Compounds containing a planar-tetracoordinate carbon atom as analogues of planar methane

(Note: The full text of this document is currently only available in the PDF Version )

Walter Siebert and Anuradha Gunale


Abstract

Over the past years the number of examples of compounds containing a planar-tetracoordinate carbon atom has increased. However, the presence of a carbon atom with a 360° sum of angles does not imply that the species is a derivative of planar methane; there must be an appropriate electronic stabilization. In the case of complexes 21a and 21b the central carbon atom is indeed stabilized by σ-donors and π-acceptors, as required for planar methane.


References

  1. J. H. van't Hoff, Arch. Neerl. Sci. Exactes Nat., 1874, 445 Search PubMed; J. A. LeBel, Bull. Soc. Chim. Fr., 1874, 22, 337 Search PubMed.
  2. R. Hoffmann, R. W. Alder and C. F. Wilcox, Jr., J. Am. Chem. Soc., 1970, 92, 4992 CrossRef CAS; R. Hoffmann, Pure Appl. Chem., 1971, 28, 181 CrossRef CAS.
  3. (a) J. B. Collins, J. D. Dill, E. D. Jemmis, Y. Apeloig, P. von R. Schleyer, R. Seeger and J. A. Pople, J. Am. Chem. Soc., 1976, 98, 5419 CrossRef CAS; (b) M.-B. Krogh-Jespersen, J. Chandrasekhar, E.-U. Würthwein, J. B. Collins and P. von R. Schleyer, ibid., 1980, 102, 2263 Search PubMed.
  4. D. Röttger and G. Erker, Angew. Chem., 1997, 109, 840 (Angew. Chem., Int. Ed. Engl., 1997, 36, 812) CrossRef and references therein.
  5. I. Hyla-Kryspin, R. Gleiter, M.-M. Rohmer, J. Devemy, A. Gunale, H. Pritzkow and W. Siebert, Chem. Eur. J., 1997, 3, 294 CAS.
  6. W. Luef and R. Keese, Adv. Strain Org. Chem., 1993, 3, 229 Search PubMed; W. C. Agosta, in The Chemistry of Alkanes and Cycloalkanes, eds. S. Patai and Z. Rappoport, Wiley, New York, 1992, p. 927 Search PubMed.
  7. J. E. Lyons, D. R. Rasmussen, M. P. McGrath, R. H. Nobes and L. Radom, Angew. Chem., 1994, 106, 1722 (Angew. Chem., Int. Ed. Engl., 1994, 33, 1667) CAS.
  8. F. A. Cotton and M. Millar, J. Am. Chem. Soc., 1977, 99, 7886 CrossRef CAS; F. A. Cotton, G. E. Lewis and G. N. Mott, Inorg. Chem., 1983, 22, 560 CrossRef CAS.
  9. R. Keese, A. Pfenninger and A. Roesle, Helv. Chim. Acta, 1979, 62, 326 CAS.
  10. H. Dietrich, W. Mahdi and W. Storck, J. Organomet. Chem., 1988, 349, 1 CrossRef CAS; S. Harder, J. Boersma, L. Brandsma, A. van Heteren, J. A. Kanters, W. Bauer and P. von R. Schleyer, J. Am. Chem. Soc., 1988, 110, 7802 CrossRef CAS.
  11. D. Thoennes and E. Weiss, Chem. Ber., 1978, 111, 3157 CAS.
  12. A. Streitwieser, S. M. Bachrach, A. Dorigo and P. von R. Schleyer, in Lithium Chemistry, eds. A.-M. Sapse and P. von R. Schleyer, Wiley, New York, 1995, p. 1 Search PubMed; K. Sorger, P. von R. Schleyer and D. Stalke, J. Am. Chem. Soc., 1996, 118, 1086 Search PubMed.
  13. S. L. Buchwald, E. A. Lucas and W. M. Davis, J. Am. Chem. Soc., 1989, 111, 397 CrossRef CAS.
  14. C. M. Poumbga, M. Bénard and I. Hyla-Kryspin, J. Am. Chem. Soc., 1994, 116, 8259 CrossRef CAS.
  15. M. A. G. M. Tinga, G. Schat, O. S. Akkerman, F. Bickelhaupt, W. J. J. Smeets and A. L. Spek, Chem. Ber., 1994, 127, 1851 CAS.
  16. A. Hergel, H. Pritzkow and W. Siebert, Angew. Chem., 1994, 106, 1342 (Angew. Chem., Int. Ed. Engl., 1994, 33, 1247) CAS.
  17. R. H. Cayton, S. T. Chacon, M. H. Chisholm, M. J. Hampden-Smith, J. C. Huffman, K. Folting, P. D. Ellis and B. A. Huggins, Angew. Chem., 1989, 101, 1547 (Angew. Chem., Int. Ed. Engl., 1989, 28, 1523) CAS; S. T. Chacon, M. H. Chisholm, K. Folting, J. C. Huffman and M. J. Hampden-Smith, Organometallics, 1991, 10, 3722 CrossRef CAS.
  18. F. A. Cotton and E. S. Shamshoum, J. Am. Chem. Soc., 1985, 107, 4662 CrossRef CAS; F. A. Cotton and E. S. Shamshoum, Polyhedron, 1985, 4, 1727 CrossRef CAS; F. A. Cotton, W. Schwotzer and E. S. Shamshoum, Organometallics, 1985, 4, 461 CrossRef CAS.
  19. S. Ogoshi, K. Tsutsumi, M. Ooi and H. Kurosawa, J. Am. Chem. Soc., 1995, 117, 10415 CrossRef CAS.
  20. P. Leoni, M. Pasquali, G. Pier, A. Albinati, P. S. Pregosin and H. Rüegger, Organometallics, 1995, 14, 3143 CrossRef CAS.
  21. (a) G. Erker, Comments Inorg. Chem., 1992, 13, 111 CAS; (b) M. Albrecht, G. Erker and C. Krüger, Synlett, 1993, 441 CrossRef CAS; (c) M. Albrecht, G. Erker, M. Nolte and C. Krüger, J. Organomet. Chem., 1992, 427, C21 CrossRef CAS; (d) G. Erker, M. Albrecht, C. Krüger, S. Werner, P. Binger and F. Langhauser, Organometallics, 1992, 11, 3517 CrossRef CAS; (e) P. Binger, F. Sandmeyer, C. Krüger, J. Kuhnigk, R. Goddard and G. Erker, Angew. Chem., 1994, 106, 213 (Angew. Chem., Int. Ed. Engl., 1994, 33, 197) CAS; (f) P. Binger, F. Sandmeyer, C. Krüger and G. Erker, Tetrahedron, 1995, 51, 4277 CrossRef CAS.
  22. R. Gleiter, I. Hyla-Kryspin, S.-Q. Niu and G. Erker, Angew. Chem., 1993, 105, 753 (Angew. Chem., Int. Ed. Engl., 1993, 32, 754) CAS.
  23. R. B. Castle and D. S. Matteson, J. Am. Chem. Soc., 1968, 90, 2194 CAS; R. B. Castle and D. S. Matteson, J. Organometal. Chem., 1969, 20, 19 CrossRef CAS.
  24. T. Ast, C. J. Porter, C. J. Proctor and J. H. Beynon, Chem. Phys. Lett., 1981, 78, 439 CrossRef CAS; C. J. Porter, C. J. Proctor, T. Ast, P. D. Bolton and J. H. Beynon, Org. Mass Spectrom., 1981, 16, 512.
  25. K. Lammertsma, P. von R. Schleyer and H. Schwarz, Angew. Chem., 1989, 101, 1313 (Angew. Chem., Int. Ed. Engl., 1989, 28, 1321) CAS.
  26. M. W. Wong and L. Radom, J. Am. Chem. Soc., 1989, 111, 1155 CrossRef CAS.
  27. H. Schmidbaur and O. Steigelmann, Z. Naturforsch., Teil B, 1992, 47, 1721.
  28. H. Schmidbaur, F. P. Gabbai, A. Schier and J. Riede, Organometallics, 1995, 14, 4969 CrossRef CAS.
  29. O. Steigelmann, P. Bissinger and H. Schmidbaur, Z. Naturforsch., Teil B, 1993, 48, 72 CAS.
  30. J. Vincente, M. T. Chicote, R. Guerrero and P. G. Jones, J. Am. Chem. Soc., 1996, 118, 699 CrossRef CAS.
  31. G. M. Smith, M. Sabat and T. J. Marks, J. Am. Chem. Soc., 1987, 109, 1854 CrossRef CAS.
  32. T. Beringhelli, G. Ciani, G. D'Alfonso, A. Sironi and M. Freni, J. Chem. Soc., Chem. Commun., 1985, 978 RSC.
  33. A. Gunale, H. Pritzkow, W. Siebert, D. Steiner and A. Berndt, Angew. Chem., 1995, 107, 1194 (Angew. Chem., Int. Ed. Engl., 1995, 34, 1111).
  34. A. Gunale, H. Pritzkow, W. Siebert, D. Steiner, A. Berndt, I. Hyla-Kryspin and R. Gleiter, in Advances in Boron Chemistry, ed. W. Siebert, The Royal Society of Chemistry, Cambridge, 1997, pp. 350–353 Search PubMed.
  35. A. Gunale, D. Steiner, D. Schweikart, H. Pritzkow, A. Berndt and W. Siebert, Chem. Eur. J., 1998, 4, 44 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.