Ring strain perturbation of the equilibria between hydroxycarbene complexes and metal acyl hydride complexes

Journal of the American Chemical Society

Volumn 119, Issue 17, 1997, Pages 3971-3978

  Casey, Charles P ^a   Czerwinski, Curtis J ^a   Fusie, Kerry A ^a   Hayashi, Randy K ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ANION; LITHIUM; METAL COMPLEX; RHENIUM;

ALKYLATION; ARTICLE; COMPLEX FORMATION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0030996172     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9637311     Document Type: Article

References (59)

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25. For other examples of hydroxycarbene complexes see: (a) Green, M. L. H.; Mitchard, L. C.; Swanwick, M. G. J. Chem. Soc. A 1971, 794. (b) Fischer, E. O.; Kreis, G.; Kreissl, F. R. J. Organomet. Chem. 1973, 56, C37. (c) Webb, M. J.; Stewart, R. P. Jr.; Graham, W. A. G. J. Organomet. Chem. 1973, 59, C21. (d) Wong, W.-K.; Tam, W.; Gladysz, J. A. J. Am. Chem. Soc. 1979, 101, 5440. (e) Darst, K. P.; Lenhert, P. G.; Lukehart, C. M.; Warfield, L. T. J. Organomet. Chem. 1980, 195, 317. (f) Buhro, W. E.; Wong, A.; Merrifield, J. H.; Lin, G.-Y.; Constable, A. C.; Gladysz, J. A. Organometallics 1983, 2, 1852. (g) Powell, J.; Farrar, D. H.; Smith, S. J. Inorg. Chim. Acta 1984, 85, L23. (h) Gibson, D. H.; Mandal, S. K.; Owens K.; Richardson, J. F. Organometallics 1990, 9, 1936 and references therein. (i) Casey, C. P.; Sakaba, H.; Underiner, T. L. J. Am. Chem. Soc. 1991, 113, 6673 and references therein. (j) Asdar, A., Lapinte, C. J. Organomet. Chem. 1987, 327, C33.
26. For other examples of hydroxycarbene complexes see: (a) Green, M. L. H.; Mitchard, L. C.; Swanwick, M. G. J. Chem. Soc. A 1971, 794. (b) Fischer, E. O.; Kreis, G.; Kreissl, F. R. J. Organomet. Chem. 1973, 56, C37. (c) Webb, M. J.; Stewart, R. P. Jr.; Graham, W. A. G. J. Organomet. Chem. 1973, 59, C21. (d) Wong, W.-K.; Tam, W.; Gladysz, J. A. J. Am. Chem. Soc. 1979, 101, 5440. (e) Darst, K. P.; Lenhert, P. G.; Lukehart, C. M.; Warfield, L. T. J. Organomet. Chem. 1980, 195, 317. (f) Buhro, W. E.; Wong, A.; Merrifield, J. H.; Lin, G.-Y.; Constable, A. C.; Gladysz, J. A. Organometallics 1983, 2, 1852. (g) Powell, J.; Farrar, D. H.; Smith, S. J. Inorg. Chim. Acta 1984, 85, L23. (h) Gibson, D. H.; Mandal, S. K.; Owens K.; Richardson, J. F. Organometallics 1990, 9, 1936 and references therein. (i) Casey, C. P.; Sakaba, H.; Underiner, T. L. J. Am. Chem. Soc. 1991, 113, 6673 and references therein. (j) Asdar, A., Lapinte, C. J. Organomet. Chem. 1987, 327, C33.
27. For other examples of hydroxycarbene complexes see: (a) Green, M. L. H.; Mitchard, L. C.; Swanwick, M. G. J. Chem. Soc. A 1971, 794. (b) Fischer, E. O.; Kreis, G.; Kreissl, F. R. J. Organomet. Chem. 1973, 56, C37. (c) Webb, M. J.; Stewart, R. P. Jr.; Graham, W. A. G. J. Organomet. Chem. 1973, 59, C21. (d) Wong, W.-K.; Tam, W.; Gladysz, J. A. J. Am. Chem. Soc. 1979, 101, 5440. (e) Darst, K. P.; Lenhert, P. G.; Lukehart, C. M.; Warfield, L. T. J. Organomet. Chem. 1980, 195, 317. (f) Buhro, W. E.; Wong, A.; Merrifield, J. H.; Lin, G.-Y.; Constable, A. C.; Gladysz, J. A. Organometallics 1983, 2, 1852. (g) Powell, J.; Farrar, D. H.; Smith, S. J. Inorg. Chim. Acta 1984, 85, L23. (h) Gibson, D. H.; Mandal, S. K.; Owens K.; Richardson, J. F. Organometallics 1990, 9, 1936 and references therein. (i) Casey, C. P.; Sakaba, H.; Underiner, T. L. J. Am. Chem. Soc. 1991, 113, 6673 and references therein. (j) Asdar, A., Lapinte, C. J. Organomet. Chem. 1987, 327, C33.
28. For other examples of hydroxycarbene complexes see: (a) Green, M. L. H.; Mitchard, L. C.; Swanwick, M. G. J. Chem. Soc. A 1971, 794. (b) Fischer, E. O.; Kreis, G.; Kreissl, F. R. J. Organomet. Chem. 1973, 56, C37. (c) Webb, M. J.; Stewart, R. P. Jr.; Graham, W. A. G. J. Organomet. Chem. 1973, 59, C21. (d) Wong, W.-K.; Tam, W.; Gladysz, J. A. J. Am. Chem. Soc. 1979, 101, 5440. (e) Darst, K. P.; Lenhert, P. G.; Lukehart, C. M.; Warfield, L. T. J. Organomet. Chem. 1980, 195, 317. (f) Buhro, W. E.; Wong, A.; Merrifield, J. H.; Lin, G.-Y.; Constable, A. C.; Gladysz, J. A. Organometallics 1983, 2, 1852. (g) Powell, J.; Farrar, D. H.; Smith, S. J. Inorg. Chim. Acta 1984, 85, L23. (h) Gibson, D. H.; Mandal, S. K.; Owens K.; Richardson, J. F. Organometallics 1990, 9, 1936 and references therein. (i) Casey, C. P.; Sakaba, H.; Underiner, T. L. J. Am. Chem. Soc. 1991, 113, 6673 and references therein. (j) Asdar, A., Lapinte, C. J. Organomet. Chem. 1987, 327, C33.
29. For other examples of hydroxycarbene complexes see: (a) Green, M. L. H.; Mitchard, L. C.; Swanwick, M. G. J. Chem. Soc. A 1971, 794. (b) Fischer, E. O.; Kreis, G.; Kreissl, F. R. J. Organomet. Chem. 1973, 56, C37. (c) Webb, M. J.; Stewart, R. P. Jr.; Graham, W. A. G. J. Organomet. Chem. 1973, 59, C21. (d) Wong, W.-K.; Tam, W.; Gladysz, J. A. J. Am. Chem. Soc. 1979, 101, 5440. (e) Darst, K. P.; Lenhert, P. G.; Lukehart, C. M.; Warfield, L. T. J. Organomet. Chem. 1980, 195, 317. (f) Buhro, W. E.; Wong, A.; Merrifield, J. H.; Lin, G.-Y.; Constable, A. C.; Gladysz, J. A. Organometallics 1983, 2, 1852. (g) Powell, J.; Farrar, D. H.; Smith, S. J. Inorg. Chim. Acta 1984, 85, L23. (h) Gibson, D. H.; Mandal, S. K.; Owens K.; Richardson, J. F. Organometallics 1990, 9, 1936 and references therein. (i) Casey, C. P.; Sakaba, H.; Underiner, T. L. J. Am. Chem. Soc. 1991, 113, 6673 and references therein. (j) Asdar, A., Lapinte, C. J. Organomet. Chem. 1987, 327, C33.
30. For other examples of hydroxycarbene complexes see: (a) Green, M. L. H.; Mitchard, L. C.; Swanwick, M. G. J. Chem. Soc. A 1971, 794. (b) Fischer, E. O.; Kreis, G.; Kreissl, F. R. J. Organomet. Chem. 1973, 56, C37. (c) Webb, M. J.; Stewart, R. P. Jr.; Graham, W. A. G. J. Organomet. Chem. 1973, 59, C21. (d) Wong, W.-K.; Tam, W.; Gladysz, J. A. J. Am. Chem. Soc. 1979, 101, 5440. (e) Darst, K. P.; Lenhert, P. G.; Lukehart, C. M.; Warfield, L. T. J. Organomet. Chem. 1980, 195, 317. (f) Buhro, W. E.; Wong, A.; Merrifield, J. H.; Lin, G.-Y.; Constable, A. C.; Gladysz, J. A. Organometallics 1983, 2, 1852. (g) Powell, J.; Farrar, D. H.; Smith, S. J. Inorg. Chim. Acta 1984, 85, L23. (h) Gibson, D. H.; Mandal, S. K.; Owens K.; Richardson, J. F. Organometallics 1990, 9, 1936 and references therein. (i) Casey, C. P.; Sakaba, H.; Underiner, T. L. J. Am. Chem. Soc. 1991, 113, 6673 and references therein. (j) Asdar, A., Lapinte, C. J. Organomet. Chem. 1987, 327, C33.
31. For other examples of hydroxycarbene complexes see: (a) Green, M. L. H.; Mitchard, L. C.; Swanwick, M. G. J. Chem. Soc. A 1971, 794. (b) Fischer, E. O.; Kreis, G.; Kreissl, F. R. J. Organomet. Chem. 1973, 56, C37. (c) Webb, M. J.; Stewart, R. P. Jr.; Graham, W. A. G. J. Organomet. Chem. 1973, 59, C21. (d) Wong, W.-K.; Tam, W.; Gladysz, J. A. J. Am. Chem. Soc. 1979, 101, 5440. (e) Darst, K. P.; Lenhert, P. G.; Lukehart, C. M.; Warfield, L. T. J. Organomet. Chem. 1980, 195, 317. (f) Buhro, W. E.; Wong, A.; Merrifield, J. H.; Lin, G.-Y.; Constable, A. C.; Gladysz, J. A. Organometallics 1983, 2, 1852. (g) Powell, J.; Farrar, D. H.; Smith, S. J. Inorg. Chim. Acta 1984, 85, L23. (h) Gibson, D. H.; Mandal, S. K.; Owens K.; Richardson, J. F. Organometallics 1990, 9, 1936 and references therein. (i) Casey, C. P.; Sakaba, H.; Underiner, T. L. J. Am. Chem. Soc. 1991, 113, 6673 and references therein. (j) Asdar, A., Lapinte, C. J. Organomet. Chem. 1987, 327, C33.
32. For other examples of hydroxycarbene complexes see: (a) Green, M. L. H.; Mitchard, L. C.; Swanwick, M. G. J. Chem. Soc. A 1971, 794. (b) Fischer, E. O.; Kreis, G.; Kreissl, F. R. J. Organomet. Chem. 1973, 56, C37. (c) Webb, M. J.; Stewart, R. P. Jr.; Graham, W. A. G. J. Organomet. Chem. 1973, 59, C21. (d) Wong, W.-K.; Tam, W.; Gladysz, J. A. J. Am. Chem. Soc. 1979, 101, 5440. (e) Darst, K. P.; Lenhert, P. G.; Lukehart, C. M.; Warfield, L. T. J. Organomet. Chem. 1980, 195, 317. (f) Buhro, W. E.; Wong, A.; Merrifield, J. H.; Lin, G.-Y.; Constable, A. C.; Gladysz, J. A. Organometallics 1983, 2, 1852. (g) Powell, J.; Farrar, D. H.; Smith, S. J. Inorg. Chim. Acta 1984, 85, L23. (h) Gibson, D. H.; Mandal, S. K.; Owens K.; Richardson, J. F. Organometallics 1990, 9, 1936 and references therein. (i) Casey, C. P.; Sakaba, H.; Underiner, T. L. J. Am. Chem. Soc. 1991, 113, 6673 and references therein. (j) Asdar, A., Lapinte, C. J. Organomet. Chem. 1987, 327, C33.
33. For other examples of hydroxycarbene complexes see: (a) Green, M. L. H.; Mitchard, L. C.; Swanwick, M. G. J. Chem. Soc. A 1971, 794. (b) Fischer, E. O.; Kreis, G.; Kreissl, F. R. J. Organomet. Chem. 1973, 56, C37. (c) Webb, M. J.; Stewart, R. P. Jr.; Graham, W. A. G. J. Organomet. Chem. 1973, 59, C21. (d) Wong, W.-K.; Tam, W.; Gladysz, J. A. J. Am. Chem. Soc. 1979, 101, 5440. (e) Darst, K. P.; Lenhert, P. G.; Lukehart, C. M.; Warfield, L. T. J. Organomet. Chem. 1980, 195, 317. (f) Buhro, W. E.; Wong, A.; Merrifield, J. H.; Lin, G.-Y.; Constable, A. C.; Gladysz, J. A. Organometallics 1983, 2, 1852. (g) Powell, J.; Farrar, D. H.; Smith, S. J. Inorg. Chim. Acta 1984, 85, L23. (h) Gibson, D. H.; Mandal, S. K.; Owens K.; Richardson, J. F. Organometallics 1990, 9, 1936 and references therein. (i) Casey, C. P.; Sakaba, H.; Underiner, T. L. J. Am. Chem. Soc. 1991, 113, 6673 and references therein. (j) Asdar, A., Lapinte, C. J. Organomet. Chem. 1987, 327, C33.
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44. 3. Reaction of the bromide with t-BuLi gave a 67:33 mixture of elimination and metal-halogen exchange products. Reaction of the iodide with n-BuLi gave a 38:62 mixture of elimination and metal-halogen exchange products. See the Supporting Information for full experimental details and characterization.
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57. 3 was observed. See the Supporting Information for details.
58. 3. Ethylene oxide from a lecture bottle was purified by condensation into a flask at -23°C and 400 mmHg. Carbon dioxide did not condense under these conditions. Pure ethylene oxide was distilled from the collection flask as needed.
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