New π-electron donor systems based on acenaphtho[1,2-b][1,4]-dithiine

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 20, 1996, Pages 2451-2459

  Bryce, Martin R ^a   Chesney, Antony ^a   Lay, Alexander K ^a   Batsanov, Andrei S ^a   Howard, Judith A K ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748956674     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960002451     Document Type: Article

References (70)

1. (a) H. Akamatsu, H. Inokuchi and Y. Matsunaga, Nature, 1953, 173, 168;
2. (b) H. P. Fritz, H. Gebaver, P. Friedrich, P. Echer, R. Artes and U. Schubert., Z. Naturforsch., Teil B, 1978, 33, 498;
3. (b) C. Krohnke, V. Enkelmann and G. Wegner, Angew. Chem., Int. Ed. Engl., 1980, 19, 912;
4. (c) K. Bechgaard, in Structure and Properties of Molecular Crystals, ed. M. Pierrot, Elsevier, Amsterdam, 1990, p. 235.
5. (a) R. C. Wheland and J. L. Gillson, J. Am. Chem. Soc., 1976, 98, 3916;
6. (b) B. Hilti, C. W. Mayer and G. Rihs, Helv. Chim. Acta, 1978, 61, 1462;
7. (c) R. Lapouyade and J.-P. Morand, J. Chem. Soc., Chem. Commun., 1987, 223;
8. (d) G. Heywang and S. Roth, Angew. Chem., Int. Ed. Engl., 1991, 30, 176;
9. (e) H. Tani, K. Nii, K. K. Masumoto, N. Azuma and N. Ono, Chem. Lett., 1993, 1055 and references cited therein.
10. (a) M. R. Bryce, Chem. Soc. Rev., 1991, 20, 355;
11. (b) A. E. Underhill, J. Mater. Chem., 1992, 2, 1;
12. M. R. Bryce, J. Mater. Chem., 1995, 5, 1481;
13. (c) Special Issue on Molecular Conductors, J. Mater. Chem., 1995, 5, 1469.
14. L. Y. Chiang and J. Weinwald, Tetrahedron Lett., 1980, 21, 4565.
15. (a) K. Bechgaard, Mol. Cryst. Liq. Cryst., 1985, 125, 81;
16. (b) K. Nakasuji, H. Kubota, T. Kotani, I, Murata, G. Saito, T. Enoki, K. Imaeda, H. Inokuchi, M. Hono, C. Katayama and J. Tanaka., J. Am. Chem. Soc., 1986, 108, 3460;
17. (c) K. Nakasuji, Pure Appl. Chem., 1990, 62, 477;
18. (d) A. Moradpour, J. Chem. Soc., Perkin Trans. 1, 1993, 7.
19. H. Tani, Y. Kamada, N. Azuma and N. Ono, Tetrahedron Lett., 1994, 35, 7051.
20. H. Tani, T. Inamasu, R. Tamaru and H. Suzuki, Chem. Lett., 1990, 1323.
21. A. D. Allen, M. Rosenbaum, N. O. L. Seto and T. T. Tidwell, J. Org. Chem., 1982, 47, 4226.
22. (a) D. C. Green, J. Org. Chem., 1979, 44, 1476;
23. (b) M. R. Bryce, G. Cooke, A. S. Dhindsa, D. Lorcy, A. J. Moore, M. C. Petty, M. B. Hursthouse and A. I. Karaulov, J. Chem. Soc., Chem. Commun., 1990, 818;
24. (c) A. J. Moore, M. R. Bryce, G. Cooke, G. J. Marshallsay, P. J. Skabara, A. S. Batsanov, J. A. K. Howard and S. T. A. K. Daley, J. Chem. Soc., Chem. Commun., 1993, 1403;
25. (d) J. Garín, J. Orduna, S. M. Uriel, A. J. Moore, M. R. Bryce, S. Wegener, D. S. Yufit and J. A. K. Howard, Synthesis, 1994, 489;
26. (e) A. S. Batsanov, M. R. Bryce, J. N. Heaton, A. J. Moore, P. J. Skabara, J. A. K. Howard, E. Ortí, P. M. Viruela and R. Viruela, J. Mater. Chem., 1995, 5, 1689.
27. (a) M. Schoufs, J. Meier, P. Vermeer and L. Brandsma, Recl. Trav. Chim. Pays-Bas, 1977, 96, 259;
28. (b) for a review of 1,4-dithiine chemistry see: K. Kobayashi and C. L. Gajurel, Sulfur Rep., 1986, 7, 123.
29. See also: S. Nakatsuji, Y. Amano, H. Kawamura and H. Anzai, J. Chem. Soc., Chem. Commun., 1994, 841.
30. A. Orahovatz, M. I. Levinson, P. J. Carroll, M. V. Lakshmikantham and M. P. Cava, J. Org. Chem., 1985, 50, 1550.
31. (a) C. A. Hunter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1548;
32. (b) C. A. Hunter, Chem. Soc. Rev., 1994, 23, 101.
33. Y. F. Khobragade and M. C. Gupta, J. Macromol. Sci., Chem., 1995, A32, 155.
34. H. P. Welzel, G. Kossmeril, H. Stein, J. Schneider and W. Plieth, Electrochim. Acta, 1995, 40, 577.
35. L. Y. Chiang, P. Shu, D. Holt and D. Cowan, J. Org. Chem., 1983, 48, 4713.
36. (a) S. Murata, T. Suzuki, A. Yanagisawa and S. Suga, J. Heterocycl. Chem., 1991, 28, 433;
37. (b) L. Engman, J. Heterocycl. Chem., 1984, 21, 413.
38. T. Wirth, Angew. Chem., Int. Ed. Engl., 1995, 34, 1726.
39. (a) Y. Kono, H. Miyamoto, Y. Aso, T. Otsubo, F. Ogura, T. Tanaka and M. Sawada, Angew. Chem., Int. Ed. Engl., 1989, 28, 1222;
40. (b) see also F. Wudl, R. C. Haddon, E. T. Zellers and F. B. Bramwell, J. Org. Chem., 1979, 44, 2491.
41. F. Wudl and M. R. Bryce, J. Chem. Educ., 1990, 67, 717.
42. J. S. Chappel, A. N. Bloch, W. A. Bryden, M. Maxfield, T. O. Poehler and D. O. Cowan, J. Am. Chem. Soc., 1981, 103, 2442.
43. M. R. Bryce, G. R. Davison, A. S. Batsanov and J. A. K. Howard, J. Chem. Soc., Perkin Trans. 1, 1992, 2295.
44. A. Orahovatz, M. I. Levinson, P. J. Carroll, M. V. Lakshmikanthan and M. P. Cava, J. Org. Chem., 1985, 50, 1550.
45. M. R. Bryce, A. M. Grainger, M. Kasan, G. J. Ashwell, P. A. Bates and M. B. Hursthouse, J. Chem. Soc., Perkin Trans. 1, 1992, 611.
46. (a) M. R. Bryce and J. A. K. Howard, Tetrahedron Lett., 1982, 23, 4273;
47. (b) M. R. Bryce and J. A. K. Howard, Tetrahedron Lett., 1983, 24, 1205.
48. (a) A. Gavezzotti, J. Am. Chem. Soc., 1983, 105, 5220;
49. (b) G. Filippini and A. Gavezzotti, Acta Crystallogr., Sect. B, 1993, 49, 868.
50. K. Kobayashi and C. L. Gajurel, Sulfur Rep., 1986, 7, 123.
51. (a) J. Kao, C. Eyermann, E. Southwick and D. Leister, J. Am. Chem. Soc., 1985, 107, 5323;
52. (b) S. Hunig, K. Sinzger, R. Bau, T. Metzenthin and J. Salbeck, Chem. Ber., 1993, 126, 465;
53. (c) D. D. Doxsee, C. P. Galloway, T. B. Ruachfuss and S. R. Wilson, Inorg. Chem., 1993, 32, 5467, and references therein.
54. N. Lozac'h, Sulfur Rep., 1989, 9, 153.
55. F. H. Allen, S. Bellard, M. D. Brice, B. A. Cartwright, A. Doubleday, H. Higgs, T. Hummelink, B. G. Hummelink-Peters, O. Kennard, W. D. S. Motherwell, J. R. Rogers and D. G. Watson, Acta Crystallogr., Sect. B, 1979, 35, 2331.
56. P. A. Howell, R. M. Curtis and W. N. Lipscomb, Acta Crystallogr., 1954, 7, 498.
57. W. A. Dollase, J. Am. Chem. Soc., 1965, 87, 879.
58. H. Kobayashi, A. Kobayashi, T. Nakamura, A. Nogami and Y. Shirota, Chem. Lett., 1987, 559.
59. H. Kim, A. Kobayashi, Y. Sasaki, R. Kato, H. Kobayashi, T. Nakamura, T. Nogami and Y. Shirota, Bull. Chem. Soc. Jpn., 1988, 61, 2559.
60. A. Hordvik, Acta Chem. Scand., 1966, 20, 1885.
61. T. G. Back and P. W. Codding, Can. J. Chem., 1983, 61, 2749.
62. H. Schmidbaur, C. E. Zybill and D. Neugebauer, Angew. Chem., Int. Ed. Engl., 1983, 22, 156.
63. L. Pauling, The Nature of the Chemical Bond, 3rd edn., Cornell Univ. Press, Ithaca, 1960.
64. G. D. Tkacheva and B. V. Suvorov, J. Org. Chem. USSR, 1985, 21, 1173.
65. J. Cosier and A. M. Glazer, J. Appl. Crystallogr., 1986, 19, 105.
66. TEXSAN: Single Crystal Structure Analysis Software, Version 5.0, Molecular Structure Corporation, USA, 1989.
67. N. W. Alcock and P. J. Marks, J. Appl. Crystallogr., 1994, 26, 200.
68. G. M. Sheldrick, Acta Crystallogr., Sect. A, 1990, 46, 467.
69. G. M. Sheldrick, SHELXL-93, Program for the refinement of crystal structures, University of Gottingen, Germany, 1993.
70. H. D. Flack, Acta Crystallogr., Sect. A, 1983, 39, 876.