Synthesis, oxidation and protonation of octamethyl-1,1′-bipyrrole

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 2, 2000, Pages 353-363

  Kuhn, Norbert ^a   Kotowski, Heike ^a   Steimann, Manfred ^a   Speiser, Bernd ^a   Würde, Marc ^a   Henkel, Gerald ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; CYCLIC VOLTAMMETRY; ELECTROCHEMISTRY; ELECTROLYSIS; ELECTROLYTES; FREE RADICALS; OXIDATION; POSITIVE IONS; PROTONS; SALTS; SYNTHESIS (CHEMICAL);

OCTAMETHYL BIPYRROLE; PROTONATION;

ORGANIC COMPOUNDS;

EID: 0034143070     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905603c     Document Type: Article

References (82)

1. A. R. Katrizky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry, Vol. 4, Pergamon, Oxford, 1984
2. R. A. Jones, Pyrroles (The Chemistry of Heterocyclic Compounds), John Wiley & Sons, New York, 1990/1992
3. A. R. Katrizky, C. W. Rees and E. F. V. Scriven, Comprehensive Heterocyclic Chemistry II, Vol. 2, Pergamon, Oxford, 1996.
4. R. Kuhn and H. Kainer, Biochim. Biophys. Acta, 1953, 12, 325
5. S. M. Blinder, M. L. Peller, N. W. Lord, L. C. Aamodt and N. S. Ivanchukov, J. Chem. Phys., 1962, 36, 540
6. R. A. Allendoerfer and A. S. Pollock, Mol. Phys., 1971, 22, 661.
7. H. Zimmermann, H. Baumgärtel and F. Bakke, Angew. Chem., 1961, 73, 808
8. K. Schilffarth and H. Zimmermann, Chem. Ber., 1965, 98, 3124.
9. M. R. C. Gerstenberger, A. Haas, B. Kirste, C. Krüger and H. Kurreck, Chem. Ber., 1982, 115, 2540.
10. W. Flitsch, H. Peeters, W. Schulten and P. Rademacher, Tetrahedron, 1978, 34, 2301
11. E. Orti, J. Sanchez-Marin, P. M. Viruela-Martin and F. Tomas, Chem. Phys. Lett., 1986, 130, 285
12. W. M. F. Fabian, J. Comput. Chem., 1988, 9, 369.
13. W. Flitsch and H. Peeters, Chem. Ber., 1973, 106, 1731
14. W. Flitsch and H. Peeterse, Chem. Ber., 1977, 110, 273.
15. N. Kuhn, Bull. Soc. Chim. Belg., 1990, 99, 707
16. Ch. Janiak and N. Kuhn, Advances in Nitrogen Heterocycles, Vol. 2, pp. 179 210, JAI Press, Greenwich, Connecticut, 1996.
17. W. A. Jung, Dissertation, Universität Giessen, 1982, ref. in G. Maier, N. H. Wiegand, S. Baum, R. Wüllner, W. Mayer and R. Boese, Chem. Ber., 1989, 122, 767.
18. N. Kuhn, E.-M. Horn, E. Zauder, D. Bläser and R. Boese, Angew. Chem., 1988, 100, 572
19. N. Kuhn, E.-M. Horn, E. Zauder, D. Bläser, and R. Boese, Angew. Chem., Int. Ed. Engl., 1988, 27, 579
20. N. Kuhn, M. Schulten, E. Zauder, N. Augart and R. Boese, Chem. Ber., 1989, 122, 1891
21. N. Kuhn, A. Kuhn and E.-M. Lampe, Chem. Ber., 1991, 24, 997
22. N. Kuhn, J. Kreutzberg, E.-M. Lampe, D. Bläser and R. Boese, J. Organomet. Chem., 1993, 458, 125.
23. G. Korschun, Ber. Dtsch. Chem. Ges., 1904, 37, 2183
24. C. Chang and R. Adams, J. Am. Chem. Soc., 1931, 53, 2353.
25. W. Flitsch, U. Krämer and H. Zimmermann, Chem. Ber., 1969, 102, 3268
26. W. Flitsch and W. Schulten, Synthesis, 1977, 414.
27. N. Kuhn, E.-M. Horn and E. Zauder, Inorg. Chim. Acta, 1988, 149, 163.
28. D. V. Avila and A. G. Davies, J. Chem. Soc., Faraday Trans., 1990, 86, 3243.
29. N. Kuhn, E.-M. Horn, R. Boese and N. Augart, Angew. Chem., 1988, 100, 1433
30. N. Kuhn, E.-M. Horn, R. Boese and N. Augart, Angew. Chem., Int. Ed. Engl., 1988, 27, 1368.
31. N. Kuhn and H. Kotowski, unpublished results.
32. A. Grimison and G. A. Simpson, J. Phys. Chem., 1968, 72, 1176.
33. M. Shiotani, Y. Nagata, M. Tasaki, J. Sohma and T. Shida, J. Phys. Chem., 1983, 87, 1170.
34. D. N. R. Rao and M. C. R. Symons, J. Chem. Soc., Perkin Trans. 2, 1983, 135.
35. A. G. Davies, L. Julia and S. N. Yazdi, J. Chem. Soc., Chem. Commun., 1987, 929
36. D. V. Avila and A. G. Davies, J. Chem. Soc., Perkin Trans. 2, 1999, 1111.
37. K. Tanaka, T. Nomura, T. Noro, H. Tatewaki, T. Takada, H. Kashigawi, F. Sasaki and K. Ohno, J. Chem. Phys., 1977, 67, 5738
38. C. Aleman, M. C. Vega and J. J. Perez, J. Mol. Struct. (THEOCHEM), 1993, 281, 39.
39. Y. Chiang and E. B. Whipple, J. Am. Chem. Soc., 1963, 85, 2763
40. F. G. Terrier, F. L. Lebleds, J. F. Verchere and A. P. Chatrousse, J. Am. Chem. Soc., 1985, 107, 307
41. F. Terrier, A.-P. Chatrousse, J. R. Jones, S. W. Hunt and E. Buncel, J. Phys. Org. Chem., 1990, 3, 684
42. Y. Nakajima, Y. Sakagishi, M. Shiibashi, Y. Suzuki and H. Kato, J. Mol. Struct. (THEOCHEM), 1993, 288, 199.
43. E. E. Havinga, K. H. Boswijk and E. H. Wiebenga, Acta Crystallogr., 1954, 7, 487.
44. 2 salt: P. K. Hon, T. C. W. Mak and J. Trotter, Inorg. Chem., 1979, 10, 2916.
45. G. Gritzner and J. Kuring;ta, Pure Appl. Chem., 1984, 56, 461.
46. A. Smie and J. Heinze, Angew. Chem., 1997, 109, 375
47. A. Smie and J. Heinze, Angew. Chem., Int. Ed. Engl., 1997, 36, 363.
48. A. Merz, J. Kronberger, L. Dunsch, A. Neudeck, A. Petr and L. Parkanyi, Angew. Chem., 1999, 111, 1533
49. A. Merz, J. Kronberger, L. Dunsch, A. Neudeck, A. Petr and L. Parkanyi, Angew. Chem., Int. Ed. Engl., 1999, 38, 1442.
50. J. M. Savéant and E. Vianello, Electrochim. Acta, 1967, 12, 1545.
51. J. Phelps and A. J. Bard, J. Electroanal. Chem., 1976, 68, 313.
52. S. Dümmling, B. Speiser, N. Kuhn and G. Weyers, Acta Chem. Scand., 1999, 53, 876.
53. K. Hesse, S. Hünig and H. Wenner, Liebigs Ann. Chem., 1982, 2079.
54. D. H. Evans and K. Hu, J. Chem. Soc., Faraday Trans., 1996, 92, 3983.
55. S. F. Nelsen, Acc. Chem. Res., 1981, 14, 131.
56. S. F. Nelsen, Adv. Electron Transfer Chem., 1993, 3, 167.
57. S. F. Nelsen, L.-J. Chen, P. A. Petillo, D. H. Evans and F. A. Neugebauer, J. Am. Chem. Soc., 1993, 115, 10611.
58. S. F. Nelsen, L.-J. Chen, M. T. Ramm, G. T. Voy, D. R. Powell, M. A. Accola, T. R. Seehafer, J. J. Sabelko and J. R. Pladziewicz, J. Org. Chem., 1996, 61, 1405.
59. M. Dietrich, J. Heinze, H. Fischer and F. A. Neugebauer, Angew. Chem., 1986, 98, 999
60. M. Dietriech, J. Heinze, H. Fischer and F. A. Neugebauer, Angew. Chem., Int. Ed. Engl., 1986, 25, 1021.
61. M. Dietrich, J. Heinze, C. Krieger and F. A. Neugebauer, J. Am. Chem. Soc., 1996, 118, 5020.
62. S. F. Nelsen, S. C. Blackstock, and K. J. Haller, Tetrahedron, 1986, 42, 6101.
63. K. Deuchert and S. Hünig, Angew. Chem., 1978, 90, 927
64. K. Deuchert and S. Hünig, Angew. Chem., Int. Ed. Engl., 1978, 17, 875.
65. M. Schmittel and A. Burghart, Angew. Chem., 1997, 109, 2658
66. M. Schmittel and A. Burghart, Angew. Chem., Int. Ed. Engl., 1997, 36, 2550.
67. N. G. Connelly and W. E. Geiger, Chem. Rev., 1996, 96, 877.
68. L. K. Bieniasz, S. Dümmling, B. Speiser and M. Würde, J. Electroanal. Chem., 1998, 447, 173.
69. R. F. Dapo and C. K. Mann, Anal. Chem., 1963, 35, 677.
70. C. D. Russell, Anal. Chem., 1963, 35, 1291.
71. K. L. Handoo, J.-P. Cheng and V. D. Parker, Acta Chem. Scand., 1993, 47, 626.
72. J. M. Savéant and E. Vianello, Electrochim. Acta, 1963, 8, 905.
73. P. Hertl and B. Speiser, J. Electroanal. Chem., 1988, 250, 237.
74. B. Speiser, in Electroanalytical Chemistry, eds. A. J. Bard and I. Rubinstein, Vol. 19, Marcel Dekker, New York, 1996, pp. 1-108.
75. W. Luo, S. W. Feldberg and M. Rudolph, J. Electroanal. Chem., 1994, 368, 109.
76. K. G. Hancock and P. L. Wylie, J. Org. Chem., 1977, 42, 1850.
77. S. Dümmling, E. Eichhorn, S. Schneider, B. Speiser and M. Würde, Curr. Sep., 1996, 15, 53.
78. T. Kuwana, D. E. Bublitz and G. Hoh, J. Am. Chem. Soc., 1960, 82, 5811.
79. J. B. Cooper and A. M. Bond, J. Electroanal. Chem., 1991, 315, 143.
80. B. Gollas, B. Krauss, B. Speiser and H. Stahl, Curr. Sep., 1994, 13, 42.
81. M. Ruddolph, D. P. Reddy and S. W. Feldberg, Anal. Chem., 1994, 66, 589A.
82. R. S. Nicholson, Anal. Chem., 1966, 38, 1406.