Homonuclear multiple bonding in heavier main group elements

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

Philip P. Power


Abstract

Recent developments in multiple bonding between heavier main group atoms are the focus of this review. Emphasis is placed on compounds with homonuclear bonds. It is clear that the Group 15 derivatives REER (E = P, As, Sb or Bi; R = alkyl or aryl ligand) display double bonding throughout the group. For the Group 14 species R2EER2 (E = Si, Ge, Sn or Pb, R = organo or related group), it is argued that, at present, only the silicon and certain germanium derivatives merit designation as ‘dimetallenes’. Data for multiply bonded heavier Group 13 compounds are currently very scarce. Nonetheless, the available structures of compounds such as (MR)n (M = Al, Ga, In or Tl; R = alkyl or aryl group; n = 1—6) indicate weakness of the M—M interaction especially for the gallium, indium and thallium compounds where monomeric species are obtained readily. The M—M bond order in the dimers RMMR is apparently less than 1 but can be increased by reduction to give [RMMR]2– but it is probable that the overall M—M bond order remains less than 2.


References

  1. (a) R. West, Science, 1984, 225, 1109 CAS; (b) G. Raabe and J. Michl, Chem. Rev., 1985, 85, 419 CrossRef CAS; (c) A. G. Brook and K. M. Baines, Adv. Organomet. Chem., 1986, 25, 1 CAS; (d) R. West, Angew. Chem., Int. Ed. Engl., 1987, 26, 1201 CrossRef; (e) The Chemistry of Organic Silicon Compounds, eds. S. Patai and Z. Rappaport, Wiley, New York, 1989 Search PubMed; (f) J. Barrau, J. Escudié and J. Satgé, Chem. Rev., 1990, 90, 283 CrossRef CAS; (g) A. G. Brook and M. A. Brook, Adv. Organomet. Chem., 1996, 39, 71 CAS; (h) T. Tsumuraya, S. A. Batcheller and S. Masamune, Angew. Chem., Int. Ed. Engl., 1991, 30, 902 CrossRef; (i) J. Escudié, C. Couret, H. Ranaivonjatovo and J. Satgé, Coord. Chem. Rev., 1994, 130, 427 CrossRef; (j) R. Okazaki and R. West, Adv. Organomet. Chem., 1996, 39, 232; (k) K. M. Baines and W. G. Stibbs, Adv. Organomet. Chem., 1996, 39, 275 CAS.
  2. (a) A. H. Cowley, Polyhedron, 1984, 3, 389 CrossRef CAS; (b) A. H. Cowley and N. C. Norman, Prog. Inorg. Chem., 1986, 34, 1 CAS; (c) M. Yoshifuji, in Multiple Bonds and Low Coordination in Phosphorus Chemistry, eds. M. Regitz and O. J. Scherer, Georg Thieme Verlag, Stuttgart, 1990 Search PubMed; (d) L. Weber, Chem. Rev., 1992, 92, 1839 CrossRef CAS; (e) N. C. Norman, Polyhedron, 1993, 12, 2431 CrossRef CAS.
  3. (a) P. J. Brothers and P. P. Power, Adv. Organomet. Chem., 1996, 39, 1 CAS for reviews of species with heavier Group 13 element-element single bonds, see,; (b) W. Uhl, Angew. Chem., Int. Ed. Engl., 1993, 32, 1386 CrossRef; (c) C. Dohmeier, D. Loos and H. Schnöckel, Angew. Chem., Int. Ed. Engl., 1996, 35, 124 CrossRef.
  4. P. J. Davidson and M. F. Lappert, J. Chem. Soc., Chem. Commun., 1973, 317 Search PubMed.
  5. (a) D. E. Goldberg, D. H. Harris, M. F. Lappert and K. M. Thomas, J. Chem. Soc., Chem. Commun., 1976, 261 RSC; (b) D. E. Goldberg, P. B. Hitchcock, M. F. Lappert, K. M. Thomas, A. J. Thorne, T. Fjelberg, A. Haaland and B. E. R. Schilling, J. Chem. Soc., Dalton Trans., 1986, 2387 RSC.
  6. A. F. Wells, Structural Inorganic Chemistry, Clarendon Press, Oxford, 5th edn., 1984, p. 1279 Search PubMed.
  7. H. J. Haupt, F. Huber and H. Pruet, Z. Anorg. Allg. Chem., 1973, 396, 81 CrossRef.
  8. K. W. Zilm, G. A. Lawless, R. M. Merrill, J. M. Millar and G. G. Webb, J. Am. Chem. Soc., 1987, 109, 7236 CrossRef CAS.
  9. J. D. Cotton, P. J. Davidson and M. F. Lappert, J. Chem. Soc., Dalton Trans., 1976, 2275 RSC; M. F. Lappert, Main Group Met. Chem., 1994, 117, 183 Search PubMed.
  10. P. B. Hitchcock, M. F. Lappert, S. J. Miles and A. J. Thorne, J. Chem. Soc., Chem. Commun., 1984, 480 RSC.
  11. G. Märkl, Angew. Chem., Int. Ed. Engl., 1966, 5, 846 CrossRef for related arsenic and antimony derivatives, see, A. J. Ashe, III, J. Am. Chem. Soc., 1971, 93, 3293 Search PubMed.
  12. E. Niecke and W. Flick, Angew. Chem., Int. Ed. Engl., 1973, 12, 585 CrossRef.
  13. G. Becker, Z. Anorg. Allg. Chem., 1976, 423, 242 CrossRef CAS.
  14. G. Becker, G. Gresser and W. Uhl, Z. Naturforsch., Teil B, 1981, 36, 16 Search PubMed; R. Appel and A. Westerhaus, Tetrahedron Lett., 1981, 22, 2159 CrossRef CAS.
  15. A. G. Brook, F. Abdesaken, B. Gutekunst, G. Gutekunst and R. K. Kallury, J. Chem. Soc., Chem. Commun., 1981, 191 RSC.
  16. R. West, M. J. Fink and J. Michl, Science, 1981, 214, 1343 CAS.
  17. H. Meyer, G. Baum, W. Massa and A. Berndt, Angew. Chem., Int. Ed. Engl., 1987, 26, 798 CrossRef; M. Lazraq, J. Escudié, J. Couret, J. Satgé, M. Dräger and R. Dammel, Angew. Chem., Int. Ed. Engl., 1988, 27, 828 CrossRef.
  18. J. T. Snow, S. Murukami, S. Masamune and D. J. Williams, Tetrahedron Lett., 1984, 25, 4191 CrossRef CAS.
  19. N. Wiberg, K. Schurz and G. Fischer, Angew. Chem., Int. Ed. Engl., 1985, 24, 1053 CrossRef; R. Boese and U. Klingebiel, J. Organomet. Chem., 1986, 315, C17 CrossRef CAS.
  20. M. Veith, S. Becker and V. Huch, Angew. Chem., Int. Ed. Engl., 1990, 29, 216 CrossRef.
  21. H. Meyer, G. Baum, W. Massa, S. Berger and A. Berndt, Angew. Chem., Int. Ed. Engl., 1987, 26, 546 CrossRef.
  22. C. N. Smit, F. M. Look and F. Bickelhaupt, Tetrahedron Lett., 1984, 25, 3011 CrossRef CAS.
  23. M. Dräger, J. Escudié, C. Couret, H. Ranaivonjatovo and J. Satgé, Organometallics, 1988, 7, 1010 CrossRef.
  24. C. Couret, J. Escudié, J. Satgé, A. Rahaarinirina and J. D. Andriamizaka, J. Am. Chem. Soc., 1985, 107, 8230.
  25. M. Yoshifuji, I. Shima, N. Inamoto, K. Hirotsu and T. Higuchi, J. Am. Chem. Soc., 1981, 103, 4587 CrossRef CAS.
  26. A. H. Cowley, J. G. Lasch, N. C. Norman, M. Pakulski and B. R. Whittlesey, J. Chem. Soc., Chem. Commun., 1983, 881 RSC.
  27. A. H. Cowley, J. G. Lasch, N. C. Norman and M. Pakulski, J. Am. Chem. Soc., 1983, 103, 5506 CrossRef.
  28. R. A. Bartlett, X. Feng and P. P. Power, J. Am. Chem. Soc., 1986, 108, 6817 CrossRef CAS.
  29. G. Linti, H. Nöth, K. Polborn and R. T. Paine, Angew. Chem., Int. Ed. Engl., 1990, 29, 622 CrossRef.
  30. M. A. Petrie, S. C. Shoner, H. V. R. Dias and P. P. Power, Angew. Chem., Int. Ed. Engl., 1990, 29, 1033 CrossRef.
  31. G. Märkl and H. Sejpka, Angew. Chem., Int. Ed. Engl., 1986, 25, 264 CrossRef.
  32. K. W. Klinkhammer and W. Schwarz, Angew. Chem., Int. Ed. Engl., 1995, 34, 1334 CrossRef CAS.
  33. K. W. Klinkhammer, T. F. Fässler and H. Grützmacher, Angew. Chem., Int. Ed. Engl., 1998, 37, 124 CrossRef CAS.
  34. M. Weidenbruch, H. Kilian, K. Peters, H. G. v. Schnering and H. Marsmann, Chem. Ber., 1995, 128, 983 CAS.
  35. U. Layh, H. Pritzkow and H. Grützmacher, J. Chem. Soc., Chem. Commun., 1992, 260 RSC.
  36. M. Weidenbruch, M. Stürmann, H. Kilian, S. Pohl and W. Saak, Chem. Ber./Recl., 1997, 130, 735 CAS.
  37. M. Kira, T. Iwamoto, T. Maruyama, C. Kabuto and H. Sakurai, Organometallics, 1996, 15, 3767 CrossRef CAS.
  38. S. A. Batcheller, T. Tsumuraya, O. Tempkin, W. M. Davis and S. Masamune, J. Am. Chem. Soc., 1990, 112, 9394 CrossRef CAS.
  39. R. S. Simons, L. Pu, M. M. Olmstead and P. P. Power, Organometallics, 1997, 16, 1920 CrossRef CAS.
  40. A. Schäfer, W. Saak, M. Weidenbruch, H. Marsmann and G. Henkel, Chem. Ber./Recl., 1997, 130, 1733 CrossRef.
  41. M. M. Olmstead, R. S. Simons and P. P. Power, J. Am. Chem. Soc., 1997, 119, 11 705 CrossRef CAS.
  42. (a) A. Sekiguchi, H. Yamazaki, C. Kabuto and H. Sakurai, J. Am. Chem. Soc., 1995, 117, 8025 CrossRef CAS; (b) A. Sekiguchi, M. Tsukamoto and M. Ichinohe, Science, 1997, 275, 60 CrossRef CAS; (c) M. M. Olmstead, L. Pu, R. S. Simons and P. P. Power, Chem. Commun., 1997, 1595 RSC.
  43. P. Arya, J. Boyer, F. Carré, R. Corriu, G. Lanneau, J. Lapasset, M. Pernot and C. Priou, Angew. Chem., Int. Ed. Engl., 1989, 28, 1010 CrossRef; H. Suzuki, N. Tokitoh, S. Nagase and R. Okazaki, J. Am. Chem. Soc., 1994, 116, 11 578 CrossRef CAS.
  44. (a) N. Tokitoh, T. Matsumoto and R. Okazaki, Chem. Lett., 1995, 1087 CAS; (b) N. Tokitoh, T. Matsumoto, K. Manmaru and R. Okazaki, J. Am. Chem. Soc., 1993, 115, 8855 CrossRef CAS; (c) T. Matsumoto, N. Tokitoh and R. Okazaki, Angew. Chem., Int. Ed. Engl., 1994, 33, 2316 CrossRef; (d) N. Tokitoh, T. Matsumoto and R. Okazaki, J. Am. Chem. Soc., 1997, 119, 2337 CrossRef CAS.
  45. M. Veith, S. Becker and V. Huch, Angew. Chem., Int. Ed. Engl., 1989, 28, 1237 CrossRef.
  46. M. C. Kuchta and G. Parkin, J. Chem. Soc., Chem. Commun., 1994, 1351 RSC.
  47. M. C. Kuchta and G. Parkin, J. Am. Chem. Soc., 1994, 116, 8372 CrossRef CAS.
  48. W.-P. Leung, W.-H. Kwok, L. T. C. Low, Z.-Y. Zhou and T. C. W. Mak, Chem. Commun., 1996, 505 RSC.
  49. N. Tokitoh, M. Saito and R. Okazaki, J. Am. Chem. Soc., 1993, 115, 2065 CrossRef CAS; M. Saito, N. Tokitoh and R. Okazaki, J. Am. Chem. Soc., 1997, 119, 11 124 CrossRef CAS.
  50. R. S. Simons and P. P. Power, J. Am. Chem. Soc., 1996, 118, 11 966 CrossRef CAS.
  51. N. Tokitoh, Y. Arai, T. S. Sasamori, R. Okazaki, S. Nagase, H. Uekusa and Y. Ohashi, J. Am. Chem. Soc., 1998, 120, 433 CrossRef CAS.
  52. N. Tokitoh, Y. Arai, R. Okazaki and S. Nagase, Science, 1997, 277, 78 CrossRef CAS.
  53. B. Twamley and P. P. Power, unpublished work.
  54. A. H. Cowley, N. C. Norman and M. Pakulski, J. Chem. Soc., Dalton Trans., 1985, 383 RSC.
  55. C. E. Laplaza, W. M. Davis and C. C. Cummins, J. Am. Chem. Soc., 1995, 34, 2044; N. C. Zanetti, R. R. Schrock and W. M. Davis, Angew. Chem., Int. Ed. Engl., 1995, 34, 2044 CrossRef CAS.
  56. W. Uhl, Z. Naturforsch., B: Chem. Sci., 1988, 43, 11 213.
  57. R. J. Wehmschulte, K. Ruhlandt-Senge, M. M. Olmstead, H. Hope, B. E. Sturgeon and P. P. Power, Inorg. Chem., 1993, 32, 2983 CrossRef CAS.
  58. (a) W. Uhl, M. Layh and T. Hildenbrand, J. Organomet. Chem., 1989, 364, 289 CrossRef CAS; (b) W. Uhl, R. Graupner, I. Hahn, T. Spies and W. Frank, Eur. J. Inorg. Chem., 1998, 355 CrossRef CAS; (c) W. Uhl, I. Hahn and R. Wartschow, Chem. Ber., 1997, 130, 417 CrossRef CAS.
  59. X. He, R. A. Bartlett, M. M. Olmstead, K. Ruhlandt-Senge, B. E. Sturgeon and P. P. Power, Angew. Chem., Int. Ed. Engl., 1993, 32, 717 CrossRef.
  60. (a) G. Linti, R. Frey and M. Schmidt, Z. Naturforsch., B: Chem. Sci., 1994, 49, 958 CAS; (b) G. Linti and W. Köstler, Angew. Chem., Int. Ed. Engl., 1996, 35, 550 CrossRef CAS.
  61. A. K. Saxena, M. Zhang, J. A. Maguire, N. S. Hosmane and A. H. Cowley, Angew. Chem., Int. Ed. Engl., 1995, 34, 332 CrossRef CAS.
  62. D. S. Brown, A. Decken and A. H. Cowley, J. Am. Chem. Soc., 1995, 117, 7578 CrossRef CAS.
  63. N. Wiberg, K. Amelunxen, H. Nöth, H. Schwenk, W. Kaim, A. Klein and T. Scheiring, Angew. Chem., Int. Ed. Engl., 1997, 36, 1213 CrossRef CAS.
  64. S. Haubrich and P. P. Power, unpublished work.
  65. W. Uhl, M. Layh and W. Hiller, J. Organomet. Chem., 1989, 368, 139 CrossRef CAS.
  66. P. J. Brothers, M. M. Olmstead and P. P. Power, Angew. Chem., Int. Ed. Engl., 1996, 35, 2355 CrossRef CAS.
  67. R. D. Schluter, A. H. Cowley, D. A. Atwood, R. A. Jones, M. R. Bond and C. J. Carrano, J. Am. Chem. Soc., 1993, 115, 2070 CrossRef CAS.
  68. M. Veith, F. Goffing, S. Becker and V. Huch, J. Organomet. Chem., 1991, 40, 105 CrossRef CAS.
  69. N. Wiberg, K. Amelunxen, H. Nöth, H. Schmidt and H. Schwenk, Angew. Chem., Int. Ed. Engl., 1996, 35, 65 CrossRef CAS.
  70. S. Henkel, K. W. Klinkhammer and W. Schwarz, Angew. Chem., Int. Ed. Engl., 1994, 33, 681 CrossRef.
  71. W. Uhl, U. Schutz, W. Kaim and E. Waldhör, J. Organomet. Chem., 1995, 501, 79 CrossRef CAS.
  72. C. Pluta, K.-R. Pörschke, C. Krüger and K. Hildebrand, Angew. Chem., Int. Ed. Engl., 1993, 32, 388 CrossRef.
  73. (a) X.-W. Li, W. T. Pennington and G. H. Robinson, J. Am. Chem. Soc., 1995, 117, 7578 CrossRef CAS; (b) X.-W. Li, Y. Xie, K. D. Gripper, R. C. Crittendon, C. F. Campana, H. F. Schaefer III and G. H. Robinson, Organometallics, 1996, 15, 3798 CrossRef CAS.
  74. J. Su, X.-W. Li, R. C. Crittendon and G. H. Robinson, J. Am. Chem. Soc., 1997, 119, 5471 CrossRef CAS.
  75. M. C. Kuchta and G. Parkin, Inorg. Chem., 1997, 36, 2492 CrossRef CAS.
  76. M. C. Kuchta and G. Parkin, J. Am. Chem. Soc., 1995, 117, 12 651 CrossRef CAS.
  77. J. Su, X.-W. Li, R. C. Crittendon, C. F. Campana and G. H. Robinson, Organometallics, 1997, 16, 4511 CrossRef CAS.
  78. F. A. Cotton, A. H. Cowley and X. Feng, J. Am. Chem. Soc., 1998, 120, 1795 CrossRef CAS.
  79. (a) T. L. Allen, W. H. Fink and P. P. Power, unpublished work; (b) Chem. Eng. News, 1997, June 16th, 9 Search PubMed.
  80. K. W. Klinkhammer, Angew. Chem., Int. Ed. Engl., 1997, 36, 2320 CrossRef CAS.
  81. Y. Xie, R. S. Grev, J. Gu, H. F. Schaefer, III, P. v. R. Schleyer, J. Su, X.-W. Li and G. H. Robinson, J. Am. Chem. Soc., 1998, 120, 3773 CrossRef.
  82. F. A. Cotton and X. Feng, Organometallics, 1998, 17, 128 CrossRef CAS.
  83. J. Weiss, D. Stelzkauf, B. Huber, R. A. Fischer, C. Bochine and G. Frenking, Angew. Chem., Int. Ed. Engl., 1997, 36, 70 CrossRef.
  84. D. L. Reger, S. S. Mason, A. L. Rheingold, B. S. Haggerty and F. P. Arnold, Organometallics, 1994, 13, 5049 CrossRef CAS.
  85. E. Urnézius and J. D. Protasiewicz, Main Group Chem., 1996, 1, 369 Search PubMed.
  86. Ref. 6; (a) p. 839; (b) p. 803; (c) p. 804; (d) p. 876; (e)cf. Sb-Sb single bond of 2.837 Å for (SbPh2)2 in: H. Bürger and R. Eujen, J. Mol. Struct., 1983, 98, 265 Search PubMed (f)cf. Bi-Bi single bond of 2.990(2) in (BiPh2)2 in: F. Calderazzo, R. Poli and G. Pelizzi, J. Chem. Soc., Dalton Trans., 1984, 2365 CrossRef.
  87. D. C. Pestana and P. P. Power, J. Am. Chem. Soc., 1989, 111, 6887 CrossRef CAS; C. Pestana and P. P. Power, Inorg. Chem., 1991, 30, 528 CrossRef CAS.
  88. W. Kutzelnigg, Angew. Chem., Int. Ed. Engl., 1984, 23, 272 CrossRef.
  89. (a) K. P. Huber and G. Herzberg, Molecular Spectra and Molecular Structures IV. Constants of Diatomic Molecules, Van Nostrand, New York, 1979 Search PubMed; (b) Sn-Sn in Sn2Me6, J. V. Davies, A. E. Pope and H. A. Skinner, Trans. Faraday Soc., 1963, 59, 2233 Search PubMed Pb-Pb in Pb2Me6, M. F. Lappert, J. B. Pedley, J. Simpson and T. R. Spalding, J. Organomet. Chem., 1971, 29, 195 RSC Sb-Sb in Sb2H4, F. E. Saalfield and H. J. Svec, Inorg. Chem., 1963, 2, 50 Search PubMed; S. R. Gunn, Inorg. Chem., 1972, 11, 786 CrossRef CAS.
  90. T. L. Allen, A. C. Scheiner, Y. Yamaguchi and H. F. Schaefer, III, J. Am. Chem. Soc., 1986, 108, 7579 CrossRef CAS.
  91. A.-M. Caminade, M. Verrier, C. Ades, N. Paillous and M. Koenig, J. Chem. Soc., Chem. Commun., 1984, 875 RSC.
  92. (a) M. Kira, T. Maruyama, C. Kabuto, K. Ebata and H. Sakurai, Angew. Chem., Int. Ed. Engl., 1994, 33, 1489 CrossRef; (b) B. D. Shepherd, D. R. Powell and R. West, Organometallics, 1989, 8, 2664 CrossRef.
  93. M. J. Fink, M. J. Michalczyk, K. J. Haller and R. West, Organometallics, 1984, 2, 793 CrossRef.
  94. Unassociated divalent organosilicon compounds have been described in: (a) P. Julzi, D. Kanne and C. Krüger, Angew. Chem., Int. Ed. Engl., 1986, 25, 164 CrossRef; (b) R. West and M. Denk, Pure Appl. Chem., 1996, 68, 785 CrossRef CAS.
  95. M. J. Michalczyk, R. West and J. Michl, Organometallics, 1985, 4, 826 CrossRef CAS Si-Si π-bond strengths in the range 24.2–26.0 kcal mol–1 have been calculated in: G. Olbrich, P. Potzinger, B. Riemann and R. Walsh, Organometallics, 1984, 3, 1267 Search PubMed; M. W. Schmidt, P. N. Truong and M. S. Gordon, J. Am. Chem. Soc., 1987, 109, 5217 CrossRef CAS; P. v. R. Schleyer and D. Kost, J. Am. Chem. Soc., 1988, 110, 2105 CrossRef CAS.
  96. (a) N. Tokitoh, H. Suzuki, R. Okazaki and K. Ogawa, J. Am. Chem. Soc., 1993, 115, 10 428 CrossRef CAS; (b) H. Suzuki, N. Tokitoh and R. Okazaki, Bull. Chem. Soc. Jpn., 1995, 68, 2471 CAS; (c) K. Kishikawa, N. Tokitoh and R. Okazaki, Chem. Lett., 1998, 239 CrossRef CAS.
  97. A π-bond strength of 25 kcal mol–1 was calculated for a Ge-Ge π bond in: R. S. Grev, H. F. Schaefer, III and K. M. Baines, J. Am. Chem. Soc., 1990, 112, 9458 Search PubMed.
  98. H. A. Skinner and L. E. Sutton, Trans. Faraday Soc., 1940, 36, 1209 RSC.
  99. W. T. Robinson and R. N. Grimes, Inorg. Chem., 1975, 14, 3056 CrossRef CAS; G. E. Herberich, B. Hessner and M. Hostalek, Angew. Chem., Int. Ed. Engl., 1986, 25, 642 CrossRef; G. E. Herberich, B. Hessner and M. Hostalek, J. Organomet. Chem., 1988, 355, 473 CrossRef CAS; J. H. Davis, E. Sinn and R. M. Grimes, J. Am. Chem. Soc., 1989, 111, 4784 CrossRef CAS; G. E. Herberich, C. Ganter, L. Weseman and R. Boese, Angew. Chem., Int. Ed. Engl., 1990, 29, 912 CrossRef.
  100. J. J. Eisch, Adv. Organomet. Chem., 1996, 39, 355 CAS.
  101. H. Meyer, G. Schmidt-Lukasch, G. Baum, W. Massa and A. Berndt, Z. Naturforsch., Teil B, 1988, 43, 801 CAS.
  102. Ref. 6, p. 1052; R. M. Minyaev and R. Hoffmann, Chem. Mater., 1991, 3, 547 Search PubMed.
  103. W. Biffar, H. Nöth and H. Pommerening, Angew. Chem., Int. Ed. Engl., 1980, 19, 56 CrossRef; K. Schlüter and A. Berndt, Angew. Chem., Int. Ed. Engl., 1980, 19, 57 CrossRef.
  104. H. Klusik and A. Berndt, Angew. Chem., Int. Ed. Engl., 1981, 20, 870 CrossRef; H. Klusik and A. Berndt, J. Organomet. Chem., 1981, 222, C25 CrossRef.
  105. (a) A. Moezzi, M. M. Olmstead and P. P. Power, J. Am. Chem. Soc., 1992, 114, 2715 CrossRef CAS; (b) A. Moezzi, R. A. Bartlett and P. P. Power, Angew. Chem., Int. Ed. Engl., 1992, 31, 1082 CrossRef.
  106. M. Pilz, J. Allwohn, P. Willershausen, W. Massa and A. Berndt, Angew. Chem., Int. Ed. Engl., 1990, 29, 1030 CrossRef.
  107. (a) E. Kaufman and P. v. R. Schleyer, Inorg. Chem., 1980, 27, 3987; (b) E. L. Hamilton, J. G. Pruis, R. L. DeKock and K. J. Jalkanen, Main Group Chem., in the press Search PubMed.
  108. (a) C. Dohmeier, C. Robl, M. Tacke and H. Schnöckel, Angew. Chem., Int. Ed. Engl., 1991, 30, 564 CrossRef; (b) A. Purath, C. Dohmeier, A. Ecker and H. Schnöckel, Organometallics, 1998, 17, 1894 CrossRef CAS.
  109. (a) W. Uhl, W. Miler, M. Layh and W. Schwarz, Angew. Chem., Int. Ed. Engl., 1992, 31, 1364 CrossRef; (b) A. Haaland, K.-G. Martinsen, H. V. Volden, W. Kaim, E. Waldhör, W. Uhl and U. Schutz, Organometallics, 1996, 15, 1146 CrossRef CAS.
  110. D. Loos, E. Baum, A. Ecker, H. Schnöckel and A. J. Downs, Angew. Chem., Int. Ed. Engl., 1997, 36, 860 CrossRef CAS.
  111. M. C. Kuchta, J. B. Bonanno and G. Parkin, J. Am. Chem. Soc., 1996, 118, 10 914 CrossRef CAS.
  112. O. T. Beachley, jun., R. Blom, M. R. Churchill, J. Fettinger, J. C. Pazik and L. Victoriano, J. Am. Chem. Soc., 1986, 108, 4666 CrossRef.
  113. (a) R. D. Schluter, A. H. Cowley, D. A. Atwood, R. J. Jones and J. L. Atwood, J. Coord. Chem., 1993, 30, 215; (b) W. Uhl, R. Graupner, M. Layh and U. Schutz, J. Organomet. Chem., 1995, 493, C1 CrossRef CAS; (c) W. Uhl, S. U. Keimling, K. W. Klinkhammer and W. Schwartz, Angew. Chem., Int. Ed. Engl., 1997, 36, 64 CrossRef CAS.
  114. (a) H. Schumann, C. Janiak, F. Görlitz, J. Loebel and A. Dietrich, J. Organomet. Chem., 1989, 363, 243 CrossRef CAS; (b) H. Schumann, C. Janiak, J. Pickhardt and U. Börner, Angew. Chem., Int. Ed. Engl., 1987, 26, 789 CrossRef.
  115. (a) M. C. Kuchta, H. V. R. Dias, S. G. Bott and G. Parkin, Inorg. Chem., 1996, 35, 943 CrossRef CAS; (b) G. Parkin, Adv. Inorg. Chem., 1995, 42, 291 CrossRef CAS.
  116. (a) S. T. Haubrich and P. P. Power, J. Am. Chem. Soc., 1998, 120, 2202 CrossRef CAS; (b) M. Niemeyer and P. P. Power, Angew. Chem., Int. Ed. Engl., 1998, 37, 1277 CrossRef CAS.
  117. (a) A. Haaland, K.-G. Martinsen, S. A. Shlykov, H. V. Volden, C. Dohmeier and H. Schnöckel, Organometallics, 1995, 14, 3116 CrossRef CAS; (b) A. Haaland, K.-G. Martinsen, H. V. Volden, D. Loos and H. Schnöckel, Acta Chem. Scand., 1994, 48, 172 CAS; (c) O. T. Beachley, jun., R. Blom, M. R. Churchill, K. Faeger, J. C. Fettinger, J. C. Pazik and L. Victoriano, Organometallics, 1989, 8, 346 CrossRef; (d) R. Blom, H. Werner and J. Wolf, J. Organomet. Chem., 1988, 354, 293 CrossRef CAS; (e) S. O. Waezsada, T. Belgardt, M. Noltemeyer and H. W. Roesky, Angew. Chem., Int. Ed. Engl., 1994, 33, 1351 CrossRef.
  118. L. Pauling, The Nature of the Chemical Bond, Cornell University Press, Ithaca, New York, 3rd edn., 1960, p. 6 Search PubMed.
  119. S. Nagase, S. Suzuki and T. Kurakake, J. Chem. Soc., Chem. Commun., 1990, 1724 RSC.
  120. A. H. Cowley, A. Decken, N. C. Norman, C. Kruger, F. Lutz, H. Jacobsen and T. Ziegler, J. Am. Chem. Soc., 1997, 119, 3389 CrossRef CAS.
  121. M. Driess and H. Grützmacher, Angew. Chem., Int. Ed. Engl., 1996, 35, 828 CrossRef CAS.
  122. R. West, J. D. Cavalieri, J. J. Buffy, C. Fry, K. W. Zilm, J. C. Duchamp, M. Kira, T. Iwamoto, T. Müller and Y. Apeloig, J. Am. Chem. Soc., 1997, 119, 4972 CrossRef CAS.
  123. M. D. Joesten and L. J. Schaad, Hydrogen Bonding, Marcel Dekker, New York, 1974 Search PubMed.
  124. (a) M. Weidenbruch, J. Schlaefke, A. Schäfer, K. Peters, H. G. v. Schnering and H. Marsmann, Angew. Chem., Int. Ed. Engl., 1994, 33, 1846 CrossRef; (b) M. Kira, R. Yauchibara, R. Hirano, C. Kabuto and H. Sakurai, J. Am. Chem. Soc., 1991, 113, 7783.
  125. (a) M. Weidenbruch, A. Schädwe, H. Kilian, S. Pohl, W. Saak and H. Marsmann, Chem. Ber., 1992, 125, 563 CAS; (b) H. Grützmacher and H. Pritzkow, Angew. Chem., Int. Ed. Engl., 1991, 30, 1017 CrossRef; (c) A. Schäfer, M. Weidenbruch, W. Saak, S. Pohl and H. Marsmann, Angew. Chem., Int. Ed. Engl., 1991, 30, 834 CrossRef.
  126. S. Masamune and L. R. Sita, J. Am. Chem. Soc., 1985, 107, 6390 CrossRef CAS.
  127. In this regard it is interesting to note that in the original investigations4, 5a,9,10 of the compounds [M{CH(SiMe3)2}2]2(M = Ge, Sn or Pb) they are generally referred to as GeII, SnII and PbII dialkyls and the terms double bond and dimetallene were used with quotation marks.
  128. (a) For further explanation of this phenomenon in some Group 14 and 15 species, see T. A. Albright, J. K. Burdett and M. H. Whangbo, Orbital Interactions in Chemistry, John Wiley, New York, 1985, p. 127 Search PubMed; (b) R. S. Grev, Adv. Organomet. Chem., 1991, 33, 125 CAS; (c) D. G. Gilheany, Chem. Rev., 1994, 94, 1339 CrossRef CAS.
  129. C. C. Levin, J. Am. Chem. Soc., 1975, 97, 5649 CrossRef CAS.
  130. R. F. W. Bader, Can. J. Chem., 1962, 40, 1164 CAS; R. G. Pearson, J. Am. Chem. Soc., 1969, 91, 4947 CrossRef CAS.
  131. D. H. Harris and M. F. Lappert, J. Chem. Soc., Chem. Commun., 1974, 895 RSC; C. D. Schaeffer and J. J. Zuckerman, J. Am. Chem. Soc., 1974, 96, 7160 CrossRef CAS; T. Fjelberg, H. Hope, M. F. Lappert, P. P. Power and A. J. Thorne, J. Chem. Soc., Chem. Commun., 1983, 639 RSC.
  132. G. Trinquier and J.-P. Malrieu, J. Am. Chem. Soc., 1987, 109, 5303 CrossRef CAS; J. Am. Chem. Soc., 1989, 11, 5916 Search PubMed; J. Am. Chem. Soc., 1991, 113, 144 Search PubMed.
  133. G. Trinquier, J.-P. Malrieu and P. Riviere, J. Am. Chem. Soc., 1982, 104, 4529 CrossRef CAS.
  134. P. J. Davidson, D. H. Harris and M. F. Lappert, J. Chem. Soc., Dalton Trans., 1976, 2268 RSC.
  135. T. Fjelberg, A. Haaland, M. F. Lappert, B. E. R. Schilling, R. Seip and A. J. Thorne, J. Chem. Soc., Chem. Commun., 1982, 1407 RSC; T. Fjelberg, A. Haaland, B. E. R. Schilling, H. V. Volden, M. F. Lappert and A. J. Thorne, J. Organomet. Chem., 1984, 254, C1 CrossRef.
  136. J. B. Pedley and J. Rylance, Sussex NPL Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, 1977 Search PubMed.
  137. J. Jacobsen and T. Ziegler, J. Am. Chem. Soc., 1994, 116, 3667 CrossRef CAS.
  138. L. Pauling, Proc. Natl. Acad. Sci. USA, 1983, 3871 CAS.
  139. G. Lendvay, Chem. Phys. Lett., 1991, 181, 88 CrossRef CAS.
  140. Ref. 118, p. 239.
  141. T. L. Allen, unpublished work.
  142. K. Kobayashi and S. Nagase, Organometallics, 1997, 16, 2489 CrossRef CAS.
  143. Z. Palágyi, R. S. Grev and H. F. Schaefer, III, J. Am. Chem. Soc., 1993, 115, 1936 CrossRef CAS.
  144. Z. Palágyi and H. F. Schaefer, III, Chem. Phys. Lett., 1993, 203, 195 CrossRef CAS; G. Treboux and J.-C. Barthelat, J. Am. Chem. Soc., 1993, 115, 4870 CrossRef CAS.
  145. C. Janiak and R. Hoffmann, Angew. Chem., Int. Ed. Engl., 1989, 28, 1688 CrossRef; C. Janiak and R. Hoffmann, J. Am. Chem. Soc., 1990, 112, 5924 CrossRef CAS.
  146. P. H. M. Budzelaar and J. Boersma, Recl. Trav. Chim. Pays-Bas, 1990, 109, 187 CAS.
  147. (a) P. Schwerdtfeger, Inorg. Chem., 1991, 30, 1660 CrossRef CAS; (b) P. Schwerdtfeger, G. A. Heath, M. Dolg and M. A. Bennett, J. Am. Chem. Soc., 1992, 114, 7518 CrossRef CAS.
  148. C. Jouany, J. C. Barthelat and J. P. Dandey, Chem. Phys. Lett., 1987, 36, 52 CrossRef; D. R. Armstrong, Theor. Chim. Acta, 1981, 60, 159 CrossRef CAS; J. D. Dill, P. v. R. Schleyer and J. Pople, J. Am. Chem. Soc., 1975, 97, 3402 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.