Wavelength-dependent selectivity in [4 + 4]-cycloaddition reactions

Journal of Organic Chemistry

Volumn 71, Issue 15, 2006, Pages 5778-5780

  Bailey, David ^a   Williams, Vance E ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHROMOPHORES; DERIVATIVES; DIMERS; MIXTURES;

ANTHRACENE DERIVATIVES; CROSS-CYCLOMER PRODUCTS; HOMODIMERS; SELECTIVE EXCITATION;

REACTION KINETICS;

2,3,6,7 TETRAPHENYLANTHRACENE; 9,10 DIMETHYL 2,3 DIPHENYLANTHRACENE; 9,10 DIMETHYLANTHRACENE; ANTHRACENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY;

EID: 33746345020     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060838q     Document Type: Article

References (18)

1. (a) Bouas-Laurent, H.; Castellan, A.; Desvergne, J. P.; Lapouyade, R. Chem. Soc. Rev. 2001, 30, 43 and references therein.
2. (b) Bouas-Laurent, H.; Castellan, A.; Desvergne, J. P.; Lapouyade, R. Chem. Soc. Rev. 2000, 29, 43-55.
3. (a) Ihara, T.; Fujii, T.; Mukae, M.; Kitamura, Y.; Jyo, A. J. Am. Chem. Soc. 2004, 126, 8880.
4. (b) de Schryver, F. C.; Anand, L.; Smets, G.; Switten, J. Polym. Lett. 1971, 9, 777.
5. (c) Jones, J. R.; Liotta, C. L.; Collard, D. M.; Schiraldi, D. A. Macromolecules 2000, 33, 1640.
6. (d) Mitsuishi, M.; Tanuma, T.; Matsui, J.; Chen, J.; Miyashita, T. Langmuir 2001, 17, 7449.
7. (e) McSkimming, G.; Tucker, J. H. R.; Bouas-Laurent, H.; Desvergne, J. P.; Coles, S. J.; Hursthouse, M. B.; Light, M. E. Chem.-Eur. J. 2002, 8, 3331.
8. (f) Nakatsuji, S.; Ojima, T.; Akutsu, H.; Yamada, J. J. Org. Chem. 2002, 67, 916.
9. (g) Ojima, T.; Akutsu, H.; Yamada, J.; Nakatsuji, S. Polyhedron 2001, 20, 1335.
10. (h) Takaguchi, Y.; Tajima, T.; Yanagimoto, Y.; Tsuboi, S.; Ohta, K.; Motoyoshiya, J.; Aoyama, H. Org. Lett. 2003, 5, 10, 1677.
11. (i) Molard, Y.; Bassani, D. M.; Desvergne, J. P.; Horton, P. H.; Hursthouse, M. B.; Tucker, J. H. R. Angew. Chem., Int. Ed. 2005, 44, 1072.
12. For other examples of approaches to improving the selectivity of these reactions, see: (a) Bailey, D.; Williams, V. E. Chem. Commun. 2005, 2569.
13. (b) Bouas-Laurent, H.; Lapouyade, R. Chem. Commun. 1969, 817.
14. (c) Lapouyade, R.; Castellan, A.; Bouas-Laurent, H. C. R. Acad. Sc. Paris 1969, 268, 217.
15. It should be noted that while the use of a fluorimeter necessarily limited the scale of the reactions studied herein, it offered the advantage of allowing us to easily change the wavelength of excitation. In principle, selective irradiation can be accomplished at larger scales using higher intensity light sources (e.g., Rayonets or immersion well systems) fitted with appropriate cutoff filters.
16. Bailey, D.; Williams, V. E. Tetrahedron Lett. 2004, 45, 2511-2513.
17. Although no other photoproducts were observed from this reaction, we did find that more DMA was consumed than anthracene, suggesting that the former decomposes via an additional, unidentified pathway. This observation may be associated with the pronounced tendency of DMA to form a 9,10-endoperoxide when irradiated in the presence of even trace quantities of oxygen. A similar observation was made for experiments involving 9,10-dimethoxyanthracene. See: Schmidt, R.; Schaffner, K.; Trost, W.; Brauer, H.-D. J. Phys. Chem. 1984, 88, 956.
18. Bouas-Laurent, H.; Lapouyade, R. C. R. Acad. Sci., Ser. C 1967, 12, 1061.