Ruthenium Carbenes Bonded to a Macrocycle: Carbon Monoxide Induced Carbene Migration Pathways from the Metal to the Ligand

Angewandte Chemie - International Edition

Volumn 37, Issue 1-2, 1998, Pages 148-150

  Klose, Alain ^a   Solari, Euro ^a   Floriani, Carlo ^a   Geremia, Silvano ^b   Randaccio, Lucio ^b  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b NONE

Author keywords

Carbenes; Macrocycles; Metathesis; Rearrangements; Ruthenium

Indexed keywords

EID: 0031929840     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980202)37:1/2<148::aid-anie148>3.0.co;2-p     Document Type: Article

References (42)

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3. U. Schubert, H. Fischer, P. Hofmann, K. Weiss, K. H. Dötz, F. R. Kreissl, Transition Metal Carbene Complexes, VCH, Weinheim, 1983; W. D. Wulff in Advances in Metal-Organic Chemistry, Vol. 1 (Ed.: L. S. Liebeskind), Jay, London, 1989, pp. 209-393; J. W. Herndon, S. U. Turner, L. A. McMullen, J. J. Matasi, W. F. K. Schnatter in Advances in Metal-Organic Chemistry, Vol. 3 (Ed.: L. S. Liebeskind), Jay, London, 1994, pp. 51-95; M. P. Doyle, W. D. Wulff, L. S. Hegedus, J. R. Stille in Comprehensive Organometallic Chemistry II, Vol. 12, (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1995, Chapters 5.1-5.5.
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23. 2 as ancillary ligand in the organometallic chemistry of the early transition metals: a) V. L. Goedken, J. A. Ladd, J. Chem. Soc. Chem. Commun. 1981, 910-911; ibid. 1982, 142-144; b) C. Floriani, S. Ciurli, A. Chiesi-Villa, C. Guastini, Angew. Chem. 1987, 99, 86-88; Angew. Chem. Int. Ed. Engl. 1987, 26, 70-72; c) E. Solari, S. De Angelis, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1992, 31, 96-101; d) S. De Angelis, E. Solari, E. Gallo, C. Floriani, A. Chiesi-Villa, C. Rizzoli. ibid. 1992, 31, 2520-2527; e) L. Giannini, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1994, 106, 2279-2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2204-2206; f) L. Giannini, E. Solari, S. De Angelis, T. R. Ward, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1995, 117, 5801-5811; g) D. G. Black, D. C. Swenson, R. F. Jordan, Organometallics 1995, 14, 3539-3550; h) A. J. Blake, P. Mountford, G. I. Nikonov, D. Swallow, Chem. Commun. 1996, 1835-1836; i) H. Schumann, Inorg. Chem. 1996, 35, 1808-1813; j) G. I. Nikonov, A. J. Blake, P. Mountford, ibid. 1997, 36, 1107-1112.
24. 2 as ancillary ligand in the organometallic chemistry of the early transition metals: a) V. L. Goedken, J. A. Ladd, J. Chem. Soc. Chem. Commun. 1981, 910-911; ibid. 1982, 142-144; b) C. Floriani, S. Ciurli, A. Chiesi-Villa, C. Guastini, Angew. Chem. 1987, 99, 86-88; Angew. Chem. Int. Ed. Engl. 1987, 26, 70-72; c) E. Solari, S. De Angelis, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1992, 31, 96-101; d) S. De Angelis, E. Solari, E. Gallo, C. Floriani, A. Chiesi-Villa, C. Rizzoli. ibid. 1992, 31, 2520-2527; e) L. Giannini, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1994, 106, 2279-2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2204-2206; f) L. Giannini, E. Solari, S. De Angelis, T. R. Ward, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1995, 117, 5801-5811; g) D. G. Black, D. C. Swenson, R. F. Jordan, Organometallics 1995, 14, 3539-3550; h) A. J. Blake, P. Mountford, G. I. Nikonov, D. Swallow, Chem. Commun. 1996, 1835-1836; i) H. Schumann, Inorg. Chem. 1996, 35, 1808-1813; j) G. I. Nikonov, A. J. Blake, P. Mountford, ibid. 1997, 36, 1107-1112.
25. 2 as ancillary ligand in the organometallic chemistry of the early transition metals: a) V. L. Goedken, J. A. Ladd, J. Chem. Soc. Chem. Commun. 1981, 910-911; ibid. 1982, 142-144; b) C. Floriani, S. Ciurli, A. Chiesi-Villa, C. Guastini, Angew. Chem. 1987, 99, 86-88; Angew. Chem. Int. Ed. Engl. 1987, 26, 70-72; c) E. Solari, S. De Angelis, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1992, 31, 96-101; d) S. De Angelis, E. Solari, E. Gallo, C. Floriani, A. Chiesi-Villa, C. Rizzoli. ibid. 1992, 31, 2520-2527; e) L. Giannini, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1994, 106, 2279-2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2204-2206; f) L. Giannini, E. Solari, S. De Angelis, T. R. Ward, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1995, 117, 5801-5811; g) D. G. Black, D. C. Swenson, R. F. Jordan, Organometallics 1995, 14, 3539-3550; h) A. J. Blake, P. Mountford, G. I. Nikonov, D. Swallow, Chem. Commun. 1996, 1835-1836; i) H. Schumann, Inorg. Chem. 1996, 35, 1808-1813; j) G. I. Nikonov, A. J. Blake, P. Mountford, ibid. 1997, 36, 1107-1112.
26. 2 as ancillary ligand in the organometallic chemistry of the early transition metals: a) V. L. Goedken, J. A. Ladd, J. Chem. Soc. Chem. Commun. 1981, 910-911; ibid. 1982, 142-144; b) C. Floriani, S. Ciurli, A. Chiesi-Villa, C. Guastini, Angew. Chem. 1987, 99, 86-88; Angew. Chem. Int. Ed. Engl. 1987, 26, 70-72; c) E. Solari, S. De Angelis, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1992, 31, 96-101; d) S. De Angelis, E. Solari, E. Gallo, C. Floriani, A. Chiesi-Villa, C. Rizzoli. ibid. 1992, 31, 2520-2527; e) L. Giannini, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1994, 106, 2279-2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2204-2206; f) L. Giannini, E. Solari, S. De Angelis, T. R. Ward, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1995, 117, 5801-5811; g) D. G. Black, D. C. Swenson, R. F. Jordan, Organometallics 1995, 14, 3539-3550; h) A. J. Blake, P. Mountford, G. I. Nikonov, D. Swallow, Chem. Commun. 1996, 1835-1836; i) H. Schumann, Inorg. Chem. 1996, 35, 1808-1813; j) G. I. Nikonov, A. J. Blake, P. Mountford, ibid. 1997, 36, 1107-1112.
27. 2 as ancillary ligand in the organometallic chemistry of the early transition metals: a) V. L. Goedken, J. A. Ladd, J. Chem. Soc. Chem. Commun. 1981, 910-911; ibid. 1982, 142-144; b) C. Floriani, S. Ciurli, A. Chiesi-Villa, C. Guastini, Angew. Chem. 1987, 99, 86-88; Angew. Chem. Int. Ed. Engl. 1987, 26, 70-72; c) E. Solari, S. De Angelis, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1992, 31, 96-101; d) S. De Angelis, E. Solari, E. Gallo, C. Floriani, A. Chiesi-Villa, C. Rizzoli. ibid. 1992, 31, 2520-2527; e) L. Giannini, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1994, 106, 2279-2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2204-2206; f) L. Giannini, E. Solari, S. De Angelis, T. R. Ward, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1995, 117, 5801-5811; g) D. G. Black, D. C. Swenson, R. F. Jordan, Organometallics 1995, 14, 3539-3550; h) A. J. Blake, P. Mountford, G. I. Nikonov, D. Swallow, Chem. Commun. 1996, 1835-1836; i) H. Schumann, Inorg. Chem. 1996, 35, 1808-1813; j) G. I. Nikonov, A. J. Blake, P. Mountford, ibid. 1997, 36, 1107-1112.
28. 2 as ancillary ligand in the organometallic chemistry of the early transition metals: a) V. L. Goedken, J. A. Ladd, J. Chem. Soc. Chem. Commun. 1981, 910-911; ibid. 1982, 142-144; b) C. Floriani, S. Ciurli, A. Chiesi-Villa, C. Guastini, Angew. Chem. 1987, 99, 86-88; Angew. Chem. Int. Ed. Engl. 1987, 26, 70-72; c) E. Solari, S. De Angelis, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1992, 31, 96-101; d) S. De Angelis, E. Solari, E. Gallo, C. Floriani, A. Chiesi-Villa, C. Rizzoli. ibid. 1992, 31, 2520-2527; e) L. Giannini, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1994, 106, 2279-2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2204-2206; f) L. Giannini, E. Solari, S. De Angelis, T. R. Ward, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1995, 117, 5801-5811; g) D. G. Black, D. C. Swenson, R. F. Jordan, Organometallics 1995, 14, 3539-3550; h) A. J. Blake, P. Mountford, G. I. Nikonov, D. Swallow, Chem. Commun. 1996, 1835-1836; i) H. Schumann, Inorg. Chem. 1996, 35, 1808-1813; j) G. I. Nikonov, A. J. Blake, P. Mountford, ibid. 1997, 36, 1107-1112.
29. 2 as ancillary ligand in the organometallic chemistry of the early transition metals: a) V. L. Goedken, J. A. Ladd, J. Chem. Soc. Chem. Commun. 1981, 910-911; ibid. 1982, 142-144; b) C. Floriani, S. Ciurli, A. Chiesi-Villa, C. Guastini, Angew. Chem. 1987, 99, 86-88; Angew. Chem. Int. Ed. Engl. 1987, 26, 70-72; c) E. Solari, S. De Angelis, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1992, 31, 96-101; d) S. De Angelis, E. Solari, E. Gallo, C. Floriani, A. Chiesi-Villa, C. Rizzoli. ibid. 1992, 31, 2520-2527; e) L. Giannini, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1994, 106, 2279-2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2204-2206; f) L. Giannini, E. Solari, S. De Angelis, T. R. Ward, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1995, 117, 5801-5811; g) D. G. Black, D. C. Swenson, R. F. Jordan, Organometallics 1995, 14, 3539-3550; h) A. J. Blake, P. Mountford, G. I. Nikonov, D. Swallow, Chem. Commun. 1996, 1835-1836; i) H. Schumann, Inorg. Chem. 1996, 35, 1808-1813; j) G. I. Nikonov, A. J. Blake, P. Mountford, ibid. 1997, 36, 1107-1112.
30. 2 as ancillary ligand in the organometallic chemistry of the early transition metals: a) V. L. Goedken, J. A. Ladd, J. Chem. Soc. Chem. Commun. 1981, 910-911; ibid. 1982, 142-144; b) C. Floriani, S. Ciurli, A. Chiesi-Villa, C. Guastini, Angew. Chem. 1987, 99, 86-88; Angew. Chem. Int. Ed. Engl. 1987, 26, 70-72; c) E. Solari, S. De Angelis, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1992, 31, 96-101; d) S. De Angelis, E. Solari, E. Gallo, C. Floriani, A. Chiesi-Villa, C. Rizzoli. ibid. 1992, 31, 2520-2527; e) L. Giannini, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1994, 106, 2279-2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2204-2206; f) L. Giannini, E. Solari, S. De Angelis, T. R. Ward, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1995, 117, 5801-5811; g) D. G. Black, D. C. Swenson, R. F. Jordan, Organometallics 1995, 14, 3539-3550; h) A. J. Blake, P. Mountford, G. I. Nikonov, D. Swallow, Chem. Commun. 1996, 1835-1836; i) H. Schumann, Inorg. Chem. 1996, 35, 1808-1813; j) G. I. Nikonov, A. J. Blake, P. Mountford, ibid. 1997, 36, 1107-1112.
31. 2 as ancillary ligand in the organometallic chemistry of the early transition metals: a) V. L. Goedken, J. A. Ladd, J. Chem. Soc. Chem. Commun. 1981, 910-911; ibid. 1982, 142-144; b) C. Floriani, S. Ciurli, A. Chiesi-Villa, C. Guastini, Angew. Chem. 1987, 99, 86-88; Angew. Chem. Int. Ed. Engl. 1987, 26, 70-72; c) E. Solari, S. De Angelis, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1992, 31, 96-101; d) S. De Angelis, E. Solari, E. Gallo, C. Floriani, A. Chiesi-Villa, C. Rizzoli. ibid. 1992, 31, 2520-2527; e) L. Giannini, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1994, 106, 2279-2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2204-2206; f) L. Giannini, E. Solari, S. De Angelis, T. R. Ward, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1995, 117, 5801-5811; g) D. G. Black, D. C. Swenson, R. F. Jordan, Organometallics 1995, 14, 3539-3550; h) A. J. Blake, P. Mountford, G. I. Nikonov, D. Swallow, Chem. Commun. 1996, 1835-1836; i) H. Schumann, Inorg. Chem. 1996, 35, 1808-1813; j) G. I. Nikonov, A. J. Blake, P. Mountford, ibid. 1997, 36, 1107-1112.
32. 2 as ancillary ligand in the organometallic chemistry of the early transition metals: a) V. L. Goedken, J. A. Ladd, J. Chem. Soc. Chem. Commun. 1981, 910-911; ibid. 1982, 142-144; b) C. Floriani, S. Ciurli, A. Chiesi-Villa, C. Guastini, Angew. Chem. 1987, 99, 86-88; Angew. Chem. Int. Ed. Engl. 1987, 26, 70-72; c) E. Solari, S. De Angelis, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1992, 31, 96-101; d) S. De Angelis, E. Solari, E. Gallo, C. Floriani, A. Chiesi-Villa, C. Rizzoli. ibid. 1992, 31, 2520-2527; e) L. Giannini, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1994, 106, 2279-2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2204-2206; f) L. Giannini, E. Solari, S. De Angelis, T. R. Ward, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1995, 117, 5801-5811; g) D. G. Black, D. C. Swenson, R. F. Jordan, Organometallics 1995, 14, 3539-3550; h) A. J. Blake, P. Mountford, G. I. Nikonov, D. Swallow, Chem. Commun. 1996, 1835-1836; i) H. Schumann, Inorg. Chem. 1996, 35, 1808-1813; j) G. I. Nikonov, A. J. Blake, P. Mountford, ibid. 1997, 36, 1107-1112.
33. 2 as ancillary ligand in the organometallic chemistry of the early transition metals: a) V. L. Goedken, J. A. Ladd, J. Chem. Soc. Chem. Commun. 1981, 910-911; ibid. 1982, 142-144; b) C. Floriani, S. Ciurli, A. Chiesi-Villa, C. Guastini, Angew. Chem. 1987, 99, 86-88; Angew. Chem. Int. Ed. Engl. 1987, 26, 70-72; c) E. Solari, S. De Angelis, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1992, 31, 96-101; d) S. De Angelis, E. Solari, E. Gallo, C. Floriani, A. Chiesi-Villa, C. Rizzoli. ibid. 1992, 31, 2520-2527; e) L. Giannini, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1994, 106, 2279-2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2204-2206; f) L. Giannini, E. Solari, S. De Angelis, T. R. Ward, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1995, 117, 5801-5811; g) D. G. Black, D. C. Swenson, R. F. Jordan, Organometallics 1995, 14, 3539-3550; h) A. J. Blake, P. Mountford, G. I. Nikonov, D. Swallow, Chem. Commun. 1996, 1835-1836; i) H. Schumann, Inorg. Chem. 1996, 35, 1808-1813; j) G. I. Nikonov, A. J. Blake, P. Mountford, ibid. 1997, 36, 1107-1112.
34. 2 as ancillary ligand in the organometallic chemistry of the early transition metals: a) V. L. Goedken, J. A. Ladd, J. Chem. Soc. Chem. Commun. 1981, 910-911; ibid. 1982, 142-144; b) C. Floriani, S. Ciurli, A. Chiesi-Villa, C. Guastini, Angew. Chem. 1987, 99, 86-88; Angew. Chem. Int. Ed. Engl. 1987, 26, 70-72; c) E. Solari, S. De Angelis, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1992, 31, 96-101; d) S. De Angelis, E. Solari, E. Gallo, C. Floriani, A. Chiesi-Villa, C. Rizzoli. ibid. 1992, 31, 2520-2527; e) L. Giannini, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1994, 106, 2279-2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2204-2206; f) L. Giannini, E. Solari, S. De Angelis, T. R. Ward, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1995, 117, 5801-5811; g) D. G. Black, D. C. Swenson, R. F. Jordan, Organometallics 1995, 14, 3539-3550; h) A. J. Blake, P. Mountford, G. I. Nikonov, D. Swallow, Chem. Commun. 1996, 1835-1836; i) H. Schumann, Inorg. Chem. 1996, 35, 1808-1813; j) G. I. Nikonov, A. J. Blake, P. Mountford, ibid. 1997, 36, 1107-1112.
35. 2 as ancillary ligand in the organometallic chemistry of the early transition metals: a) V. L. Goedken, J. A. Ladd, J. Chem. Soc. Chem. Commun. 1981, 910-911; ibid. 1982, 142-144; b) C. Floriani, S. Ciurli, A. Chiesi-Villa, C. Guastini, Angew. Chem. 1987, 99, 86-88; Angew. Chem. Int. Ed. Engl. 1987, 26, 70-72; c) E. Solari, S. De Angelis, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1992, 31, 96-101; d) S. De Angelis, E. Solari, E. Gallo, C. Floriani, A. Chiesi-Villa, C. Rizzoli. ibid. 1992, 31, 2520-2527; e) L. Giannini, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1994, 106, 2279-2281; Angew. Chem. Int. Ed. Engl. 1994, 33, 2204-2206; f) L. Giannini, E. Solari, S. De Angelis, T. R. Ward, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Am. Chem. Soc. 1995, 117, 5801-5811; g) D. G. Black, D. C. Swenson, R. F. Jordan, Organometallics 1995, 14, 3539-3550; h) A. J. Blake, P. Mountford, G. I. Nikonov, D. Swallow, Chem. Commun. 1996, 1835-1836; i) H. Schumann, Inorg. Chem. 1996, 35, 1808-1813; j) G. I. Nikonov, A. J. Blake, P. Mountford, ibid. 1997, 36, 1107-1112.
36. a) F. A. Cotton, J. Czuchajowska, Polyhedron 1990, 9, 1221-1224;
37. b) L. Luo, E. D. Stevens, S. P. Nolan, Inorg. Chem. 1996, 35, 252-254.
38. Correct analytical data are available for 3-6 and 8.
39. -1, final R1, wR2, and S are 0.0365, 0.1117, and 1.896 for 467 parameters and 4986 unique observed reflections with I >2σ(I). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-179-177. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: int. code + (44) 1223-336033; e-mail: deposit@CCDC.cam.ac.uk).
40. J.-P. Djukic, D. A. Smith, V. G. Young, Jr., L. K. Woo, Organometallics 1994, 13, 3020-3026.
41. [5d]
42. C. Floriani, unpublished results.