Organometallic Chemistry of Ph3PC=C=O. Synthesis, Characterization, X-ray Structure Determination, and Density Functional Study of the First Stable Bis-η1-ketenyl Complex, trans-[PtCl2{η1-C(PPh3)CO}2]

Organometallics

Volumn 19, Issue 7, 2000, Pages 1373-1383

  Bertani, Roberta ^a   Casarin, Maurizio ^a   Ganis, Paolo ^a   Maccato, Chiara ^a   Pandolfo, Luciano ^b   Venzo, Alfonso ^c   Vittadini, Andrea ^c   Zanotto, Livio ^c  

^a UNIVERSITY OF PADOVA   (Italy)

^b UNIVERSITY OF BASILICATA   (Italy)

^c CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000353503     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990826d     Document Type: Article

References (106)

1. Staudinger, H. Chem. Ber. 1905, 38, 1735.
2. (a) Staudinger, H. Die Ketene; VerlagEnke: Stuttgart, 1912.
3. (b)-The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; Wiley: New York, 1980.
4. (c) Tidwell, T. T. Ketenes; Wiley: New York, 1995.
5. Gong, L.; McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1991, 113, 6021, and references therein.
6. Geoffroy, G. L.; Bassner, S. L. Adv. Organomet. Chem. 1988, 28, 1.
7. Calderazzo, F.; Englert, U.; Guarini, A.; Marchetti, F.; Pampaloni, G.; Segre, A.; Tripepi, G. Chem. Eur. J. 1996, 2, 41
8. (a) Hanford, W. E.; Sauer, J. C. Org. React. 1946, 3, 108.
9. (b) Ward, R. S. In The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; Wiley: New York, 1980; pp 223-277.
10. (c) Schaumann, E.; Scheiblich, S. Methoden der Organischen Chemie; Theime Verlag: Stuttgart, 1993; Vol. E15, pp 2353-2530, 2818-2881, 2933-2957.
11. (d) Tidwell, T. T. Ketenes; Wiley: New York, 1995; pp 52-149.
12. 2-ketenylidene compounds (Paiaro, G.; Pandolfo, L. Angew. Chem., Int. Ed. Engl. 1980, 20, 289. Pandolfo, L.; Paiaro, G. Gazz. Chim. Ital. 1985, 115, 561).
13. 2-ketenylidene compounds (Paiaro, G.; Pandolfo, L. Angew. Chem., Int. Ed. Engl. 1980, 20, 289. Pandolfo, L.; Paiaro, G. Gazz. Chim. Ital. 1985, 115, 561).
14. 2-ketenylidene compounds (Paiaro, G.; Pandolfo, L. Angew. Chem., Int. Ed. Engl. 1980, 20, 289. Pandolfo, L.; Paiaro, G. Gazz. Chim. Ital. 1985, 115, 561).
15. 2-ketenylidene compounds (Paiaro, G.; Pandolfo, L. Angew. Chem., Int. Ed. Engl. 1980, 20, 289. Pandolfo, L.; Paiaro, G. Gazz. Chim. Ital. 1985, 115, 561).
16. 2-ketenylidene compounds (Paiaro, G.; Pandolfo, L. Angew. Chem., Int. Ed. Engl. 1980, 20, 289. Pandolfo, L.; Paiaro, G. Gazz. Chim. Ital. 1985, 115, 561).
17. 3-ketenylidene derivatives, in which the C=C=O fragment interacts with three metal centers of some carbonylic clusters.
18. (a) Kreissl, F. R.; Frank, A.; Shubert, U.; Lindner, T. L.; Huttner, G. Angew. Chem., Int. Ed. Engl. 1976, 15, 632.
19. (b) Kreissl, F. R.; Eberl, I.; Uedelhoven, W. Chem. Ber. 1977, 110, 3782.
20. (c) Kreissl, F. R.; Friedrich, P.; Huttner, G. Angew. Chem., Int. Ed. Engl. 1977, 16, 102.
21. (d) Kreissl, F. R.; Uedelhoven, W.; Eberl, I. Angew. Chem., Int. Ed. Engl. 1978, 17, 859.
22. (e) Kreissl, F. R.; Eberl, I.; Uedelhoven, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 860.
23. (f) Uedelhoven, W.; Eberl, I.; Kreissl, F. R. Chem. Ber. 1979, 112, 3376.
24. (g) Eberl, I.; Uedelhoven, W.; Karsch, H.; Kreissl, F. R. Chem. Ber. 1980, 113, 3377.
25. (h) Kreissl, F. R.; Reber, G.; Müller, G. Angew. Chem., Int. Ed. Engl. 1986, 25, 643.
26. (a) Paiaro, G.; Pandolfo, L. Angew. Chem., Int. Ed. Engl. 1980, 20, 288.
27. (b) Pandolfo, L.; Morandini, F.; Paiaro, G. Gazz. Chim. Ital. 1985, 115, 711.
28. (c) List, A. K.; Smith, M. R., II; Hillhouse, G. L. Organometallics 1991, 10, 361.
29. Pandolfo, L.; Paiaro, G.; Valle, G.; Ganis, P. Gazz. Chim. Ital. 1985, 115, 59.
30. (a) Hillhouse, G. L. J. Am. Chem. Soc. 1985, 107, 7772.
31. (b) Pandolfo L.; Paiaro, G. Gazz. Chim. Ital. 1990, 120, 531.
32. (c) Ganis, P.; Paiaro, G.; Pandolfo, L.; Valle, G. Gazz. Chim. Ital. 1990, 120, 541.
33. (a) Mattews, C. N.; Birum, G. H. Tetrahedron Lett. 1966, 46, 5707.
34. (b) Bestmann, H. J. Angew. Chem., Int. Ed. Engl. 1977, 16, 349.
35. (c) Bestmann, H. J.; Sandmeier, D. Chem. Ber. 1980, 113, 274.
36. (a) Berke, H.; Lindner, E. Angew. Chem., Int. Ed. Engl. 1973, 12, 667.
37. (b) Lindenberger, H.; Birk, R.; Orama, O.; Huttner, G.; Berke, H. Z. Naturforsch. 1988, 43b, 749.
38. (a) Bestmann, H.-J.; Schmid, G.; Sandmeier, D.; Kisielowski, L. Angew. Chem., Int. Ed. Engl. 1977, 16, 268.
39. (b) Bestmann, H. J.; Geismann, C.; Zimmermann, R. Chem. Ber. 1994, 127, 1501.
40. (a) Pandolfo, L.; Paiaro, G.; Dragani, L. K.; Maccato, C.; Bertani, R.; Facchin, G.; Zanotto, L.; Ganis, P.; Valle, G. Organometallics 1996, 15, 3250.
41. (b) Bertani, R.; Meneghetti, F.; Pandolfo, L.; Scarmagnan, A.; Zanotto, L. J. Organomet. Chem. 1999, 583, 146.
42. Chock, F. B.; Halpern, J.; Paulik, F. E. Inorg. Synth. 1973, 15, 90.
43. Hartley, F. R. Organomet. Chem. Rev. A 1970, 6, 119.
44. Ramirez, F.; Dershowitz, S. J. Org. Chem. 1957, 22, 41.
45. Bax, A.; Subramanian, S. J. Magn. Reson. 1986, 67, 565.
46. (a) Otting, C.; Wüthrich, K. J. Magn. Reson. 1988, 76, 569.
47. (b) Drobny, G.; Pines, A.; Sinton, S.; Weitekamp, D.; Wemmer, D. Faraday Symp. Chem. Soc. 1979, 13, 49.
48. Bax, A.; Summers, M. S. J. Am. Chem. Soc. 1986, 108, 2093.
49. ADF 2.3.0, Department of Theoretical Chemistry, Vrije Universiteit, Amsterdam, 1997.
50. (a) Post, D.; Baerends, E. J. J. Chem. Phys. 1983, 78, 5663.
51. (b) Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1988, 2, 41.
52. (c) Boerrigter, P. M.; te Velde, G.; Baerends, E. J. Int. J. Quantum Chem. 1988, 33, 87.
53. (d) van der Hoek, P. J.; Klein, A. W.; Baerends, E. J. Commun. At. Mol. Phys. 1989, 23, 93.
54. (e) te Velde, G.; Baerends, E. J. J. Comput. Chem. 1992, 99, 84.
55. Vosko, S. J.; Wilk, M.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
56. (a) Snijdeders, J. G.; Baerends, E. J. Mol. Phys. 1978, 36, 1789.
57. (b) Snijdeders, J. G.; Baerends, E. J.; Ros, P. Mol. Phys. 1979, 38, 1909.
58. (c) Ziegler, T.; Tschinke, V.; Baerends, E. J.; Snijdeders, J. G.; Ravenek, W. J. Phys. Chem. 1989, 93, 3050.
59. Ziegler, T.; Rauk, A. Theor. Chim. Acta 1977, 46, 1.
60. Cromer, D. T.; Waber, J. T. Acta Crystallogr. 1965, 18, 104.
61. Cromer, D. T. Acta Crystallogr. 1965, 18, 17.
62. Sheldrix, G. M. SHELX-76, Program for Crystal Structure Determination; Cambridge University, 1976.
63. Pregosin, P. S.; Kunz, R. W. In NMR. Basic Principles and Progress; Vol. 16, Springer-Verlag: Berlin, 1979.
64. (a) Facchin, G.; Zanotto, L.; Bertani, R.; Nardin, G. Inorg. Chim. Acta 1996, 245, 157.
65. (b) Hall, P. W.; Puddephat, R. J.; Tipper, C. F. H. J. Organomet. Chem. 1974, 71, 145.
66. (c) Plutino, M. R.; Otto, S.; Roodt, A.; Elding, L. J. Inorg. Chem. 1999, 38, 1233.
67. (a) Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335.
68. (b) Meester, M. A. M.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1976, 16, 191.
69. (c) Meester, M. A. M.; Stufkens, D. J.; Vrieze, K. Inorg. Chim. Acta 1977, 21, 25.
70. (d) Pregosin, P. S.; Sze, S. N.; Salvadori, P.; Lazzaroni, R. Helv. Chim. Acta 1977, 60, 2514.
71. Fracarollo, D.; Bertani, R.; Mozzon, M.; Belluco, U.; Michelin, R. A. Inorg. Chim. Acta 1992, 201, 15.
72. Johnson, A. W. Ylides and Imines of Phosphorus; Wiley: New York, 1993, and references therein.
73. (a) Gil, J. M.; Howard, J. A. K.; Navarro, R.; Stone, F. G. A. J. Chem. Soc., Chem. Commun. 1979, 1168.
74. (b) Casey, C. P.; Fagan, P. J. J. Am. Chem. Soc. 1982, 104, 7360.
75. Ziegler, T. Chem. Rev. 1991, 91, 651.
76. Bertoncello, R.; Bettinelli, M.; Casarin, M.; Maccato, C.; Pandolfo, L.; Vittadini, A. Inorg. Chem. 1997, 36, 4707.
77. 39 during the geometry optimization.
78. Daly, J. J.; Wheatley, P. J. J. Chem Soc. (A) 1966, 1703.
79. 3PC=C=O.
80. Albright, T. A.; Hofmann, P.; Rossi, A. R. Z. Naturforsch. 1980, 35b, 343.
81. (a) Hirshfeld, F. L. Theor. Chim. Acta 1977, 44, 1703.
82. (b) Wiberg, K. B.; Rablen, P. R. J. Comput. Chem. 1993, 14, 1504.
83. 1 levels is not displayed in the figure because it is negligibly affected by θ.
84. 3PC=C=O groups around the x axis.
85. (a) Purcell, K. F.; Kotz, J. C. Inorganic Chemistry; Hot-Saunders International Edition, Japan, 1985.
86. (b) Cotton, F. A.; Wilkinson, G. Advances in Inorganic Chemistry, 5th ed.; Wiley-Interscience: New York, 1988.
87. Diels, O.; Wolf, B. Chem. Ber. 1906, 39, 689.
88. (a) Tidwell, T. T. Ketenes; Wiley: New York, 1995; pp 405-428.
89. (b) Allen, A. D.; Ma, J.; McAllister, M. A.; Tidwell, T. T.; Zhao, D.-c. Acc. Chem. Res. 1995, 28, 265.
90. (a) Zhao, D.; Tidwell, T. T. J. Am. Chem. Soc. 1992, 114, 10980.
91. (b) Zhao, D.; Allen, A. D.; Tidwell, T. T. J. Am. Chem. Soc. 1993, 115, 10097.
92. (c) McAllister, M. A., Tidwell, T. T. J. Org. Chem. 1994, 59, 4506.
93. (a) Meier, G.; Reisenauer, H. P.; Shäfer, U.; Balli, H. Angew. Chem., Int. Ed. Engl. 1988, 27, 566.
94. (b) Meier, G.; Reisenauer, H. P.; Ulrich, A. Tetrahedron Lett. 1991, 32, 4469.
95. (a) Beringer, F. M.; Winter R. E. K.; Castellano, J. A. Tetrahedron Lett. 1968, 6183.
96. (b) Vierling, R. A. Ph.D. Thesis, Cornell University, 1962; Chem. Abstr. 1963, 58, 7838a.
97. (b) Vierling, R. A. Ph.D. Thesis, Cornell University, 1962; Chem. Abstr. 1963, 58, 7838a.
98. McDonald, R. N.; Morris, D. L.; Petty, H. E.; Hoskins, T. L. Chem. Commun. 1971, 743.
99. Sung, K.; Tidwell, T. T. J. Am. Chem. Soc. 1996, 118, 2768.
100. 4 (ref 15b), which, although stable only at low temperature, is another example of a 1,3-bisketene.
101. 2 the transoid form is 1.6 kcal/mol more stable than the cisoid form.
102. Tidwell, T. T. Acc. Chem. Res. 1990, 23, 273.
103. (a) Sung, K.; Tidwell, T. T. J. Am. Chem. Soc. 1998, 120, 3034.
104. (b) Allen, A. D.; Tidwell, T. T. J. Org. Chem. 1999, 64, 266.
105. Tidwell, T. T. Ketenes; Wiley: New York, 1995; p 581.
106. Allen, A. D.; Ma, J.; McAllister, M. A.; Tidwell, T. T.; Zhao, D.-c. J. Chem. Soc., Perkin Trans. 2 1995, 847.