Synthesis and characterization of highly fluorinated tungsten(II) metallacyclopropene complexes. Kinetics and mechanism of an unprecedented η2-vinyl isomerization

Organometallics

Volumn 15, Issue 6, 1996, Pages 1545-1564

  Kiplinger, Jaqueline L ^a   Richmond, Thomas G ^a   Arif, Atta M ^a   Dücker Benfer, Carlos ^b   Van Eldik, Rudi ^b  

^a UNIVERSITY OF UTAH   (United States)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007869481     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9509251     Document Type: Article

References (103)

1. Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373-431.
2. Kiplinger, J. L.; King, M. A.; Arif, A. M.; Richmond, T. G. Organometallics 1993, 12, 3382-3384.
3. Kiplinger, J. L.; Richmond, T. G. J. Am. Chem. Soc. 1996, 118, 1805-1806.
4. 4-Pia refers to the ligand chelate fragment equation presented
5. 4 alkyne complexes and their related chemistry see: Templeton, J. L. Adv. Organomet. Chem. 1989, 29, 1-100.
6. Feng, S. G.; Templeton, J. L. Organometallics 1992, 11, 2168-2175.
7. Morrow, J. R.; Tonker, T. L.; Templeton, J. L. J. Am. Chem. Soc. 1985, 107, 6956-6963.
8. Feng, S. G.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1992, 114, 2951-2960.
9. (a) Allen, S. R.; Green, M.; Orpen, A. G.; Williams, I. D. J. Chem. Soc., Chem. Commun. 1982, 826-828.
10. (b) Green, M.; Norman, N. C.; Orpen, A. G. J. Am. Chem. Soc. 1981, 103, 1267-1269.
11. (c) Allen, S. R.; Beevor, R. G.; Green, M.; Norman, N. C.; Orpen, A. G.; Williams, I. D. J. Chem. Soc., Dalton Trans. 1985, 435-450.
12. (d) Beevor, R. G.; Green, M.; Orpen, A.; Williams, I. D. J. Chem. Soc., Chem. Commun. 1983, 673-675.
13. Allen, S. R.; Green, M.; Norman, N. C.; Paddick, K. E.; Orpen, A. G. J. Chem. Soc., Chem. Commun. 1983, 1625-1633.
14. (a) Reger, D. L.; Belmore, K. A.; Mintz, E.; McElligot, P. J. Organometallics 1984, 3, 134-140.
15. (b) Reger, D. L.; McElligot, P. J. J. Am. Chem. Soc. 1990, 102, 5923-5924.
16. (c) Reger, D. L. Acc. Chem. Res. 1988, 21, 229-235.
17. (a) Davidson, J. L.; Vasapollo, G.; Manojlovic-Muir, L.; Muir, K. W. J. Chem. Soc., Chem. Commun. 1982, 1025-1027.
18. (b) Davidson, J. L.; Vasapollo, G.; Manojlović-Muir, L.; Muir, K. W. J. Chem. Soc., Chem. Commun. 1982, 1025-1027.
19. (c) Agh-Atabay, N. M.; Canoira, L. J.; Carlton, L.; Davidson, J. L. J. Chem. Soc., Dalton Trans. 1991, 1175-1182.
20. (d) Carlton, L.; Davidson, J. L. J. Chem. Soc., Dalton Trans. 1987, 895-905.
21. Feng, S. G.; Gamble, A. S.; Templeton, J. L. Organometallics 1989, 8, 2024-2031.
22. Gamble, A. S.; White, P. S.; Templeton, J. L. Organometallics 1991, 10, 693-702.
23. Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis, 2nd ed.; Wiley: New York, 1992.
24. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, 2nd ed.; University Science Books: Mill Valley, CA, 1987.
25. Carlton, L.; Davidson, J. L.; Miller, J. C.; Muir, K. W. J. Chem. Soc., Chem. Commun. 1984, 11-13.
26. Davidson, J. L.; Wilson, W. F.; Manojlović-Muir, L.; Muir, K. W. J. Organomet. Chem. 1983, 254, C6-C10.
27. (a) Osterberg, C. E.; King, M. A.; Arif, A. M.; Richmond, T. G. Angew. Chem., Int. Ed. Engl. 1990, 29, 888-890.
28. (b) Richmond, T. G. Coord. Chem. Rev. 1990, 105, 221-250.
29. Frenz, B. A. The Enraf-Nonius CAD 4 SPD-A Real-Time System for Concurrent X-ray Data Collection and Crystal Structure Determination. In Computing and Crystallography; Schenk, H., Olthof-Hazelkamp, R., van Konigveld, H., Bassi, G. C., Eds.; Delft University Press: Delft, Holland, 1978; pp 64-71.
30. Comer, D. T.; Waber, J. T. In International Tables for X-ray Crystallography; Ibers, J. A., Hamilton, W. C., Eds.; Kynoch: Birmingham, England, 1974; Vol. IV, Tables 2.2B and 2.3.1, pp 72-98, 149-150.
31. Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds; Wiley: New York, 1988.
32. 13C NMR Data for Organometallic Compounds; Academic Press: New York, 1981.
33. (a) Blake, A. J.; Cockman, R. W.; Ebsworth, E. A. V.; Holloway, J. H. J. Chem. Soc., Chem. Commun, 1988, 529-530.
34. (b) Darensbourg, D. J.; Klausmeyer, K. K.; Reibenspies, J. H. Inorg. Chem. 1995, 34, 4933-4934.
35. Allen, S. R.; Baker, P. K.; Barnes, S. G.; Bottrill, M.; Green, M.; Orpen, A. G.; Welch, A. J. J. Chem. Soc., Dalton Trans. 1983, 927-939.
36. (a) Green, R. D. Hydrogen Bonding by C-H Groups; Wiley: New York, 1974; Chapter 5.
37. (b) Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1990, 454-455.
38. (c) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296.
39. Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
40. (a) Servis, K. L.; Fang, K. N. J. Am. Chem. Soc. 1968, 90, 6712-6717.
41. (b) Servis, K. L.; Jerome, F. R. J. Am. Chem. Soc. 1971, 93, 1535-1537.
42. (c) Mallory, F. B.; Mallory, C. W.; Ricker, W. M. J. Org. Chem. 1985, 50, 457-461.
43. Benn, R.; Rufińska, A.; King, M. A.; Osterberg, C. E.; Richmond, T. G. J. Organomet. Chem. 1989, 376, 359-366.
44. CAChe Worksystem 3.0 (CAChe Scientific, Beaverton, OR).
45. -1) obtained from: Lühring, P.; Schumpe, A. J. Chem. Eng. Data 1989, 34, 250-252.
46. (a) Bassetti, M.; Mannina, L.; Monti, D. Organometallics 1994, 13, 3293-3299.
47. (b) Wax, M. J.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 7028-7030.
48. (c) Monti, D.; Bassetti, M. J. Am. Chem. Soc. 1993, 115, 4658-4664.
49. Sigma Plot Version 1.02, Windows 3.10 Enhanced (Jandel Scientific, Corte Madera, CA).
50. Beck, M. T. Chemistry of Complex Equilibria; Van Nostrand Reinhold: London, 1970; p 86.
51. (a) Albéniz, A. C.; Espinet, P.; Jeannin, Y.; Philoche-Levisalles, M.; Mann, B. E. J. Am. Chem. Soc. 1990, 112, 6594-6600.
52. (b) Albéniz, A. C.; Espinet, P.; Foces-Foces, C.; Cano, F. H. Organometallics 1990, 9, 1079-1085.
53. (c) Albéniz, A. C.; Espinet, P. Organometallics 1991, 10, 2987-2988.
54. (d) Gipson, S. L.; Kneten, K. Inorg. Chim. Acta 1989, 157, 143-145.
55. Osterberg, C. E. Ph.D. Thesis, University of Utah, 1990.
56. Kiplinger, J. L. Unpublished results (data to appear in an upcoming paper).
57. 4N see: (a) Davidson, J. L.; Murray, I. E. P.; Preston, P. N.; Russo, M. V.; Manojlović-Muir, L.; Muir, K. W. J. Chem. Soc., Chem. Commun. 1981, 1059-1061. (b) Davidson, J. L.; Murray, I. E. P.; Preston, P. N.; Russo, M. V. J. Chem Soc., Dalton Trans. 1983, 1783-1787.
58. 4N see: (a) Davidson, J. L.; Murray, I. E. P.; Preston, P. N.; Russo, M. V.; Manojlović-Muir, L.; Muir, K. W. J. Chem. Soc., Chem. Commun. 1981, 1059-1061. (b) Davidson, J. L.; Murray, I. E. P.; Preston, P. N.; Russo, M. V. J. Chem Soc., Dalton Trans. 1983, 1783-1787.
59. Cohen, S. C.; Massey, A. Adv. Fluorine Chem. 1970, 6, 83-285.
60. Brower, D. C.; Birdwhistell, K. R.; Templeton, J. L. Organometallics 1986, 5, 94-98.
61. Wehman-Ooyevaar, I. C. M.; Kapteijn, G. M,; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Chem. Soc., Dalton Trans. 1994, 703-711.
62. A similar process has been reported for five-coordinate chiral tin complexes that contain a bidentate C,N ligand: (a) van Koten, G.; Jastrzebski, J. T. B. H.; Noltes, J. G.; Pontenagel, W. M. G. F.; Kroon, J.; Spek, A. L. J. Am. Chem. Soc. 1978, 100, 5021-5028. (b) Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. J. Organomet. Chem. 1991, 413, 43-53.
63. A similar process has been reported for five-coordinate chiral tin complexes that contain a bidentate C,N ligand: (a) van Koten, G.; Jastrzebski, J. T. B. H.; Noltes, J. G.; Pontenagel, W. M. G. F.; Kroon, J.; Spek, A. L. J. Am. Chem. Soc. 1978, 100, 5021-5028. (b) Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. J. Organomet. Chem. 1991, 413, 43-53.
64. (a) Doherty, N. M.; Hoffman, N. W. Chem. Rev. 1991, 91, 553-573.
65. (b) Simpson, R. D.; Bergman, R. G. Organometallics 1993, 12, 781-796.
66. (a) Maassarani, F.; Pfeffer, M.; Le Borgne, G. Organometallics 1987, 6, 2029-2043.
67. (b) Wu, G.; Rheingold, A. L.; Heck, R. F. Organometallics 1986, 5, 1922-1924.
68. (c) Bahsoun, A.; Dehand, J.; Pfeffer, M.; Zinsius, M.; Bouaoud, S. E.; Le Borgne, G. J. Chem. Soc., Dalton Trans. 1979, 547-556.
69. (d) Arien, C.; Pfeffer, M.; Fischer, J.; Mitschler, A. J. Chem. Soc., Chem. Commun. 1983, 928-929.
70. Carlton, L.; Davidson, J. L.; Ewing, P.; Manojlović-Muir, L.; Muir, K. J. Chem. Soc., Chem. Commun. 1985, 1474-1476.
71. (a) Richmond, T. G.; King, M. A.; Kelson, E. P.; Arif, A. M. Organometallics 1987, 6, 1995-1996.
72. (b) Poss, M. J.; Arif, A. M.; Richmond, T. G. Organometallics 1988, 7, 1669-1670.
73. Churchill, M. R.; Youngs, W. J. Inorg. Chem. 1979, 18, 2454-2458.
74. Schilling, B. E. R.; Hoffmann, R.; Lichtenberger, D. L. J. Am. Chem. Soc. 1979, 101, 585-591.
75. Kiplinger, J. L.; Arif, A. M.; Richmond, T. G. Inorg. Chem. 1995, 34, 399-401.
76. (a) Birdwhistell, K. R.; Nieter Burgmayer, S. J.; Templeton, J. L. J. Am. Chem. Soc. 1983, 105, 7789-7790.
77. (b) Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335-422.
78. (c) Shustorovich, E. M.; Porai-Koshits, M. A.; Buslaev, Y. A. Coord. Chem. Rev. 1975, 17, 1-98.
79. (a) Bruce, M. I. Angew. Chem., Int. Ed. Engl. 1977, 16, 73-86.
80. (b) Richmond, T. G.; Osterberg, C. E.; Arif, A. M. J. Am. Chem. Soc. 1987, 109, 8091-8092.
81. (52)(a) Buffin, B. P.; Arif, A. M.; Richmond, T. G. J. Chem. Soc., Chem. Commun. 1993, 1432-1434.
82. (b) Buffin, B. P.; Poss, M. J.; Arif, A. M.; Richmond, T. G. Inorg. Chem. 1993, 32, 3805-3806.
83. (a) Anderson, C. M.; Puddephatt, R. J.; Ferguson, G.; Lough, A. J. J. Chem. Soc., Chem. Commun. 1989, 1297-1298.
84. (b) Anderson, C. M.; Crespo, M.; Ferguson, G.; Lough, A. J. Organometullics 1992, 11, 1177-1181.
85. (a) Basolo, F. Polyhedron 1990, 9, 1503-1535.
86. (b) Darensbourg, D. J. Adv. Organomet. Chem. 1982, 21, 113-150.
87. (c) Howell, J. A. S.; Burkinshaw, P. M. Chem. Rev. 1983, 83, 557-599.
88. Schneider, K. J.; van Eldik, R. Organometallics 1990, 9, 1235-1240.
89. Taube, D. J.; van Eldik, R.; Ford, P. C. Organometallics 1987, 6, 125-129.
90. Reddy, K. B.; van Eldik, R. Organometallics 1990, 9, 1418-1421.
91. Simões, J. A. M.; Beauchamp, J. L. Chem. Rev. 1990, 90, 629-688.
92. (a) Atwood, J. D.; Brown, T. L. J. Am. Chem. Soc. 1976, 98, 3160-3166.
93. (b) Lichtenberger, D. L.; Brown, T. L. J. Am. Chem. Soc. 1978, 100, 366-373.
94. (c) Hoffman, N. W.; Prokopuk, N.; Robbing, M. J.; Jones, C. M.; Doherty, N. M. Inorg. Chem. 1991, 30, 4177-4181.
95. Davidson, J. L.; Shiralian, M.; Manojlovié-Muir, L.; Muir, K. W. J. Chem. Soc., Dalton Trans. 1984, 2167-2176.
96. O'Connor, J. M.; Casey, C. P. Chem. Rev. 1987, 87, 307-318.
97. Wilkins, R. G. Kinetics and Mechanism of Reactions of Transition Metal Complexes, 2nd ed.; VCH Publishers: New York, 1991.
98. Wilhelm, E.; Battino, R. Chem. Rev. 1973, 73, 1-9.
99. (a) van Eldik, R.; Merbach, A. E. Comments Inorg. Chem. 1992, 12, 341-378.
100. (b) van Eldik, R.; Asano, T.; le Noble, W. J. Chem. Rev. 1989, 89, 549-688
101. Zhang, S.; Zang, V.; Dobson, G. R.; van Eldik, R. Inorg. Chem. 1991, 30, 355-356.
102. (a) Lawrence, G. A.; Suvachittanont, S. Inorg. Chim. Acta 1979, 32, L13-L15.
103. (b) Lawrance, G. A.; Stranks, D. R. Inorg. Chem. 1977, 16, 929-935.