Strikingly different reactivity patterns of fischer alkoxycarbene and thiocarbene complexes in experimental and theoretical studies

Organometallics

Volumn 26, Issue 20, 2007, Pages 4983-4996

  Karatas, Betül ^a   Hyla Kryspin, Isabella ^a   Aumann, Rudolf ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMIUM COMPOUNDS; COMPLEXATION; CYCLIZATION; POTENTIAL ENERGY SURFACES; REACTION KINETICS; TUNGSTEN COMPOUNDS;

FISCHER ALKOXYCARBENE; PYRROLES; REACTION CHANNELS; THIOCARBENE COMPLEXES;

OLEFINS;

EID: 34948857577     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700391t     Document Type: Article

References (85)

1. Fischer, E. O.; Maasböl, A. Angew. Chem. 1964, 76, 645;
2. Angew. Chem., Int. Ed. Engl. 1964, 3, 580.
3. (a) Dötz, K. H. Angew. Chem. 1984, 96, 573-594;
4. Angew. Chem., Int. Ed. Engl. 1984, 23, 587-608.
5. (b) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M. Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 5, pp 1065-1113.
6. (c) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, pp 469-547.
7. (d) Doyle, M. D. In Comprehensive Organometallic Chemistry 11; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, pp 387-420.
8. (e) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1.
9. (f) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271-288.
10. (g) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596.
11. (h) de Meijere, A. Schirmer, H. Duetsch, M. Angew. Chem. 2000, 112, 4124-4162;
12. Angew. Chem., Int. Ed. 2000, 39, 3964-4002.
13. (i) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689-1706.
14. (j) Wu, Y.-T.; Kurahashi, T.; de Meijere, A. J. Organomet. Chem. 2005, 690, 5900-5911.
15. (k) Barluenga, J.; Rodriguez, F.; Fananas, J. F.; Florez, J. Top. Organomet. Chem. 2004, 13, 59-121.
16. (l) Gomez-Gallego, M.; Mancheno, M. J.; Sierra, M. A. Acc Chem. Res. 2005, 38, 44-53.
17. (m) Barluenga, J. Pure Appl. Chem. 2002, 74, 1317-1325.
18. (n) Rudler, H.; Parlier, A. Trends Organomet. Chem. 1999, 3, 113-164.
19. (o) Schwindt, M. A.; Miller, J. R.; Hegedus, L. S. J. Organomet. Chem. 1991, 413, 143-153.
20. (p) Grotjahn, D. B. Dötz, K. H. Synlett 1991, 6, 381-390.
21. (q) Hegedus, L. S. Pure Appl. Chem. 1990, 62, 691-698.
22. (a) Linford, L.; Raubenheimer, H. G. Adv. Organomet. Chem. 1991, 32, 1-119.
23. (b) Linford, L.; Raubenheimer. H. G. Comments Inorg. Chem. 1991, 12, 113-138.
24. Fischer, E. O.; Kreiter, C. G.; Müller, J.; Leupold, M. Chem. Ber. 1972, 105, 150-161.
25. (a) Raubenheimer, H. G.; Kruger, G. J.; Lombard, A.; Linford, L.; Viljoen, J. C. Organometallics 1985, 4, 275-284.
26. (b) Raubenheimer, H. G.; Kruger, G. J.; Marais, C. F.; Otte, R.; Hattingh, J. T. Z. Organometallics 1988, 7, 1853-1858.
27. (c) Raubenheimer, H. G.; Kruger, G. J.; Viljoen, H. W. J. Chem. Soc., Dalton Trans. 1985, 1963-1966.
28. (a) Aumann, R.; Schröder, J. J. Organomet. Chem. 1989, 378, 57-65.
29. (b) Aumann, R.; Schröder, J. Chem. Ber. 1990, 123, 2053-2058.
30. (c) Aumann, R.; Schröder, J.; Krüger, C.; Goddard, R. J. Organomet. Chem. 1989, 378, 185-197.
31. (d) Aumann, R.; Schröder, J.; Heinen, H. Chem. Ber. 1990, 123, 1369-1374.
32. Dötz, K. H.; Leue, V. J. Organomet. Chem. 1991, 407, 337-351.
33. Kreissl, F. R.; Fischer, E. O.; Kreiter, C. G.; Fischer, H. Chem. Ber. 1973, 106, 1262-1276.
34. Fischer, E. O.; Kreis, G. Chem. Ber. 1973, 106, 2310-2314.
35. (a) Raubenheimer, H. G.; Kruger, G. J.; Marais, C. F.; Otte, R.; Scott, F. S. Afr. J. Chem. 1987, 40, 207-208.
36. (b) Raubenheimer, H. G.; Kruger, G. J.; Linford, L.; Marais, C. F.; Otte, R.; Hattingh, J. T. Z.; Lombard, A. J. Chem. Soc., Dalton Trans. 1989, 1565-1577.
37. (c) Raubenheimer, H. G.; Kruger, G. J.; Scott, F.; Otte, R. Organometallics 1987, 6, 1789-1795.
38. (a) Pickering, R. A.; Jacobson, R. A.; Angelici, R. J. J. Am. Chem. Soc. 1981, 103, 817-821.
39. (b) Pickering, R. A.; Angelici, R. J. lnorg. Chem. 1981, 20, 2977-2983.
40. (a) Kim, H. P.; Kim, S.; Jacobson, R. A.; Angelici, R. J. Organometallics 1986, 5, 2481-2488.
41. (b) Kim, H. P.; Angelici, R. J. Organometallics 1986, 5, 2489-2496.
42. (c) Ullrich, N.; Keller, H.; Stegmair, C.; Kreissl, F. R. J. Organomet. Chem. 1989, 378, C19-C22.
43. (d) Schutt, W.; Herdtweck, E.; Kreissl, F. R. J. Organomet. Chem. 1993, 456, C15-C17.
44. (e) Ogric, C.; Schütt, W.; Lehotkay, T.; Herdtweck, E.; Kreissl, F. R. Z. Naturforsch., B: Chem. Sci. 1995, 50, 1839-1844.
45. (f) Ogric, C.; Lehotkay, T.; Wurst, K.; Jaitner, P.; Kreissl, F. R. J. Organomet. Chem. 1997, 541, 71-75.
46. (g) Ullrich, N.; Stegmair, C.; Keller, H.; Herdtweck, E.; Kreissl, F. R. Z. Naturforsch. B: Chem. Sci. 1990, 45, 921-925.
47. Ostermeier, J.; Schutt, W.; Stegmair, C. M.; Ullrich, N.; Kreissl, F. R. J. Organomet. Chem. 1994, 464, 77-81.
48. (a) Doyle, R. A.; Angelici, R. J. Organometallics 1989, 8, 2207-2214.
49. (b) Doyle, R. A.; Angelici, R. J. J. Organomet. Chem. 1989, 375, 73-84.
50. Kreissl, F. R.; Müller, F. X.; Wilkinson, D. L.; Müller, G. Chem. Ber. 1989, 122, 289-290.
51. Ogric, C.; Ostermeier, J.; Heckel, M.; Hiller, W.; Kreissl, F. R. Inorg. Chim. Acta 1994, 222, 77-84.
52. Nitsche, F.; Aumann, R.; Fröhlich, R. J. Organomet. Chem. 2007, 692, 2971-2989.
53. (a) Aumann, R.; Hinterding, P. Chem. Ber. 1990, 123, 2047-2051.
54. (b) Aumann, R.; Fu, X.; Vogt, D.; Fröhlich, R.; Kataeva, O. Organometallics 2002, 21, 2736-2742.
55. (c) Aumann, R.; Hinterding, P. Chem. Ber. 1990, 123, 611-620.
56. Ünaldi, S.; Aumann, R.; Fröhlich, R. Chem.-Eur. J. 2003, 9, 3300-3309.
57. Nerdel, F.; Weyerstahl, P.; Dahl, R. Liebigs Ann. Chem. 1968, 716, 127-134.
58. (a) Aumann, R.; Heinen, H.; Krüger, C.; Betz, P. Chem. Ber. 1990, 123, 599-604.
59. (b) Aumann, R.; Heinen, H.; Goddard, R.; Krüger, C. Chem. Ber. 1991, 124, 2587-2593.
60. (c) Aumann, R.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 2571-2580.
61. (a) Aumann, R.; Runge, M. Chem. Ber. 1992, 125, 259-264.
62. (b) Aumann, R.; Läge, M.; Krebs, B. Chem. Ber. 1994, 127, 731-738.
63. (c) Aumann, R.; Fischer, E. O. Angew. Chem. 1967, 79, 900-901;
64. Angew. Chem., Int. Ed. Engl. 1967, 6, 879-880.
65. Axenrod, T.; Milne, G. W. A. Tetrahedron 1968, 24, 5775-5783.
66. 2-9e.
67. (a) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
68. (b) Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory; Wiley-VCH: Weinheim, 2000.
69. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
70. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
71. (a) Dunlap, B. I. J. Chem. Phys. 1983. 78, 3140-3142.
72. (b) Eichkorn, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 242, 652-660.
73. (c) Treutler, O.; Ahlrichs, R. J. Chem. Phys. 1995, 102, 346-354.
74. (d) Dunlap, B. I. J. Mol. Struct. (THEOCHEM) 2000, 529, 37-40.
75. (e) Dunlap, B. I. Phys. Chem. Chem. Phys. 2000, 2, 2113-2116.
76. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Oritz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin. R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzales, C.; Pople, J. A. Gaussian 03 Rev. COI; Gaussian, Inc.: Wallingford, CT, 2004.
77. (a) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284-298.
78. (b) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
79. Dunning, T. H., Jr.; Hay, P. J. In Modem Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; Vol. 3, pp 1-28.
80. Andrae, D.; Häussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123-141.
81. The basis sets are available from the TURBOMOLE homepage http://www.turbomole.com via the FTP Server Button in the subdirectory basen.
82. (a) Peng, C.; Schlegel, H. B. Isr. J. Chem. 1994, 33, 449-454.
83. (b) Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49-56.
84. (a) Del Bene, J. E. In Molecular Structure and Energetics: Bonding Models; Liebmann, J. F., Greenberg, A., Eds.; VCH: Deerfield Beach, FL, 1986; Vol. 1, pp 319-348.
85. (b) Pitzer, K. S. Quantum Chemistry; Prentice Hall: Englewood Cliffs, NJ, 1961.