Regioselective photodimerization of 9-substituted acridizinium salts in the solid state

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5715-5718

  Ihmels, Heiko ^a   Leusser, Dirk ^a   Pfeiffer, Matthias ^a   Stalke, Dietmar ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDIZINIUM SALT; ORGANIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CRYSTAL STRUCTURE; DIMERIZATION; NUCLEAR MAGNETIC RESONANCE IMAGING; ORGANIC CHEMISTRY; PHOTOCHEMISTRY; PHOTOREACTIVITY; SOLID STATE; STRUCTURE ANALYSIS;

EID: 0033597807     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990465b     Document Type: Article

References (37)

1. For reviews, see: (a) Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991. (b) Reactivity in Molecular Crystals; Ohashi, Y., Ed.; VCH Publishers: New York, 1994. (c) Sakamoto, M. Chem. Eur. J. 1997, 3, 684. (d) Ito, Y. Synthesis 1998, 1. (e) Ihmels, H.; Scheffer, J. R. Tetrahedron 1999, 55, 885.
2. For reviews, see: (a) Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991. (b) Reactivity in Molecular Crystals; Ohashi, Y., Ed.; VCH Publishers: New York, 1994. (c) Sakamoto, M. Chem. Eur. J. 1997, 3, 684. (d) Ito, Y. Synthesis 1998, 1. (e) Ihmels, H.; Scheffer, J. R. Tetrahedron 1999, 55, 885.
3. For reviews, see: (a) Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991. (b) Reactivity in Molecular Crystals; Ohashi, Y., Ed.; VCH Publishers: New York, 1994. (c) Sakamoto, M. Chem. Eur. J. 1997, 3, 684. (d) Ito, Y. Synthesis 1998, 1. (e) Ihmels, H.; Scheffer, J. R. Tetrahedron 1999, 55, 885.
4. For reviews, see: (a) Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991. (b) Reactivity in Molecular Crystals; Ohashi, Y., Ed.; VCH Publishers: New York, 1994. (c) Sakamoto, M. Chem. Eur. J. 1997, 3, 684. (d) Ito, Y. Synthesis 1998, 1. (e) Ihmels, H.; Scheffer, J. R. Tetrahedron 1999, 55, 885.
5. For reviews, see: (a) Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991. (b) Reactivity in Molecular Crystals; Ohashi, Y., Ed.; VCH Publishers: New York, 1994. (c) Sakamoto, M. Chem. Eur. J. 1997, 3, 684. (d) Ito, Y. Synthesis 1998, 1. (e) Ihmels, H.; Scheffer, J. R. Tetrahedron 1999, 55, 885.
6. (a) Sieburth, S.; Cunard, N. T. Tetrahedron 1996, 52, 6251.
7. (b) Kaupp, G. Angew. Chem. 1992, 104, 435; Angew. Chem., Int. Ed. Engl. 1992, 31, 422.
8. (b) Kaupp, G. Angew. Chem. 1992, 104, 435; Angew. Chem., Int. Ed. Engl. 1992, 31, 422.
9. Bradsher, C. K. In Comprehensive Heterocyclic Chemistry; Boultier, A. J., McKillop, A., Eds.; Pergamon Press: Oxford, U.K., 1985; Vol. 2, p 525.
10. (a) Wang, W. N.; Jones, W. Tetrahedron 1987, 43, 1273.
11. (b) Wang, W. N.; Jones, W. Mol. Cryst. Liq. Cryst. 1994, 242, 227.
12. (c) Kearsley, D. K. In Organic Solid State Chemistry; Desiraju, G. R., Ed.; Elsevier: Amsterdam, 1987; p 69.
13. Lehnberger, C.; Scheller, D.; Wolff, T. Heterocycles 1997, 10, 2033.
14. (a) Kaupp, G.; Frey, H.; Behmann, G. Chem. Ber. 1988, 121, 2135.
15. (b) Vansant, J.; Toppet, S., Smets, G.; Declerq, J. P.; Germain, G.; Van Meersche, M. J. Org. Chem. 1980, 45, 1565.
16. Ihmels, H. Tetrahedron Lett. 1998, 39, 8641.
17. 1H NMR spectroscopic data of the isolated dimers anti-ht-2a,f have already been reported, see refs 5 and 7.
18. Ramamurthy, V. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991; p 133.
19. Some geometric parameters of the compounds 1a and 1b with varying anions have been reported, but the actual crystallographic data have not been published so far; see ref 4.
20. For single-crystal-to-single-crystal photoreactions, see: (a) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1998, 120, 12755. (b) Suzuki, T.; Fukushima, T.; Yamashita, T. J. Am. Chem. Soc. 1994, 116, 2793. (c) Enkelmann, V.; Wegner, G.; Novak, K. Wagener, K. B. J. Am. Chem. Soc. 1998, 115, 10390. (d) Ohashi, Y. Acc. Chem. Res. 1988, 21, 268. (e) Reference 4a. (f) Hasegawa, M. Chem. Rev. 1983, 83, 507. (g) Thomas, J. M. Nature 1981, 289, 633. (h) Thomas, J. M.; Morsi, S. E.; Desvergne, J. P. Adv. Phys. Org. Chem. 1977, 75, 63. (i) Wegner, G. Pure Appl. Chem. 1977, 49, 443. (j) Schmidt, G. M. Pure Appl. Chem. 1971, 27, 647.
21. For single-crystal-to-single-crystal photoreactions, see: (a) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1998, 120, 12755. (b) Suzuki, T.; Fukushima, T.; Yamashita, T. J. Am. Chem. Soc. 1994, 116, 2793. (c) Enkelmann, V.; Wegner, G.; Novak, K. Wagener, K. B. J. Am. Chem. Soc. 1998, 115, 10390. (d) Ohashi, Y. Acc. Chem. Res. 1988, 21, 268. (e) Reference 4a. (f) Hasegawa, M. Chem. Rev. 1983, 83, 507. (g) Thomas, J. M. Nature 1981, 289, 633. (h) Thomas, J. M.; Morsi, S. E.; Desvergne, J. P. Adv. Phys. Org. Chem. 1977, 75, 63. (i) Wegner, G. Pure Appl. Chem. 1977, 49, 443. (j) Schmidt, G. M. Pure Appl. Chem. 1971, 27, 647.
22. For single-crystal-to-single-crystal photoreactions, see: (a) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1998, 120, 12755. (b) Suzuki, T.; Fukushima, T.; Yamashita, T. J. Am. Chem. Soc. 1994, 116, 2793. (c) Enkelmann, V.; Wegner, G.; Novak, K. Wagener, K. B. J. Am. Chem. Soc. 1998, 115, 10390. (d) Ohashi, Y. Acc. Chem. Res. 1988, 21, 268. (e) Reference 4a. (f) Hasegawa, M. Chem. Rev. 1983, 83, 507. (g) Thomas, J. M. Nature 1981, 289, 633. (h) Thomas, J. M.; Morsi, S. E.; Desvergne, J. P. Adv. Phys. Org. Chem. 1977, 75, 63. (i) Wegner, G. Pure Appl. Chem. 1977, 49, 443. (j) Schmidt, G. M. Pure Appl. Chem. 1971, 27, 647.
23. For single-crystal-to-single-crystal photoreactions, see: (a) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1998, 120, 12755. (b) Suzuki, T.; Fukushima, T.; Yamashita, T. J. Am. Chem. Soc. 1994, 116, 2793. (c) Enkelmann, V.; Wegner, G.; Novak, K. Wagener, K. B. J. Am. Chem. Soc. 1998, 115, 10390. (d) Ohashi, Y. Acc. Chem. Res. 1988, 21, 268. (e) Reference 4a. (f) Hasegawa, M. Chem. Rev. 1983, 83, 507. (g) Thomas, J. M. Nature 1981, 289, 633. (h) Thomas, J. M.; Morsi, S. E.; Desvergne, J. P. Adv. Phys. Org. Chem. 1977, 75, 63. (i) Wegner, G. Pure Appl. Chem. 1977, 49, 443. (j) Schmidt, G. M. Pure Appl. Chem. 1971, 27, 647.
24. For single-crystal-to-single-crystal photoreactions, see: (a) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1998, 120, 12755. (b) Suzuki, T.; Fukushima, T.; Yamashita, T. J. Am. Chem. Soc. 1994, 116, 2793. (c) Enkelmann, V.; Wegner, G.; Novak, K. Wagener, K. B. J. Am. Chem. Soc. 1998, 115, 10390. (d) Ohashi, Y. Acc. Chem. Res. 1988, 21, 268. (e) Reference 4a. (f) Hasegawa, M. Chem. Rev. 1983, 83, 507. (g) Thomas, J. M. Nature 1981, 289, 633. (h) Thomas, J. M.; Morsi, S. E.; Desvergne, J. P. Adv. Phys. Org. Chem. 1977, 75, 63. (i) Wegner, G. Pure Appl. Chem. 1977, 49, 443. (j) Schmidt, G. M. Pure Appl. Chem. 1971, 27, 647.
25. For single-crystal-to-single-crystal photoreactions, see: (a) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1998, 120, 12755. (b) Suzuki, T.; Fukushima, T.; Yamashita, T. J. Am. Chem. Soc. 1994, 116, 2793. (c) Enkelmann, V.; Wegner, G.; Novak, K. Wagener, K. B. J. Am. Chem. Soc. 1998, 115, 10390. (d) Ohashi, Y. Acc. Chem. Res. 1988, 21, 268. (e) Reference 4a. (f) Hasegawa, M. Chem. Rev. 1983, 83, 507. (g) Thomas, J. M. Nature 1981, 289, 633. (h) Thomas, J. M.; Morsi, S. E.; Desvergne, J. P. Adv. Phys. Org. Chem. 1977, 75, 63. (i) Wegner, G. Pure Appl. Chem. 1977, 49, 443. (j) Schmidt, G. M. Pure Appl. Chem. 1971, 27, 647.
26. For single-crystal-to-single-crystal photoreactions, see: (a) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1998, 120, 12755. (b) Suzuki, T.; Fukushima, T.; Yamashita, T. J. Am. Chem. Soc. 1994, 116, 2793. (c) Enkelmann, V.; Wegner, G.; Novak, K. Wagener, K. B. J. Am. Chem. Soc. 1998, 115, 10390. (d) Ohashi, Y. Acc. Chem. Res. 1988, 21, 268. (e) Reference 4a. (f) Hasegawa, M. Chem. Rev. 1983, 83, 507. (g) Thomas, J. M. Nature 1981, 289, 633. (h) Thomas, J. M.; Morsi, S. E.; Desvergne, J. P. Adv. Phys. Org. Chem. 1977, 75, 63. (i) Wegner, G. Pure Appl. Chem. 1977, 49, 443. (j) Schmidt, G. M. Pure Appl. Chem. 1971, 27, 647.
27. For single-crystal-to-single-crystal photoreactions, see: (a) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1998, 120, 12755. (b) Suzuki, T.; Fukushima, T.; Yamashita, T. J. Am. Chem. Soc. 1994, 116, 2793. (c) Enkelmann, V.; Wegner, G.; Novak, K. Wagener, K. B. J. Am. Chem. Soc. 1998, 115, 10390. (d) Ohashi, Y. Acc. Chem. Res. 1988, 21, 268. (e) Reference 4a. (f) Hasegawa, M. Chem. Rev. 1983, 83, 507. (g) Thomas, J. M. Nature 1981, 289, 633. (h) Thomas, J. M.; Morsi, S. E.; Desvergne, J. P. Adv. Phys. Org. Chem. 1977, 75, 63. (i) Wegner, G. Pure Appl. Chem. 1977, 49, 443. (j) Schmidt, G. M. Pure Appl. Chem. 1971, 27, 647.
28. For single-crystal-to-single-crystal photoreactions, see: (a) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1998, 120, 12755. (b) Suzuki, T.; Fukushima, T.; Yamashita, T. J. Am. Chem. Soc. 1994, 116, 2793. (c) Enkelmann, V.; Wegner, G.; Novak, K. Wagener, K. B. J. Am. Chem. Soc. 1998, 115, 10390. (d) Ohashi, Y. Acc. Chem. Res. 1988, 21, 268. (e) Reference 4a. (f) Hasegawa, M. Chem. Rev. 1983, 83, 507. (g) Thomas, J. M. Nature 1981, 289, 633. (h) Thomas, J. M.; Morsi, S. E.; Desvergne, J. P. Adv. Phys. Org. Chem. 1977, 75, 63. (i) Wegner, G. Pure Appl. Chem. 1977, 49, 443. (j) Schmidt, G. M. Pure Appl. Chem. 1971, 27, 647.
29. Earley, W. G.; Dority, J. A., Jr.; Kumar, V.; Mallamo, J. P. Heterocycles 1995, 41, 309.
30. Bradsher, C. K; Sherer, J. P.; Parham, J. H. J. Chem. Eng. Data 1965, 10, 180.
31. (a) Gries, W.-K.; Günther, E.; Hünig, S. Liebigs Ann. 1991, 1021.
32. (b) Geuder, W.; Hünig, S. Angew. Chem. 1983, 85, 501; Angew. Chem., Int. Ed. Engl. 1983, 22, 489.
33. (b) Geuder, W.; Hünig, S. Angew. Chem. 1983, 85, 501; Angew. Chem., Int. Ed. Engl. 1983, 22, 489.
34. Stalke, D. Chem. Soc. Rev. 1998, 27, 171.
35. North, A. C. T.; Philipps, D. C.; Mathews, F. S. Acta Crystallogr., Sect. A 1968, 24, 351.
36. Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467.
37. Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement. University of Göttingen, 1997.