Parallel vs. perpendicular alkyne coordination in binuclear complexes. The first examples of reactivity differences in isomers differing in their alkyne coordination modes

Canadian Journal of Chemistry

Volumn 74, Issue 11, 1996, Pages 2289-2303

  George, Darren S A ^a   McDonald, Robert ^a   Cowie, Martin ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Diiridium alkyne complexes; Parallel and perpendicular alkyne coordination

Indexed keywords

BENZENE; COORDINATION REACTIONS; CRYSTAL STRUCTURE; DECOMPOSITION; IRIDIUM; PHASE EQUILIBRIA; X RAY ANALYSIS;

ALKYNE COORDINATION; BINUCLEAR COMPLEXES; DIIRIDIUM ALKYNE COMPLEXES; DIMETHYL ACETYLENEDICARBOXYLATE; ISOMER; PROTONATION;

ORGANOMETALLICS;

EID: 0030288894     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-257     Document Type: Article

References (109)

1. J.P. Collman, L.S. Hegedus, J.R. Norton, and R.G. Finke. Principles and applications of organotransition metal chemistry. University Science Books, Mill Valley, Calif. 1987. Chaps. 11 and 18, and references therein.
2. J.L. Davidson. In Reactions of coordinated ligands. Vol. 1. Edited by P.S. Braterman. Plenum Press, New York. 1986. p. 825.
3. (a) E.L. Muetterties. Bull. Soc. Chim. Belg. 84, 953 (1975);
4. (b) Bull Soc. Chim. Belg. 85, 451 (1976);
5. (c) Angew. Chem. Int. Ed. Engl. 17, 545 (1978);
6. (d) E.L. Muetterties, R.N. Rhodin, E. Band, C.F. Brucker, and W.R. Pretzer. Chem. Rev. 79, 91 (1979);
7. (e) E. Sappa, A. Tiripicchio, and P. Braunstein. Chem. Rev. 83, 203 (1983).
8. R.S. Dickson. Polyhedron, 10, 1995 (1991).
9. (a) M.J.S. Dewar. Bull. Soc. Chim. Fr. 18, C79 (1951);
10. (b) Annu. Rep. Chem. Soc. 48, 112 (1951);
11. (c) J. Chatt and L.A. Duncanson. J. Chem. Soc. 2339 (1953);
12. (d) M.J.S. Dewar, R.C. Haddon, A. Komornicki, and H. Rzepa. J. Am. Chem. Soc. 99, 377 (1977);
13. (e) M.J.S. Dewar and G.P. Ford. J. Am. Chem. Soc. 101, 783 (1979).
14. D.M. Hoffman, R. Hoffmann, and C.R. Fisel. J. Am. Chem. Soc. 104, 3858 (1982).
15. (a) R.S. Dickson and G.N. Pain. J. Chem. Soc. Chem. Commun. 277 (1979);
16. (b) M.R. Gagné and J. Takats. Organometallics, 7, 561 (1988).
17. (a) M. Cowie and T.G. Southern. Inorg. Chem. 21, 246 (1982);
18. (b) B.R. Sutherland and M. Cowie. Organometallics, 3, 1869 (1984);
19. (c) M. Cowie, R.S. Dickson, and B.W. Hames. Organometallics, 3, 1879 (1984);
20. (d) B.R. Sutherland and M. Cowie. Organometallics, 4, 1801 (1985);
21. (e) J.A. Jenkins, J.P. Ennett, and M. Cowie. Organometallics, 7, 1845 (1988);
22. (f) I.R. McKeer, S.J. Sherlock, and M. Cowie. J. Organomet. Chem. 352, 205 (1988);
23. (g) B.A. Vaartstra and M. Cowie. Organometallics, 8, 2388 (1989);
24. (h) B.A. Vaartstra and M. Cowie. Organometallics, 9, 1594 (1990);
25. (i) R.W. Hilts, R.A. Franchuk, and M. Cowie. Organometallics, 10, 304 (1991);
26. (j) B.A. Vaartstra, J. Xiao, J.A. Jenkins, R. Verhagen, and M. Cowie. Organometallics, 10, 2708 (1991);
27. (k) J.A. Jenkins and M. Cowie. Organometallics, 11, 2767 (1992);
28. (l) J. Xiao and M. Cowie. Organometallics, 12, 463 (1993);
29. (m) B.T. Sterenberg, R.W. Hilts, G. Moro, R. McDonald, and M. Cowie. J. Am. Chem. Soc. 117, 245 (1995);
30. (n) L.-S. Wang and M. Cowie. Can. J. Chem. 73; 1058 (1995);
31. (o) Organometallics, 14, 3040 (1995);
32. (p) F.H. Antwi-Nsiah, O. Oke, and M. Cowie. Organometallics, 15, 506 (1996).
33. (a) D.H. Berry and R. Eisenberg. Organometallics, 6, 1796 (1987);
34. (b) S.I. Hommeltoft, D.H. Berry, and R. Eisenberg. J. Am. Chem. Soc. 108, 5345 (1986).
35. (a) R.P. Aggarwal, N.G. Connelly, M.C. Crespo, B.J. Dunne, P.J. Hopkins, and A.G. Orpen. J. Chem. Soc. Chem. Commun. 33 (1989);
36. (b) P.H. Bird, A.R. Fraser, and D.N. Hall. Inorg. Chem. 16, 1923 (1977);
37. (c) W.G. Sly. J. Am. Chem. Soc. 81, 18 (1959);
38. (d) F.A. Cotton, J.D. Jamerson, and B.R. Stults. J. Am. Chem. Soc. 98, 1774 (1976).
39. (a) A.L. Balch, C.-L. Lee, C.H. Lindsay, and M.M. Olmstead. J. Organomet. Chem. 177, C22 (1979);
40. (b) C.-L. Lee, C.T. Hunt, and A.L. Balch. Inorg. Chem. 20, 2498 (1981).
41. P.G. Pringle and B.L. Shaw. J. Chem. Soc. Dalton Trans. 889 (1983).
42. R.J. Puddephatt and M.A. Thomson. Inorg. Chem. 21, 725 (1982).
43. B.R. Sutherland and M. Cowie. Organometallics, 4, 1637 (1985).
44. J.R. Torkelson and M. Cowie. Manuscript in preparation.
45. N. Walker and D. Stuart. Acta Crystallogr. Sect. A: Found. Crystallogr. A39, 158 (1983).
46. C.P. Kubiak and R. Eisenberg. Inorg. Chem. 19, 2726 (1980).
47. C.P. Kubiak, C. Woodcock, and R. Eisenberg. Inorg. Chem. 19, 2733 (1980).
48. B.A. Vaartstra and M. Cowie. Inorg. Chem. 28, 3138 (1989).
49. (a) C.P. Casey, R.S. Cariño, R.K. Hayashi, and K.D. Schladetzky. J. Am. Chem. Soc. 118, 1617 (1996);
50. (b) N.M. Boag, M. Green, J.A.K. Howard, F.G.A. Stone, and H. Wadepohl. J. Chem. Soc. Dalton Trans. 862 (1981);
51. (c) N.M. Boag, M. Green, J.A.K. Howard, J.L. Spencer, R.F.D. Stansfield, M.D.O. Thomas, F.G.A. Stone, and P. Woodward. J. Chem. Soc. Dalton Trans. 2181 (1980);
52. (d) G.M. Villacorta, D. Gibson, I.D. Williams, and S.J. Lippard. J. Am Chem. Soc. 107, 6732 (1985);
53. (e) GM. Villacorta, D. Gibson, I.D. Williams, E. Whang, and S.J. Lippard, Organometallics, 6, 2426 (1987);
54. (f) H.L. Aalten, G. van Koten, E. Reithorst, and C.H. Stam. Inorg. Chem. 28, 4140 (1989);
55. (g) C. Bianchini, D. Masi, A. Meli, M. Peruzzini, A. Vaaca, F. Laschi, and P. Zanello. Organometallics, 10, 636 (1991);
56. (h) E. Spaltenstein and J. M. Mayer. J. Am. Chem. Soc. 113, 7744 (1991);
57. (i) J. Krause, W. Bonrath, and K.R. Pörchke. Organometallics, 11, 1158 (1992);
58. (j) D.L. Reger and M.F. Huff. Organometallics, 11, 69 (1992).
59. J. Clemens, M. Green, M.-C. Kuo, C.J. Fritchie, J. Mague, and F.G.A. Stone. J. Chem. Soc. Chem. Commun. 53 (1972).
60. L.E. Smart, J. Browning, M. Green, A. Laguna, J.L. Spencer, and F.G.A. Stone. J. Chem. Soc. Dalton Trans. 1777 (1977).
61. R. McDonald and M. Cowie. Organometallics, 9, 2468 (1990).
62. (a) W.-D. Wang, S.I. Hommeltoft and R. Eisenberg. Organometallics, 7, 2417 (1988);
63. (b) W.-D. Wang and R. Eisenberg. J. Am. Chem. Soc. 112, 1833 (1990).
64. F.A. Cotton, K.R. Dunbar, and M.G. Verbruggen, J. Am. Chem. Soc. 109, 5498 (1987).
65. J.T. Mague. Inorg. Chem. 28, 2215 (1989).
66. L. Manojlović-Muir, K.A. Muir, A.A. Frew, S.S.M. Ling, M.A. Thomson, and R.J. Puddephatt. Organometallics, 3, 1637 (1984).
67. J. Wu, P.E. Fanwick, and C.P. Kubiak. J. Am. Chem. Soc. 111, 7812 (1989).
68. (a) J. Wu, P.E. Fanwick, and C.P. Kubiak. J. Am. Chem. Soc. 110, 1319 (1988);
69. (b) P. Braunstein, B. Oswald, A. DeCian, and J. Fischer, J. Chem. Soc. Dalton Trans. 2685 (1991).
70. M.P. Brown, S.J. Cooper, A.A. Frew, L. Manojlović-Muir, K.W. Muir, R.J. Puddephatt, K.R. Seddon, and M.A. Thornson. Inorg. Chem. 20, 1500 (1981);
71. (b) R.J. Haines, E. Meintjies, M. Laing, and P. Sommerville. J. Organomet. Chem. 216, C19 (1981);
72. (c) W.S. McDonald, P.G. Pringle, and B.L. Shaw. J. Chem. Soc. Chem. Commun. 861 (1982);
73. (d) A.T. Hutton, P.G. Pringle, and B.L. Shaw. Organometallics, 2, 1889 (1983);
74. (e) C. Woodcock and R. Eisenberg. Inorg. Chem. 24, 1287 (1985);
75. (f) A.L. Balch, R.R. Guimerans, J. Linehan, M.M. Olmstead, and D.E. Oram. Organometallics, 4, 1445 (1985);
76. (g) D.L. DeLaet, R. Del Rosario, P.E. Fanwick, and C.P. Kubiak. J. Am. Chem. Soc. 109, 754 (1987);
77. (h) D.J. Elliot, G. Ferguson, D.G. Holah, A.N. Hughes, M.C. Jennings, V.R. Magnuson, D. Potter, and R.J. Puddephatt. Organometallics, 9, 1336 (1990);
78. (i) M.K. Reining. Ph.D. Thesis, Purdue University, 1989. Chap. 3.
79. G.G. Sumner, H.P. Klug, and L.E. Alexander. Acta Crystallogr. 17, 732 (1964).
80. H. van Dam, D.J. Stufkens, A. Oskan, M. Doran, and I.H. Hillier. Electron Spectrosc. Relat. Phenom. 21, 47 (1980).
81. K.A. Johnson and W.L. Gladfelter. Organometallics, 8, 2866 (1989).
82. J.L. Davidson, W. Harrison, D.W.A. Sharp, and G.A. Sim. J. Organomet. Chem. 46, C42 (1972).
83. Y. Koie, S. Shinoda, Y. Saito, B.J. Fitzgerald, and G.G. Pierpont. Inorg. Chem. 19, 770 (1980).
84. R.S. Dickson, S.H. Johnson, H.P. Kirsch, and D.J. Lloyd. Acta Crystallogr. Sect. B: Crystallogr. Cryst. Chem. Struct. B33, 2057 (1977).
85. J.T. Mague, Organometallics, 5, 918 (1986).
86. J.T. Mague, C.L. Klein, R.J. Majeste, and E.D. Stevens. Organometallics, 3, 1860 (1984).
87. R.J. Puddephatt and M.A. Thomson. Inorg. Chem. 21, 725 (1982).
88. M.A. Bennett, R.N. Johnson, G.B. Robertson, T.W. Turney, and P.O. Whimp. Inorg. Chem. 15, 97 (1976).
89. T.R. Jack, C.J. May, and J. Powell. J. Am. Chem. Soc. 99, 4707 (1977).
90. E.L. Muetterties, W.R. Pretzer, M.G. Thomas, B.F. Beier, D.L. Thorn, VW. Day, and A.B. Anderson. J. Am. Chem. Soc. 100, 2090 (1978).
91. B.H. Freeland, J.E. Huz, N.C. Payne, and K.G. Tyers. Inorg. Chem. 19, 693 (1980).
92. N.A. Bailey and R. Mason. J. Chem. Soc. A, 1293 (1968).
93. (a) C.P. Kubiak, C. Woodcock, and R. Eisenberg. Inorg. Chem. 19, 2733 (1980);
94. (b) B.R. Sutherland and M. Cowie. Inorg. Chem. 23, 2324 (1984);
95. (c) Can. J. Chem. 64, 464 (1986);
96. (d) J. Wu, M.K. Reinking, P.E. Fanwick, and C.P. Kubiak. Inorg. Chem. 26, 247 (1987);
97. (e) R. McDonald, B.R. Sutherland, and M. Cowie. Inorg. Chem. 26, 3333 (1987).
98. (j) J. Wu, P.E. Fanwick, and C.P. Kubiak. Organometallics, 6, 1805 (1987);
99. (g) A.L. Balch, K.M. Waggoner, and M.M. Olmstead. Inorg. Chem. 27, 4511 (1988).
100. M. Angoletta, P.L. Bellon, F. Demartin, and M. Sansoni. J. Organomet. Chem. 208, C12 (1981).
101. 13C NMR data for organometallic compounds. Academic Press; London. 1981. pp. 14-15.
102. J.R. Torkelson, F.H. Antwi-Nsiah, and M. Cowie. Manuscript in preparation.
103. H. Friebolin. Basic one- and two-dimensional NMR spectroscopy. VCH Verlagsgesellschaft mbH, Weinheim. 1991. pp. 54, 284.
104. M.J. Burn, G.-Y. Kiel, F. Seils, J. Takats, and J. Washington. J. Am. Chem. Soc. 111, 6850 (1989).
105. R. Cramer, J.B. Kline, and J.D. Roberts. J. Am. Chem. Soc. 91, 2519 (1969).
106. (a) R.S. Dickson, C. Mok, and G. Pain. J. Organomet. Chem. 166, 385 (1979);
107. (b) J.J. Bonnet, R. Mathieu, and J.A. Ibers. Inorg. Chem. 19, 2448 (1980);
108. (c) N.M. boag, M. Green, and F.G.A. Stone. J. Chem. Soc. Chem. Commun. 1281 (1980);
109. (d) S.A.R. Knox. J. Organomet. Chem. 400, 255 (1990).