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Paper | Special issue | Vol 42, No. 1, 1996, pp.341-346
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S42
Effect of Bromides on the Anomalous Photoarylation of 5-Halo-1,3-dimethyluracils

Koh-ichi Seki, Kazue Ohkura, Yuki Fukai, and Masanao Terashima

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan

Abstract

Photolysis of 5-chloro- and 5-fluoro-1,3-dimethyluracil in toluene in the presence of a bromide (e.g.,p-dibromobenzene, 1,2-dibromoethane, and benzyl bromide) and an acid (hifluoroacetic acid, HBr) afforded 1,3-dimethyl-5-tolyluracils and the 6-isomers as the isomeric mixture. 5-Arylation occurred most favorably at ortho, while meta-isomers were preferential products in 6-arylation. The 5-isomers are suggested to be derived from uracils excited in the singlet states, while the 6-isomers are presumed to result from the uracils excited in the triplet states.