Enhanced Photodecarboxylation of an Aryl Ester in Polyethylene Films

Organic Letters

Volumn 5, Issue 24, 2003, Pages 4661-4664

  Mori, Tadashi ^a,b   Inoue, Yoshihisa ^a,c   Weiss, Richard G ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 METHYLPROPYL) 2,4,6 TRIMETHYLBENZENE; 2,4,6 TRIMETHYLPHENYL 2 METHYLBUTANOATE; BENZENE DERIVATIVE; BETA CYCLODEXTRIN; BUTYRIC ACID DERIVATIVE; ESTER DERIVATIVE; ORGANIC COMPOUND; POLYETHYLENE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CONFORMATION; DECARBOXYLATION; DENSITY; FILM; PHOTOACTIVATION; PHOTOREACTIVITY; STEREOCHEMISTRY;

EID: 0346780583     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035852t     Document Type: Article

References (39)

1. Miranda, M. A.; Galindo, F. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed; Horspool, W. M., Lenci, F., Eds.; CRC Press LLC: Boca Raton, FL, 2004; Chapter 42, in press. Miranda, M. A.; Galindo, F. In Molecular and Supramolecular Photochemistry; Ramamurthy, V., Schanze, K. S., Eds.; Marcel Dekker: New York, 2003; Vol. 9, pp 43-131 and references therein.
2. Miranda, M. A.; Galindo, F. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed; Horspool, W. M., Lenci, F., Eds.; CRC Press LLC: Boca Raton, FL, 2004; Chapter 42, in press. Miranda, M. A.; Galindo, F. In Molecular and Supramolecular Photochemistry; Ramamurthy, V., Schanze, K. S., Eds.; Marcel Dekker: New York, 2003; Vol. 9, pp 43-131 and references therein.
3. For a review on photodecarboxylation, see: Budac, D.; Wan, P. J. Photochem. Photobiol. A 1992, 67, 135-166.
4. (a) Mori, T.; Takamoto, M.; Wada, T. Inoue, Y. Photochem. Photobiol. Sci. 2003, in press.
5. (b) Mori, T.; Wada, T.; Inoue, Y. Org. Lett. 2000, 2, 3401-3404.
6. Finnegan, R. A.; Knutson, D. J. Am. Chem. Soc. 1967, 89, 1970-1972.
7. Mori, T.; Saito, H.; Inoue, Y. Chem. Commun. 2003, 2302-2303. See also ref 4.
8. For examples, see: (a) Tung, C.-H.; Wu, L.-Z., Zhang, L.-P.; Chen, B. Acc. Chem. Res. 2003, 36, 39-47. (b) Weiss, R. G., Ramamurthy, V.; Hammond, G. S. Acc. Chem. Res. 1993, 26, 530-536.
9. For examples, see: (a) Tung, C.-H.; Wu, L.-Z., Zhang, L.-P.; Chen, B. Acc. Chem. Res. 2003, 36, 39-47. (b) Weiss, R. G., Ramamurthy, V.; Hammond, G. S. Acc. Chem. Res. 1993, 26, 530-536.
10. (a) Turro, N. J. Acc. Chem. Res. 2000, 33, 637-646.
11. (b) Scaiano, J. C.; Garcia, H. Acc. Chem. Res. 1999, 32, 783-793.
12. (c) Ramamurthy, V.; Garcia-Garibay, M. A. Comput. Supramol. Chem. 1996, 7, 693-719.
13. (a) Ueno, A.; Ikeda, H. Mol. Supramol. Photochem. 2001, 8, 461-503.
14. (b) Bortolus, P.; Monti, S. Adv. Photochem. 1996, 21, 1-133.
15. (c) Bortolus, P.; Grabner, G.; Koehler, G.; Monti, S. Coord. Chem. Rev. 1993, 125, 261-268.
16. (d) Ramamurthy, V.; Eaton, D. F. Acc. Chem. Res. 1988, 21, 300-306.
17. (a) Sivaguru, J.; Natarajan, A.; Kaanumalle, L. S.; Shailaja, J.; Uppili, S.; Joy, A.; Ramamurthy, V. Acc. Chem. Res. 2003, 36, 509-521.
18. (b) Turro, N. J. Proc. Nat. Acad. Sci. U.S.A. 2002, 99, 4805-4809.
19. (c) Brunet, E. Chirality 2002, 14, 135-143.
20. (d) Constable, E. C.; Housecraft, C. E. Chimia 1999, 53, 187-191.
21. (e) Inoue, Y. Chem. Rev. 1992, 92, 741-770.
22. (a) Gu, W.; Warrier, M.; Ramamurthy, V.; Weiss, R. G. J. Am. Chem. Soc. 1999, 121, 9467-9468.
23. (b) Gu, W.; Warrier, M.; Schoon, B.; Ramamurthy, V.; Weiss, R. G. Langmuir 2000, 16, 6977-6981.
24. Gu, W.; Abdallah, D. J.; Weiss, R. G. J. Photochem. Photobiol. A 2001, 139, 79-87.
25. (a) Gao, F.; Boyles, D.; Sullivan, R.; Compton, R. N. Pagni, R. M. J. Org. Chem. 2002, 67, 9361-9367.
26. (b) Griesbeck, A. G.; Kramer, W.; Lex, J. Angew. Chem., Int. Ed. 2001, 40, 577-579.
27. (c) Bhanthumnavin, W.; Bentrude, W. G. J. Org. Chem., 2001, 66, 980-990.
28. Xu, J.; Weiss, R. G. Org. Lett. 2003, 5, 3077-3080.
29. Details will be discussed in full paper. See Supporting Information for typical data.
30. Films employed in this study are an amorphous polymer from DuPont-Dow Elastomers (PEO; Nordel IP 3430 containing 42.5 wt % ethylene, 57 wt % propylene, 0.5 wt % ethylidenenorbornene), low-density PE (PE46; Sclairfilm SL-1) from DuPont of Canada and linear low-density PE (PE50; LL-3001.63) from Exxon Chemical Co., and high-density PE from Polialden Petroquimica, Brazil (PE68; type ES-300) or from Exxon Chemical Co. (PE74; Exxon HDPE 7745.10). Films were cold-stretched by hand to ca. three (PE46 and PE50) or four (PE68 and PE70) times their original lengths. All films were extracted with chloroform at least three times each before use to remove antioxidants, plasticizers, and other additives, rinsed with fresh hexanes, and dried in vacuo.
31. By X-ray diffraction with MDI Jade 5 software for X-ray diffraction pattern processing from Materials Data, Inc., Livermore, CA. Also see: (a) Matthews, J. L.; Peiser, H. S.; Richards, R. B. Acta Crystallogr. 1949, 2, 85-90. (b) Reference 13.
32. By X-ray diffraction with MDI Jade 5 software for X-ray diffraction pattern processing from Materials Data, Inc., Livermore, CA. Also see: (a) Matthews, J. L.; Peiser, H. S.; Richards, R. B. Acta Crystallogr. 1949, 2, 85-90. (b) Reference 13.
33. Wang, C.; Xu, J.; Weiss, R. G. J. Phys. Chem. B 2003, 107, 7015-7025.
34. Some chiral induction (2.0% ee) was obtained in 2 when racemic ester 1 was irradiated in aqueous β-cyclodextrin. Details will be presented elsewhere.
35. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision A.1; Gaussian, Inc.: Pittsburgh, PA, 2003.
36. Gu, W.; Hill, A. J.; Wang, X.; Cui, C.; Weiss, R. G. Macromolecules 2000, 33, 7801-7811.
37. (a) Lamotte, M.; Joussot-Dubien, J.; Mantione, M. J.; Claverie, P. Chem. Phys. Lett. 1974, 27, 515-520.
38. (b) Lamotte, M.; Joussot-Dubien, J. Chem. Phys. 1973, 2, 245-248.
39. Tung, C.-H.; Yuan, Z.-Y.; Wu, L.-Z.; Weiss, R. G. J. Org. Chem. 1999, 64, 5156-5161.