Cyclopropanes from Reactions of Transition-Metal-Carbene Complexes with Olefins

Chemical Reviews

Volumn 87, Issue 2, 1987, Pages 411-432

  Brookhart, Maurice ^a   Studabaker, William B ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845281753     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr00078a008     Document Type: Article

References (93)

1. Fischer, E.O.; Maasbol, A. Angew. Chem. 1964, 76, 645.
2. Brown, F. J. Prog. Inorg. Chem. 1980, 27, 1.
3. Casey, C.P. In Reactive Intermediates; Jones, M., Moss, R.A., Eds.; Wiley: New York, 1981; Vol. 2, 135.
4. Dotz, K.H.; Fischer, H.; Hoffmann, P.; Kreissl, F.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield Beach, FL, 1983.
5. Dotz, K. press H. Angew. Chem., Int. Ed. Eng. 1984, 23, 587.
6. Ivin, J.J. Olefin Metathesis; Academic Press: New York, 1983.
7. Anderson, R.B. The Fischer-Tropsch Synthesis; Academic Press: New York, 1984; 174–228.
8. Hayes, J.C.; Jernakoff, P.; Miller, G.A.; Cooper, N.J. Pure Appl. Chem. 1984, 56, 25.
9. Schrock, R.R. Science 1983, 219, 13.
10. Schrock, R.R. Acc. Chem. Res. 1979, 12, 98.
11. Herrmann, W.A. J. Organomet. Chem. 1983, 250, 319.
12. Doyle, M.I. Chem. Rev., in (Catalytic applications).
13. Ho, T.H.; Katz, T.J.J. Mol, Cat. 1985, 28, 359.
14. Clark, T.C.; Yannoni, C.S.; Katz, T.J. J. Am. Chem. Soc. 1983, 105, 7787.
15. Katz, T.J.; Sivavec, T.M. J. Am. Chem. Soc. 1985, 107, 737.
16. Semmelhack, M.F.; Tamura, R.; Schantter, W.; Springer, J. J. Am. Chem. Soc. 1984, 106, 5363.
17. Semmelhack, M.F.; Tamura, R. J. Am. Chem. Soc. 1983, 105, 4099.
18. Semmelhack, M.F.; Tamura, R. J. Am. Chem. Soc. 1983, 105, 6750.
19. Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823.
20. Wulff, W.D.; Tang, P.C.; Chan, K.S.; McCallum, J.S.; Yang, D.C.; Gilbertson, S.R. Tetrahedron 1985, 41, 5813.
21. Wulff, W.D.; Kaesler, R.W.; Peterson, G.A.; Tang, P.C. Tetrahedron. 1985, 107, 1060.
22. Wulff, W.D.; Kaesler, R.W. Organometallics 1985, 4, 1461.
23. Dotz, K.H.; Popall, M. Tetrahedron 1985, 41, 5797.
24. Wulff, W.D.; Gilbertson, S.R. J. Am. Chem. Soc. 1985, 107, 503.
25. Fischer, H.; Schmid, J.; Markel, R. J. Chem. Soc., Chem. Commun. 1985, 572.
26. Hegedus, L.S.; Schultze, L.M.; Toro, J.; Yijum, C. Tetrahedron 1985, 41, 5833.
27. Grubbs, R.H. Prog. Inorg. Chem. 1978, 24, 1.
28. Jolly, P.W.; Pettit, R. J. Am. Chem. Soc. 1955, 88, 5044.
29. Riley, P.E.; Capshew, C.E.; Pettit, R.; Davis, R.E. Inorg. Chem. 1978, 17, 408.
30. Markham, J.; Tolman, W.; Menard, K.; Cutler, A. J. Organomet. Chem. 1985, 294, 45.
31. Guerchais, V.; Astruc, D. J. Chem. Soc., Chem. Commun. 1985, 835.
32. Guerchais, V.; Lapinte, C. J. Chem. Soc., Chem. Commun. 1986, 894.
33. Dotz, K. Fischer, H.; Fischer, E.O. Chem. Ber. 1970, 103, 1273.
34. Chem. Ber. 1972, 105, 1356.
35. Dotz, K.H.; Fischer, E.O. Chem. Ber. 1972, 105, 3966.
36. Dorrer, B.; Fischer, E.O.; Kalbfus, W. J. Organomet. Chem. 1974, 81, 20.
37. Cooke, M.D.; Fischer, E.O. J. Organomet. Chem. 1973, 56, 279.
38. Burkhardt, T.J.; Casey, C.P. J. Am. Chem. Soc. 1973, 95, 5833.
39. Casey, C.P.; Tuinstra, H.E.; Saeman, M.C. J. Am. Chem. Soc. 1976, 98, 608.
40. Casey, C.P.; Cesa, M.C. Organometallics 1982, 1, 87.
41. Casey, C.P.; Polichnowski, S.W. J. Am. Chem. Soc. 1977, 99, 6097.
42. Casey, C.P.; Polichnowski, S.W.; Shusterman, A.J.; Jones, C.R. J. Am. Chem. Soc. 1979, 101, 7282.
43. Fischer, H.; Zeuner, S.; Ackermann, K. J. Chem. Soc., Chem. Commun. 1984, 684, (16)
44. Brookhart, M.; Nelson, G.O. J. Am. Chem. Soc. 1977, 99, 6099.
45. Brookhart, M.; Humphrey, M.B.; Kratzer, H.J.; Nelson, G.O. J. Am. Chem. Soc. 1980, 102, 7802.
46. Green, M.L.H.; Mitchard, L.C.; Swanwick, M.G. J. Chem. Soc. A 1971, 794.
47. Davison, A.; Reger, D. J. Am. Chem. Soc. 1972, 94, 9237.
48. Baird, G.J.; Davies, S.G.; Jones, R.H.; Prout, K.; Warner, P. J. Chem. Soc., Chem. Commun. 1984, 745.
49. Baird, G.J.; Davies, S.G.; Maberly, T.R. Organometallics 1984, 3, 1764.
50. Felkin, H.; Meunier, B.; Pascard, C.; Prange, T. J. Organomet. Chem. 1977, 135, 361.
51. Cutler, A.R. J. Organomet. Chem. 1981, 213, 31.
52. Bodnar, T.; Brookhart, M.; Tucker, J.R.; Husk, G.R. J. Am. Chem. Soc. 1981, 103, 979.
53. Brookhart, M.; Tucker, J.R.; Husk, G.R. J. Am. Chem. Soc. 1983, 105, 258.
54. Casey, C.P.; Miles, W.H.; Tukada, H.; O’Connor, J.M. J. Am. Chem. Soc. 1982, 104, 3761.
55. Casey, C.P.; Miles, W.H. Organometallics 1984, 3, 808.
56. Casey, C.P.; Miles, W.H.; Tukada, H. J. Am. Chem. Soc. 1985, 107, 2924.
57. Casey, C.P.; Miles, W.H. J. Organomet. Chem. 1984, 254, 333.
58. Kegley, S.E.; Brookhart, M.; Husk, G.R. Organometallics 1982, 1, 760.
59. Brandt, S.; Helquist, P. J. Am. Chem. Soc. 1979, 101, 6473.
60. Wender, P.A.; Eck, S.L. Tetrahedron Lett. 1982, 23, 1871.
61. Kremer, K.A.M.; Helquist, P.; Kerber, R.C. J. Am. Chem. Soc. 1981, 103, 1862.
62. Kremer, K.A.M.; Helquist, P. J. Organomet. Chem. 1985, 285, 231.
63. Davidson, J.G.; Barefield, E.K.; Van Derveer, D.G. Organometallics 1985, 4, 1178.
64. Barefield, E.K.; McCarten, P.; Hillhouse, M.C. Organometallics. 1985, 4, 1682.
65. Kremer, K.A.M.; Kuo, G.H.; O’Connor, E.J.; Helquist, P.; Kerber, R.C. J. Am. Chem. Soc. 1982, 104, 6119.
66. Iyer, R.S.; Kuo, G.H.; Helquist, P. J. Org. Chem. 1985, 50, 5898.
67. Brookhart, M.; Timmers, D.; Tucker, J.R.; Williams, G.D.; Husk, G.R. J. Am. Chem. Soc. 1983, 105, 6721.
68. Davison, A.; Krussell, W.C.; Michaelson, R.C. J. Organomet. Chem. 1974, 72, 7.
69. Brookhart, M.; Tucker, J.R.; Flood, T.C.; Jensen, J. J. Am. Chem. Soc. 1980, 102, 1203.
70. Flood, T.C.; DiSanti, F.J.; Miles, D.L. Inorg. Chem. 1976, 15, 1910.
71. Doyle, M.P.; Griffin, J.H.; Bagheri, V.; Dorow, R.L. Organometallics 1984, 3, 56.
72. Brookhart, M.; Kegley, S.E.; Husk, G.R. Organometallics 650, 1984.
73. Kuo, G.H.; Helquist, P.; Kerber, R.C. Organometallics 1984, 3, 806.
74. Brookhart, M.; Studabaker, W.B.; Husk, G.R. Organometallics 1985, 4, 943.
75. Casey, C.P.; Shusterman, A.J. J. Mol. Catal. 1980, 8, 1.
76. Casey, C.P.; Shusterman, A.J. Organometallics 1985, 4, 736.
77. Casey, C.P.; Shusterman, A.J.; Vollendorf, N.W.; Haller, K.J. J. Am. Chem. Soc. 1982, 104, 2417.
78. Casey, C.P.; Vollendorf, N.W.; Haller, K.J. J. Am. Chem. Soc. 1984, 106, 375.
79. Toledano, C.A.; Rudler, H.; Karan, J.C.; Jeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574.
80. McGeary, M.J.; Tonker, T.L.; Templeton, J.L. Organometallics 1985, 4, 2102.
81. Schilling, B.E.R.; Hoffmann, R.; Lichtenberger, D.L. J. Am. Chem. Soc. 1979, 101, 585.
82. Kostic, N.M.; Fenske, R.F. J. Am. Chem. Soc. 1982, 104, 3879.
83. Kostic, N.M.; Fenske, R.F. Organometallics 1982, 1, 974.
84. Crespi, A.M.; Shriver, D.F. Organometallics 1985, 4, 1830.
85. Knors, C.J.; Kuo, G.H.; Helquist, P. Abstracts of Papers 191st National Meeting of the American Chemical Society New York, NY; American Chemical Society: Washington, DC; ORGN 126.
86. Kiel, W.A.; Lin, G.Y.; Bodner, G.S.; Gladysz, J.A. J. Am. Chem. Soc. 1983, 105, 4958.
87. Kiel, W.A.; Lin, G.Y.; Constable, A.G.; McCormick, F.B.; Strouse, C.E.; Eisenstein, O.; Gladysz, J.A. J. Am. Chem. Soc. 1982, 104, 4865.
88. Dominey, E.W.G.; Brookhart, M. Presented at the Eleventh International Conference on Organometallic Chemistry, Callaway Gardens, GA, October 10–14, 1983.
89. Davis, D.D.; Johnson, H.T. J. Am. Chem. Soc. 1974, 96, 7576.
90. McWilliam, D.C.; Balasubramanian, T.R.; Kuivila, H.G. J. Am. Chem. Soc. 1978, 100, 6407.
91. Dotz, K.H.; Pruskil, I. Chem. Ber. 1981, 114, 1980.
92. Stevens, A.E.; Beauchamp, J.L. J. Am. Chem. Soc. 1978, 100, 2584.
93. Weiss, K.; Hoffmann, K. J. Organomet. Chem. 1983, 255, 24.