Stable o-quinone methide complexes of iridium: Synthesis, structure, and reversed reactivity imparted by metal complexation

Organometallics

Volumn 19, Issue 9, 2000, Pages 1740-1748

  Amouri, Hani ^a   Vaissermann, Jacqueline ^a   Rager, Marie Noelle ^b   Grotjahn, Douglas B ^c  

^a CNRS   (France)

^b PSL RESEARCH UNIVERSITY   (France)

^c SAN DIEGO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COMPLEXATION; DERIVATIVES; ISOMERS; MOLECULAR STRUCTURE; ORGANIC ACIDS; ORGANIC POLYMERS; SYNTHESIS (CHEMICAL);

OXODIENYL COMPLEXES; QUINONE METHIDE; TRICYCLIC IRIDIUM COMPLEX;

METALLORGANIC POLYMERS;

EID: 0033743279     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om000073r     Document Type: Article

References (76)

1. (a) Wagner, H.-U.; Gompper, R. In The Chemistry of the Quinonoid Compounds; Patai, S., Ed.; Wiley: New York, 1974; Part 2, Chapter 18.
2. (b) Desimoni, G.; Tacconi, G. Chem. Rev. 1975, 75, 651-692, especially pp 654-655.
3. (c) Boger, D. L.; Weinreb, S. N. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: New York, 1987; p 193.
4. (d) Berson, J. In The Chemistry of the Quinonoid Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1988; Vol. 2, Part 1, pp 455-536.
5. (e) Thompson, D. C.; Thompson, J. A.; Sugumaran, M.; Moldeus, P. Chem.-Biol. Interact. 1993, 86, 129-162.
6. (f) Wan, P.; Barker, B.; Diao, L.; Fischer, M.; Shi, Y.; Yang, C. Can. J. Chem. 1996, 74, 465-475.
7. Smith, D. A.; Dimmel, D. R. J. Org. Chem. 1988, 53, 5428-5434.
8. Pardini, V. L.; Smith, C. Z.; Utley, J. H. P.; Vargas, R. R.; Viertler, H. J. Org. Chem. 1991, 56, 7305-7313, and references therein.
9. Leading references: (a) Angle, S. R.; Arnaiz, D. O.; Boyce, J. P.; Frutos, R. P.; Louie, M. S.; Mattson-Arnaiz, H. L.; Rainer, J. D.; Turnbull, K. D.; Yang, W. J. Org,. Chem. 1994, 59, 6322-6337.
10. (b) Angle, S. R.; Arnaiz, D. O. J. Org. Chem. 1992, 57, 5937-5947.
11. (c) Angle, S. R.; Rainier, J. D. J. Org. Chem. 1992, 57, 6883-6890.
12. (a) Padwa, A.; Lee, G. A.; J. Chem. Soc., Chem. Commun. 1972, 795-796.
13. (b) Padwa, A.; Au, A.; Lee, G. A.; Owens, W. J. Org. Chem. 1975, 40, 1142-1149.
14. (c) Padwa, A.; Lee, G. A.; Owens, W. J. Am. Chem. Soc. 1976, 98, 3555-3564.
15. (d) Karabelas, K.; Moore, H. W. J. Am. Chem. Soc. 1990, 112, 5372-5373.
16. (e) Huang, C.-G.; Beveridge, K. A.; Wan, P. J. Am. Chem. Soc. 1991, 113, 7676-7684.
17. (f) Huang, C.-G.; Shukla, D.; Wan, P. J. Org. Chem. 1991, 56, 5437-5442.
18. (g) Katritzky, A. R.; Zhang, Z.; Lan, X.; Lang, H. J. Org. Chem. 1994, 59, 1900-1903.
19. (a) Chapman, O. L.; Engel, O. R.; Springer, J. P.; Clardy, J. C. J. Am. Chem. Soc. 1971, 93, 6696-6698.
20. (b) Chauhan, M. S.; Dean, F. M.; McDonald, S.; Robinson, M. S. J. Chem. Soc., Perkin Trans. 1 1973, 359-363.
21. (c) Balasubramanian, K. K.; Selvaraj, S. J. Org. Chem. 1980, 45, 3726-3727.
22. (d) Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1981, 22, 4437-4440.
23. (e) Marino, J. P.; Dax, S. L. J. Org. Chem. 1984, 49, 3671-3672.
24. (f) Katada, T.; Eguchi, S.; Esaki, T.; Sasaki T. J. Chem. Soc., Perkin Trans. 1 1984, 2649-2653.
25. (g) Talley, J. J. J. Org. Chem. 1985, 50, 1695-1699.
26. (h) Inoue, T.; Inoue, S.; Sato, K. Chem. Lett. 1989, 653-656.
27. Chambers, J. D.; Crawford, J.; Williams, H. W. R.; Dufresne, C.; Scheigetz, J.; Bernstein, M. A.; Lau, C. K. Can. J. Chem. 1992, 70, 1717-1732.
28. (j) Génisson, Y.; Tyler, P. C.; Young, R. N. J. Am. Chem. Soc. 1994, 116, 759-760.
29. (k) Diao, L.; Yang, C.; Wan, P. J. Am. Chem. Soc. 1995, 117, 5369-5370.
30. Chiba. K.; Hirano, T.; Kitano, Y.; Tada, M. J. Chem. Soc., Chem. Commun. 1999, 691-692.
31. (a) Egberston, M. Danishefsky, S. J. J. Am. Chem. Soc. 1987, 109, 2204-2205.
32. (b) Tomasz, A. K. Chawla, A. K. Lipman, R. Biochemistry, 1988, 27, 3182-3187.
33. (c) Ouyang, A.; Skibo, E. B. J. Org. Chem. 1998, 63, 1893-1900.
34. (d)Alkylations of DNA by related quinone methides: Chatterjee M.; Rokita, E. S. J. Am. Chem. Soc. 1990, 112, 6397-6398.
35. Chatterjee M.; Rokita, E. S. J. Am. Chem. Soc. 1991, 113, 5116-5117.
36. Chatterjee M.; Rokita, E. S. J. Am. Chem. Soc. 1994, 116, 1690-1697.
37. (e) Lin, A. J.; Pradini, R. S.; Cosby, L. A.; Lillis, B. J.; Shansky, C. W.; Sartorelli, A. C. J. Med. Chem. 1973, 16, 1268-1271.
38. (f) Antonini, I.; Lin, T.-S.; Cosby, L. A.; Dai, Y.-R. Sartorelli, A. C. J. Med. Chem. 1982, 25, 730-735, and previous papers.
39. (a) McIntosh, C. L.; Chapman, O. L. J. Chem. Soc., Chem. Commun. 1971, 771.
40. Chapman, O. L.; McIntosh, C. L. J. Chem. Soc., Chem. Commun., Ibid. 1971, 383-384.
41. (b) Eck, V.; Schweig, A.; Vermeer, H. Tetrahedron Lett. 1978, 2433-2436.
42. (c) Letulle, M.; Guenot, P.; Rippol, J.-L. Tetrahedron Lett. 1991, 32, 2013-2016.
43. (d) Tomioka, H. Pure Appl. Chem. 1997, 69, 837-840.
44. (e) Tomioka, H.; Matsushita, T. Chem. Lett. 1997, 399-400.
45. (f) Qiao, G. G.-H.; Lenghaus, K.; Solomon, D. H.; Reisinger, A.; Bytheway, I.; Wentrup, C. J. Org. Chem. 1998, 63, 9806-9811.
46. (a) Kopach, M. E.; Harman, W. D. J. Am. Chem. Soc. 1994, 116, 6581-6592.
47. (b) Vigalok, A.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 7873-7874.
48. (c) Vigalok, A.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 477-483.
49. (d) Rabin, O.; Vigalok, A.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 7119-7120.
50. Amouri, H.; Besace, Y.; Le Bras, J.; Vaissermann, J. J. Am. Chem. Soc. 1998, 120, 6171-6172.
51. Bennett, M. A.; Bown, M.; Byrnes, M. J. J. Organomet. Chem. 1998, 571, 139-144.
52. Bennett, M. A.; Bown, M.; Hockless, D. C. R.; McGrady, J. E.; Schranz, H. W.; Stranger, R.; Willis, A. C. Organometallics 1998, 17, 3784-3797.
53. Le Bras, J.; Amouri, H., Vaissermann, J. Organometallics 1996, 15, 5706-5712.
54. Le Bras, J.; Rager, M. N.; Besace, Y.; Vaissermann, J.; Amouri, H. Organometallics 1997, 16, 1765-1771.
55. (a) Cp*Ir and Cp*Rh-cyclohexadiene: Grundy, S. L.; Smith, A. J.; Adams, S. H.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1984, 1747-1754.
56. Moseley, K.; Maitlis, P. M. J. Chem. Soc. A 1970, 2884-2888.
57. (b) CpCo-diene complexes: Sternberg, E. D.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 1564-1573, and references therein,
58. 3-diene complexes: Pearson, A. J. Aust. J. Chem. 1977, 30, 407-410.
59. Pearson, A. J. Metallo-organic Chemistry; Wiley: Chichester, 1985; pp 262-264.
60. 13C NMR-Spektroskopie; Georg Thieme Verlag: Stuttgart, 1984; pp 262-269.
61. (b) Breitmeier, E.; Voelter, W. Carbon-13 NMR Spectroscopy; VCH: Weinheim, 1987; p 214.
62. (c) Rojas, A. C. Crandall, J. K. J. Org. Chem. 1975, 40, 2225-2229.
63. (d) Taskinen, E. Tetrahedron 1978, 34, 425-427.
64. (e) Taskinen, E. Tetrahedron 1978, 34, 433-436.
65. Silverstein, R. M.; Webster, F. X. Spectrometric Identification of Organic Compounds, 6th ed.; Wiley: New York, 1998; p 206.
66. Iodinations: (a) Gambie, R. C.; Hayward, R. C.; Jurlina, J. L.; Rutledge, P. S.; Woodgate, P. D. J. Chem. Soc., Perkin Trans, 1 1978, 126-130.
67. (b) Rubottom, G. M.; Mott, R. C. J. Org. Chem. 1979, 44, 1731-1734. Other electrophilic reactions:
68. (c) Reuss, R. H.; Hassner, A. J. Org. Chem. 1974, 39, 1785-1787.
69. (d) Blanco, L.; Amice, P.; Conia, J. M. Synthesis 1976, 194-196.
70. (e) Horiuchi, C. A.; Satoh, J. Y. Synthesis 1981, 312-314.
71. (f) Mukaiyama, T. Pure Appl. Chem. 1983, 55, 1749-1758.
72. Schei, H.; Hagen, K.; Traetteberg, M.; Seip, R. J. Mol. Struct. 1980, 62, 121-130, and references therein.
73. Reference 14a, pp 149-154.
74. Cromer, D. T. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, Vol. IV, 1974.
75. Walker, N.; Stuart, D. Acta Crystallogr. A 1983, A39, 158-166.
76. Watkin, D. J.; Prout, C. K.; Betteridge P. W. Crystals Issue 10; Chemical Crystallography Laboratory: University of Oxford, Oxford, U.K., 1996.