Radical-type reactivity of metalla[1.1.1]propellanes of group 14: Syntheses, structures, and reduction chemistry of transition metal-terminated bicyclo[1.1.1]pentastannanes

Organometallics

Volumn 29, Issue 22, 2010, Pages 6028-6037

  Nied, Dominik ^a   Matern, Eberhard ^a   Berberich, Helga ^a   Neumaier, Marco ^a   Breher, Frank ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BOND-BREAKING; COBALTOCENIUM; ELECTROCHEMICAL STUDIES; ISOLATED YIELD; ISOLATION AND CHARACTERIZATION; LIGAND-FREE; MAKING PROCESS; PROPELLANES; REDOX CYCLES; TIN ATOMS; TITLE COMPOUNDS; X RAY STRUCTURE ANALYSIS;

CHEMICAL BONDS; GERMANIUM; REDUCTION; TRANSITION METALS;

TIN;

EID: 78650139711     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100779b     Document Type: Article

References (109)

1. Wiberg, K. B. Chem. Rev. 1989, 89, 975
2. Yeston, J. Science 2009, 323, 563
3. Breher, F. Coord. Chem. Rev. 2007, 251, 1007
4. Schleyer, P.; von, R.; Janoschek, R. Angew. Chem. 1987, 99, 1312
5. Angew. Chem., Int. Ed. 1987, 26, 1267.
6. Schoeller, W. W.; Dabisch, T.; Busch, T. Inorg. Chem. 1987, 26, 4383
7. Nagase, S.; Kudo, T. Organometallics 1987, 6, 2456
8. Nagase, S.; Kudo, T. Organometallics 1988, 7, 2534
9. Nagase, S. Polyhedron 1991, 10, 1299
10. Gordon, M. S.; Nguyen, K. A.; Carroll, M. T. Polyhedron 1991, 10, 1247
11. Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem. 1991, 103, 916
12. Angew. Chem., Int. Ed. 1991, 30, 902.
13. Gallego-Planas, N.; Whitehead, M. A. J. Mol. Struct. (THEOCHEM) 1992, 260, 419
14. Gallego-Planas, N.; Whitehead, M. A. J. Mol. Struct. (THEOCHEM) 1997, 391, 51
15. Holder, A. J.; Earley, C. W. J. Mol. Struct. (THEOCHEM) 1993, 281, 131
16. Wiberg, K. B.; Walker, F. H. J. Am. Chem. Soc. 1982, 104, 5239
17. Semmler, K.; Szeimies, G.; Belzner, J. J. Am. Chem. Soc. 1985, 107, 6410
18. Levin, M. D.; Kaszynski, P.; Michl, J. Chem. Rev. 2000, 100, 169
19. Messerschmidt, M.; Scheins, S.; Grubert, L.; Pätzel, M.; Szeimies, G.; Paulmann, C.; Luger, P. Angew. Chem. 2005, 117, 3993
20. Angew. Chem., Int. Ed. 2005, 44, 3925.
21. Coppens, P. Angew. Chem. 2005, 117, 6970
22. Angew. Chem., Int. Ed. 2005, 44, 6810.
23. Wu, W.; Gu, J.; Song, J.; Shaik, S.; Hiberty, P. C. Angew. Chem. 2009, 121, 1435
24. Angew. Chem., Int. Ed. 2009, 48, 1407.
25. Shaik, S.; Danovich, D.; Wu, W.; Hiberty, P. C. Nat. Chem. 2009, 1, 443
26. Grützmacher, H.; Breher, F. Angew. Chem. 2002, 114, 4178
27. Angew. Chem., Int. Ed. 2002, 41, 4006.
28. Karni, M.; Apeloig, Y.; Kapp, J.; Schleyer, P.; von, R. In The Chemistry of Organic Silicon Compounds, Vol. 3; Rappoport, Z.; Apeloig, Y., Eds.; Wiley: Chichester, 2001.
29. Power, P. P. Nature 2010, 463, 171
30. Chivers, T.; Konu, J. Comm. Inorg. Chem. 2009, 30, 131
31. "A biradical oid is a closed shell species derived from a singlet biradical by a weak interaction between the radical centers." Dewar, M. J. S.; Healy, E. F. Chem. Phys. Lett. 1987, 141, 521
32. Bonaić-Koutecký, V.; Koutecký, J.; Michl, J. Angew. Chem. 1987, 99, 216
33. Angew. Chem., Int. Ed. Engl. 1987, 26, 170.
34. Borden, W. T. In Enzyclopedia of Computational Chemistry; Schleyer, P. v. R., Ed.; Wiley: New York, 1998; p 708.
35. Biradicals; Borden, W. T., Ed.; Wiley: New York, 1982.
36. Berson, J. A. Acc. Chem. Res. 1997, 30, 238
37. Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88
38. Salem, L.; Rowland, C. Angew. Chem. 1972, 84, 86
39. Angew. Chem., Int. Ed. 1972, 11, 92
40. Borden, W. T.; Iwamura, H.; Berson, J. A. Acc. Chem. Res. 1994, 27, 109
41. Rajca, A. Chem. Rev. 1994, 94, 871
42. Review on REER (E = group 14 element) showing in some cases biradicaloid behavior: Power, P. P. Organometallics 2007, 26, 4362
43. See for example: Nguyen, K. A.; Carroll, M. T.; Gordon, M. S. J. Am. Chem. Soc. 1991, 113, 7924
44. Sandström, N.; Ottosson, H. Chem. - Eur. J. 2005, 11, 5067
45. Wang, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2005, 46, 5567
46. Ebrahimi, A.; Deyhimi, F.; Roohi, H. J. Mol. Struct. (THEOCHEM) 2003, 626, 223
47. Kitchen, D. B.; Jackson, J. E.; Allen, L. C. J. Am. Chem. Soc. 1990, 112, 3408
48. Fischer, G.; Huch, V.; Mayer, P.; Vasisht, S. K.; Veith, M.; Wiberg, N. Angew. Chem. 2005, 117, 8096
49. 2) consisting of only one ligand-free Si atom see
50. Scheschkewitz, D. Angew. Chem. 2005, 117, 3014
51. Angew. Chem., Int. Ed. 2005, 44, 2954.
52. Schnepf, A.; Köppe, R. Angew. Chem. 2003, 115, 940
53. Angew. Chem., Int. Ed. 2003, 42, 911.
54. Schnepf, A.; Drost, C. Dalton Trans. 2005, 3277 See also: Schnepf, A. Chem. Soc. Rev. 2007, 36, 745
55. Wiberg, N.; Lerner, H.-W.; Wagner, S.; Nöth, H.; Seifert, T. Z. Naturforsch. B 1999, 54, 877
56. See also: Wiberg, N.; Power, P. P. In Molecular Clusters of the Main Group Elements; Driess, M.; Nöth, H., Eds.; Wiley-VCH: Weinheim, 2004.
57. Reviews: Sita, L. R. Adv. Organomet. Chem. 1995, 38, 189
58. Sita, L. R. Acc. Chem. Res. 1994, 27, 191
59. Sita, L. R.; Kinoshita, I. J. Am. Chem. Soc. 1992, 114, 7024
60. Sita, L. R.; Kinoshita, I. J. Am. Chem. Soc. 1991, 113, 5070
61. Sita, L. R.; Kinoshita, I. J. Am. Chem. Soc. 1990, 112, 8839
62. Sita, L. R.; Bickerstaff, R. D. J. Am. Chem. Soc. 1989, 111, 6454
63. Drost, C.; Hildebrand, M.; Lönnecke, P. Main Group Met. Chem. 2002, 25, 93
64. Richards, A. F.; Brynda, M.; Power, P. P. Organometallics 2004, 23, 4009 See also: Richards, A. F.; Brynda, M.; Olmstead, M. M.; Power, P. P. Organometallics 2004, 23, 2841
65. Nied, D.; Klopper, W.; Breher, F. Angew. Chem. 2009, 121, 1439
66. Angew. Chem., Int. Ed. 2009, 48, 1411.
67. Nied, D.; Köppe, R.; Klopper, W.; Schnöckel, H.; Breher, F. J. Am. Chem. Soc. 2010, 131, 10264
68. It is important to note that the quantity of radical character is fundamentally different from the theory of radical behavior. Radical character serves as a theoretical measure, whereas radical behavior is experimentally observed for such species.
69. Bitterwolf, T. E. Coord. Chem. Rev. 2000, 206-207, 419
70. Bitterwolf, T. E. J. Organomet. Chem. 2004, 689, 3939
71. Meyer, T. J.; Caspar, J. V. Chem. Rev. 1985, 85, 197
72. Szaciowski, K.; Macyk, W.; Stochel, G.; Stasicka, Z.; Sostero, S.; Traverso, O. Coord. Chem. Rev. 2000, 208, 277
73. Dessy, R. E.; Weissman, P. M.; Pohl, R. L. J. Am. Chem. Soc. 1966, 88, 5117
74. Miholová, D.; Vlček, A. A. Inorg. Chim. Acta 1980, 41, 119
75. Bullock, J. P.; Palazotto, M. C.; Mann, K. R. Inorg. Chem. 1991, 30, 1284
76. Pugh, J. R.; Meyer, T. J. J. Am. Chem. Soc. 1992, 114, 3784
77. 2} entities).
78. Nied, D.; Klopper, W.; Breher, F. Manuscript in preparation.
79. For a closely related bicyclo[1.1.1]pentasilane derivative see: Kabe, Y.; Kawase, T.; Okada, J.; Yamashita, O.; Goto, M.; Masamune, S. Angew. Chem. 1990, 102, 823
80. 2,5]pentane derivatives
81. Lee, V. A.; Yokoyama, T.; Takanashi, K.; Sekiguchi, A. Chem. - Eur. J. 2009, 15, 8401
82. Lee, V. A.; Ichinoe, M.; Sekiguchi, A. J. Am. Chem. Soc. 2002, 124, 9962
83. 1H NMR chemical shifts (see Supporting Information).
84. 2 showed M-M bond homolysis and CO-loss photochemical channels. It is by far out of the scope of this article to cite all original papers dealing with the photochemistry of these types of molecules. The reader is referred to excellent review articles cited in ref 25. We thank one referee for helpful comments.
85. Unfortunately, 3 and 4 could not be analyzed by mass spectrometry because the electron impact (EI) ionization method tends to result in decomposition of the compounds. The smoother electrospray ionization method (ESI), however, was shown to be too gentle to ionize the compounds.
86. -1. Fischer, R. D.; Vogler, A.; Noack, K. J. Organomet. Chem. 1967, 7, 135
87. Programs WinNMR and WinDaisy, Bruker Daltonik: Bremen, 1999.
88. Hägele, G.; Engelhardt, M.; Boenigk, W. Simulation und Automatisierte Analyse von NMR-Spektren; VCH: Weinheim, 1987.
89. Hoffmann, R. Acc. Chem. Res. 1971, 4, 1
90. Hahn, T. International Tables for Crystallography, Vol. A, 5 th ed.; Kluwer Academic Publishers: Dordrecht, 2002.
91. 9], see: McNeese, T. J.; Wreford, S. S.; Tipton, D. L.; Bau, R. J. Chem. Soc., Chem. Commun. 1977, 390
92. Values for the second independent molecule in the asymmetric unit are given in brackets.
93. 3]. Itazaki, M.; Kamitani, M.; Nakazawa, H. Acta Crystallogr. Sect. E 2008, 64, m1578
94. 2]. Akita, M.; Hua, R.; Oku, T.; Tanaka, M.; Moro-oka, Y. Organometallics 1996, 15, 4162
95. Geiger, W. E. Organometallics 2007, 26, 5738
96. Evans, D. H. Chem. Rev. 2008, 108, 2113
97. Braunschweig, H.; Breher, F.; Kaupp, M.; Gross, M.; Kupfer, T.; Nied, D.; Radacki, K.; Schinzel, S. Organometallics 2008, 27, 6427 (and cited references).
98. Krossing, I.; Raabe, I. Angew. Chem. 2004, 116, 2116
99. Angew. Chem., Int. Ed. 2004, 43, 2066.
100. 2 to furnish 5.
101. Harris, R. K.; Becker, E. D.; Cabral de Menezes, S. M.; Goodfellow, R.; Granger, P. Pure Appl. Chem. 2001, 73, 1795
102. Hinkelmann, K.; Heinze, J.; Schacht, H.-T.; Field, J. S.; Vahrenkamp, H. J. Am. Chem. Soc. 1989, 111, 5078
103. Heinze, J. Angew. Chem. 1984, 96, 823
104. Angew. Chem., Int. Ed. 1984, 23, 831.
105. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877
106. Sita, L. R.; Bickerstaff, R. D. J. Am. Chem. Soc. 1989, 111, 3769
107. Doherty, N. M.; Knox, S. A. R.; Morris, M. J. Inorg. Synth. 1990, 28, 189
108. SHELXTL v6.12; Bruker AXS Inst. Inc.: Madison, WI, USA, 2000.
109. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112