Synthesis and reactivity of low-valent group 14 element compounds

Zeitschrift fur Anorganische und Allgemeine Chemie

Volumn 636, Issue 7, 2010, Pages 1275-1285

  Johnson, Brian P ^a   Almstätter, Stefan ^a   Dielmann, Fabian ^a   Bodensteiner, Michael ^a   Scheer, Manfred ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Density functional calculations; Germanium; Multiple bonding; Phosphorus; Tin

Indexed keywords

EID: 77954340280     PISSN: 00442313     EISSN: 15213749     Source Type: Journal    
DOI: 10.1002/zaac.201000029     Document Type: Article

References (131)

1. G. Becker, G. Cesser, W. UhI, Z. Naturforsch. 1981, 36b, 16.
2. T. Allspach, M. Regitz, G. Becker, W. Becker, Synthesis 1986, 31;
3. M. Regitz, P. Binger, Angew. Chem. 1988, 100, 1541;
4. Angew. Chem. Int. Ed. Engl. 1988, 27, 1484;
5. M. Regitz, Chem. Rev. 1990, 90, 191.
6. Some examples: a) A. M. Arif, A. Barron, A. H. Cowley, S. W. Hall, J. Chem. Soc., Chem. Commun. 1988, 171;
7. b) G. Becker, M. Bohringer, R. Gleiter, K.-H. Pfeifer, J. Grobe, D. LeVan, M. Hegemann, Chem. Ber. 1994, 127, 1041;
8. c) G. Becker, K. Hubler, Z. Anorg. Allg. Chem. 1994, 620, 405;
9. d) G. Becker, W. Schwarz, N. Seidler, M. Westerhausen, Z. Anorg. Allg. Chem. 1992, 612, 72.
10. G. Märkl, H. Sejpka, Angew. Chem. 1986, 98, 286;
11. Angew. Chem. Int. Ed. Engl. 1986, 25, 264.
12. M. Finze, E. Bernhardt, H. Willner, C. W. Lehmann, Angew. Chem. 2004, 116,
13. Angew. Chem. Int. Ed. 2004, 43, 4160.
14. a) M. Regitz, P. Binger, Angew. Chem. 1988, 100, 1541;
15. Angew. Chem. Int. Ed. Engl. 1988, 27, 1484;
16. b) M. Regitz, P. Binger, in: Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds.: M. Regitz, O. J. Scherer), Thieme, Stuttgart, 1990, p. 58;
17. c) M. Regitz, Chem. Rev. 1990, 90, 191;
18. d) A. Mack, M. Regitz, Chem. Ber. Recueil 1997, 130, 823;
19. e) T. W. Mackewitz, M. Regitz, Synthesis 1998, 125;
20. for synthesis of different phosphaalkynes cf.: J.-C. Guillemin, T. Janati, J.-M. Denis, J. Org. Chem. 2001, 66, 7864;
21. for short living phosphaalkynes: A. C. Gaumont, J.-M. Denis, Chem. Rev. 1994, 94, 1413.
22. a) J. F. Nixon, Chem. Rev. 1988, 88, 1327;
23. b) P. Binger, in: Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds.: M. Regitz, O. J. Scherer), Thieme, Stuttgart, 1990,p. 90;
24. c) J. F. Nixon, Chem. Ind. 1993, 404;
25. d) J. F. Nixon, Coord. Chem. Rev. 1995, 145, 201;
26. e) J. F. Nixon, Chem. Soc. Rev. 1995, 24, 319;
27. f) K. B. Dillon, F. Mathey, J. F. Nixon, in: Phosphorus, The Carbon Copy, Wiley, Chichester, 1998,pp 40;
28. g) F. Mathey, Angew. Chem. 2003, 115, 1616;
29. Angew. Chem. Int. Ed. 2003, 42, 1578.
30. a) P. P. Power, J. Chem. Soc., Dalton Trans. 1998, 18, 2939;
31. b) P. P. Power, Chem. Rev. 1999, 99, 3463.
32. a) C. N. Smit, F. M. Lock, F. Bickelhaupt, Tetrahedron Lett. 1984, 25, 3011;
33. b) C. N. Smit, F. Bickelhaupt, Organometallics 1987, 6, 1156;
34. c) E. Niecke, E. Klein, M. Nieger, Angew. Chem. 1989, 101, 792;
35. Angew. Chem. Int. Ed. Engl. 1989, 28, 751.
36. a) J. Escudié, C. Couret, J. Satgé, M. Andrianarison, J. D. Andriamizaka, J. Am. Chem. Soc. 1985, 107, 3378;
37. b) H. Ranaivonjatovo, J. Escudié, C. Couret, J. Satgé, M. Dräger, New J. Chem. 1989, 13, 389;
38. c) H. Ranaivonjatovo, J. Escudié, C. Couret, J. Satgé, J. Organomet. Chem. 1991, 415, 327.
39. a) C. Couret, J. Escudié, J. Satgé, A. Raharinirina, J. D. Andriamizaka, J. Am. Chem. Soc. 1985, 107, 8280;
40. b) H. Ranaivonjatovo, J. Escudié, C. Couret, J. Satgé, J. Chem. Soc. Chem. Commun. 1992, 1047.
41. a) M. Driess, Angew. Chem. 1991, 103, 979;
42. Angew. Chem. Int. Ed. Engl 1991, 30, 1022;
43. b) M. Driess, U. Winkler, W. Imhof, L. Zsolnai, G. Huttner, Chem. Ber. 1994, 127, 1031.
44. W. Setaka, K. Hirai, H. Tomioka, K. Sakamoto, M. Kira, J. Am. Chem. Soc. 2004, 126, 2696
45. B. Twamley, P. P. Power, Chem. Commun. 1998, 1979.
46. R. C. Smith, P. Gantzel, A. L. Rheingold, J. D. Protasiewicz, J. Am. Chem. Soc. 2003, 125, 40.
47. a) M. Scheer, K. Schuster, T. A. Budzichowski, M. H. Chisholm, W E. Streib, J. Chem. Soc., Chem. Commun. 1995, 1671;
48. b) P. Kramkowski, M. Scheer, G. Baum, J. Organomet. Chem. 1998, 553, 511;
49. c) M. Scheer, J. Krug, Z. Anorg. Allg. Chem. 1998, 624, 399;
50. d) T. Gröer, G. Baum, M. Scheer, Organometallics 1998, 17, 5916;
51. e) M. Scheer, E. Leiner, P. Kramkowski, M. Schiffer, G. Baum, Chem. Eur. J. 1998, 4, 1917;
52. f) P. Kramkowski, M. Scheer, Angew. Chem. 1999, 111, 3384;
53. Angew. Chem. Int. Ed. 1999, 38, 3183;
54. g) M. Scheer, P. Kramkowski, K. Schuster, Organometallics 1999, 18, 2874;
55. h) P. Kramkowski, G. Baum, U. Radius, M. Kaupp, M. Scheer, Chem. Eur. J. 1999, 5, 2890;
56. i) R Kramkowski, M. Scheer, Angew. Chem. 2000, 112, 959;
57. Angew. Chem. Int. Ed. 2000, 39, 928;
58. j) M. Scheer, D. Himmel, B. P. Johnson, C. Kuntz, M. Schiffer, Angew. Chem. 2007, 119, 4045;
59. Angew. Chem. Int. Ed. 2007, 46, 3971.
60. A. S. Ionkin, W. J. Marshall, Organometallics 2003, 22, 4136.
61. J. Glatthaar, G. Maier, Angew. Chem. 2004, 116, 1314;
62. Angew. Chem. Int. Ed. 2004, 43, 1294.
63. M. Driess, S. Block, M. Brym, M. T. Gamer, Angew. Chem. 2006, 118, 2351;
64. Angew. Chem. Int. Ed. 2006, 45, 2293.
65. a) M. Bender, E. Niecke, M. Nieger, R. Pietschnig, Eur. J. Inorg. Chem, 2006, 380;
66. b) R. Pietschnig,J. J. Tirreé, in: Organosilicon Chemistry - From Molecules to Materials VI, Vol. 1 (Eds.: N. Auner, J. Weis), Wiley-VCH, 2005, pp. 222.
67. Y-H. Hu, M.-D. Su, Chem. Phys. Lett. 2003, 378, 289.
68. M. Saito, H. Hashimoto, T. Tajima, M. Ikeda, J. Organomet. Chem. 2007, 692, 2729.
69. H. Schumann, R. Fischer, J. Organomet. Chem. 1975, 88, C13.
70. a) M. Scheer, F. Uhlig, T. T. Nam, M. Dargatz, H.-D. Schädler, E. Herrmann, Z. Anorg. Allg. Chem. 1990, 585, 177;
71. b) M. Scheer, St. Gremler, E. Herrmann, U. Grünhagen, M. Dargatz, E. Kleinpeter, Z. Anorg. Allg. Chem. 1991, 600, 203;
72. c) M. Scheer, St. Gremler, E. Herrmann, P. G. Jones, J. Organomet. Chem. 1991, 414, 337;
73. d) S. Gremler, M. Scheer, Z. Anorg. Allg. Chem. 1993, 619, 466;
74. e) M. Scheer, S. Gremler, Z. Anorg. Allg. Chem. 1993, 619, 471;
75. f) M. Scheer, St. Gremler, E. Herrmann, M. Dargatz, H.-D. Schädler, Z. Anorg. Allg. Chem. 1993, 619, 1047.
76. B. E. Eichler, L. Pu, M. Stender, P. P. Power, Polyhedron 2001, 20, 551.
77. a) W.-W. du Mont, H. Schumann, Angew. Chem. 1975, 87, 354;
78. Angew. Chem. Int. Ed. Engl. 1975, 14, 368;
79. b) W.-W. du Mont, M. Grenz, Chem. Ber. 1985, 118, 1045.
80. K. Izod, J. Stewart, W. Clegg, R. W. Harrington, Organometallics 2010, 29, 108.
81. M. F. Lappert, P. P. Power, J. Chem. Soc., Dalton Trans. 1985, 51.
82. M. F. Lappert, M. C. Misra, M. Onyszchuk, R. S. Rowe, P. P. Power, M. J. Slade, J. Organomet. Chem. 1987, 330, 31.
83. P. B. Hitchcock, H. A. Jasim, M. F. Lappert, W.-P. Leung, A. K. Rai, R. E. Taylor, Polyhedron 1991, 10, 1203.
84. B. Twamley, N. J. Hardman, P. P. Power, Acta Crystallogr., Sect. C 2000, 56, E514.
85. B. Twamley, P. P. Power, Chem. Commun. 1998, 1979.
86. L. Pu, A. D. Phillips, A. F. Richards, M. Stender, R. S. Simons, M. M. Olmstead, P. P. Power, J. Am. Chem. Soc. 2003, 125, 11626.
87. a) M. Driess, Chem. Unserer Zeit 1993, 27, 141;
88. b) M. Yoshifuji, I. Shima, N. Inamoto, K. Hirotsu, T. Higuchi, J. Am. Chem. Soc. 1981, 103, 4587;
89. c) A. H. Cowley, Polyhedron 1984, 3, 389;
90. d) L. Weber, Coord. Chem. Rev. 1992, 92, 1839;
91. e) N. C. Norman, Polyhedron 1993, 12, 2431;
92. f) A. H. Cowley, J. G. Lasch, N. C. Norman, M. Pakulski, J. Am. Chem. Soc. 1983, 105, 5506;
93. g) C. Couret, J. Escudie, Y. Madaule, H. Ranaivonjatovo, J.-G. Wolf, Tetrahedron Lett. 1983, 24, 2769;
94. h) N. Tokitoh, Y. Arai, T. Sasamori, R. Okazaki, S. Nagase, H. Uekusa, Y. Ohashi, J. Am. Chem. Soc. 1998, 120, 443;
95. i) N. Tokitoh, Y. Arai, R. Okazaki, S. Nagase, Science 1997, 277, 78.
96. Gaussian 03, Revision B.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 2003. For a current listing of basis sets and ECPs, see http://www.gaus-sian.com.
97. a) D. Agustin, G. Rima, H. Gornitzka, J. Barrau, Eur. J. Inorg. Chem. 2000, 693;
98. b) A. L. Balch, M. M. Olmstead, D. P. Oram, Inorg. Chem. 1988, 27, 4309;
99. c) M. Weidenbruch, A. Stilter, J. Schläfke, K. Peters, H. G. von Schnering, J. Organomet. Chem. 1995, 501, 67;
100. d) H.-P. Abicht, K. Jurkschat, A. Tzschach, K. Peters, E.-M. Peters, H. G. von Schnering, J. Organomet. Chem. 1987, 326, 357.
101. J. Beckmann, K. Jurkschat, S. Rabe, M. Schürmann, Z. Anorg. Allg. Chem. 2001, 627, 2413.
102. G. H. Spikes, Y. Peng, J. C. Fettinger, J. Steiner, P. P. Power, Chem. Commun. 2005, 6041.
103. a) D. Brandes, A. Blaschette, J. Organomet. Chem. 1974, 73, 217;
104. b) D. Brandes, A. Blaschette, J. Organomet. Chem. 1973, 49, C6;
105. c) A. Tzschach, M. Scheer, K. Jurkschat, Z. Anorg. Allg. Chem. 1984, 508, 73.
106. L. Pu, N. J. Hardman, P. P. Power, Organometallics 2001, 20, 5105.
107. M. A. Edelman, P. B. Hitchcock, M. F. Lappert, J. Chem. Soc., Chem. Commun. 1990, 1116.
108. H. Puff, R. Gattermayer, R. Hundt, R. Zimmer, Angew. Chem. 1977, 89, 556;
109. Angew. Chem. Int. Ed. Engl. 1977, 16, 547.
110. P. Brown, M. F. Mahon, K. C. Molloy, J. Chem. Soc., Chem. Commun. 1989, 1621.
111. J. Janssen, J. Maguli, H. W. Roesky, Angew. Chem. 2002, 114, 1425;
112. Angew. Chem. Int. Ed. 2002, 41, 1365.
113. a) F. Uhlig, St. Gremler, M. Dargatz, M. Scheer, E. Herrmann, Z. Anorg. Allg. Chem. 1991, 606, 105;
114. b) H. H. Karsch, F. Bienlein, T. Rupprich, F. Uhlig, E. Herrmann, M. Scheer, Synth. Methods Organomet. Inorg. Chem. 1996, 3, 58;
115. c) G. Fritz, W. Hölderlin, Z. Anorg. Allg. Chem. 1976, 422, 104.
116. B. Schiemenz, P. P. Power, Organometallics 1996, 15, 958.
117. L. Pu, M. M. Olmstead, P. P. Power, B. Schiemenz, Organometallics 1998, 17, 5602.
118. B. E. Eichler, L. Pu, M. Stender, P. R Power, Polyhedron 2001, 20, 551.
119. CrysAlis RED, Oxford Diffraction Ltd. Version. 1.171.33.52, 2009.
120. STOE IPDS-software, version 2.89, program Facelt, STOE & CIE GmbH, Darmstadt, Germany, 1998.
121. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Cryst. 1999, 32, 115.
122. L. Palatinus, G. Chapuis, J. Appl. Cryst. 2007, 40, 786.
123. a) G. M. Sheldrick, SHELXL-97, University of Göttingen, 1997;
124. b) G. M. Sheldrick, Acta Crystallogr., Sect. A 2008, 64, 112.
125. A. L. Spek, J. Appl. Cryst. 2003, 36, 7.
126. a) A. D. Becke, Phys. Rev. A 1988, 38, 3098;
127. b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785;
128. c) A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
129. A. Bergner, M. Dolg, H. Stall, H. Preuss, Mol. Phys. 1993, 80, 1431.
130. T. H. Dunning Jr., P. J. Hay, in: Modern Theoretical Chemistry (Ed.: H. F. Schaefer III), Vol. 3, Plenum, New York, 1976.
131. Bond lengths and angles for 2 are not listed, because the molecular structure of 2 is disordered due to contamination of the product with the starting material Ph*GeCl.