Synthesis of a New Family of Metallafurans from (Oxapentadienyl)metal Precursors

Organometallics

Volumn 14, Issue 11, 1995, Pages 5127-5137

  Bleeke, John R ^a   New, Pamela R ^a   Blanchard, Jonathan M B ^a   Haile, Tesfamichael ^a   Beatty, Alicia M ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038063118     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00011a035     Document Type: Article

References (9)

1. Bleeke, J. R.; Peng, W.-J. Organometallics 1987, 6, 1576. (b) Bleeke, J. R.; Peng, W.-J.; Xie, Y.-F.; Chiang, M. Y. Organometallics 1990, 9, 1113. (c) Bleeke, J. R.; Rohde, A. M.; Boorsma, D. W. Organometallics 1993, 12, 970.
2. Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740. (b) Bleeke, J. R.; Ortwerth, M. F.; Rohde, A. M. Organometallics 1995, 14, 2813.
3. 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.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. Y. J. Am. Chem. Soc. 1989, 111, 4118. (b) Bleeke, J. R. Acc. Chem. Res. 1991, 24, 271.
5. Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1993, 12, 985. (b) Bleeke, J. R.; Ortwerth, M. F.; Rohde, A. M. Organometallics 1995, 14, 2813.
6. A sizable number of compounds containing the metallafuran structure have been reported, although the extent to which these species exhibit aromatic character varies widely. The largest classes of metallafurans are metal-carbonyl complexes of the group VI and VII metals. Key references include the following: (a) Green, M.; Nyathi, J. Z.; Scott, C.; Stone, F. G. A.; Welch, A. J.; Woodward, P. J. Chem. Soc., Dalton Trans. 1978, 1067. (b) Allen, S. R.; Green, M.; Norman, N. C.; Paddick, K. E.; Orpen, A. G. J. Chem. Soc., Dalton Trans. 1983, 1625. (c) Watson, P. L.; Bergman, R. G. J. Am. Chem. Soc. 1979, 101, 2055. (d) Alt, H. G. J. Organomet. Chem. 1985, 288, 149. (e) Alt, H. G.; Herrmann, G. S.; Engelhardt, H. E.; Rogers, R. D. J. Organomet. Chem. 1987, 331, 329. (f) Burkhardt, E. R.; Doney, J. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 2022. (g) Chaona, S.; Lalor, F. J.; Ferguson, G.; Hunt, M. M. J. Chem. Soc., Chem. Commun. 1988, 1606. (h) Rusik, C. A.; Collins, M. A.; Gamble, A. S.; Tonker, T. L.; Templeton, J. L. J. Am. Chem. Soc. 1989, 111, 2550. (i) Garrett, K. E.; Sheridan, J. B.; Pourreau, D. B.; Feng, W. C.; Geoffroy, G. L.; Staley, D. L.; Rheingold, A. L. J. Am. Chem. Soc. 1989, 111, 8383. (j) Van der Zeijden, A. A. H.; Bosch, H. W.; Berke, H. Organometallics 1992, 11, 563. (k) Carter, J. D.; Schoch, T. K.; McElwee-White, L. Organometallics 1992, 11, 3571. (l) Masters, A. P.; Parvez, M.; Sorensen, T. S.; Sun, F. Can. J. Chem. 1993, 71, 230. (m) Booth, B. L.; Hargreaves, R. G. J. Chem. Soc. A 1970, 308. (n) Herrmann, W. A.; Ziegler, M. L.; Serhadli, O. Organometallics 1983, 2, 958. (o) DeShong, P.; Sidler, D. R.; Rybczynski, P. J.; Slough, G. A.; Rheingold, A. L. J. Am. Chem. Soc. 1988, 110, 2575. (p) 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. (q) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716. (r) O'Connor, J. M.; Uhrhammer, R.; Rheingold, A. L.; Roddick, D. M. J. Am. Chem. Soc. 1991, 113, 4530. (s) Adams, R. D.; Chen, G.; Chen, L.; Wu, W.; Yin, J. J. Am. Chem. Soc. 1991, 113, 9406. (t) Adams, R. D.; Chen, L.; Wu, W. Organometallics 1992, 11, 3505. (u) Padolik, L. L.; Gallucci, J. C.; Wojcicki, A. J. Am. Chem. Soc. 1993, 115, 9986. A substantial number of Group VIII metallafurans have also been reported. Key references include the following: (v) Komiya, S.; Ito, T.; Cowie, M.; Yamamoto, A.; Ibers, J. A. J. Am. Chem. Soc. 1976, 98, 3874. (w) Deeming, A. J.; Manning, P. J.; Rothwell, I. P.; Hursthouse, M. B.; Walker, N. P. C. J. Chem. Soc., Dalton Trans. 1984, 2039. (x) Werner, H.; Weinand, R.; Otto, H. J. Organomet. Chem. 1986, 307, 49. (y) Romero, A.; Vegas, A.; Dixneuf, P. H. Angew. Chem., Int. Ed. Engl. 1990, 29, 215. (z) Akita, M.; Terada, M.; Oyama, S.; Sugimoto, S.; Moro-oka, Y. Organometallics 1991, 10, 1561. (aa) Espuelas, J.; Esteruelas, M. A.; Lahoz, F. J.; Oro, L. A.; Valero, C. Organometallics 1993, 12, 663. (bb) Werner, H.; Dirnberger, T.; Schulz, M. Angew. Chem., Int. Ed. Engl. 1988, 27, 948. (cc) Sunley, G. J.; Menanteau, P. C.; Adams, H.; Bailey, N. A.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1989, 2415. (dd) Bianchini, C.; Innocenti, P.; Masi, D.; Meli, A.; Sabat, M. Organometallics 1986, 5, 72. (ee) Carmona, E.; Gutierrez-Puebla, E.; Monge, A.; Marin, J. M.; Paneque, M.; Poveda, M. L. Organometallics 1989, 8, 967. (ff) Allevi, C.; Garlaschelli, L.; Malatesta, M. C.; Ganazzoli, F. Organometallics 1990, 9, 1383. One example of a metallafuran in which the oxygen atom resides beta to the metal center has been reported. See (gg) Shih, K.-Y.; Fanwick, P. E.; Walton, R. A. J. Am. Chem. Soc. 1993, 115, 9319.
7. The chemical shifts for the β proton in furan and the proton β in the nonaromatic analogue 4,5-dihydrofuran are δ 6.41 and 4.95, respectively. See Bird, C. W.; Cheeseman, G. W. H. Comprehensive Heterocyclic Chemistry; Pergamon Press: Oxford, 1984; Vol. 4.
8. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G.; Taylor, R. J. Chem. Soc., Dalton Trans. 1989, S1. (b) Huheey, J. E. Inorganic Chemistry, 3rd ed.; Harper and Row: New York, 1983; Appendix E and references cited therein.
9. Atomic scattering factors were obtained from the following: International Tables for X-Ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. 4.