The reversible [4 + 4] photocycloaddition of acridizinium derivatives

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 200, Issue 1, 2008, Pages 3-9

  Ihmels, Heiko ^a   Luo, Jia ^a  

^a UNIVERSITY OF SIEGEN   (Germany)

Author keywords

4 + 4 photocycloaddition; Azoniaanthracene; Nitrogen heterocycles; Photocycloreversion; Solid state photochemistry

Indexed keywords

EID: 52749092103     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2008.04.008     Document Type: Article

References (67)

1. Bouas-Laurent H., Castellan A., Desvergne J.-P., and Lapouyade R. Chem. Soc. Rev. 29 (2000) 43
2. Bouas-Laurent H., and Desvergne J.-P. In: Dürr H., and Bouas-Laurent H. (Eds). Photochromism, Molecules and Systems (1990), Elsevier, Amsterdam 561
3. Cross-dimerizations: D.E. Bailey, V.E. Williams, J. Org. Chem. 71 (2006) 5778.
4. [4 + 4] Cycloaddition in organic synthesis: S.McN. Sieburth, N.T. Cunard, Tetrahedron 52 (1996) 6251.
5. Theoretical aspects: S. Grimme, C. Diedrich, D. Korth, Angew. Chem. 118 (2006) 641.
6. [4 + 4] Cycloaddition by photochemical upconversion: R. Islangulov, F.N. Casterllano, Angew. Chem. 118 (2006) 6103.
7. Schäfer C., Eckel R., Ros R., Mattay J., and Anselmetti D. J. Am. Chem. Soc. 129 (2007) 1488
8. Masu H., Mizutani I., Kato T., Azumaya I., Yamaguchi K., Kishikawa K., and Kohmoto S. J. Org. Chem. 71 (2006) 8037
9. Schäfer C., and Mattay J. Photochem. Photobiol. Sci. 3 (2004) 331
10. Al-Kaysi R.O., Müller A.M., and Bardeen C.J. J. Am. Chem. Soc. 128 (2006) 15938
11. Ihara T., Fuji T., Mukae M., Kitamura Y., and Jyo A. J. Am. Chem. Soc. 124 (2004) 8880
12. Daub J., Beck M., Knorr A., and Spreitzer H. Pure Appl. Chem. 68 (1996) 1399
13. Irie M. Pure Appl. Chem. 68 (1996) 1367
14. de Silva A.P., and McCoy C.P. Chem. Ind. (1994) 992
15. Dvornikov A.S., Cokgor I., McCormick F., Piyaket R., Esener S., and Rentzepis P.M. Opt. Commun. 128 (1996) 205
16. Dvornikov A.S., and Rentzepis P.M. Res. Chem. Intermed. 22 (1996) 115
17. McSkimming G., Tucker J.H.R., Bouas-Laurent H., Desvergne J.-P., Coles S.J., Hursthouse M.B., and Light M.E. Chem. Eur. J. 8 (2002) 3331
18. Ihmels H. In: Black D. (Ed). Science of Synthesis, vol. 15. Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom (2004), Georg Thieme Verlag, Stuttgart 907
19. Jones G. Adv. Heterocycl. Chem. 31 (1982) 1
20. Bradsher C.K. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry, vol. 2. Six-Membered Rings with One Nitrogen Atom (1984), Pergamon, Oxford 525
21. Arai S., and Hida M. Adv. Heterocycl. Chem. 55 (1992) 261
22. Bradsher C.K., Beavers L.E., and Jones J.H. J. Org. Chem. 129 (1957) 1740
23. Bradsher C.K., and Beavers L.E. J. Am. Chem. Soc. 77 (1955) 4812
24. Lehnberger C., Scheller D., and Wolff T. Heterocycles 45 (1997) 2033
25. Ihmels H., Leusser D., Pfeiffer M., and Stalke D. J. Org. Chem. 64 (1999) 5715
26. Ihmels H., Mohrschladt C.J., Schmitt A., Bressanini M., Leusser D., and Stalke D. Eur. J. Org. Chem. (2002) 2624
27. Ihmels H. Tetrahedron Lett. 39 (1998) 8641
28. Ihmels H., Engels B., Faulhaber K., and Lennartz C. Chem. Eur. J. 6 (2000) 2854
29. Warrner R.W., Golic M., and Butler D.N. Tetrahedron Lett. 39 (1998) 4717
30. Bradsher C.K., and Solomons T.W.G. J. Am. Chem. Soc. 82 (1960) 1808
31. Bendig J., Bauer U., and Kreysig D. Z. Phys. Chem. 262 (1981) 1041
32. Ihmels H., Otto D., Faccio A., and Viola G. J. Org. Chem. 71 (2006) 8401
33. Zee-Cheng R.K.Y., and Cheng C.C. J. Med. Chem. 19 (1976) 883
34. Bendig J., Geppert B., and Kreysig D. J. Prakt. Chem. 320 (1978) 739
35. Bendig J., and Kreysig D. Z. Phys. Chem. 260 (1979) 663
36. Buchwitz J.W., Fischer J., and Kreysig D. J. Prakt. Chem. 323 (1981) 485
37. Wagner J., Bendig J., and Kreysig D. J. Prakt. Chem. 326 (1984) 757
38. Wagner J., Bendig J., Felber A., Sommerer A., and Kreysig D. Z. Chem. 25 (1985) 64
39. Schmidt G.M.J. Pure Appl. Chem. 27 (1971) 647
40. Weiss R.G., Ramamurthy V., and Hammond G.S. Acc. Chem. Res. 26 (1993) 530
41. For a critical view on topochemical photoreactions in the solid state and the postulation of a "phase rebuilding concept", that considers dynamic effects during the photoreaction, see: G. Kaupp, in: J.E.D. Davies, J.A. Ripmeester (Eds.), Comprehensive Supramolecular Chemistry, vol. 8. Physical Methods in Supramolecular Chemistry, Elsevier, Oxford, 1996, p. 381.
42. Keating A.E., and Garcia-Garibay M.A. In: Ramamurthy V., and Schanze K.S. (Eds). Organic and Inorganic Photochemistry (1998), Marcel Dekker Inc., New York 195
43. Toda F. Top. Curr. Chem. 254 (2005) 1
44. Sakamoto M. Top. Curr. Chem. 254 (2005) 207
45. Scheffer J.R., and Xia W. Top. Curr. Chem. 254 (2005) 233
46. Ihmels H., and Scheffer J.R. Tetrahedron 55 (1999) 885
47. Craig D.P., and Sarti-Fantoni P. J. Chem. Soc., Chem. Commun. (1966) 742
48. Cohen M.D., Ludmer Z., Thomas J.M., and Williams J.O. J. Chem. Soc., Chem. Commun. (1969) 1172
49. Cohen M.D., and Schmidt G.M.J. J. Am. Chem. Soc. 86 (1964) 1996
50. Gamlin J.G., Jones R., Leibovitch M., Patrick B., Scheffer J.R., and Trotter J. Acc. Chem. Res. 29 (1996) 203
51. Kearsley D.K. In: Desiraju G.R. (Ed). Organic Solid State Chemistry (1987), Elsevier, Amsterdam 69
52. Wang W.N., and Jones W. Tetrahedron 43 (1987) 1273
53. Wang W.N., and Jones W. Mol. Cryst. Liq. Cryst. 242 (1994) 227
54. Glusker J.P. Top. Curr. Chem. 198 (1998) 1
55. Nangia A., and Desiraju G.R. Top. Curr. Chem. 198 (1998) 57
56. Sharma C.V.K., Panneerselvam K., Shimoni L., Katz H., Carrell H.L., and Desiraju G.R. Chem. Mater. 6 (1994) 1282
57. Ihmels H., Leusser D., Pfeiffer M., and Stalke D. Mol. Cryst. Liq. Cryst. 356 (2001) 433
58. Ihmels H., Bosio S., Bressanini M., Schmitt A., Wissel K., Leusser D., and Stalke D. Mol. Cryst. Liq. Cryst. 390 (2003) 105
59. Bouas-Laurent H., Castellan A., Desvergne J.-P., and Lapouyade R. Chem. Soc. Rev. 29 (2001) 248
60. Barber R.A., de Mayo P., Okada K., and Wong S.K. J. Am. Chem. Soc. 104 (1982) 4995
61. Masnovi J.M., and Kochi J.K. J. Am. Chem. Soc. 107 (1985) 6781
62. Mitzner R., Bendig J., Ziebig R., Graichen F., Kreysig D., and Pragst F. J. Prakt. Chem. 327 (1985) 241
63. Tomlinson W.J., Chandross E.A., Fork R.L., Pryde C.A., and Lamola A.A. Appl. Opt. 11 (1972) 533
64. Smets G. J. Polym. Sci. Polym. Chem. Ed. 13 (1975) 2223
65. Kuckling D., Ivanova I.G., Adler H.P., and Wolff T. Polymer 43 (2002) 1813
66. Lehnberger C., Scheller D., and Wolff T. J. Colloid Interface Sci. 213 (1999) 187
67. Nees D., Cichos U., and Wolff T. Ber. Bunsenges. Phys. Chem. 100 (1996) 1372