Thiapentadienyl-Iridium-Phosphine Chemistry

Organometallics

Volumn 14, Issue 6, 1995, Pages 2813-2826

  Bleeke, John R ^a   Ortwerth, Michael F ^a   Rohde, Alicia M ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751156972     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00006a030     Document Type: Article

References (23)

1. Pentadienyl—Metal—Phosphine Chemistry. 30. Part 29: Bleeke, J. R.; Rohde, A. M.; Robinson, K. D. Organometallics 1995, 14, 1674.
2. For recent reviews, see: (a) Ernst, R. D. Chem. Rev. 1988, 88, 1251. (b) Yasuda, H.; Nakamura, A. J. Organomet. Chem. 1985, 285, 15. (c) Powell, P. Adv. Organomet. Chem. 1986, 26, 125.
3. See, for example: (a) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19. (b) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517.
4. Bleeke, J. R.; Luaders, S. T.; Robinson, K. D. Organometallics 1994, 13, 1592.
5. Bleeke, J. R.; Rohde, A. M.; Robinson, K. Organometallics 1994, 13, 401.
6. Two communications on this subject have already appeared: (a) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (b) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1993, 12, 985.
7. Kloosterziel, H.; Van Drunen, J. A. A.; Galama, P. J. Chem. Soc., Chem. Commun. 1969, 885.
8. Several thiapentadienyl (or “butadienethiolate”) metal complexes have recently been obtained from (thiophene)metal precursors: (a) Spies, G. H.; Angelici, R. J. Organometallics 1987, 6, 1897. (b) Hachgenei, J. W.; Angelici, R. J. Angew. Chem., Int. Ed. Engl. 1987, 26, 909. (c) Hachgenei, J. W.; Angelici, R. J. J. Organomet. Chem. 1988, 355, 359. (d) Skaugset, A. E.; Rauchfuss, T. B.; Wilson, S. R. Organometallics 1990, 9, 2875. (e) Bianchini, C.; Meli, A.; Peruzzini, M.; Vizza, F.; Frediani, P.; Herrera, V.; Sanchez-Delgado, R. A. J. Am. Chem. Soc. 1993, 115, 2731.
9. 4-bound α,β-unsaturated thioaldehyde or thioketone ligands have been reported. (a) Harlow, R. L.; Pfluger, C. E. Acta Crystallogr., Sect. B 1973, B29, 2633. (b) Dittmer, D. C.; Takahashi, K.; Iwanami, M.; Tsai, A. I.; Chang, P. L.; Blidner, B. B.; Stamos, I. K. J. Am. Chem. Soc. 1976, 98, 2795. (c) Skaugset, A. E.; Rauchfuss, T. B.; Wilson, S. R. J. Am. Chem. Soc. 1992, 114, 8521.
10. Derome, A. E. Modern NMR Techniques for Chemistry Research; pergamon Press: Oxford, 1987; p 113.
11. 4-butadiene ligands. (a) Faller, J. W.; Rosan, A. M. J. Am. Chem. Soc. 1977, 99, 4858. (b) Benn, R,; Schroth, G. J. Organomet. Chem. 1982, 228, 71. (c) Erker, G.; Krüger, C.; Müller, G. Adv. Organomet. Chem. 1985, 24, 1. See also: Hersh, W. H.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1983, 105, 5834.
12. Gutsche, C. D.; Pasto, D. J. Fundamentals of Organic Chemistry, Prentice-Hall: Englewood Cliffs, NJ, 1975; pp 446–448.
13. Compound 5 is structurally related to a family of metallathiacyclopentene complexes which contain an oxygen atom in place of the exocyclic methylene carbon. (a) Davidson, J. L.; Shiralian, M.; Manojlovic-Muir, L.; Muir, K. W. J. Chem. Soc., Chem. Commun. 1979, 30. (b) Manojlovic-Muir, L.; Muir, K. W. J. Organomet. Chem. 1979, 168, 403. (c) Guerchais, J. E.; LeFloch-Perennou, F.; Petillon, F. Y.; Keith, A. N.; Manojlovic-Muir, L.; Muir, K. W.; Sharp, D. W. A. J. Chem. Soc., Chem. Commun. 1979, 410. (d) Petillon, F. Y.; LeFloch-Perennou, F.; Guerchais, J. E.; Sharp, D. W. A. J. Organomet. Chem. 1979, 173, 89. (e) Ashby, M. T.; Enemark, J. H. Organometallics 1987, 6, 1318.
14. Huheey, J. E. Inorganic Chemistry, 3rd ed.; Harper and Row: New York, 1983; Appendix E and references therein.
15. Anderson, K.K. In The Chemistry of the Sulphonium Group; Stirling, C. J. M., Ed.; Wiley: Chichester, England, 1981; Part 1, pp 229–266.
16. The ring in 9 is expected to be essentially planar, based on the structures of close carbon and oxygen analogues. See: Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576, and ref 3a.
17. Other related metallathiacyclohexadienes have been synthesized via metal-centered cleavage of C-S bonds in thiophenes: (a) Ogilvy, A. E.; Draganjac, M.; Rauchfuss, T. B.; Wilson, S. R. Organometallics 1988, 7, 1171. (b) Chen, J.; Daniels, L. M.; Angelici, R. J. J. Am. Chem. Soc. 1990, 112, 199. (c) Chen, J.; Daniels, L. M.; Angelici, R. J. Polyhedron 1990, 9, 1883. (d) Jones, W. D.; Dong, L. J. Am. Chem. Soc. 1991, 113, 559. (e) Dong, L.; Duckett, S. B.; Ohman, K. F.; Jones, W. D. J. Am. Chem. Soc. 1992, 114, 151. (f) Jones, W. D.; Chin, R. M. Organometallics 1992, 11, 2698. (g) Luo, S.; Skaugset, A. E.; Rauchfuss, T. B.; Wilson, S. R. J. Am. Chem. Soc. 1992, 114, 1732. (h) Selnau, H. E.; Merola, J. S. Organometallics 1993, 12, 1583. (i) Bianchini, C.; Meli, A.; Peruzzini, M.; Vizza, F.; Frediani, P.; Herrera, V.; Sanchez-Delgado, R. A. J. Am. Chem. Soc. 1993, 115, 2731. (j) Garcia, J. J.; Maitlis, P. M. J. Am. Chem. Soc. 1993, 115, 12200. (k) Buys, I. E.; Field, L. D.; Hambley, T. W.; McQueen, A. E. D. J. Chem. Soc., Chem. Commun. 1994, 557. (l) Bianchini, C.; Meli, A.; Peruzzini, M.; Vizza, F.; Moneti, S.; Herrera, V.; Sanchez-Delgado, R. A. J. Am. Chem. Soc. 1994, 116, 4370. (m) Jones, W. D.; Chin, R. M.; Crane, T. W.; Baruch, D. M. Organometallics 1994, 13, 4448.
18. Fenske—Hall molecular orbital calculations have been performed on a related manganafuran system. See: DeShong, P.; Slough, G. A.; Sidler, D. R.; Rybczynski, P. J.; von Philipsborn, W.; Kunz, R. W.; Bursten, B. E.; Clayton, T. W., Jr. Organometallics 1989, 8, 1381.
19. Analogous bromination of a related manganafuran system has been reported. See: Deshong, P.; Sidler, D. R.; Rybczynski, P. J.; Slough, G. A.; Rheingold, A. L. J. Am. Chem. Soc. 1988, 110, 2575.
20. Herde, J. L.; Lambert, J. C.; Senoff, C. V. In Inorganic Syntheses; Parshall, G. W., Ed.; McGraw-Hill: New York, 1974; Vol. 15, pp 18–20.
21. Atomic scattering factors were obtained from the following: International Tables for X-Ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. 4.
22. Pople, J. A.; Schneider, W. G.; Bernstein, H. J. High-Resolution Nuclear Magnetic Resonance; McGraw-Hill: New York, 1959; p 223.
23. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry; Harper and Row: New York, 1976; p 194.