, in particular the deep red ortho-dilithiobenzene, to its magnesium analogue, the tetrameric ortho-phenylenemagnesium. The latter was applied in the synthesis of novel 1,2-disubstituted benzene derivatives such as 9,10-dimetallatriptycenes.

References

  1. Ch. Elschenbroich and A. Salzer, Organometallics, A Concise Introduction, VCH, Weinheim, 2nd edn., 1992 Search PubMed.
  2. K. Ziegler and H. Colonius, Liebigs Ann. Chem., 1930, 479, 135 Search PubMed.
  3. G. Wittig and M. Leo, Ber. Dtsch. Chem. Ges., 1931, 64, 2395.
  4. G. Wittig, M. Leo and W. Wiemer, Ber. Dtsch. Chem. Ges., 1930, 64, 2405.
  5. W. Tochtermann, Liebigs Ann./Recueil, 1997, I Search PubMed.
  6. G. Wittig, R. Ludwig and R. Polster, Chem. Ber., 1955, 88, 264.
  7. G. Wittig and F. Bickelhaupt, Chem. Ber., 1958, 91, 865 CAS.
  8. U. Schümann and E. Weiss, Angew. Chem., 1988, 100, 573.
  9. L. Vecchiotti, Ber. Dtsch. Chem. Ges., 1930, 63, 2395.
  10. D. S. Brown, A. G. Massey and D. A. Wickens, Inorg. Chim. Acta, 1980, 44, L193 CrossRef CAS.
  11. G. Wittig and F. Bickelhaupt, Chem. Ber., 1958, 91, 883 CAS.
  12. A. D. Vreugdenhil and C. Blomberg, Recl. Trav. Chim. Pays-Bas, 1963, 82, 453; 461 CAS.
  13. F. Bickelhaupt, Angew. Chem., 1987, 99, 1020 (Angew. Chem., Int. Ed. Engl., 1987, 26, 990) CAS.
  14. F. Bickelhaupt, J. Organomet. Chem., 1994, 475, 1 CrossRef CAS.
  15. N. J. R. van Eikema Hommes, F. Bickelhaupt and G. W. Klumpp, Recl. Trav. Chim. Pays-Bas, 1988, 107, 393 CAS.
  16. M. A. M. G. Tinga, G. Schat, O. S. Akkerman, F. Bickelhaupt, E. Horn, W. J. J. Smeets and A. L. Spek, J. Am. Chem. Soc., 1993, 115, 2808 CrossRef CAS.
  17. M. Schreuder Goedheijt, T. Nijbakker, O. S. Akkerman, F. Bickelhaupt, N. Veldman and A. L. Spek, Angew. Chem., 1996, 108, 1651 (Angew. Chem., Int. Ed. Endl., 1996, 35, 1550).
  18. M. A. Dam, PhD Thesis, Vrije Universiteit, Amsterdam, 1997.
  19. M. A. Dam, T. Nijbacker, B. T. de Pater, F. J. J. de Kanter, O. S. Akkerman, F. Bickelhaupt, W. J. J. Smeets and A. L. Spek, Organometallics, 1997, 16, 511 CrossRef CAS.
  20. N. Rot, PhD Thesis, Vrije Universiteit, Amsterdam, 1998.
  21. N. P. McCleland and J. B. Whitworth, J. Chem. Soc., 1927, 2753 RSC.
  22. M. A. Dam, F. J. J. de Kanter, F. Bickelhaupt, W. J. J. Smeets, A. L. Spek, J. Fornies-Camer and C. Cardin, J. Organomet. Chem., 1998, 550, 347 CrossRef CAS.
  23. N. Rot and M. Oberhoff, unpublished results.
  24. K. Nützel, in Methoden der Organischen Chemie (Houben-Weyl), ed. E. Müller, Thieme, Stuttgart, 1973, vol. 13/2a, p. 47 Search PubMed.
  25. W. E. Lindsell, in Comprehensive Organometallic Chemistry, eds. G. Wilkinson, F. G. A. Stone, E. W. Abel, Pergamon, Oxford, 1982, vol. 1, p. 155 Search PubMed.
  26. W. E. Lindsell, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone, G. Wilkinson, Pergamon/Elsevier, Oxford, 1995, vol. 1, p. 57 Search PubMed.
  27. G. S. Silverman and P. E. Rakita, Handbook of Grignard Reagents, Marcel Dekker, New York, 1996 Search PubMed.
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