1-Metalla-1,3,5-hexatrienes and related compounds

European Journal of Organic Chemistry

Volumn , Issue 1, 2000, Pages 17-31

  Aumann, Rudolf ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Alkyn es; Azahexatrienes; Carbene complexes; Chromium; Hexatrienes; Polyenes; Transmetallation; Tungsten

Indexed keywords

CARBENE; CHROMIUM DERIVATIVE; ORGANOMETALLIC COMPOUND; TUNGSTEN DERIVATIVE;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC CHEMISTRY; SHORT SURVEY; SYNTHESIS;

EID: 0033986474     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200001)2000:1<17::AID-EJOC17>3.0.CO;2-T     Document Type: Short Survey

References (108)

1. R. Aumann, H. Heinen, Chem. Ber. 1987, 120, 537.
2. [2a] K. H. Dötz, Angew. Chem. 1984, 96, 573; Angew. Chem. Int. Ed. Engl. 1984, 23, 587.
3. [2a] K. H. Dötz, Angew. Chem. 1984, 96, 573; Angew. Chem. Int. Ed. Engl. 1984, 23, 587.
4. [2b] W. D. WulfF, in: Comprehensive Organometallic Chemistry II (Eds.: E. Abel. F. G. A. Stone, G. Wilkinson), Pergamon Press, 1995, vol. 12, p. 469.
5. [2c] K. H. Dötz, R. Ehlenz, Chem. Eur. J. 1997, 3, 1751.
6. [2d] M. L. Waters, T. A. Brandvold, L. Isaacs, W. D. Wulff, Organometallics 1998, 17, 4298.
7. M. Torrent, M. Duran, M. Sola, J. Am. Chem. Soc. 1999, 121, 1309.
8. L. Knauss, E. O. Fischer, J. Organomet. Chem. 1971, 31, C71.
9. Recent reviews: -[5a] W. Beck, B. Niemer, M. Wieser, Angew. Chem. 1993, 105, 969; Angew. Chem. Int. Ed. Engl. 1993, 32, 923.
10. Recent reviews: -[5a] W. Beck, B. Niemer, M. Wieser, Angew. Chem. 1993, 105, 969; Angew. Chem. Int. Ed. Engl. 1993, 32, 923.
11. [5b] H. Lang, Angew. Chem. 1994, 106, 569; Angew. Chem. Int. Ed. Engl. 1994, 33, 547.
12. [5b] H. Lang, Angew. Chem. 1994, 106, 569; Angew. Chem. Int. Ed. Engl. 1994, 33, 547.
13. [5c] U. H. F. Bunz, Angew. Chem. 1996, 108, 1047; Angew. Chem. Int. Ed. Engl. 1996, 35, 969.
14. [5c] U. H. F. Bunz, Angew. Chem. 1996, 108, 1047; Angew. Chem. Int. Ed. Engl. 1996, 35, 969.
15. [5d] O. Briel, A. Fehn, W. Beck. J. Organomet. Chem. 1998, 578, 247.
16. [6a] R. Aumann, P. Hinterding, Chem. Ber. 1989, 122, 365.
17. [6b] R. Aumann, P. Hinterding, Chem. Ber. 1990, 123, 611.
18. [6c] R. Aumann, P. Hinterding, Chem. Ber. 1990, 123, 2047.
19. [6d] L. Lattuada, E. Licandro, A. Papagni, S. Maiorana, A. C. Villa, C. Guastini, J. Chem. Soc., Chem. Commun. 1988, 1092.
20. R. Aumann, K. Roths, M. Kößmeier, R. Fröhlich, J. Organomet. Chem. 1998, 556, 119.
21. R. Aumann, D. Vogt, R. Fröhlich, unpublished results.
22. J. Barluenga, F. Aznar, M. Fernández, Chem. Eur. J. 1997, 3, 1629.
23. R. Aumann, Chem. Ber. 1992, 125, 1141.
24. A. Geisbauer, S. Mihan, W. Beck, J. Organomet. Chem. 1995, 501, 61.
25. R. Aumann, B. Jasper, R. Fröhlich, S. Kotila, J. Organomet. Chem. 1995, 502, 137.
26. R. Aumann, H. Heinen, P. Hinterding, N. Sträter, B. Krebs, Chem. Ber. 1991, 124, 1229.
27. For related reactions see: [14a] K. H. Dötz, C. G. Kreiter, J. Organomet. Chem. 1975, 99, 309.
28. [14b] K. H. Dötz, C. G. Kreiter, Chem. Ber. 1976, 109, 2026.
29. [14c] K. H. Dötz, Chem. Ber. 1977, 110, 78.
30. [14d] H. Fischer, K. H. Dötz, Chem. Ber. 1980, 113, 193.
31. [14e] K. H. Dötz, R. Ehlenz, Chem. Eur. J. 1977, 3, 1751.
32. [14f] C. P. Casey, S. W. Polichnowsky, A. J. Shusterman, C. R. Jonas. J. Am. Chem. Soc. 1979, 101, 7282.
33. R. Aumann, B. Jasper, M. Läge, B. Krebs, Organometallics 1994, 13, 3510.
34. For a review see: R. Aumann, H. Nienaber, Adv. Organomet. Chem. 1997, 41, 161.
35. H. Fischer, T. Meisner, J. Hofmann, J. Chem. Ber. 1990, 123, 1799.
36. K. H. Dötz, C. Christoffers, P. Knochel, J. Organomet. Chem. 1995, 489, C84.
37. [19a] R. Aumann, K. Roths, M. Grehl, Synlett 1993, 669.
38. [19b] R. Aumann, M. Kößmeier, K. Roths, R. Fröhlich, Synlett 1994, 1041.
39. [19C] A. G. Meyer, R. Aumann, Synlett 1995, 1011.
40. [19d] R. Aumann, K. Roths. B. Jasper, R. Fröhlich, Organometallics 1996, 15, 1257.
41. [19e] R. Aumann, M. Kößmeier, F. Zippel, Synlett 1997, 621.
42. [19f] Z. Yu, R. Aumann, R. Fröhlich, K. Roths, J. Hecht, J. Organomet. Chem. 1997, 541, 187.
43. [19g] R. Aumann, A. G. Meyer, R. Fröhlich, Organometallics 1996, 15, 5018.
44. [19h] R. Aumann, M. Kößmeier, A. Jäntti, Synlett 1998, 1120.
45. R. Aumann, R. Fröhlich, J. Prigge, O. Meyer, Organometallics 1999, 18, 1369.
46. C. A. Merlic, E. E. Burns, D. Xu, S. Y. Chen, J. Am. Chem. Soc. 1992, 114, 8722.
47. H. H. Fox, J.-K. Lee, L. Y. Park, R. R. Schrock, Organometallics 1993, 12, 759.
48. D. Pilette, K. Ouzzine, H. Le Bozec, P. Dixneuf, Organometallics 1992, 11, 809.
49. R. Aumann, H. Heinen, M. Dartmann, B. Krebs, Chem. Ber. 1991, 124, 2343.
50. For a review see: K. L. Habermas, S. E. Denmark, T. K. Jones, Org. Reactions 1994, 45, 1.
51. For reactions of [(2-amino)alkenyl]carbene complexes with alkynes see: [26a] M. Duetsch, R. Lackmann, F. Stein, A. de Meijere, Synlett, 1991, 324.
52. [2b] F. Stein, M. Duetsch, M. Noltemeyer, A. de Meijere, Synlett 1993, 486.
53. [26c] M. Duetsch, S. Vidoni, F. Stein, F. Funke, M. Noltemeyer, A. de Meijere, J. Chem. Soc., Chem. Commun. 1994, 1679.
54. [26d] A. de Meijere, L. Wessjohann, Synlett 1990, 20.
55. [26e] B. L. Flynn, C. C. Silveira, A. de Meijere, Synlett 1995, 812.
56. [26f] F. Stein, M. Duetsch, R. Lackmann, M. Noltemeyer, A. de Meijere, Angew. Chem. 1991, 103, 1669; Angew. Chem. Int. Ed. Ensgl. 1991, 30, 1658.
57. [26f] F. Stein, M. Duetsch, R. Lackmann, M. Noltemeyer, A. de Meijere, Angew. Chem. 1991, 103, 1669; Angew. Chem. Int. Ed. Ensgl. 1991, 30, 1658.
58. [26g] M. Duetsch, F. Stein, F. Funke, E. Pohl, R. Herbst-Irmer, A. de Meijere, Chem. Ber. 1993, 126, 2535.
59. [26h] B. L. Flynn, C. C. Silveira, A. de Meijere, Synlett 1995, 1007.
60. [26i] M. Duetsch, F. Stein, A. de Meijere, Tetrahedron Lett. 1993, 34, 5875.
61. [26k] B. L. Flynn, F. Funke, M. Noltemeyer, A. de Meijere, Tetrahedron 1995, 51, 11141.
62. [26l] review: de Meijere, A. Pure Appl. Chem. 1996, 68, 61.
63. K.-H. Dötz, I. Pruskil, Chem. Ber. 1978, 111, 2059.
64. A. Yamashita, Tetrahedr. Lett. 1986, 27, 5915.
65. S. L. B. Wang, W. D. Wulff, J. Am. Chem. Soc. 1990, 112, 4550.
66. R. Aumann, A. G. Meyer, R. Fröhlich, J. Am. Chem. Soc. 1996, 118, 10861.
67. [31a] C. A. Merlic, D. Xu, J. Am. Chem. Soc. 1991, 113, 7418.
68. [31b] C. A. Merlic, D. Xu, B. G. Gladstone, J. Org. Chem. 1993, 58, 538.
69. For photo-induced insertion of carbon monoxide into the M = C bond of aminocarbene complexes see: [32a] L. S. Hegedus, G. de Weck, S. D'Andrea, J. Am. Chem. Soc. 1988, 110, 2122.
70. [32b] L. S. Hegedus, M. A. Schwindt, S. De Lombaert, R. Imwinkelried, J. Am. Chem. Soc. 1990, 112, 2264.
71. [32c] B. C. Söderberg, L. S. Hegedus, M. A. Sierra, J. Am. Chem. Soc. 1990, 112, 4364.
72. For review on reactions of ketene imine complexes, generated from carbene complexes by addition of isocyanides, see: [33a] R. Aumann, Angew. Chem. 1988, 100, 1512; Angew. Chem. Int. Ed. Engl. 1988, 100, 1456.
73. For review on reactions of ketene imine complexes, generated from carbene complexes by addition of isocyanides, see: [33a] R. Aumann, Angew. Chem. 1988, 100, 1512; Angew. Chem. Int. Ed. Engl. 1988, 100, 1456.
74. [33b] R. Aumann, in: Organometallics in Organic Synthesis: Aspects of a Modern Interdisciplinary Field (Eds.: A. de Meijere, H. tom Dieck), Springer-Verlag, Berlin, Heidelberg, 1987, pp. 69-83.
75. R. Aumann, Chem. Ber. 1993, 126, 1867.
76. C. A. Merlic, E. E. Burns, Tetrahedron Lett. 1993, 34, 5401.
77. [36a] R. Aumann, Chem. Ber. 1992, 125, 1141.
78. [36b] R. Aumann, B. Jasper, R. Fröhlich, Organometallics 1995, 14, 231.
79. [37a] R. Aumann, H. Heinen, C. Krüger, Y.-H. Tsay, Chem. Ber. 1986, 119, 3141.
80. [37b] R. Aumann, H. Heinen, Chem. Ber. 1986, 119, 3801.
81. N. Hoa Tran Huy, F. Mathey, L. Ricard, Tetr. Lett. 1988, 29, 4289.
82. C. K. Murray, D. Y. Yang, W. D. Wulff, J. Am. Chem. Soc. 1990, 112, 5660.
83. [40a K.-H Dötz, R. Noack, K. Harms, Tetrahedron 1990, 46, 1235.
84. [40b] F. Camps, J. M. Moretó, S. Ricart, J. M. Viñas, Angew. Chem. 1991, 103, 1540; Angew. Chem. Int. Ed. Engl. 1991, 30, 1470.
85. [40b] F. Camps, J. M. Moretó, S. Ricart, J. M. Viñas, Angew. Chem. 1991, 103, 1540; Angew. Chem. Int. Ed. Engl. 1991, 30, 1470.
86. [40c] L. Jordi, A. Segundo, F. Camps, S. Ricart, J. M. Moretó, Organometallics 1993, 12, 3795.
87. R. Aumann, M. Kößmeier, Eur. J. Org. Chem., in preparation.
88. For somewhat related α-cyclizations of tertiary amines involving π systems see, e.g.: B. DeBoeck, S. J. Z. Janousek, H. G. Viehe, Tetrahedron 1994, 50, 7075.
89. R. Aumann, H. Wu, R. Fröhlich, B. Wibbeling, Eur. J. Org. Chem. submitted.
90. R. Aumann, B. Hildmann, R. Fröhlich, Organometallics 1998, 17, 1197.
91. A protonation/deprotonation of the (4-aminocyclobutenyl)carbene unit would in principal lead to the same result.
92. R. Aumann, R. Fröhlich, S. Kotila, Organometallics 1996, 15, 4842.
93. R. Aumann, B. Trentmann, C. Krüger, F. Lutz, Chem. Ber. 1991, 124, 2595.
94. R. Aumann, H. Heinen, C. Krüger, P. Betz, Chem. Ber. 1990, 123, 605.
95. R. Aumann, Z. Yu, R. Fröhlich, Organometallics 1998, 17, 2897.
96. R. Aumann, B. Jasper, R. Goddard, C. Krüger, Chem. Ber. 1994, 127, 717.
97. R. Aumann, K. Roths, R. Fröhlich, Organometallics 1997, 16, 5893.
98. For related studies on the addition of enol derivatives to (1-alkynyl)carbene complexes see: W. D. Wulff, K. L. Faron, J. Su, J. P. Springer, A. L. Rheingold, J. Chem. Soc., Perkin Trans. 1 1999, 197.
99. R. Aumann, I. Göttker-Schnetmann, Eur. J. Org. Chem. 1999, 2545.
100. M. A. Sierra, M. J. Mancheño, E. Sáez, J. C. del Amo, J. Am. Chem. Soc. 1998, 120, 6812.
101. [55a] R. Aumann, H. Heinen, J. Organomet. Chem. 1990, 389, Cl.
102. [55b] R. Aumann, H. Heinen, J. Organomet. Chem. 1990. 391, C7.
103. [55c] R. Aumann, H. Heinen, M. Dartmann, B. Krebs, Chem. Ber. 1991, 124, 2587.
104. V. Dragisich, C. K. Murray, B. P. Warner, W. D. Wulff, D. C. Yang, J. Am. Chem. Soc. 1990, 112, 1251.
105. F. Funke, M. Duetsch, F. Stein, M. Noltemeyer. A. de Meijere, Chem. Ber. 1994, 127, 911.
106. R. Aumann, R. Fröhlich, F. Zippel, Organometallics 1997, 16, 2571.
107. R. Aumann, B. Jasper, R. Fröhlich, F. Zippel, Organometallics 1995, 14, 3167.
108. R. Aumann, Z. Yu, R. Fröhlich, F. Zippel, Eur. J. Inorg. Chem. 1998, 1623.