Unprecedented ROMP activity of low-valent rhenium-nitrosyl complexes: Mechanistic evaluation of an electrophilic olefin metathesis system

Chemistry - A European Journal

Volumn 12, Issue 12, 2006, Pages 3325-3338

  Frech, Christian M ^a   Blacque, Olivier ^a   Schmalle, Helmut W ^a   Berke, Heinz ^a   Adlhart, Christian ^b   Chen, Peter ^b  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b ETH ZURICH   (Switzerland)

Author keywords

Density functional calculations; Metathesis; Reaction mechanisms; Rhenium; Ring opening polymerization

Indexed keywords

BENZENE; COMPLEXATION; MOLECULAR WEIGHT; OLEFINS; POSITIVE IONS; REACTION KINETICS; RING OPENING POLYMERIZATION;

PHOSPHINE OXIDE; RHENIUM-NITROSYL COMPLEXES; RING-OPENING METATHESIS POLYMERIZATION (ROMP);

RHENIUM COMPOUNDS;

EID: 33646027292     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501025     Document Type: Article

References (138)

1. K. J. Ivin, J. C. Mol in Olefin Metathesis and Metathesis Polymerization (Eds.: K.J. Ivin, J. C. Mol), Academic Press, San Diego, 1997.
2. F. Zaragoza Dörwald in Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999.
3. A. Fürstner, Angew. Chem. 2000, 112, 3140;
4. Angew. Chem. Int. Ed. 2000, 39, 3012.
5. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18.
6. a) H. S. Eleuterio, US Patent 3074918, 1963;
7. b) H. S. Eleuterio, J. Mol. Catal. 1991, 65, 55;
8. c) there is earlier evidence for the discovery of the metathesis reaction in polymer chemistry (ROMP): A. W. Anderson, N. G. Merckling, US Patent 2721189, 1955;
9. d) for a comprehensive review: K. J. Ivin, J. C. Mol in Olefin Metathesis and Metathesis Polymerization (Eds.: K.J. Ivin, J. C. Mol), Academic Press, San Diego, 1997.
10. N. Calderon, H. Y. Chen, R.W. Scott, Tetrahedron Lett. 1967, 8, 3327.
11. S. T. Nguyen, L. K. Johnson, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1992, 114, 3974.
12. A. Demonceau, A. F. Noels, E. Saive, A. J. Hubert, J. Mol. Catal. 1992, 76, 123.
13. P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100.
14. a) S. M. Hansen, F. Rominger, M. Metz, P. Hofmann, Chem. Eur. J. 1999, 5, 557;
15. b) S. M. Hansen, M. A. O. Volland, F. Rominger, F. Eisenträger, P. Hofmann, Angew. Chem. 1999, 111, 1360;
16. Angew. Chem. Int. Ed. 1999, 38, 1273;
17. c) P. Hofmann, M. A. O. Volland, S. M. Hansen, F. Eisenträger, J. H. Gross, K. Stengel, J. Organomet. Chem. 2000, 606, 88.
18. a) M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247;
19. b) M. Scholl, S. Ding, W. C. Lee, R. H. Grubbs, Org. Lett. 1999, 1. 953.
20. a) J. Huang, E. D. Stevens, S. P. Nolan, J. L. Petersen, J. Am. Chem. Soc. 1999, 121, 2674;
21. b) J. Huang, H.-J. Schanz, S. P. Nolan, Organometallics 1999, 18, 5375.
22. a) T. Weskamp, F. J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. 1999, 111, 2573;
23. Angew. Chem. Int. Ed. 1999, 38, 2416;
24. b) L. Ackermann, A. Fürstner, T. Weskamp, F. J. Kohl, W. A. Herrmann, Tetrahedron Lett. 1999, 40, 4787:
25. c) T. Weskamp, F. J. Kohl, W. A. Herrmann, J. Organomet. Chem. 1999, 582, 362.
26. Reviews of NHC: a) W. A. Herrmann, C. Köher, Angew. Chem. 1997, 109, 2256;
27. Angew. Chem. Int. Ed. 1997, 36, 2162;
28. b) A. J. Ar-duengo, Acc. Chem. Res. 1999, 32, 913.
29. R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446.
30. a) R. R. Schrock, J. S. Murdzek, G. C. Bazan, J. Robbins, J. Dimare, M. B. O'Regan, J. Am. Chem. Soc. 1990, 112, 3875;
31. b) G. C. Bazan, E. Khosravi, R. R. Schrock. W. J. Feast, V. C. Gibson, M. B. O'Regan, J. K. Thomas, W. M. Davis, J. Am. Chem. Soc. 1990, 112, 8378;
32. c) G. C. Bazan, H. Oskam, H. N. Cho, L. Y. Park, R. R. Schrock, J. Am. Chem. Soc. 1991, 113, 6899.
33. P. E. Romero, W. E. Piers, R. McDonald, Angew. Chem. 2004, 116, 6287;
34. Angew. Chem. Int. Ed. 2004, 43, 6161.
35. E. L. Dias, S. T. Nguyen, R. H. Grubbs, J. Am. Chem. Soc. 1997, 119. 3887.
36. M. Ulman, R. H. Grubbs, Organometallics 1998, 17, 2484.
37. M. Ulman, R. H. Grubbs, J. Org. Chem. 1999, 64, 7202.
38. M. S. Sanford, M. Ulman, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 749.
39. M. S. Sanford, J. A. Love, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 6543.
40. C. Hinderling, C. Adlhart, P. Chen, Angew. Chem. 1998, 110, 2831:
41. Angew. Chem. Int. Ed. 1998, 37, 2685.
42. C. Adlhart, C. Hinderling, H. Baumann, P. Chen, J. Am. Chem. Soc. 2000, 122, 8204.
43. C. Adlhart, M. A. O. Volland, P. Hofmann, P. Chen, Helv. Chim. Acta 2000, 83, 3306.
44. M. A. O. Volland, C. Adlhart, C. A. Kiener, P. Chen, P. Hofmann, Chem. Eur. J. 2001, 7, 4621.
45. J. A. Tallarico, P. J. Bonitatebus Jr., M. L. Snapper. J. Am. Chem. Soc. 1997, 119, 7157.
46. M. S. Sanford, L. M. Henling, M. W. Day, R. H. Grubbs, Angew. Chem. 2000, 112, 3593;
47. Angew. Chem. Int. Ed. 2000, 39, 3451.
48. M. T. Reetz, M. H. Becker, M. Liebl, A. Fürstner, Angew. Chem. 2000, 112, 1294;
49. Angew. Chem. Int. Ed. 2000, 39, 1236.
50. A. Fürstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer, O. R. Thiel, Chem. Eur. J. 2001, 7, 3236.
51. a)E. J. Howman, L. Turner, Dutch Patent 6605328, 1966;
52. b) J. Cosyns, J. Chodorge, D. Commereuc, B. Torck, Hydrocarbon Process. 1998, 60.
53. X. Chen, X. Zhang, P. Chen, Angew. Chem. 2003, 115, 3928;
54. Angew. Chem. Int. Ed. 2003, 42, 3798.
55. a) W. A. Herrmann, J. Organomet. Chem. 1995, 500, 149;
56. b) C. C. Romao, F. E. Kühn, W. A. Herrmann, Chem. Rev. 1997, 97, 3197;
57. c) R. R. Schrock, R. T. Depue. J. Feldman, C. J. Schaverien, J. C. Dewan, A. H. Liu, J. Am. Chem. Soc. 1988, 110, 1423;
58. d) M. H. Schofield, R. R. Schrock, L. Y. Park, Organometallics 1991, 10, 1844;
59. e) A. Weinstock, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1991, 113, 135;
60. f) R. Toreki, R. R. Schrock, J. Am. Chem. Soc. 1990, 112, 2448;
61. g) R. Toreki, R. R. Schrock, J. Am. Chem. Soc. 1992, 114, 3367;
62. h) R. Toreki, G. A. Vaughan, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 127;
63. i) R. Toreki, R. R. Schrock, W. M. Davis, J. Organomet. Chem. 1996, 520, 69;
64. j) G. A. Vaughan, R. Toreki, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 2980;
65. k) A. M. LaPointe, R. R. Schrock, Organometallics 1995, 14, 1875.
66. a) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 17, 4251;
67. b) M. Doherty, A. Siove, A. Parlier, H. Rudler, M. Fontanillc, Makromol. Chem. Macromol. Symp. 1986, 6, 33;
68. c) S. Warwel, V. Siekermann, Makromol. Chem. Rapid Comm. 1983, 4, 423.
69. a) H. Jacobsen, K. Heinze, A. Llamazares, H. W. Schmalle, G. Artus, H. Berke, J. Chem. Soc. Dalton Trans. 1999, 1717;
70. b) A. Llamazares, H. W. Schmalle, H. Berke, Organometallics 2001, 20, 5277;
71. c) D. G. Gusev, A. Llamazares, G. Artus, H. Jacobsen, H. Berke, Organometallics 1999, 18, 75.
72. a) E. A. Zuech, Chem. Commun. 1968, 1182;
73. b) E. A. Zuech, W. B. Hughes, D. H. Kubicek, E. T. Kittleman, J. Am. Chem. Soc. 1970, 92. 528;
74. c)R. Taube, K. Z. Seyferth, Chem. Br. 1977, 13, 300;
75. d) R. Taube, K. Seyferth, Z. Anorg. Allg. Chem. 1973, 437, 213;
76. e) M. Leconte, J.-M. Basset, J. Am. Chem. Soc. 1979, 101, 7296;
77. f) K. Seyferth, K. Rosenthal, G. Kühn, R. Taube, Z. Anorg. Allg. Chem. 1984, 513, 57;
78. g) K. Seyferth, R. Taube, J. Organomet. Chem. 1984, 262, 191:
79. h) A. Keller, L. Szterenberg, J. Mol. Catal. 1989, 57, 207;
80. i) A. Keller, J. Organomet. Chem. 1990, 407, 237;
81. j) A. Keller, L. Szterenberg, Z. Naturforsch. Teil B 1991, 47, 1469;
82. k) A. Keller, J. Organomet. Chem. 1992, 436, 199;
83. l) A. Keller, J. Mol. Catal. 1993, 78, L15;
84. m) A. Keller, R. Matusiak, J. Mol. Catal. A 1996, 104, 213;
85. n) A. Keller, J. M. Sobczak, R. Matusiak, J. Mol. Catal. A 1998, 136, 115;
86. o) A. Keller, R. Matusiak, J. Mol. Catal. A 1999, 142, 317;
87. p) R. Matusiak, A. Keller, Polym. Bull. 1999, 43, 199.
88. a) W. Beck, A. Melnikoff, R. Stahl, Chem. Ber. 1966, 99, 3721;
89. b) A. Poletti, A. Foffani, R. Cataliotti, Spectrochim. Acta 1970, 26A, 1063.
90. a) J. M. E. Matos, B. S. Lima-Neto, J. Mol. Catal. A 2004, 222, 81;
91. b) N. Cobo, M. A. Esteruelas, F. Gonzalez, J. Herrero, A. M. Lopez, P. Lucio, M. Olivan, J. Catal. 2004, 223, 319;
92. c) L. Bencze, N. Biro, B. Szabo-Ravasz, L. Mihichuk, Can. J. Chem. 2004, 82, 499.
93. a) K. J. Ivin, B. S. R. Reddy, J. J. Rooney, J. Chem. Soc. Chem. Commun. 1981, 1062;
94. b) G. J. Spivak, J. N. Coalter, Organometallics 1998, 17, 999;
95. c) J. N. Coalter, G. J. Spivak, H. Gérard, E. Clot, E. R. Davidson, O. Eisenstein, K. C. Caulton, J. Am. Chem. Soc. 1998, 720, 9388;
96. d) J. N. Coalter, J. C. Bollinger, O. Eisenstein, K. G. Caulton, New J. Chem. 2000, 24, 925;
97. e) G. Ferrando-Miguel, J. N. Coalter, H. Gerard, J. C. Huffman, O. Eisenstein, K. G. Caulton, New J. Chem. 2002, 26, 687;
98. f) G. Ferrando, H. Gerard, G. J. Spivak, J. N. Coalter, J. C. Huffman, O. Eisenstein, K. G. Caulton, Inorg. Chem. 2001, 40, 6610;
99. g) J. N. Coalter, J. C. Bollinger, J. C. Huffman, U. Werner-Zwanziger, K. G. Caulton, E. R. Davidson, E. Clot, O. Eisenstein, New J. Chem. 2000, 24, 9;
100. h) N. Dolker, G. Frenking, J. Organomet. Chem. 2001, 677, 225.
101. a) O. Dereli, B. Duz, B. Zümreoglu-Karan, Y. Imanoglu, Appl. Organomet. Chem. 2004, 18, 130;
102. b) Y. Nakayama, K. Katsuda, H. Yasuda, Polym. J. 2003, 35, 896;
103. c) E. P. Bokaris, M. M. Kosmas, J. Mol. Catal. A 2003, 192, 263;
104. d) S. Hayano, H. Kurakata, Y. Tsunogae, Y. Nakayama, Y. Sato, H. Yasuda, Macromolecules 2003, 36, 7422.
105. a) S. M. Hansen, F. Rominger, M. Metz, P. Hofmann, Chem. Eur. J. 1999, 5, 557.
106. carbene nucleophilically, resulting in the formation of an alkyl unit, which could be labile, bonded to the metal center. If dissociation occurs, immediate protonation of the alkyl unit and liberation of the polymer chain would be accompanied by formation of an alkoxy-rhenium species. However, no experimental evidence has been obtained, nor theoretical investigation performed, which could support the proposed polymer liberation mechanism.
107. The basic electrospray source for mass spectrometry is described by: C. M. Whitehouse, R. N. Dreyer, M. M. Yamashita, J. B. Fenn, Anal. Chem. 1985, 57, 675.
108. A complete monograph on the technique is: Electrospray Ionization Mass Spectrometry (Ed.: R. D. Cole), Wiley, New York, 1997.
109. a) C. Adlhart, C. Hinderung, H. Baumann, P. Chen, J. Am. Chem. Soc. 2000, 122, 8204;
110. b) C. Hinderung, C. Adlhart, P. Chen, Angew. Chem. 1998, 110, 2831;
111. Angew. Chem. Int. Ed. 1998, 37, 2685.
112. M. A. O. Volland, C. Adlhart, C. A. Kiener, P. Chen, P. Hofmann, Chem. Eur. J. 2001, 7, 4621.
113. T. T. Cue, T. Bastelberger, H. Höcker, J. Mol. Catal. 1985, 28, 279.
114. a) H. Katayama, H. Urushima, F. Ozawa, J. Organomet. Chem. 2000, 606, 16;
115. b) P. A. van der Schaaf, R. Kolly, H. J. Kirner, F. Rime, A. Muhlebach, A. Hafner, J. Organomet. Chem. 2000, 606, 65.
116. C. Adlhart, Ph.D. Thesis, ETH Zürich, 2003.
117. M. S. Sanford, J. A. Love, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 6543.
118. M. J. Szabo, H. Berke, T. Weiss, T. Ziegler, Organometallics 2003, 22, 3671.
119. X. Creary, Synthesis 1986, 207.
120. Stoe IPDS software for data collection, cell refinement, and data reduction, Version 2.92, Stoe & Cie GmbH, Darmstadt, Germany, 1999.
121. P. Coppens, L. Leiserowitz, D. Rabinovich, Acta Crystallogr. 1965, 78(6), 1035.
122. G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467.
123. A. L. Spek, Acta Crystallogr. Sect. A 1990, 46, C34.
124. Y. Le Page, J. Appl. Crystallogr. 1987, 20, 264.
125. G. M. Sheldrick, SHELXL-97: Software package for crystal structure determination and refinement, University of Göttingen, Göttingen, Germany, 1997.
126. C. K. Johnson, ORTEPII, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge (TN), 1976.
127. TURBOMOLE, Program package for ab initio electronic structure calculations, Theoretical Chemistry Groups, University of Karlsruhe, Germany; http://www.turbomole.com;
128. a) R. Ahlrichs, M. Bär, M. Häser, H. Horn, C. Kölmel, Chem. Phys. Lett. 1989, 162, 165;
129. b) O. Treutler, R. Ahlrichs, J. Chem. Phys. 1995, 102, 346;
130. c) M. von Arnim, R. Ahlrichs, J. Comput. Chem. 1998, 19, 1746.
131. S. H. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 1980, 58, 1200.
132. A. D. Becke, Phys. Rev. A 1988, 38, 3098.
133. a) J. P. Perdew, Phys. Rev. B 1986, 33, 8822;
134. b) J. P. Perdew, Phys. Rev. B 1986, 34, 7406.
135. a) K. Eichkorn, O. Treutier, H. Öhm, M. Häser, R. Ahlrichs, Chem. Phys. Lett. 1995, 240, 283;
136. b) K. Eichkorn, O. Treutler, H. Ohm, M. Häser, R. Ahlrichs, Chem. Phys. Lett. 1995, 242, 652;
137. c) K. Eichkorn, F. Weigand, O. Treutler, R. Ahlrichs, Theor. Chem. Acc. 1997, 97, 119.
138. A. Schäfer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829.