References
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- Hüttermann , J. 1977 . “ Excited States in Organic Chemistry and Biochemistry ” . Edited by: Pullman , B. and Goldblum , N. 85 Reidel, Dordrecht, , Holland b) D. J. Deebel, S. Das, and C. Sonntag, J. Phys. Chem., 89, 5784 (1985); c) K. Bhatia and R. H. Schuler, ibid., 77, 1888 (1975); d) B. J. Swenson, J. C. Kutzer, and T. H. Koch, J. Am. Chem. Soc., 103, 1274 (1981); e) T. M. Dietz and T. H. Koch, Photochem. Photobiol., 46, 971 (1987)
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- In view of the ESR study2c,8) and the MO calculation9) for 1[.−] and its protonated derivative, showing that 1[.−] would be difficult to dissociate to 1,3-dimethyluracyl-5-yl radical (8) under acidic conditions, it seems unlikely that the formation of 3 is the result of the coupling of 8, derived from 1[.−] by elimination of fluoride ion (F−), and 2[.+] (Scheme 4). The fact that no formation of 1,3-dimethyluracil (9) was detected may support the above basis. Scheme 4
- Various photochemical studies including hydration, cycloaddition and dimerization have been reported for 5-fluorouracil and its dimethyl derivative 5-FDMU which, however, can be regarded as chemistry of the olefinic part: see references in; S. Y. Wang, “Photochemistry and Photobiology of Nucleic Acid“ Vol. 1, ed. by S. Y. Wang, Academic Press, New York, 1976, Chapter 6; W. M. Horspool, “Enone Cycloadditions and Rearrangements: Photoreactions of Dienones and Quinones” in “Photochemistry”, ed. by D. Bryce-Smith, The Royal Society of Chemistry, London, Vols. 12, 16, and 17, 1982, 1985, and 1986; A. J. Wexler, R. J. Balchunis, and J. S. Swenton, J. Org. Chem.49, 2733 (1984).
- Sevilla , M. D. , Failor , R. and Zorman , G. 1974 . J. Phys. Chem. , 74 : 696
- Unpublished data. For chloro derivatives, see ref. 3b).