New Molecular Devices: In Search of a Molecular Ratchet

Journal of Organic Chemistry

Volumn 63, Issue 11, 1998, Pages 3655-3665

  Ross Kelly, T ^a   Sestelo, José Pérez ^a,b   Tellitu, Imanol ^a,c  

^a BOSTON COLLEGE   (United States)

^b UNIVERSITY OF A CORUÑA   (Spain)

^c UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542497894     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9723218     Document Type: Article

References (56)

1. (a) For a leading reference see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994.
2. (b) See also: Oki, M. Top. Stereochem. 1983, 14, 1-81 (note especially Section III).
3. (a) Iwamura, H.; Mislow, K. Ace. Chem. Res. 1988, 21, 175-182.
4. (b) Mislow, K. Chemtracts: Org. Chem. 1989, 2, 151-174.
5. (c) Nakamura, M ; Oki, M. Bull. Chem. Soc. Jpn. 1975, 48, 2106-2111.
6. (d) Oki, M.; Fukuda, T.; Asakura, M.; Toyota, S. Ibid. 1996, 69, 3267-3272.
7. (e) Yamamoto, G. Tetrahedron 1990, 46, 2761-2772.
8. (f) Kawada, Y.; Sakai, H.; Oguri, M.; Koga, G. Tetrahedron Lett. 1994, 35, 139-143.
9. (g) Stevens, A. M.; Richards, C. J. Ibid. 1997, 38, 7805-7808.
10. (h) Gakh, A. A.; Sachleben, R. A.; Bryan, J. C. Chem Tech 1997, 27, 26-33
11. (a) Kelly, T. R.; Bowyer, M. C.; Bhaskar, K. V.; Bebbington, D.; García, A.; Lang, F.; Kim, M. H.; Jette, M. P. J. Am. Chem. Soc. 1994, 116, 3657-3658.
12. See the supplementary material appended thereto for detailed synthetic procedures. See also: (b) Casares, J. A.; Coco, S.; Espinet, P.; Lin, Y.-S. Organometallics 1995, 14, 3058-3067. (c) Fanizzi, F. P.; Lanfranchi, M.; Natile, G.; Tiripicchio, A. Inorg. Chem. 1994, 33, 3331-3339.
13. See the supplementary material appended thereto for detailed synthetic procedures. See also: (b) Casares, J. A.; Coco, S.; Espinet, P.; Lin, Y.-S. Organometallics 1995, 14, 3058-3067. (c) Fanizzi, F. P.; Lanfranchi, M.; Natile, G.; Tiripicchio, A. Inorg. Chem. 1994, 33, 3331-3339.
14. Bedard, T. C.; Moore, J. S. J. Am. Chem. Soc. 1995, 117, 10662-10671.
15. Kelly, T. R.; Tellitu, I.; Sestelo, J. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 1866-1868. For a "Highlight" featuring this paper see: Davis, A. P. Ibid. 1998, 37, 909-910.
16. Kelly, T. R.; Tellitu, I.; Sestelo, J. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 1866-1868. For a "Highlight" featuring this paper see: Davis, A. P. Ibid. 1998, 37, 909-910.
17. For a review of triptycenes see: Skvarchenko, V. R.; Shalaev, V. K.; Klabunovskii, E. I. Russ. Chem. Rev. 1974, 43, 951-966.
18. For reviews of helicene chemistry, see: (a) Martin, R. H. Angew. Chem., Int. Ed. Engt. 1974, 13, 649-660. (b) Laarboven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 725, 63-130. (c) Meurer, K. P.; Vögtle F. Ibid. 1985, 127, 1-76. Some more recent papers: (d) Liu L.; Kate, T. J. Tetrahedron Lett. 1990, 31, 3983-3986. (e) Wilimore, N. D.; Liu, L.; Katz, T. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1093-1094. (f) Janke, R. H.; Haufe, G.; Würthwein, E.; Borkent, J. H. J. Am. Chem. Soc. 1996, 118, 6031-6035.
19. For reviews of helicene chemistry, see: (a) Martin, R. H. Angew. Chem., Int. Ed. Engt. 1974, 13, 649-660. (b) Laarboven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 725, 63-130. (c) Meurer, K. P.; Vögtle F. Ibid. 1985, 127, 1-76. Some more recent papers: (d) Liu L.; Kate, T. J. Tetrahedron Lett. 1990, 31, 3983-3986. (e) Wilimore, N. D.; Liu, L.; Katz, T. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1093-1094. (f) Janke, R. H.; Haufe, G.; Würthwein, E.; Borkent, J. H. J. Am. Chem. Soc. 1996, 118, 6031-6035.
20. For reviews of helicene chemistry, see: (a) Martin, R. H. Angew. Chem., Int. Ed. Engt. 1974, 13, 649-660. (b) Laarboven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 725, 63-130. (c) Meurer, K. P.; Vögtle F. Ibid. 1985, 127, 1-76. Some more recent papers: (d) Liu L.; Kate, T. J. Tetrahedron Lett. 1990, 31, 3983-3986. (e) Wilimore, N. D.; Liu, L.; Katz, T. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1093-1094. (f) Janke, R. H.; Haufe, G.; Würthwein, E.; Borkent, J. H. J. Am. Chem. Soc. 1996, 118, 6031-6035.
21. For reviews of helicene chemistry, see: (a) Martin, R. H. Angew. Chem., Int. Ed. Engt. 1974, 13, 649-660. (b) Laarboven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 725, 63-130. (c) Meurer, K. P.; Vögtle F. Ibid. 1985, 127, 1-76. Some more recent papers: (d) Liu L.; Kate, T. J. Tetrahedron Lett. 1990, 31, 3983-3986. (e) Wilimore, N. D.; Liu, L.; Katz, T. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1093-1094. (f) Janke, R. H.; Haufe, G.; Würthwein, E.; Borkent, J. H. J. Am. Chem. Soc. 1996, 118, 6031-6035.
22. For reviews of helicene chemistry, see: (a) Martin, R. H. Angew. Chem., Int. Ed. Engt. 1974, 13, 649-660. (b) Laarboven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 725, 63-130. (c) Meurer, K. P.; Vögtle F. Ibid. 1985, 127, 1-76. Some more recent papers: (d) Liu L.; Kate, T. J. Tetrahedron Lett. 1990, 31, 3983-3986. (e) Wilimore, N. D.; Liu, L.; Katz, T. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1093-1094. (f) Janke, R. H.; Haufe, G.; Würthwein, E.; Borkent, J. H. J. Am. Chem. Soc. 1996, 118, 6031-6035.
23. For reviews of helicene chemistry, see: (a) Martin, R. H. Angew. Chem., Int. Ed. Engt. 1974, 13, 649-660. (b) Laarboven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 725, 63-130. (c) Meurer, K. P.; Vögtle F. Ibid. 1985, 127, 1-76. Some more recent papers: (d) Liu L.; Kate, T. J. Tetrahedron Lett. 1990, 31, 3983-3986. (e) Wilimore, N. D.; Liu, L.; Katz, T. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1093-1094. (f) Janke, R. H.; Haufe, G.; Würthwein, E.; Borkent, J. H. J. Am. Chem. Soc. 1996, 118, 6031-6035.
24. (a) Martin, R. H.; Marchant, M. J. Tetrahedron Lett. 1972, 3707-3708.
25. (b) Martin, R. H.; Marchant, M. J. Tetrahedron 1974, 30, 347-349.
26. (c) Scherübl, H.; Fritzsche, U.; Mannschreck, A. Chem. Ber. 1984, 117, 336-343.
27. (a) Calculations (AMI) were carried out using the coordinate drive feature of the Spartan molecular modeling program (Wavefunction, Inc., Irvine, CA), Version 4,0, on a Silicon Graphics workstation. (b) The same calculations (Spartan AMI coordinate drive) give a significantly different potential energy curve for counterclockwise (120° →0° dihedral angle) rotation. The calculations for counterclockwise rotation give an energy maximum ca. 5 kcal/mol higher than for clockwise rotation and, in contrast to clockwise rotation, are accompanied by inversion of the helicity of the helicene. In contrast, experimental determinations (vide infra) indicate that helicene inversion is an appreciably higher energy process7 than triptycene rotation. Given the principle of microscopic reversibility, we attribute the clockwise/counterclockwise difference to a limitation of the calculational program, at least as employed by us.
28. Laarhoven, W. H.; Peters, W. H. M.; Tinnemans, A. H. A. Tetrahedron 1978, 34, 769-777.
29. Mallory, F. B.; Mallory, C. W. Org. React. 1984, 30, 1-456.
30. (a) Tinnemans, A. H. A.; Laarhoven, W. H. Tetrahedron Lett. 1973, 817-820.
31. (b) Tinnemans, A. H. A.; Laarhoven, W. H. J. Chem. Soc., Perkin Trans. 2 1976, 1111-1115.
32. (c) Tinnemans, A. H. A.; Laarhoven, W. H. Ibid. 1976, 1115-1121.
33. Stoilov, I.; Watt, D. S.; Goodman, J. P.; Pyrek, J. St. J. Heterocycl. Chem. 1993, 30, 1645-1651.
34. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769-3772.
35. (a) Akiyama, S.; Nakasuji, N.; Nakagama, M. Bull. Chem. Soc. Jpn. 1971, 44, 2231-2236.
36. (b) Mallory, F. B.; Mallory, C. W. J. Org. Chem. 1983, 48, 526-532.
37. We note, however, that when we replaced the 9-triptycyl unit in 6 by an anthracene (21) the results of the attempted photocyclization were equivalent (eq i). Propargylic aldehyde 20 was prepared from the corresponding dibromide (38): see the Experimental Section. chemical equation presented.
38. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
39. 3a from 9-bromoanthracene by metalation with n-BuLi and reaction of the resulting aryilithium with tributyltin chloride (98% yield).
40. Logullo, F. M.; Seitz, A. H.; Friedman, L. Organic Syntheses; 1973; Collect. Vol. 5, pp 54-59.
41. Geerts, J. P.; Martin, R. H. Bull. Soc. Chim. Belg. 1960, 60, 563-569.
42. See the Experimental Section for general conditions of irradiation. See also: Lui, L.; Yang, B.; Katz, T. J.; Poindexter, M. K. J. Org. Chem. 1991, 56, 3769-3775.
43. (a) Sudhakar, A.; Katz, T. J. Tetrahedron Lett. 1986, 27, 2231-2234.
44. (b) Sudhakar, A.; Katz, T. J.; Yang, B.-W. J. Am. Chem. Soc. 1986, 108, 2790-2791.
45. (c) Liu, T.; Katz, T. J. Tetrahedron Lett. 1991, 32, 6831-6834.
46. Compound 25 was identified by MS; its :H NMR spectrum suggests a mixture of two compounds.
47. Haworth, R. D. J. Chem. Soc. 1932, 1125-1133.
48. Huggenberg, S.; Hesse, M. Helv. Chem. Acta 1980, 63, 2295-2301.
49. Tashiro, M.; Yamato, T.; Kobayashi, K.; Arimura,T. J. Org. Chem. 1987, 52, 3196-3199.
50. For leading references to the spin polarization transfer method, see: (a) Dahlquist, F. W.; Longmur, K. J.; Du Vernet, R. B. J. Magn. Reson. 1975, 17, 406-410. (b) Frim, R.; Zilber, G.; Rabinovitz, M. J. Chem. Soc., Chem. Commun. 1991, 1202-1203. (c) Abdourazak, A. H.; Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-3011. For a more general review of the application of 2D NMR spectroscopy to the kinetics of exchange processes, see: Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967.
51. For leading references to the spin polarization transfer method, see: (a) Dahlquist, F. W.; Longmur, K. J.; Du Vernet, R. B. J. Magn. Reson. 1975, 17, 406-410. (b) Frim, R.; Zilber, G.; Rabinovitz, M. J. Chem. Soc., Chem. Commun. 1991, 1202-1203. (c) Abdourazak, A. H.; Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-3011. For a more general review of the application of 2D NMR spectroscopy to the kinetics of exchange processes, see: Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967.
52. For leading references to the spin polarization transfer method, see: (a) Dahlquist, F. W.; Longmur, K. J.; Du Vernet, R. B. J. Magn. Reson. 1975, 17, 406-410. (b) Frim, R.; Zilber, G.; Rabinovitz, M. J. Chem. Soc., Chem. Commun. 1991, 1202-1203. (c) Abdourazak, A. H.; Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-3011. For a more general review of the application of 2D NMR spectroscopy to the kinetics of exchange processes, see: Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967.
53. For leading references to the spin polarization transfer method, see: (a) Dahlquist, F. W.; Longmur, K. J.; Du Vernet, R. B. J. Magn. Reson. 1975, 17, 406-410. (b) Frim, R.; Zilber, G.; Rabinovitz, M. J. Chem. Soc., Chem. Commun. 1991, 1202-1203. (c) Abdourazak, A. H.; Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-3011. For a more general review of the application of 2D NMR spectroscopy to the kinetics of exchange processes, see: Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967.
54. The value of ΔG‡ is calculated from the half-life obtained from the data in Figure 5, See, for example, Scudder, P. H. Electron Flow in Organic Chemistry; Wiley: New York, 1992; pp 38-40.
55. Feynman, R. P.; Leighton, R. B.; Sands, M. The Feynman Lectures on Physics; Addison-Wesley: Reading, MA, 1963; Vol. 1, Chapter 46.
56. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.