Synthesis, structure, and reactivity of iridacyclohexadienone and iridaphenol complexes

Journal of the American Chemical Society

Volumn 119, Issue 36, 1997, Pages 8503-8511

  Bleeke, John R ^a   Behm, Robert ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IRIDIUM COMPLEX;

ARTICLE; CRYSTALLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 0030882572     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971721+     Document Type: Article

References (30)

1. Metallacyclohexadiene and Metallabenzene Chemistry. 14. For previous papers in this series, see: (a) Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118. (c) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (d) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (e) Bleeke, J. R.; Xie, Y.-F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703. (f) Bleeke, J. R.; Bass, L. A.; Xie, Y.-F.; Chiang, M. Y. J. Am. Chem. Soc. 1992, 114, 4213. (g) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (h) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517. (i) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970. (j) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, Jr., T. W.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093. (k) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606. (l) Bleeke, J. R.; Behm, R.; Beatty, A. M. Organometallics 1997, 16, 1103. (m) Bleeke, J. R.; Blanchard, J. M. B. J. Am. Chem. Soc. 1997, 119, 5443. See also: Bleeke, J. R. Acc. Chem. Res. 1991, 24. 271.
2. Metallacyclohexadiene and Metallabenzene Chemistry. 14. For previous papers in this series, see: (a) Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118. (c) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (d) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (e) Bleeke, J. R.; Xie, Y.-F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703. (f) Bleeke, J. R.; Bass, L. A.; Xie, Y.-F.; Chiang, M. Y. J. Am. Chem. Soc. 1992, 114, 4213. (g) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (h) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517. (i) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970. (j) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, Jr., T. W.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093. (k) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606. (l) Bleeke, J. R.; Behm, R.; Beatty, A. M. Organometallics 1997, 16, 1103. (m) Bleeke, J. R.; Blanchard, J. M. B. J. Am. Chem. Soc. 1997, 119, 5443. See also: Bleeke, J. R. Acc. Chem. Res. 1991, 24. 271.
3. Metallacyclohexadiene and Metallabenzene Chemistry. 14. For previous papers in this series, see: (a) Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118. (c) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (d) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (e) Bleeke, J. R.; Xie, Y.-F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703. (f) Bleeke, J. R.; Bass, L. A.; Xie, Y.-F.; Chiang, M. Y. J. Am. Chem. Soc. 1992, 114, 4213. (g) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (h) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517. (i) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970. (j) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, Jr., T. W.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093. (k) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606. (l) Bleeke, J. R.; Behm, R.; Beatty, A. M. Organometallics 1997, 16, 1103. (m) Bleeke, J. R.; Blanchard, J. M. B. J. Am. Chem. Soc. 1997, 119, 5443. See also: Bleeke, J. R. Acc. Chem. Res. 1991, 24. 271.
4. Metallacyclohexadiene and Metallabenzene Chemistry. 14. For previous papers in this series, see: (a) Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118. (c) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (d) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (e) Bleeke, J. R.; Xie, Y.-F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703. (f) Bleeke, J. R.; Bass, L. A.; Xie, Y.-F.; Chiang, M. Y. J. Am. Chem. Soc. 1992, 114, 4213. (g) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (h) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517. (i) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970. (j) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, Jr., T. W.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093. (k) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606. (l) Bleeke, J. R.; Behm, R.; Beatty, A. M. Organometallics 1997, 16, 1103. (m) Bleeke, J. R.; Blanchard, J. M. B. J. Am. Chem. Soc. 1997, 119, 5443. See also: Bleeke, J. R. Acc. Chem. Res. 1991, 24. 271.
5. Metallacyclohexadiene and Metallabenzene Chemistry. 14. For previous papers in this series, see: (a) Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118. (c) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (d) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (e) Bleeke, J. R.; Xie, Y.-F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703. (f) Bleeke, J. R.; Bass, L. A.; Xie, Y.-F.; Chiang, M. Y. J. Am. Chem. Soc. 1992, 114, 4213. (g) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (h) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517. (i) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970. (j) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, Jr., T. W.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093. (k) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606. (l) Bleeke, J. R.; Behm, R.; Beatty, A. M. Organometallics 1997, 16, 1103. (m) Bleeke, J. R.; Blanchard, J. M. B. J. Am. Chem. Soc. 1997, 119, 5443. See also: Bleeke, J. R. Acc. Chem. Res. 1991, 24. 271.
6. Metallacyclohexadiene and Metallabenzene Chemistry. 14. For previous papers in this series, see: (a) Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118. (c) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (d) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (e) Bleeke, J. R.; Xie, Y.-F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703. (f) Bleeke, J. R.; Bass, L. A.; Xie, Y.-F.; Chiang, M. Y. J. Am. Chem. Soc. 1992, 114, 4213. (g) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (h) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517. (i) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970. (j) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, Jr., T. W.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093. (k) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606. (l) Bleeke, J. R.; Behm, R.; Beatty, A. M. Organometallics 1997, 16, 1103. (m) Bleeke, J. R.; Blanchard, J. M. B. J. Am. Chem. Soc. 1997, 119, 5443. See also: Bleeke, J. R. Acc. Chem. Res. 1991, 24. 271.
7. Metallacyclohexadiene and Metallabenzene Chemistry. 14. For previous papers in this series, see: (a) Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118. (c) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (d) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (e) Bleeke, J. R.; Xie, Y.-F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703. (f) Bleeke, J. R.; Bass, L. A.; Xie, Y.-F.; Chiang, M. Y. J. Am. Chem. Soc. 1992, 114, 4213. (g) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (h) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517. (i) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970. (j) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, Jr., T. W.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093. (k) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606. (l) Bleeke, J. R.; Behm, R.; Beatty, A. M. Organometallics 1997, 16, 1103. (m) Bleeke, J. R.; Blanchard, J. M. B. J. Am. Chem. Soc. 1997, 119, 5443. See also: Bleeke, J. R. Acc. Chem. Res. 1991, 24. 271.
8. Metallacyclohexadiene and Metallabenzene Chemistry. 14. For previous papers in this series, see: (a) Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118. (c) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (d) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (e) Bleeke, J. R.; Xie, Y.-F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703. (f) Bleeke, J. R.; Bass, L. A.; Xie, Y.-F.; Chiang, M. Y. J. Am. Chem. Soc. 1992, 114, 4213. (g) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (h) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517. (i) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970. (j) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, Jr., T. W.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093. (k) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606. (l) Bleeke, J. R.; Behm, R.; Beatty, A. M. Organometallics 1997, 16, 1103. (m) Bleeke, J. R.; Blanchard, J. M. B. J. Am. Chem. Soc. 1997, 119, 5443. See also: Bleeke, J. R. Acc. Chem. Res. 1991, 24. 271.
9. Metallacyclohexadiene and Metallabenzene Chemistry. 14. For previous papers in this series, see: (a) Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118. (c) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (d) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (e) Bleeke, J. R.; Xie, Y.-F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703. (f) Bleeke, J. R.; Bass, L. A.; Xie, Y.-F.; Chiang, M. Y. J. Am. Chem. Soc. 1992, 114, 4213. (g) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (h) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517. (i) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970. (j) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, Jr., T. W.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093. (k) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606. (l) Bleeke, J. R.; Behm, R.; Beatty, A. M. Organometallics 1997, 16, 1103. (m) Bleeke, J. R.; Blanchard, J. M. B. J. Am. Chem. Soc. 1997, 119, 5443. See also: Bleeke, J. R. Acc. Chem. Res. 1991, 24. 271.
10. Metallacyclohexadiene and Metallabenzene Chemistry. 14. For previous papers in this series, see: (a) Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118. (c) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (d) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (e) Bleeke, J. R.; Xie, Y.-F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703. (f) Bleeke, J. R.; Bass, L. A.; Xie, Y.-F.; Chiang, M. Y. J. Am. Chem. Soc. 1992, 114, 4213. (g) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (h) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517. (i) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970. (j) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, Jr., T. W.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093. (k) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606. (l) Bleeke, J. R.; Behm, R.; Beatty, A. M. Organometallics 1997, 16, 1103. (m) Bleeke, J. R.; Blanchard, J. M. B. J. Am. Chem. Soc. 1997, 119, 5443. See also: Bleeke, J. R. Acc. Chem. Res. 1991, 24. 271.
11. Metallacyclohexadiene and Metallabenzene Chemistry. 14. For previous papers in this series, see: (a) Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118. (c) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (d) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (e) Bleeke, J. R.; Xie, Y.-F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703. (f) Bleeke, J. R.; Bass, L. A.; Xie, Y.-F.; Chiang, M. Y. J. Am. Chem. Soc. 1992, 114, 4213. (g) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (h) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517. (i) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970. (j) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, Jr., T. W.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093. (k) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606. (l) Bleeke, J. R.; Behm, R.; Beatty, A. M. Organometallics 1997, 16, 1103. (m) Bleeke, J. R.; Blanchard, J. M. B. J. Am. Chem. Soc. 1997, 119, 5443. See also: Bleeke, J. R. Acc. Chem. Res. 1991, 24. 271.
12. Metallacyclohexadiene and Metallabenzene Chemistry. 14. For previous papers in this series, see: (a) Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118. (c) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (d) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (e) Bleeke, J. R.; Xie, Y.-F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703. (f) Bleeke, J. R.; Bass, L. A.; Xie, Y.-F.; Chiang, M. Y. J. Am. Chem. Soc. 1992, 114, 4213. (g) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (h) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517. (i) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970. (j) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, Jr., T. W.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093. (k) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606. (l) Bleeke, J. R.; Behm, R.; Beatty, A. M. Organometallics 1997, 16, 1103. (m) Bleeke, J. R.; Blanchard, J. M. B. J. Am. Chem. Soc. 1997, 119, 5443. See also: Bleeke, J. R. Acc. Chem. Res. 1991, 24. 271.
13. Metallacyclohexadiene and Metallabenzene Chemistry. 14. For previous papers in this series, see: (a) Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118. (c) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (d) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (e) Bleeke, J. R.; Xie, Y.-F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703. (f) Bleeke, J. R.; Bass, L. A.; Xie, Y.-F.; Chiang, M. Y. J. Am. Chem. Soc. 1992, 114, 4213. (g) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (h) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517. (i) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970. (j) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, Jr., T. W.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093. (k) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606. (l) Bleeke, J. R.; Behm, R.; Beatty, A. M. Organometallics 1997, 16, 1103. (m) Bleeke, J. R.; Blanchard, J. M. B. J. Am. Chem. Soc. 1997, 119, 5443. See also: Bleeke, J. R. Acc. Chem. Res. 1991, 24. 271.
14. Metallacyclohexadiene and Metallabenzene Chemistry. 14. For previous papers in this series, see: (a) Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118. (c) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (d) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (e) Bleeke, J. R.; Xie, Y.-F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703. (f) Bleeke, J. R.; Bass, L. A.; Xie, Y.-F.; Chiang, M. Y. J. Am. Chem. Soc. 1992, 114, 4213. (g) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (h) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517. (i) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970. (j) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, Jr., T. W.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093. (k) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606. (l) Bleeke, J. R.; Behm, R.; Beatty, A. M. Organometallics 1997, 16, 1103. (m) Bleeke, J. R.; Blanchard, J. M. B. J. Am. Chem. Soc. 1997, 119, 5443. See also: Bleeke, J. R. Acc. Chem. Res. 1991, 24. 271.
15. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; pp 512-513.
16. 2-aldehyde)metal complex, and dissociation of the aldehyde CO bond from the iridium center may precede C5-H bond activation.
17. 3 complexes (see ref 1f).
18. Several other (1,2,5-η-penta-1,3-dien-5-oyl)metal complexes have been previously characterized by X-ray diffraction: (a) Brammer, L.; Crocker, M.; Dunne, B. J.; Green, M.; Morton, C. E.; Nagle, K. R.; Orpen, A. G. J. Chem. Soc., Chem. Commun. 1986, 1226. (b) Crocker, M.; Dunne, B. J.; Green, M.; Orpen, A. G. J. Chem. Soc. Dalton Trans. 1991, 1589. (c) Garlaschelli, L.; Malatesta, M. C.; Panzeri, S. Organometallics 1987, 6, 63.
19. Several other (1,2,5-η-penta-1,3-dien-5-oyl)metal complexes have been previously characterized by X-ray diffraction: (a) Brammer, L.; Crocker, M.; Dunne, B. J.; Green, M.; Morton, C. E.; Nagle, K. R.; Orpen, A. G. J. Chem. Soc., Chem. Commun. 1986, 1226. (b) Crocker, M.; Dunne, B. J.; Green, M.; Orpen, A. G. J. Chem. Soc. Dalton Trans. 1991, 1589. (c) Garlaschelli, L.; Malatesta, M. C.; Panzeri, S. Organometallics 1987, 6, 63.
20. Several other (1,2,5-η-penta-1,3-dien-5-oyl)metal complexes have been previously characterized by X-ray diffraction: (a) Brammer, L.; Crocker, M.; Dunne, B. J.; Green, M.; Morton, C. E.; Nagle, K. R.; Orpen, A. G. J. Chem. Soc., Chem. Commun. 1986, 1226. (b) Crocker, M.; Dunne, B. J.; Green, M.; Orpen, A. G. J. Chem. Soc. Dalton Trans. 1991, 1589. (c) Garlaschelli, L.; Malatesta, M. C.; Panzeri, S. Organometallics 1987, 6, 63.
21. 1-buta-1,3-dienyl) complexes: Yongskulrote, W.; Bramlett, J. M.; Mike, C. A.; Durham, B.; Allison, N. T. Organometallics 1989, 8, 556.
22. C-P value increases with increasing s character in the carbon hybridization.
23. 3.
24. Huheey, J. E. Inorganic Chemistry: Principles of Structure and Reactivity; Harper and Row: New York, 1972; pp 423-440.
25. To our knowledge, there have been no prior reports of metallaphenols. Perhaps the closest reported relative is an metallathiaphenol, synthesized by Roper: Elliott, G. P.; Roper, W. R.; Waters, J. M. J. Chem. Soc., Chem. Commun. 1982, 811.
26. 3.
27. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G.; Taylor, R. J. Chem. Soc., Dalton Trans. 1989, S1.
28. Compound 1 and related aromatic metallacycles are typically orange or red in color (see ref 1).
29. Stout, G. H.; Jensen, L. H. X-Ray Structure Determination; Macmillan Publishing Co., Inc.: New York, 1968; pp 302-303.
30. Atomic scattering factors were obtained from the following: International Tables for X-Ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. IV.