Carbene complexes of chromium bearing nitrogen substituents

Synlett

Volumn 1991, Issue 6, 1991, Pages 381-390

  Grotjahn, D B ^a,b   Dotz K H ^a,b  

^a ARIZONA STATE UNIVERSITY   (United States)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84985734564     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1991-20736     Document Type: Article

References (83)

1. Fischer, E.O.; Maasbol, A. Angew. Chem. 1964, 76, 645
2. Angew. Chem., Int. Ed. Engl. 1964, 3, 580.
3. Dotz, K.H.; Fischer, H.; Hofmann, P.; Kreissl, F.; Schubert, U.; Weiss, K.; Transition Metal Carbene Complexes; Verlag Chemie: Weinheim, 1983.
4. Dotz, K.H. Angew. Chem. 1984,86, 573
5. Angew. Chem. Int. Ed. Engl. 1984, 23, 587.
6. Wulff, W.D. In Advances in Metal-Organic Chemistry; Liebes-kind, L.S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1.
7. Klabunde, U., Experimental Station, Dupont, Wilmington, Delaware, USA; Connor, J. A., University of Kent, Canterbury, England; personal communications.
8. Grotjahn, D.B., unpubtished observations.
9. Klabunde, U.; Fischer, E.O. J. Am. Chem. Soc. 1967, 89, 7141.
10. Baikie, P.E.; Fischer, E.O.; Mills, O.S. J. Chem. Soc, Chem. Common. 1967,1199.
11. Connor, J.A.; Fischer, E.O. J. Chem. Soc, Chem. Common. Ibid. 1967,1024
12. Connor, J. A.; Fischer, E.O. J. Chem. Soc. A 1969, 578.
13. Dotz, K.H.; Schafer, X; Harms, K. Angew. Chem. 1990 102, 188
14. Angew. Chem., Int. Ed. Engl. 1990, 29,176.
15. Hoffmann, R. Angew. Chem. 1982, 94, 725
16. Angew. Chem., Int. Ed. Engl. 1982,21, 711.
17. Stone, F.G.A., Angew. Chem., Int. Ed. Engl. Ibid. 1984, 96, 85; 1984, 23, 89.
18. For recent examples: Hegedus, L.S.; Schultze, L.M.; Montgomery, J. Organometallics 1989, 8, 2189 and references therein.
19. Alvarez, C; Parlier, A.; Rudler, H.; Yefsah, R.; Daran, J.C.; Knobler, C. Organometallics 1989,8, 2253.
20. Casey, CP.; Hornung, N.L.; Vollendorf, N.W. /. Organomet. Chem. 1986, 303, 375.
21. Audouin, M.; Blandinieres, S.; Parlier, A.; Rudler, H. /. Chem. Soc, Chem. Common. 1990, 23.
22. Hegedus, L.S.; Schwindt, M.A.; DeLombaert, S.; Imwinkel-ricd, R. /. Am. Chem. Soc 1990,112, 2264.
23. Wulff, W.D.; Anderson, B.A.; Toole, A.J. /. Am. Chem. Soc 1989, 111, 5485.
24. Montgomery, J.; Wieber, G.M.; Hegedus, L.S. J. Am. Chem. Soc. 1990, 112, 6255.
25. Schwindt, M.A.; Lejon, T.; Hegedus, L.S. Organometallics 1990, 9, 2814 and references therein.
26. Dotz, K.H. Angew. Chem. WIS, 87, 672
27. Angew. Chem., Int. Ed. Engl. 1975,14, 644
28. Dotz, K.H.; Dietz, R. Chem. Ber. 1977, 110, 1555.
29. Wulff, W.D.; Tang, P.-C; McCallum, J.S. J. Am. Chem. Soc. 1981, 103, 7677. :i7)
30. Dotz, K.H.; Pruskil, I. Chem. Ber. 1978, ///, 2059.
31. Yamashita, A. Tetrahedron Lett. 1986,27, 5915.
32. Fischer, H.; Muhlemeier, J.; Markl, R.; Dotz, K.H. Chem. Ber. 1982,115,1355.
33. Dotz, K.H.; Erben, H.-G.; Harms, K. J. Chem. Soc. Chem. Commun. 1989, 692.
34. Casey, CP.; Shusterman, A.J.; Vollendorf, N.W.; Haller, K.J. J. Am. Chem. Soc 1982,104, 2417.
35. Sakano, K.; Ishimaru, K.; Nakamura, S. J. Antibiot. 1980,33, 683.
36. Sakano, K.; Nakamura, S. J. Antibiot. Ibid. 1980,33,961.
37. Kaneda, M.; Sakano, K.; Nakamura, S.; Kushi, Y.; litaka, Y. Heterocycles 1981,15,993.
38. Knolker, H.-J.; Bauermeister, M.; Blaser, D.; Boesc. R.; Pannek, J.-B. Angew. Chem. 1989, 101, 227
39. Angew. Chem., Int. Ed. Engl. 1989, 28, 223.
40. Moody, C.J.; Shah, P. /. Chem. Soc. Perkin TYans. I 1989. 2463.
41. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
42. Austin, W. B.; Bilow, N.; Kelleghan, W. J.; Lau, K.S. Y. J. Org. Chem. 1981,46, 2280.
43. Castro, C.E.; Gaughan, E.J.; Owsley, D.C /. Org. Chem. 1966, 31, 4071.
44. Fujiwara, J.; Fukutani, Y.; Sano, H.; Marnoka, K.; Yama-moto, H. /. Am. Chem. Soc. 1983,105, 7177.
45. Taylor, E.C.; Katz, A.H.; Salgado-Zagora, H.; McKillop, A. Tetrahedron Lett. 1985, 26, 5963.
46. Larock, R.C; Harrison, L.W. J. Am. Chem. Soc 1984,106, 4218.
47. Sakamoto, X; Kondo, Y.; Yamanaka, H. Heterocycles 1986, 24, 31.
48. Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 2581.
49. Muchowski, J.M.; Venuti, M.C. /. Org. Chem. 1980,45,4798.
50. Hofle, G.; Steglich, W.; Vorbruggen, H. Angew. Chem. 1978, 90, 602
51. Angew. Chem., Int. Ed. Engl. 1978, 17. 569.
52. Wender, P.A.; White, A.W. Tetrahedron 1983, 39, 3767.
53. Connell, R.D.; Helquist, P.; Akermark, B. J. Org. Cltem. 1989,54, 3359.
54. Olah, G.A.; Narang, S.C.; Balaram Gupta. B.G.; Malhotra, R. /. Org. Chem. 1979, 44,1247.
55. Macomber, D.W.; Madhukar, P.; Rogers, R.D. Organometallics 1989, 8, 1275.
56. In a separate experiment, 44 was dcmetallated in rcfluxing acetonitrile to 43 completely within 5 minutes. Xhus, in acetonitrile as cyclization solvent the metal may be lost either from 33 or from complex 44.
57. Traylor, T.G.; Goldberg, M.J. J. Am. Chem. Soc. 1987.109, 3968.
58. Traylor, T.G.; Stewart, K.J.; Goldberg, M.J. Organometallics 1986, 5, 2062.
59. Semmelhack, M.F.; Bozcll, J.J. Tetrahedron Lett. 1982, 23, 2931.
60. Semmelhack, M.F.; Bozell, J. J.; Keller, L.; Sato. X; Spiess, E.J.; Wulff, W.D.; Zask, A. Tetrahedron 1985, 41. 5803.
61. Wulff, W.D.; McCallum, J.S.; Kunng, F.-A. /. Am. Chem. Soc. 1988,110, 7419.
62. Hoye, T.R.; Rehberg, G.M. Organometallics 1989, 8, 2070.
63. Hegedus, L.S.; Miller, D.B., Jr. J. Org. Chem. 1989,54,1241.
64. Denise, B.; Goumont, R.; Parlier, A.; Rudler, H.; Daran, J.C.; Vaissermann, J. /. Chem. Soc, Chem. Commun. 1990. 1238.
65. Parlier, A.; Ycfsah, R.; Rudler, M.; Rudler, H.; Daran, J.C.; Vaissermann, J. /. Organomet. Chem. 1990,381,191.
66. Rudler, H.; Parlier, A.; Yefsah, R.; Denise. B.; Daran, J.C.; Vaissermann, J.; Knobler, C. J. Organomet. Chem. 1988,358. 245.
67. Hegedus, L.S.; Imwinkelried, R.; Alarid-Sargent, M.; Dvorak, D.; Satoh, Y. /. Am. Chem. Soc. 1990, 112, 1109.
68. Wulff, W.D.; Yang, D.C. J. Am. Chem. Soc. 1983,105, 6726
69. Chan, K.S.; Wulff, W.D. J. Am. Chem. Soc. Ibid. 1986. 108. 5229.
70. Wulff, W.D.; Banta, W.E.; Kaesler, R.W.; Lankford, P.J.; MiUer, R.A.; Murray, C.K.; Yang, CD. J. Am. Chem. Soc. Ibid.1990,112,3642.
71. Dotz, K.H.; Noack, R.; Harms, K.; Mfiller, G. Tetrahedron 1990,46, 1235.
72. Parker, K. A.; Adamchuk, M. R. Tetrahedron Lett. 1978,1689.
73. Winter, C.H.; Veal, W.R.; Garner, CM.; Arif, A.M.; Gladysz, J.A. /. Am. Chem. Soc. 1989, 111, 4766 and references therein.
74. Dotz, K.H.; Grotjahn, D.; Harms, K. /. Organomet. Chem. 1989, 375, C47.
75. Aumann, R.; Althaus, S.; Kruger, C; Betz, P. Chem. Ber. 1989, 122, 357.
76. Wulff, W.D.; Dragisich, V.; Huffman, J.C; Kaesler, R.W.; Yang, D.C. Organometallics 1989,8, 2196 and 1990, 9, 3006.
77. Dragisich, V.; Murray, C.K.; Warner, B.P.; Wulff, W.D.; Yang, D.C. J. Am. Chem. Soc. 1990,112,1251.
78. Dragisich, V.; Wulff, W.D.; Hoogstccn, K. Organometallics 1990, 9, 2867.
79. Grehn, L.; Gunnarsson, K.; Ragnarsson, U. Acta Chem. Scand. Ser. B, 1986, B40, 745.
80. Dotz, K.H.; Grotjahn, D.B.; Harms, K. Angew. Chem. 1989, 101,1425
81. Angew. Chem. Int. Ed. Engl. 1989,28,1384.
82. Grotjahn, D.B.; Kroll, E; Schafer, T.; Harms, K.; Dotz, K.H.; unpublished results.
83. Casey, CP.; Cesa, M.C Organometallics 1982, /, 87.