Diels-Alder Reactions of 3-Ferrocenyl-2,4,5-triphenylcyclopentadienone: Syntheses and Structures of the Sterically Crowded Systems C6Ph5Fc, C7Ph6FcH, and [C7Ph6FcH][SbCl6]

Organometallics

Volumn 18, Issue 2, 1999, Pages 115-122

  Gupta, Hari K ^a   Brydges, Stacey ^a   McGlinchey, Michael J ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000679843     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980645w     Document Type: Article

References (67)

1. Iwamura, H.; Mislow, K. Acc. Chem. Res. 1988, 21, 175.
2. Mislow, K. Chemtracts: Org. Chem. 1989, 2, 151.
3. Rouhi, A. M. Chem. Eng. News 1998, 76, 6(16), 57-62 (April 20).
4. (a) Kelly, T. R.; Bowyer, M. C.; Bhaskar, K. V.; Bebbington, D.; Garcia, A.; Lang, F.; Kim, M. H.; Jette, M. P. J. Am. Chem. Soc. 1994, 116, 3657.
5. (b) Kelly, T. R.; Tellitu, I.; Sestelo, J. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 1866.
6. (c) Kelly, T. R.; Sestelo, J. P.; Tellitu, I., J. Org. Chem. 1998, 63, 3655.
7. Bedard, T. C.; Moore, J. S. J. Am. Chem. Soc. 1995, 117, 10662.
8. For a review of molecular propellers, refer to: Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 3-75.
9. (a) Gust, D.; Mislow, K. J. Am. Chem. Soc. 1973, 95, 1535, and references therein.
10. (b) Finocchiaro, P.; Gust, D.; Mislow, K. J. Am. Chem. Soc. 1974, 96, 3198.
11. (c) Mislow, K.; Gust, D.; Finocchiaro, P.; Boettcher, R. Top. Curr. Chem. 1974, 47, 1.
12. (d) Finocchiaro, P. Gazz. Chim. Ital. 1975, 105, 149.
13. (e) Mislow, K. Acc. Chem. Res. 1976, 9, 26.
14. (f) Glaser, R.; Blount, J. F.; Mislow, K. J. Am. Chem. Soc. 1980, 102, 2777.
15. (g) Willem, R.; Gielen, M.; Hoogzand, C.; Pepermans, H. Adv. Dyn. Stereochem. 1985, 1, 207.
16. ± systems, see: Olah, G. A.; Mateescu, G. D. J. Am. Chem. Soc. 1970, 92, 1430.
17. Li, L.; Decken, A.; Sayer, B. G.; McGlinchey, M. J.; Brégaint, P.; Thépot, J.-Y.; Toupet, L.; Hamon, J.-R.; Lapinte, C. Organometallics 1994, 13, 682.
18. Mailvaganam, B.; Sayer, B. G.; McGlinchey, M. J. J. Organomet. Chem. 1990, 395, 177.
19. Brydges, S.; Gupta, H. K.; Chao, L. C. F.; Pole, D. L.; Britten, J. F.; McGlinchey, M. J. Chem. Eur. J. 1998, 7, 1199.
20. (a) Gust, D. J. Am. Chem. Soc. 1977, 99, 6980.
21. (b) Gust, D.; Patton, J. J. Am. Chem. Soc. 1978, 100, 8175.
22. (a) Mailvaganam, B.; McCarry, B. E.; Sayer, B. G.; Perrier, R. E.; Faggiani, R.; McGlinchey, M. J. J. Organomet. Chem. 1987, 335, 213.
23. (b) Malisza, K. L.; Chao, L. C. F.; Britten, J. F.; Sayer, B. G.; Jaouen, G.; Top, S.; Decken, A.; McGlinchey, M. J. Organometallics 1993, 12, 2462.
24. Siegel, A.; Rausch, M. D. Synth. React. Inorg. Met.-Org. Chem. 1978, 8 (3), 209.
25. For details of the synthesis, refer to: Rausch, M. D.; Siegel, A. J. Org. Chem. 1968, 33, 4545.
26. (a) Morgenroth, F.; Reuther, E.; Müllen, K. Angew. Chem. 1997, 109, 1067.
27. (b) Morgenroth, F.; Reuther, E.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 361.
28. (c) Morgenroth, F.; Kübel, C.; Müllen, K. J. Mater. Chem. 1997, 7, 1207.
29. (d) Morgenroth, F.; Berresheim, A. J.; Wagner, M.; Müllen, K. Chem. Commun. 1998, 1139.
30. (a) Qiao, X.; Padula, M. A.; Ho, D. M.; Vogelaar, N. J.; Schutt, C. E.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1996, 118, 741.
31. (b) Qiao, X.; Ho, D. M.; Pascal, R. A., Jr. Angew. Chem., Int. Ed. Engl. 1997, 36, 1531.
32. (c) Tong, L.; Ho, D. M.; Vogelaar, N. J.; Schutt, C. E.; Pascal, R. A., Jr. Tetrahedron Lett. 1997, 38, 7.
33. (d) Tong, L.; Ho, D. M.; Vogelaar, N. J.; Schutt, C. E.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1997, 119, 7291.
34. (e) Tong, L.; Lau, H.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120, 6000.
35. (a) Iyer, V. S.; Wehmeier, M.; Brand, J. D.; Keegstra, M. A.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1604.
36. (b) Müller, M.; Iyer, V. S.; Kübel, C.; Enkelmann, V.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1607.
37. (a) Bart, J. C. J. Acta Crystallogr. 1968, B24, 1277.
38. (b) Larson, E. M.; Von Dreele, R. B.; Hansen, P.; Gust, J. D. Acta Crystallogr. 1990, C46, 784.
39. Early electron diffraction studies of hexaphenylbenzene vapor found that the peripheral phenyl rings oscillate at ±10° from the orthogonal form. Almenningen, A.; Bastiansen, O.; Skancke, P. N. Acta Chem. Scand. 1958, 12, 1215.
40. n ring to the centroid of the ligand base (h).
41. (a) Battiste, M. A. J. Am. Chem. Soc. 1961, 83, 4101.
42. (b) Battiste, M. A. Chem. Ind. 1961, 550.
43. Chao, L. C. F.; Gupta, H. K.; Hughes, D. W.; Britten, J. F.; Rigby, S. S.; Bain, A. D.; McGlinchey, M. J. Organometallics 1995, 14, 1139.
44. 6: Biagini, P.; Funaioli, T.; Fachinetti, G.; Laschi, F.; Zanazzi, P. F. J. Chem. Soc., Chem. Commun. 1989, 405.
45. 6: Biagini, P.; Funaioli, T.; Fachinetti, G.; Laschi, F.; Zanazzi, P. F. J. Chem. Soc., Chem. Commun. 1989, 405.
46. 6: Biagini, P.; Funaioli, T.; Fachinetti, G.; Laschi, F.; Zanazzi, P. F. J. Chem. Soc., Chem. Commun. 1989, 405.
47. 6: Biagini, P.; Funaioli, T.; Fachinetti, G.; Laschi, F.; Zanazzi, P. F. J. Chem. Soc., Chem. Commun. 1989, 405.
48. Dunn, J. A.; Gupta, H. K.; Bain, A. D.; McGlinchey, M. J. Can. J. Chem. 1996, 74, 2258.
49. For examples, see: (a) Lupon, S.; Kapon, M.; Cais, M.; Herbstein, F. H. Angew. Chem., Int. Ed. Engl. 1972, 11, 1025. (b) Behrens, U. J. Organomet. Chem. 1979, 182, 89.
50. For examples, see: (a) Lupon, S.; Kapon, M.; Cais, M.; Herbstein, F. H. Angew. Chem., Int. Ed. Engl. 1972, 11, 1025. (b) Behrens, U. J. Organomet. Chem. 1979, 182, 89.
51. (a) Hill, E. A.; Wiesner, R. J. Am. Chem. Soc. 1969, 91, 510.
52. (b) Gleiter, R.; Seeger, R.; Binder, H.; Fluck, E.; Cais, M. Angew. Chem., Int. Ed. Engl. 1972, 11, 1028.
53. (c) Dannenberg, J. J.; Levenberg, M. K.; Richards, J. H. Tetrahedron 1973, 29, 1575.
54. (a) Caffyn, A. J. M.; Nicholas, K. M. In Comprehensive Organometallic Chemistry II; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, Chapter 7.1, pp 685-702.
55. (b) El Amouri, H.; Gruselle, M. Chem. Rev. 1996, 96, 1077.
56. (c) McGlinchey, M. J.; Girard, L.; Ruffolo, R. Coord. Chem. Rev. 1995, 143, 331.
57. Albright, T.; Hoffmann, R.; Hofmann, P. Chem. Ber. 1978, 111, 1591.
58. Brownstein, S. K.; Gabe, E. J.; Hynes, R. C. Can. J. Chem. 1992, 70, 1011.
59. Malisza, K. L.; Top, S.; Vaissermann, J.; Caro, B.; Sénéchal-Tocquer, M.-C.; Sénéchal, D.; Saillard, J.-Y.; Triki, S.; Kahlal, S.; Britten, J. F.; McGlinchey, M. J.; Jaouen, G. Organometallics 1995, 14, 5273.
60. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 2nd ed.; Wiley: New York, 1993; p 131.
61. Deeming, A. J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, U.K., 1982; Vol. 4, Chapter 31.3, pp 479-481.
62. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals, 2nd ed.; Pergamon Press: New York, 1980.
63. Prepared according to the procedure outlined in: Broadhead, G. D.; Osgerby, J. M.; Pauson, P. L. J. Chem. Soc. 1958, 650.
64. SMART, Release 4.05; Siemens Energy and Automation Inc., Madison, WI 53719, 1996.
65. SAINT, Release 4.05; Siemens Energy and Automation Inc., Madison, WI 53719, 1996.
66. Sheldrick, G. M. SADABS (Siemens Area Detector Absorption Corrections); Siemens Energy and Automation, Madison, WI, 1996.
67. Sheldrick, G. M. SHELXTL, Version 5.03; Siemens Analytical X-ray Instruments Inc.: Madison, WI, 1994.