Allenylidene complexes of ruthenium: Synthesis, spectroscopy and electron transfer properties

Coordination Chemistry Reviews

Volumn 248, Issue 15-16 SPEC. ISS., 2004, Pages 1565-1583

  Winter, Rainer F ^a   Záliš, Stanislav ^a,b  

^a UNIVERSITY OF STUTTGART   (Germany)

^b J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

Author keywords

Allenylidene complexes of ruthenium; Electron transfer; Spectroscopy

Indexed keywords

METAL COMPLEX; RUTHENIUM COMPLEX;

CARBON NUCLEAR MAGNETIC RESONANCE; DENSITY FUNCTIONAL THEORY; ELECTROLYSIS; ELECTRON TRANSPORT; INFRARED SPECTROMETRY; INFRARED SPECTROSCOPY; OXIDATION REDUCTION REACTION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; REVIEW; SPECTROSCOPY; SPECTRUM; STOICHIOMETRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE MEASUREMENT; X RAY CRYSTALLOGRAPHY;

EID: 5444240389     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2004.05.005     Document Type: Review

References (126)

1. Fischer E.O. Pure Appl. Chem. 24:1970;407
2. Fischer E.O., Leupold M., Kreiter C.G., Müller J. Chem. Ber. 105:1972;150
3. Fischer E.O., Kreis G., Kreißl F.R., Kreiter C.G., Müller J. Chem. Ber. 106:1973;3910
4. Fischer E.-O., Kalder H.J., Frank A., Köhler F.H., Huttner G. Angew. Chem. 88:1976;683
5. 4-Liganden aus Diacetylen, Verlag Grauer, Beuren Stuttgart, 2002.
6. Re N., Sgamellotti A., Floriani C. Organometallics. 19:2000;1115
7. Marrone A., Re N. Organometallics. 21:2002;3562
8. Cadierno V., Gamasa M.P., Gimeno J., González-Cueva M., Lastra E., Borge J., García-Granda S., Pérez-Carreño E. Organometallics. 15:1996;2137
9. Esteruelas M.A., Gómez A.V., López A.M., Modrego J., Oñate E. Organometallics. 16:1997;5826
10. Baya M., Crochet P., Esteruelas M.A., Gutiérrez-Puebla E., López A.M., Modrego J., Oñate E., Vela N. Organometallics. 19:2000;2585
11. Winter R.F., Klinkhammer K.-W., Záliš S. Organometallics. 20:2001;1317
12. Touchard D., Haquette P., Daridor A., Toupet L., Dixneuf P.H. J. Am. Chem. Soc. 116:1994;11157
13. Péron D., Romero A., Dixneuf P.H. Gazz. Chim. Ital. 124:1994;497
14. Péron D., Romero A., Dixneuf P.H. Organometallics. 14:1995;3319
15. Touchard D., Pirio N., Toupet L., Fettouhi M., Ouahab L., Dixneuf P.H. Organometallics. 14:1995;5263
16. Roth G., Fischer H. Organometallics. 15:1996;1139
17. Roth G., Fischer H. Organometallics. 15:1996;5766
18. Roth G., Fischer H., Meyer-Friedrichsen T., Heck J., Houbrechts S., Persoons A. Organometallics. 17:1998;1511
19. R.M. Bullock, J. Chem. Soc., Chem. Commun. (1989) 165.
20. Bruce M.I. Chem. Rev. 91:1991;107
21. de los Ríos I., Tenorio M.J., Puerta M.C., Valerga P. J. Am. Chem. Soc. 119:1997;6529
22. E. Peréz-Carreño, P. Paoli, A. Ienco, C. Mealli, Eur. J. Inorg. Chem. (1999) 1315.
23. Cadierno V., Gamasa M.P., Gimeno J., González-Bernardo C., Pérez-Carreño E., García-Granda S. Organometallics. 20:2001;5177
24. de Angelis F., Sgamellotti A., Re N. Organometallics. 21:2002;5944
25. Lomprey J.R., Selegue J.P. Organometallics. 12:1993;616
26. M.I. Bruce, P. Hinterding, P.J. Low, B.W. Skelton, A.H. White, J. Chem. Soc., Chem. Commun. (1996) 1009.
27. M.I. Bruce, P. Hinterding, P.J. Low, B.W. Skelton, A.H. White, J. Chem. Soc., Dalton Trans. (1998) 467.
28. M.I. Bruce, P. Hinterding, M. Ke, P.J. Low, B.W. Skelton, A.H. White, Chem. Commun. (1997) 715.
29. Bruce M.I., Ke M., Kelly B.D., Low P.J., Smith M.E., Skelton B.W., White A.H. J. Organomet. Chem. 590:1999;184
30. Winter R.F. Organometallics. 16:1997;4248
31. R.F. Winter, Chem. Commun. (1998) 2209.
32. R.F. Winter, Eur. J. Inorg. Chem. (1999) 2121.
33. Winter R.F., Hornung F.M. Organometallics. 18:1999;4005
34. R.F. Winter, S. Hartmann, S. Záliš, K.W. Klinkhammer, Dalton Trans. (2003) 2342.
35. Hartmann S., Winter R.F., Scheiring T., Wanner M. J. Organomet. Chem. 637-639:2001;240
36. Harbort R.-C., Hartmann S., Winter R.F., Klinkhammer K.W. Organometallics. 22:2003;3171
37. K. Venkatesan, F.J. Fernández, O. Blacque, T. Fox, M. Alfonso, H.W. Schmalle, H. Berke, Chem. Commun. (2003) 2006.
38. Ilg K., Werner H. Angew. Chem. 112:2000;1691
39. Coat F., Guillemot M., Paul F., Lapinte C. J. Organomet. Chem. 578:1999;76
40. C.J. Adams, M.I. Bruce, B.W. Skelton, A.H. White, Chem. Commun. (1996) 2663.
41. Adams C.J., Bruce M.I., Skelton B.W., White A.H. J. Organomet. Chem. 584:1999;254
42. Guillaume V., Thominot P., Coat F., Mari A., Lapinte C. J. Organomet. Chem. 565:1998;75
43. Haquette P., Touchard D., Toupet L., Dixneuf P. J. Organomet. Chem. 565:1998;63
44. S. Hartmann, Synthese, Dissertation, Universität Stuttgart, 2003.
45. Bustelo E., Jimenez-Tenorio M., Mereiter K., Puerta M.C., Valerga P. Organometallics. 21:2002;1903
46. Barrett A.G.M., Carpenter N. Organometallics. 6:1987;2249
47. Jung S., Brandt C.D., Werner H. New. J. Chem. 25:2001;1101
48. Rigaut S., Touchard D., Dixneuf P.H. Organometallics. 22:2003;3980
49. Castarlenas R., Dixneuf P.H. Angew. Chem. 115:2003;4662
50. Fischer H., Szesni N., Roth G., Burzlaff N., Weibert B. J. Organomet. Chem. 683:2003;301
51. Selegue J.P. Organometallics. 1:1982;217
52. H. Le Bozec, K. Ouzzine, P.H. Dixneuf, J. Chem. Soc., Chem. Commun. (1989) 219.
53. Pilette D., Ouzzine K., Le Bozec H., Dixneuf P.H., Rickard C.E.F., Roper W.R. Organometallics. 11:1992;809
54. Esteruelas M.A., Gómez A.V., Lahoz F.M., López A.M., Oñate E., Oro L.A. Organometallics. 15:1996;3423
55. Esteruelas M.A., Gómez A.V., López A.M., Modrego J., Oñate E. Organometallics. 17:1998;5434
56. Bernad J., Esteruelas M.A., López A.M., Modrego J., Puerta M.C., Valerga P. Organometallics. 18:1999;4005
57. Fischer H., Reindl D., Troll C., Leroux F. J. Organomet. Chem. 490:1995;221
58. Werner H., Stark A., Steinert P., Grünwald C., Wolf J. Chem. Ber. 128:1995;49
59. Cadierno V., Gamasa M.P., Gimeno J., López-González M.C., Borge J., García-Granda S. Organometallics. 16:1997;4453
60. Touchard D., Dixneuf P.H. Coord. Chem. Rev. 178-180:1998;409
61. B. Buriez, D.J. Cook, K.J. Harlow, A.F. Hill, T. Welton, A.J.P. White, D.J. Williams, J.D.E.T. Wilton-Ely, J. Organomet. Chem. (1999) 264.
62. Bianchini C., Mantovani N., Marvelli L., Peruzzini M., Rossi R., Romerosa A. J. Organomet. Chem. 617-618:2001;233
63. Buil M.L., Esteruelas M.A., López A.M., Oñate E. Organometallics. 22:2003;162
64. Mantovani N., Marvelli L., Rossi R., Bertolasi V., Bianchini C., Rios I.D.L., Peruzzini M. Organometallics. 21:2002;2382
65. S. Rigaut, O. Maury, D. Touchard, P.H. Dixneuf, Chem. Commun. (2001) 373.
66. W. Runge, in: S.R. Landor (Ed.), The Chemistry of Allenes: Stereochemical, Spectroscopic and Special Aspects, vol. 3, Academic Press, London, 1982.
67. Moreau J.-L., Gaudemar M. J. Organomet. Chem. 108:1976;159
68. Craig J.C., Ekwuribe N.N. Tetrahedron Lett. 21:1980;2587
69. G. Maas, T. Mayer, Synthesis (1991) 1209.
70. G. Pourcelot, P. Cadiot, Bull. Soc. Chim. Fr. (1966) 3024.
71. Tamm M., Jentzsch T., Werncke W. Organometallics. 16:1997;1418
72. Touchard D., Pirio N., Dixneuf P.H. Organometallics. 14:1995;4920
73. H. Fischer, N. Szesni, Coord. Chem. Rev. 248 (2004) 1659.
74. D. Lin-Vien, N.B. Colthup, W.G. Fateley, J.G. Grasselli, in: The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules, Academic Press, San Diego, 1991.
75. Manna J., John K.D., Hopkins M.D. Adv. Organomet. Chem. 38:1995;79
76. Wu I.-Y., Linn J.T., Luo J., Li C.-S., Tsai C., Wen Y.S., Hsu C.-C., Yeh F.-F., Liou S. Organometallics. 17:1998;2188
77. Denis R., Toupet L., Paul F., Lapinte C. Organometallics. 19:2000;4240
78. Bianchini C., Laschi F., Masi D., Ottavani F.M., Pastor A., Peruzzini M., Zanobini F. J. Am. Chem. Soc. 115:1993;2723
79. Lin C., Ren T., Valente E.J., Zubkowski J.D. J. Organomet. Chem. 579:1999;114
80. Hodge A.J., Ingham S.L., Kakkar A.K., Khan M.S., Lewis J., Long N.J., Parker D.G., Raithby P.R. J. Organomet. Chem. 488:1995;205
81. Whittall I.R., Humphrey M.G., Hockless D.C.R., Skelton B.W., White A.H. Organometallics. 14:1995;3970
82. McDonagh A.M., Whittall I.R., Humphrey M.G., Skelton B.W., White A.H. J. Organomet. Chem. 519:1996;229
83. Duetsch M., Stein F., Lackmann R., Pohl E., Herbst-Irmer R., Meijere A.d. Chem. Ber. 125:1992;2051
84. Stein F., Duetsch M., Pohl E., Herbst-Irmer R., Meijere A.D. Organometallics. 12:1993;2556
85. Aumann R., Roths K., Fröhlich R. Organometallics. 16:1997;5893
86. C. Rabiller, J.P. Renou, G.J. Martin, J. Chem. Soc., Perkin Trans. II (1977) 536.
87. Conejero S., Díez J., Gamasa M.P., Gimeno J., García-Granda S. Angew. Chem. 114:2002;3589
88. Wolinska A., Touchard D., Dixneuf P.H. J. Organomet. Chem. 420:1991;217
89. Bustelo E., Jiménez-Tenorio M., Puerta M.C., Valerga P. Organometallics. 18:1999;4563
90. Gamasa M.P., Gimeno J., González-Bernardo C., Borge J., García-Granda S. Organometallics. 16:1997;2483
91. K. Urtel, A. Frick, G. Huttner, L. Zsolnai, P. Kircher, P. Rutsch, E. Kaifer, A. Jacobi, Eur. J. Inorg. Chem. (2000) 33.
92. A. Fürstner, M. Picquet, C. Bruneau, P.H. Dixneuf, Chem. Commun. (1998) 1315.
93. Buriez B., Burns I.D., Hill A.F., White A.J.P., Williams D.J., Wilton-Ely J.D.E.T. Organometallics. 18:1999;1504
94. M. Martín, O. Gevert, H. Werner, J, Chem. Soc., Dalton Trans. (1996) 2275.
95. S. Jung, K. Ilg, C.D. Brandt, J. Wolf, H. Werner, Dalton Trans. (2002) 318.
96. Werner H., Grünwald C., Steinert P., Gevert O., Wolf J. J. Organomet. Chem. 565:1998;231
97. de los Ríos I., Jiménez-Tenorio M., Puerta M.C., Valerga P. J. Organomet. Chem. 549:1997;221
98. M.C. Colbert, J. Lewis, N.J. Long, P.R. Raithby, M. Younus, A.J.P. White, D.J. Williams, N.N. Payne, L. Yellowlees, D. Beljonne, N. Chawdhury, R.H. Friend, J. Chem. Soc., Dalton Trans. (1998) 3034.
99. E. Bustelo, M. Jiménez-Tenorio, M.C. Puerta, P. Valerga, Eur. J. Inorg. Chem. (2001) 2391.
100. Cadierno V., Gamasa M.P., Gimeno J., Lastra E., Borge J., García-Granda S. Organometallics. 13:1994;745
101. Berke H., Huttner G., Seyerl J.v. Z. Naturforsch. B. 36B:1981;1277
102. Clark R.J.H., Dines T.J. Angew. Chem. Int. Ed. Engl. 25:1986;131
103. van Slageren J., Winter R.F., Klein A., Hartmann S. J. Organomet. Chem. 670:2003;137
104. Olah G.A., Pittman C.U. Jr., Waack R., Doran M. J. Am. Chem. Soc. 88:1966;1488
105. Runge W., Firl J. Ber. Bunsenges Phys. Chem. 79:1975;913
106. Czech P.T., Ye X.-Q., Fenske R.F. Organometallics. 9:1990;2016
107. Olah G.A., Spear R.J., Westerman P.W., Denis J.-M. J. Am. Chem. Soc. 98:1974;5855
108. Olah G.A., Berrier A.L., Field L.D., Prakash G.K.S. J. Am. Chem. Soc. 104:1982;1349
109. Krishnamurty V.V., Prakash G.K.S., Iyer P.D., Olah G.A. J. Am. Chem. Soc. 108:1986;1575
110. Komatsu K., Takai T., Aonuma S., Takeuchi K.i. Tetrahedron Lett. 29:1988;5157
111. Gleiter R., Hyla-Kryspin I., Binger P., Regitz M. Organometallics. 11:1992;177
112. Stoll M.E., Lovelace S.R., Geiger W.E., Schimanke H., Hyla-Kryspin I., Gleiter R. J. Am. Chem. Soc. 121:1999;9343
113. Sczepura L.F., Giambra J., See R.F., Lawson H., Janik T.S., Jircitano A.J., Churchill M.R., Takeuchi K.J. Inorg. Chim. Acta. 84:1984;91
114. Krejcik M., Danek M., Hartl F. J. Electroanal. Chem. 317:1991;179
115. S. Hartmann, R.F. Winter, B.M. Brunner, B. Sarkar, A. Knödler, I. Hartenbach, Eur. J. Inorg. Chem. (2003) 876.
116. Schilling B.E.R., Hoffmann R., Lichtenberger D.L. J. Am. Chem. Soc. 101:1979;585
117. Kostic N.M., Fenske R.F. Organometallics. 1:1982;974
118. Fonseca Guerra C., Snijders J.G., te Velde G., Baerends E.J. Theor. Chim. Acc. 99:1998;391
119. van Gisbergen S.J.A., Snijders J.G., Baerends E.J. Comput. Phys. Commun. 118:1999;119
120. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Revision A.11, Gaussian. Inc., Pittsburgh, PA, 1998.
121. Woon D.E., Dunning T.H. Jr. J. Chem. Phys. 98:1993;1358
122. Bergner A., Dolg M., Kuechle W., Stoll H., Preuss H. Mol. Phys. 80:1993;1431
123. Andrae D., Häussermann U., Dolg M., Stoll H., Preuss H. Theor. Chim. Acta. 77:1990;123
124. Stephens P.J., Devlin F.J., Cabalowski C.F., Frisch M.J. J. Phys. Chem. 98:1994;11623
125. Becke A.D. Phys. Rev. A. 38:1988;3098
126. Perdew J.P. Phys. Rev. A. 33:1986;8822