Homonuclear multiple bonding in heavier main group elements

Journal of the Chemical Society - Dalton Transactions

Volumn , Issue 18, 1998, Pages 2939-2951

  Power, Philip P ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33749099793     PISSN: 03009246     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (236)

1. (a) R. West, Science, 1984, 225, 1109;
2. (b) G. Raabe and J. Michl, Chem. Rev., 1985, 85, 419;
3. (c) A. G. Brook and K. M. Baines, Adv. Organomet. Chem., 1986, 25, 1;
4. (d) R. West, Angew. Chem., Int. Ed. Engl., 1987, 26, 1201;
5. (e) The Chemistry of Organic Silicon Compounds, eds. S. Patai and Z. Rappaport, Wiley, New York, 1989;
6. (f) J. Barrau, J. Escudié and J. Satgé, Chem. Rev., 1990, 90, 283;
7. (g) A. G. Brook and M. A. Brook, Adv. Organomet. Chem., 1996, 39, 71;
8. (h) T. Tsumuraya, S. A. Batcheller and S. Masamune, Angew. Chem., Int. Ed. Engl., 1991, 30, 902;
9. J. Escudié, C. Couret, H. Ranaivonjatovo and J. Satge, Coord. Chem. Rev., 1994, 130, 427;
10. (j) R. Okazaki and R. West, Adv. Organomet. Chem., 1996, 39, 232;
11. (k) K. M. Baines and W. G. Stibbs, Adv. Organomet. Chem., 1996, 39, 275.
12. (a) A. H. Cowley, Polyhedron, 1984, 3, 389;
13. (b) A. H. Cowley and N. C. Norman, Prog. Inorg. Chem., 1986, 34, 1;
14. (c) M. Yoshifuji, in Multiple Bonds and Low Coordination in Phosphorus Chemistry, eds. M. Regitz and O. J. Scherer, Georg Thieme Verlag, Stuttgart, 1990;
15. (d) L. Weber, Chem. Rev., 1992, 92, 1839;
16. (e) N. C. Norman, Polyhedron, 1993, 12, 2431.
17. (a) P. J. Brothers and P. P. Power, Adv. Organomet. Chem., 1996, 39, 1; for reviews of species with heavier Group 13 element-element single bonds, see,
18. (b) W. Uhl, Angew. Chem., Int. Ed. Engl., 1993, 32, 1386;
19. (c) C. Dohmeier, D. Loos and H. Schnockel, Angew. Chem., Int. Ed. Engl., 1996, 35, 124.
20. P. J. Davidson and M. F. Lappert, J. Chem. Soc., Chem. Commun., 1973, 317.
21. (a) D. E. Goldberg, D. H. Harris, M. F. Lappert and K. M. Thomas, J. Chem. Soc., Chem. Commun., 1976, 261;
22. (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.
23. A. F. Wells, Structural Inorganic Chemistry, Clarendon Press, Oxford, 5th edn., 1984, p. 1279.
24. H. J. Haupt, F. Huber and H. Pruet, Z. Anorg. Allg. Chem., 1973, 396, 81.
25. K. W. Zilm, G. A. Lawless, R. M. Merrill, J. M. Millar and G. G. Webb, J. Am. Chem. Soc., 1987, 109, 7236.
26. J. D. Cotton, P. J. Davidson and M. F. Lappert, J. Chem. Soc., Dalton Trans., 1976, 2275;
27. M. F. Lappert, Main Group Met. Chem., 1994, 117, 183.
28. P. B. Hitchcock, M. F. Lappert, S. J. Miles and A. J. Thorne, J. Chem. Soc., Chem. Commun., 1984, 480.
29. G. Märkl, Angew. Chem., Int. Ed. Engl., 1966, 5, 846; for
30. related arsenic and antimony derivatives, see, A. J. Ashe, III, J. Am. Chem. Soc., 1971, 93, 3293.
31. E. Niecke and W. Flick, Angew. Chem., Int. Ed. Engl., 1973, 12, 585.
32. G. Becker, Z. Anorg. Allg. Chem., 1976, 423, 242.
33. G. Becker, G. Gresser and W. Uhl, Z. Naturforsch., Teil B, 1981, 36, 16;
34. R. Appel and A. Westerhaus, Tetrahedron Lett., 1981, 22, 2159.
35. A. G. Brook, F. Abdesaken, B. Gutekunst, G. Gutekunst and R. K. Kallury, J. Chem. Soc., Chem. Commun., 1981, 191.
36. R. West, M. J. Fink and J. Michl, Science, 1981, 214, 1343.
37. H. Meyer, G. Baum, W. Massa and A. Berndt, Angew. Chem., Int. Ed. Engl., 1987, 26, 798;
38. M. Lazraq, J. Escudié, J. Couret, J. Satgé, M. Dräger and R. Dammel, Angew. Chem., Int. Ed. Engl., 1988, 27, 828.
39. J. T. Snow, S. Murukami, S. Masaraune and D. J. Williams, Tetrahedron Lett., 1984, 25, 4191.
40. N. Wiberg, K. Schurz and G. Fischer, Angew. Chem., Int. Ed. Engl., 1985, 24, 1053;
41. R. Boese and U. Klingebiel, J. Organomet. Chem., 1986, 315, C17.
42. M. Veith, S. Becker and V. Huch, Angew. Chem., Int. Ed. Engl., 1990, 29, 216.
43. H. Meyer, G. Baum, W. Massa, S. Berger and A. Berndt, Angew. Chem., Int. Ed. Engl., 1987, 26, 546.
44. C. N. Smit, F. M. Look and F. Bickelhaupt, Tetrahedron Lett., 1984, 25, 3011.
45. M. Dräger, J. Escudié, C. Couret, H. Ranaivonjatovo and J. Satgé, Organometallics, 1988, 7, 1010.
46. C. Couret, J. Escudié, J. Satgé, A. Rahaarinirina and J. D. Andriamizaka, J. Am. Chem. Soc., 1985, 107, 8230.
47. M. Yoshifuji, I. Shima, N. Inamoto, K. Hirotsu and T. Higuchi, J. Am. Chem. Soc., 1981, 103, 4587.
48. A. H. Cowley, J. G. Lasch, N. C. Norman, M. Pakulski and B. R. Whittlesey, J. Chem. Soc., Chem. Commun., 1983, 881.
49. A. H. Cowley, J. G. Lasch, N. C. Norman and M. Pakulski, J. Am. Chem. Soc., 1983, 103, 5506.
50. R. A. Bartlett, X. Feng and P. P. Power, J. Am. Chem. Soc., 1986, 108, 6817.
51. G. Linti, H. Nöth, K. Polborn and R. T. Paine, Angew. Chem., Int. Ed. Engl., 1990, 29, 622.
52. M. A. Petrie, S. C. Shoner, H. V. R. Dias and P. P. Power, Angew. Chem., Int. Ed. Engl., 1990, 29, 1033.
53. G. Märkl and H. Sejpka, Angew. Chem., Int. Ed. Engl., 1986, 25, 264.
54. K. W. Klinkhammer and W. Schwarz, Angew. Chem., Int. Ed. Engl., 1995, 34, 1334.
55. K. W. Klinkhammer, T. F. Fässler and H. Grützmacher, Angew. Chem., Int. Ed. Engl., 1998, 37, 124.
56. M. Weidenbruch, H. Kilian, K. Peters, H. G. v. Schnering and H. Marsmann, Chem. Ber., 1995, 128, 983.
57. U. Layh, H. Pritzkow and H. Grützmacher, J. Chem. Soc., Chem. Commun., 1992, 260.
58. M. Weidenbruch, M. Sturmann, H. Kilian, S. Pohl and W. Saak, Chem. Ber./Recl., 1997, 130, 735.
59. M. Kira, T. Iwamoto, T. Maruyama, C. Kabuto and H. Sakurai, Organometallics, 1996, 15, 3767.
60. S. A. Batcheller, T. Tsumuraya, O. Tempkin, W. M. Davis and S. Masamune, J. Am. Chem. Soc., 1990, 112, 9394.
61. R. S. Simons, L. Pu, M. M. Olmstead and P. P. Power, Organometallics, 1997, 16, 1920.
62. A. Schäfer, W. Saak, M. Weidenbruch, H. Marsmann and G. Henkel, Chem. Ber./Recl., 1997, 130, 1733.
63. M. M. Olmstead, R. S. Simons and P. P. Power, J. Am. Chem. Soc., 1997, 119, 11 705.
64. (a) A. Sekiguchi, H. Yamazaki, C. Kabuto and H. Sakurai, J. Am. Chem. Soc., 1995, 117, 8025;
65. (b) A. Sekiguchi, M. Tsukamoto and M. Ichinohe, Science, 1997, 275, 60;
66. (c) M. M. Olmstead, L. Pu, R. S. Simons and P. P. Power, Chem. Commun., 1997, 1595.
67. P. Arya, J. Boyer, F. Carré, R. Corriu, G. Lanneau, J. Lapasset, M. Pemot and C. Priou, Angew. Chem., Int. Ed. Engl., 1989, 28, 1010;
68. H. Suzuki, N. Tokitoh, S. Nagase and R. Okazaki, J. Am. Chem. Soc., 1994, 116, 11 578.
69. (a) N. Tokitoh, T. Matsumoto and R. Okazaki, Chem. Lett., 1995, 1087;
70. (b) N. Tokitoh, T. Matsumoto, K. Manmaru, R. Okazaki, J. Am. Chem. Soc., 1993, 115, 8855;
71. (c) T. Matsumoto, N. Tokitoh and R. Okazaki, Angew. Chem., Int. Ed. Engl., 1994, 33, 2316;
72. (d) N. Tokitoh, T. Matsumoto and R. Okazaki, J. Am. Chem. Soc., 1997, 119, 2337.
73. M. Veith, S. Becker and V. Huch, Angew. Chem., Int. Ed. Engl., 1989, 28, 1237.
74. M. C. Kuchta and G. Parkin, J. Chem. Soc., Chem. Commun., 1994, 1351.
75. M. C. Kuchta and G. Parkin, J. Am. Chem. Soc., 1994, 116, 8372.
76. W.-P. Leung, W.-H. Kwok, L. T. C. Low, Z.-Y. Zhou and T. C. W. Mak, Chem. Commun., 1996, 505.
77. N. Tokitoh, M. Saito and R. Okazaki, J. Am. Chem. Soc., 1993, 115, 2065;
78. M. Saito, N. Tokitoh and R. Okazaki, J. Am. Chem. Soc., 1997, 119, 11124.
79. R. S. Simons and P. P. Power, J. Am. Chem. Soc., 1996, 118, 11 966.
80. N. Tokitoh, Y. Arai, T. S. Sasamori, R. Okazaki, S. Nagase, H. Uekusa and Y. Ohashi, J. Am. Chem. Soc., 1998, 120, 433.
81. N. Tokitoh, Y. Arai, R. Okazaki and S. Nagase, Science, 1997, 277, 78.
82. B. Twamley and P. P. Power, unpublished work.
83. A. H. Cowley, N. C. Norman and M. Pakulski, J. Chem. Soc., Dalton Trans., 1985, 383.
84. C. E. Laplaza, W. M. Davis and C. C. Cummins, J. Am. Chem. Soc., 1995, 34, 2044;
85. N. C. Zanetti, R. R. Schrock and W. M. Davis, Angew. Chem., Int. Ed. Engl., 1995, 34, 2044.
86. W. Uhl, Z. Naturforsch., B: Chem. Sci., 1988, 43, 11 213.
87. R. J. Wehmschulte, K. Ruhlandt-Senge, M. M. Olmstead, H. Hope, B. E. Sturgeon and P. P. Power, Inorg. Chem., 1993, 32, 2983.
88. (a) W. Uhl, M. Layh and T. Hildenbrand, J. Organomet. Chem., 1989, 364, 289;
89. (b) W. Uhl, R. Graupner, I. Hahn, T. Spies and W. Frank, Eur. J. Inorg. Chem., 1998, 355;
90. (e) W. Uhl, I. Hahn and R. Wartschow, Chem. Ber., 1997, 130, 417.
91. 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.
92. (a) G. Lint, R. Frey and M. Schmidt, Z. Naturforsch., B: Chem. Sci., 1994, 49, 958;
93. (b) G. Linti and W. Köstler, Angew. Chem., Int. Ed. Engl., 1996, 35, 550.
94. A. K. Saxena, M. Zhang, J. A. Maguire, N. S. Hosmane and A. H. Cowley, Angew. Chem., Int. Ed. Engl., 1995, 34, 332.
95. D. S. Brown, A. Decken and A. H. Cowley, J. Am. Chem. Soc., 1995, 117, 7578.
96. N. Wiberg, K. Amelunxen, H. Nöth, H. Schwenk, W. Kaim, A. Klein and T. Scheiring, Angew. Chem., Int. Ed. Engl., 1997, 36, 1213.
97. S. Haubrich and P. P. Power, unpublished work.
98. W. Uhl, M. Layh and W. Hiller, J. Organomet. Chem., 1989, 368, 139.
99. P. J. Brothers, M. M. Olmstead and P. P. Power, Angew. Chem., Int. Ed. Engl., 1996, 35, 2355.
100. 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.
101. M. Veith, F. Goffing, S. Becker and V. Huch, J. Organomet. Chem., 1991, 40, 105.
102. N. Wiberg, K. Amelunxen, H. Nöth, H. Schmidt and H. Schwenk, Angew. Chem., Int. Ed. Engl., 1996, 35, 65.
103. S. Henkel, K. W. Klinkhammer and W. Schwarz, Angew. Chem., Int. Ed. Engl., 1994, 33, 681.
104. W. Uhl, U. Schutz, W. Kaim and E. Waldhör, J. Organomet. Chem., 1995, 501, 79.
105. C. Pluta, K.-R. Pörschke, C. Krüger and K. Hildebrand, Angew. Chem., Int. Ed. Engl., 1993, 32, 388.
106. (a) X.-W. Li, W. T. Pennington and G. H. Robinson, J. Am. Chem. Soc., 1995, 117, 7578;
107. (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.
108. J. Su, X.-W. Li, R. C. Crittendon and G. H. Robinson, J. Am. Chem. Soc., 1997, 119, 5471.
109. M. C. Kuchta and G. Parkin, Inorg. Chem., 1997, 36, 2492.
110. M. C. Kuchta and G. Parkin, J. Am. Chem. Soc., 1995, 117, 12 651.
111. J. Su, X.-W. Li, R. C. Crittendon, C. F. Campana and G. H. Robinson, Organometallics, 1997, 16, 4511.
112. F. A. Cotton, A. H. Cowley and X. Feng, J. Am. Chem. Soc., 1998, 120, 1795.
113. (a) T. L. Allen, W. H. Fink and P. P. Power, unpublished work;
114. (b) Chem. Eng. News, 1997, June 16th, 9.
115. K. W. Klinkhammer, Angew. Chem., Int. Ed. Engl., 1997, 36, 2320.
116. 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.
117. F. A. Cotton and X. Feng, Organometallics, 1998, 17, 128.
118. J. Weiss, D. Stelzkauf, B. Huber, R. A. Fischer, C. Bochine and G. Frenking, Angew. Chem., Int. Ed. Engl., 1997, 36, 70.
119. D. L. Reger, S. S. Mason, A. L. Rheingold, B. S. Haggerty and F. P. Arnold, Organometallics, 1994, 13, 5049.
120. E. Urnézius and J. D. Protasiewicz, Main Group Chem., 1996, 1, 369.
121. Ref. 6; E. Urnézius and J. D. Protasiewicz, Main Group Chem., 1996, (a) p. 839;
122. (b) E. Urnézius and J. D. Protasiewicz, Main Group Chem., 1996, p. 803;
123. E. Urnézius and J. D. Protasiewicz, Main Group Chem., 1996, p. 804;
124. E. Urnézius and J. D. Protasiewicz, Main Group Chem., 1996, p. 876;
125. 2 in: H. Bürger and R. Eujen, J. Mol. Struct., 1983, 98, 265;
126. 2 in: F. Calderazzo, R. Poli and G. Pelizzi, J. Chem. Soc., Dalton Trans., 1984, 2365.
127. D. C. Pestana and P. P. Power, J. Am. Chem. Soc., 1989, 111, 6887;
128. D. C. Pestana and P. P. Power, Inorg. Chem., 1991, 30, 528.
129. W. Kutzelnigg, Angew. Chem., Int. Ed. Engl., 1984, 23, 272.
130. (a) K. P. Huber and G. Herzberg, Molecular Spectra and Molecular Structures IV. Constants of Diatomic Molecules, Van Nostrand, New York, 1979;
131. 4, J. V. Davies, A. E. Pope and H. A. Skinner, Trans. Faraday Soc., 1963, 59, 2233;
132. 6, M. F. Lappert, J. B. Pedley, J. Simpson and T. R. Spalding, J. Organomet. Chem., 1971, 29, 195;
133. 4, F. E. Saalfield and H. J. Svec, Inorg. Chem., 1963, 2, 50;
134. S. R. Gunn, Inorg. Chem., 1972, 11, 786.
135. T. L. Allen, A. C. Scheiner, Y. Yamaguchi and H. F. Schaefer, III, J. Am. Chem. Soc., 1986, 108, 7579.
136. A.-M. Caminade, M. Verrier, C. Ades, N. Paillous and M. Koenig, J. Chem. Soc., Chem. Commun., 1984, 875.
137. (a) M. Kira, T. Maruyama, C. Kabuto, K. Ebata and H. Sakurai, Angew. Chem., Int. Ed. Engl., 1994, 33, 1489;
138. (b) B. D. Shepherd, D. R. Powell and R. West, Organometallics, 1989, 8, 2664.
139. M. J. Fink, M. J. Michalczyk, K. J. Haller and R. West, Organometallics, 1984, 2, 793.
140. Unassociated divalent organosilicon compounds have been described in: (a) P. Julzi, D. Kanne and C. Krüger, Angew. Chem., Int. Ed. Engl., 1986, 25, 164;
141. (b) R. West and M. Denk, Pure Appl. Chem., 1996, 68, 785.
142. M. J. Michalczyk, R. West and J. Michl, Organometallics, 1985, 4, 826;
143. -1 have been calculated in: G. Olbrich, P. Potzinger, B. Riemann and R. Walsh, Organometallics, 1984, 3, 1267;
144. M. W. Schmidt, P. N. Truong and M. S. Gordon, J. Am. Chem. Soc., 1987, 109, 5217;
145. P. v. R. Schleyer and D. Kost, J. Am. Chem. Soc., 1988, 110, 2105.
146. (a) N. Tokitoh, H. Suzuki, R. Okazaki and K. Ogawa, J. Am. Chem. Soc., 1993, 115, 10428;
147. (b) H. Suzuki, N. Tokitoh and R. Okazaki, Bull. Chem. Soc. Jpn., 1995, 68, 2471;
148. (c) K. Kishikawa, N. Tokitoh and R. Okazaki, Chem. Lett., 1998, 239.
149. -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.
150. H. A. Skinner and L. E. Sutton, Trans. Faraday Soc., 1940, 36, 1209.
151. W. T. Robinson and R. N. Grimes, Inorg. Chem., 1975, 14, 3056;
152. G. E. Herberich, B. Hessner and M. Hostalek, Angew. Chem., Int. Ed. Engl., 1986, 25, 642;
153. G. E. Herberich, B. Hessner and M. Hostalek, J. Organomet. Chem., 1988, 355, 473;
154. J. H. Davis, E. Sinn and R. M. Grimes, J. Am. Chem. Soc., 1989, 111, 4784;
155. G. E. Herberich, C. Ganter, L. Weseman and R. Boese, Angew. Chem., Int. Ed. Engl., 1990, 29, 912.
156. J. J. Eisch, Adv. Organomet. Chem., 1996, 39, 355.
157. H. Meyer, G. Schmidt-Lukasch, G. Baum, W. Massa and A. Berndt, Z. Naturforsch., Teil B, 1988, 43, 801.
158. Ref. 6, H. Meyer, G. Schmidt-Lukasch, G. Baum, W. Massa and A. Berndt, Z. Naturforsch., Teil B, 1988, p. 1052;
159. R. M. Minyaev and R. Hoffmann, Chem. Mater., 1991, 3, 547.
160. W. Biffar, H. Nōth and H. Pommerening, Angew. Chem., Int. Ed. Engl., 1980, 19, 56;
161. K. Schlüter and A. Berndt, Angew. Chem., Int. Ed. Engl., 1980, 19, 57.
162. H. Klusik and A. Berndt, Angew. Chem., Int. Ed. Engl., 1981, 20, 870;
163. H. Klusik and A. Berndt, J. Organomet. Chem., 1981, 222, C25.
164. (a) A. Moezzi, M. M. Olmstead and P. P. Power, J. Am. Chem. Soc., 1992, 114, 2715;
165. (b) A. Moezzi, R. A. Bartlett and P. P. Power, Angew. Chem., Int. Ed. Engl., 1992, 31, 1082.
166. M. Pilz, J. Allwohn, P. Willershausen, W. Massa and A. Berndt, Angew. Chem., Int. Ed. Engl., 1990, 29, 1030.
167. (a) E. Kaufman and P. v. R. Schleyer, Inorg. Chem., 1980, 27, 3987;
168. (b) E. L. Hamilton, J. G. Pruis, R. L. DeKock and K. J. Jalkanen, Main Group Chem., in the press.
169. (a) C. Dohmeier, C. Robl, M. Tacke and H. Schnöckel, Angew. Chem., Int. Ed. Engl., 1991, 30, 564;
170. (b) A. Purath, C. Dohmeier, A. Ecker and H. Schnöckel, Organometallics, 1998, 17, 1894.
171. (a) W. Uhl, W. Miler, M. Layh and W. Schwarz, Angew. Chem., Int. Ed. Engl., 1992, 31, 1364;
172. (b) A. Haaland, K.-G. Martinsen, H. V. Volden, W. Kaim, E. Waldhör, W. Uhl and U. Schutz, Organometallics, 1996, 15, 1146.
173. D. Loos, E. Baum, A. Ecker, H. Schnöckel and A. J. Downs, Angew. Chem., Int. Ed. Engl., 1997, 36, 860.
174. M. C. Kuchta, J. B. Bonanno and G. Parkin, J. Am. Chem. Soc., 1996, 118, 10 914.
175. O. T. Beachley, jun., R. Blom, M. R. Churchill, J. Fettinger, J. C. Pazik and L. Victoriano, J. Am. Chem. Soc., 1986, 108, 4666.
176. (a) R. D. Schluter, A. H. Cowley, D. A. Atwood, R. J. Jones and J. L. Atwood, J. Coord. Chem., 1993, 30, 215;
177. (b) W. Uhl, R. Graupner, M. Layh and U. Schutz, J. Organomet. Chem., 1995, 493, Cl;
178. (c) W. Uhl, S. U. Keimling, K. W. Klinkhammer and W. Schwartz, Angew. Chem., Int. Ed. Engl., 1997, 36, 64.
179. (a) H. Schumann, C. Janiak, F. Görlitz, J. Loebel and A. Dietrich, J. Organomet. Chem., 1989, 363, 243;
180. (b) H. Schumann, C. Janiak, J. Pickhardt and U. Börner, Angew. Chem., Int. Ed. Engl., 1987, 26, 789.
181. (a) M. C. Kuchta, H. V. R. Dias, S. G. Bott and G. Parkin, Inorg. Chem., 1996, 35, 943;
182. (b) G. Parkin, Adv. Inorg. Chem., 1995, 42, 291.
183. (a) S. T. Haubrich and P. P. Power, J. Am. Chem. Soc., 1998, 120, 2202;
184. (b) M. Niemeyer and P. P. Power, Angew. Chem., Int. Ed. Engl., 1998, 37, 1277.
185. (a) A. Haaland, K.-G. Martinsen, S. A. Shlykov, H. V. Volden, C. Dohmeier and H. Schnöckel, Organometallics, 1995, 14, 3116;
186. (b) A. Haaland, K.-G. Martinsen, H. V. Volden, D. Loos and H. Schnöckel, Acta Chem. Scand., 1994, 48, 172;
187. (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;
188. (d) R. Blom, H. Werner and J. Wolf, J. Organomet. Chem., 1988, 354, 293;
189. (e) S. O. Waezsada, T. Belgardt, M. Noltemeyer and H. W. Roesky, Angew. Chem., Int. Ed. Engl., 1994, 33, 1351.
190. L. Pauling, The Nature of the Chemical Bond, Cornell University Press, Ithaca, New York, 3rd edn., 1960, p. 6.
191. S. Nagase, S. Suzuki and T. Kurakake, J. Chem. Soc., Chem. Commun., 1990, 1724.
192. A. H. Cowley, A. Decken, N. C. Norman, C. Kruger, F. Lutz, H. Jacobsen and T. Ziegler, J. Am. Chem. Soc., 1997, 119, 3389.
193. M. Driess and H. Grützmacher, Angew. Chem., Int. Ed. Engl., 1996, 35, 828.
194. 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.
195. M. D. Joesten and L. J. Schaad, Hydrogen Bonding, Marcel Dekker, New York, 1974.
196. (a) M. Weidenbruch, J. Schlaefke, A. Schäfer, K. Peters, H. G. v. Schnering and H. Marsmann, Angew. Chem., Int. Ed. Engl., 1994, 33, 1846;
197. (b) M. Kira, R. Yauchibara, R. Hirano, C. Kabuto and H. Sakurai, J. Am. Chem. Soc., 1991, 113, 7783.
198. (a) M. Weidenbruch, A. Schadwe, H. Kilian, S. Pohl, W. Saak and H. Marsmann, Chem. Ber., 1992, 125, 563;
199. (b) H. Grützmacher and H. Pritzkow, Angew. Chem., Int. Ed. Engl., 1991, 30, 1017;
200. (c) A. Schäfer, M. Weidenbruch, W. Saak, S. Pohl and H. Marsmann, Angew. Chem., Int. Ed. Engl., 1991, 30, 834.
201. S. Masamune and L. R. Sita, J. Am. Chem. Soc., 1985, 107, 6390.
202. II dialkyls and the terms double bond and dimetallene were used with quotation marks.
203. For further explanation of this phenomenon in some Group 14 and 15 species, see (a) T. A. Albright, J. K. Burdett and M. H. Whangbo, Orbital Interactions in Chemistry, John Wiley, New York, 1985, p. 127;
204. (b) R. S. Grev, Adv. Organomet. Chem., 1991, 33, 125;
205. (c) D. G. Gilheany, Chem. Rev., 1994, 94, 1339.
206. C. C. Levin, J. Am. Chem. Soc., 1975, 97, 5649.
207. R. F. W. Bader, Can. J. Chem., 1962, 40, 1164;
208. R. G. Pearson, J. Am. Chem. Soc., 1969, 91, 4947.
209. D. H. Harris and M. F. Lappert, J. Chem. Soc., Chem. Commun., 1974, 895;
210. C. D. Schaeffer and J. J. Zuckerman, J. Am. Chem. Soc., 1974, 96, 7160;
211. T. Fjelberg, H. Hope, M. F. Lappert, P. P. Power and A. J. Thorne, J. Chem. Soc., Chem. Commun., 1983, 639.
212. G. Trinquier and J.-P. Malrieu, J. Am. Chem. Soc., 1987, 109, 5303;
213. J. Am. Chem. Soc., 1989, 11, 5916;
214. J. Am. Chem. Soc., 1991, 113, 144.
215. G. Trinquier, J.-P. Malrieu and P. Riviere, J. Am. Chem. Soc., 1982, 104, 4529.
216. P. J. Davidson, D. H. Harris and M. F. Lappert, J. Chem. Soc., Dalton Trans., 1976, 2268.
217. T. Fjelberg, A. Haaland, M. F. Lappert, B. E. R. Schilling, R. Seip and A. J. Thorne, J. Chem. Soc., Chem. Commun., 1982, 1407;
218. T. Fjelberg, A. Haaland, B. E. R. Schilling, H. V. Volden, M. F. Lappert and A. J. Thorne, J. Organomet. Chem., 1984, 254, Cl.
219. J. B. Pedley and J. Rylance, Sussex NPL Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, 1977.
220. J. Jacobsen and T. Ziegler, J. Am. Chem. Soc., 1994, 116, 3667.
221. L. Pauling, Proc. Natl. Acad. Sci. USA, 1983, 3871.
222. G. Lendvay, Chem. Phys. Lett., 1991, 181, 88.
223. Ref. 118, p. 239.
224. T. L. Allen, unpublished work.
225. K. Kobayashi and S. Nagase, Organometallics, 1997, 16, 2489.
226. Z. Palagyi, R. S. Grev and H. F. Schaefer, III, J. Am. Chem. Soc., 1993, 115, 1936.
227. Z. Palagyi and H. F. Schaefer, III, Chem. Phys. Lett., 1993, 203, 195;
228. G. Treboux and J.-C. Barthelat, J. Am. Chem. Soc., 1993, 115, 4870.
229. C. Janiak and R. Hoffmann, Angew. Chem., Int. Ed. Engl., 1989, 28, 1688;
230. C. Janiak and R. Hoffmann, J. Am. Chem. Soc., 1990, 112, 5924.
231. P. H. M. Budzelaar and J. Boersma, Recl. Trav. Chim. Pays-Bas, 1990, 109, 187.
232. (a) P. Schwerdtfeger, Inorg. Chem., 1991, 30, 1660;
233. (b) P. Schwerdtfeger, G. A. Heath, M. Dolgand M. A. Bennett, J. Am. Chem. Soc., 1992, 114, 7518.
234. C. Jouany, J. C. Barthelat and J. P. Dandey, Chem. Phys. Lett., 1987, 36, 52;
235. D. R. Armstrong, Theor. Chim. Acta, 1981, 60, 159;
236. J. D. Dill, P. v. R. Schleyer and J. Pople, J. Am. Chem. Soc., 1975, 97, 3402.