Competition between inter- and intramolecular photocycloaddition reactions of 9-substituted anthracenes

Synthesis

Volumn , Issue 13, 2007, Pages 1995-2001

  Cao, Derong ^a,b   Gao, Chunmei ^a   Dobis, Silvia ^c   Meier, Herbert ^b,c  

^a GUANGZHOU INSTITUTE OF CHEMISTRY   (China)

^b SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^c JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Cycloaddition; Cyclodimerization; Ether cleavage; Regioselectivity; Retrocycloaddition

Indexed keywords

CYCLODIMERIZATION; ETHER CLEAVAGE; RETROCYCLOADDITION;

CYCLOADDITION; DIMERIZATION; MOLECULAR STRUCTURE; PHOTOREACTIVITY; REGIOSELECTIVITY;

SUBSTITUTION REACTIONS;

9 [(2,5 DIMETHOXYBENZYLOXY)METHYL]ANTHRACENE; 9 [(3 BROMOBENZYLOXY)METHYL]ANTHRACENE; 9 [(3,5 DICHLOROBENZYLOXY)METHYL]ANTHRACENE; 9 [(3,5 DIFLUOROBENZYLOXY)METHYL]ANTHRACENE; 9 [(3,5 DIMETHYLBENZYLOXY)METHYL]ANTHRACENE; 9 [(4 METHOXYBENZYLOXY)METHYL]ANTHRACENE; 9 [(ARYL METHOXY)METHYL]ANTHRACENE; 9 [(BENZYLOXY)METHYL]ANTHRACENE; ANTHRACENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLOADDITION; DIMERIZATION; ELECTRON TRANSPORT; IRRADIATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOREACTIVITY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 34447558263     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983734     Document Type: Article

References (42)

1. Books and reviews which recently appeared on this topic, see: (a) Raymo, F. M.; Tomasulo, M. Chem. Eur. J. 2006, 12, 3186.
2. (b) Raymo, F. M.; Tomasulo, M. Chem. Soc. Rev. 2005, 24, 327.
3. (c) Raymo, F. M.; Tomasulo, M. J. Phys. Chem. A 2005, 109, 7343.
4. (d) Minkin, V. I. Chem. Rev. 2004, 104, 2751.
5. (e) Photochromism: Molecules and Systems; Dürr, H.; Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 2003.
6. (f) Bouas-Laurent, H.; Dürr, H. Pure Appl. Chem. 2001, 73, 639.
7. (g) Nolte, D. D. Mind at Light Speed: A New Kind of Intelligence; Free Press: New York, 2001.
8. (h) Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Weinheim, 2001.
9. (i) Kasap, S. O. Optoelectronic and Photonics: Principles and Practices; Prentice-Hall: Upper Saddle River, 2001.
10. (j) Special issue on Photochromism: Memories and Switches, Chem. Rev. 2000, 100, 1683-1890.
11. (k) Organic Photochromic and Thermochromic Compounds; Crano, J. C.; Guglielmetti, R. J., Eds.; Plenum Press/Kluwer Academic: New York, 1999.
12. (l) Photo-Reactive Materials for Ultrahigh Density Optical Memory; Irie, M., Ed.; Elsevier: Amsterdam, 1994.
13. (m) Applied Photochromic Polymer Systems; McArdle, C. B., Ed.; Blackie: Glasgow, 1992.
14. (n) Organic Photochromes; El'tsov, A. V., Ed.; Consultants Bureau: New York, 1990.
15. Cao, D.; Dobis, S.; Meier, H. Tetrahedron Lett. 2002, 43, 6853.
16. (a) Bouas-Laurent, H.; Castellan, A.; Desvergne, J.-P.; Lapouyade, R. Chem. Soc. Rev. 2001, 30, 248.
17. (b) Bouas-Laurent, H.; Castellan, A.; Desvergne, J.-P.; Lapouyade, R. Chem. Soc. Rev. 2000, 29, 43.
18. (c) Becker, H. D. Chem. Rev. 1993, 93, 145.
19. (d) Becker, H. D. In Advances in Photochemistry, Vol. 15; Volman, D. H.; Hammond, G. S.; Gollnik, K., Eds.; Wiley: New York, 1990, 139-227.
20. Desvergne, J.-P.; Castellan, A.; Bouas-Laurent, H. Tetrahedron Lett. 1981, 22, 3529.
21. Dobis, S.; Schollmeyer, D.; Gao, C.; Cao, D.; Meier, H. Eur. J. Org. Chem. 2007, 2964.
22. Cao, D.; Dobis, S.; Schollmeyer, D.; Meier, H. Tetrahedron 2003, 59, 5323.
23. Tsujiya, N.; Kitaura, K.; Kumamoto, Y. J. Phys. Chem. A 1997, 101, 31.
24. Desvergne, J.-P.; Bitit, N.; Castellan, A.; Bouas-Laurent, H. J. Chem Soc., Perkin Trans. 2 1983, 109.
25. 10 and can be ruled out here under the reaction conditions used.
26. Cao, D.; Meier, H. Angew. Chem. Int. Ed. 2001, 40, 186;
27. Angew. Chem. 2001, 113, 193.
28. (a) De Schryver, F. C.; Anand, L.; Smets, G.; Switten, J. J. Polym. Sci., Part B: Polym. Lett. 1971, 9, 777.
29. (b) Kaupp, G.; Teufel, E. Chem. Ber. 1980, 113, 3669.
30. (c) Wolff, T.; Müller, N. J. Photochem. 1983, 23, 131.
31. (d) Ito, Y. Mol. Cryst. Liq. Cryst. 1996, 277, 247.
32. (e) Ito, Y.; Fujita, H. J. Org. Chem. 1996, 61, 5677.
33. (f) Mori, Y.; Maeda, K. Bull. Chem. Soc. Jpn. 1997, 70, 869.
34. (g) Ito, Y.; Olovsson, G. J. Chem. Soc., Perkin Trans. 1 1997, 127.
35. (h) Tung, C.-H.; Guan, J.-Q. J. Org. Chem. 1998, 63, 5857.
36. (i) Wu, D.-Y.; Zhang, L.-P.; Wu, L.-Z.; Wang, B.; Tung, C.-H. Tetrahedron Lett. 2002, 43, 1281.
37. (j) Wu, D.-Y.; Chen, B.; Fu, X.-G.; Wu, L.-Z.; Zhang, L.-P.; Tung, C.-H. Org. Lett. 2003, 5, 1075.
38. (k) Takaguchi, Y.; Tajima, T.; Yanagimoto, Y.; Tsuboi, S.; Ohta, K.; Motoyoshiya, J.; Aoyama, H. Org. Lett. 2003, 5, 1677.
39. Becker, H.-D.; Langer, V. J. Org. Chem. 1993, 58, 4703.
40. We attribute the quantitatively different concentration effects to different aggregation tendencies.
41. Commercially available.
42. The bromo compound 3k is thermolabile and light-sensitive, correct elemental analysis could not be obtained.