Abstract
SOME interesting observations on the reaction of bromine with pyrimidine compounds were recently reported by Cohn1. Since 1907, when Wheeler and Johnson2 first observed the coloured reaction product obtained by the action of bromine with uracil or cytosine and isolated the intermediate, the bromine reaction has been utilized for structural determinations, analyses and the preparation of derivatives3. In 1940, Johnson concluded that “5,5-dibromo-4(6)-hydroxyhydrouracil decomposed spontaneously and quantitatively to 5-bromouracil and HOBr”4. I have been unable to confirm this observation. Due to the renewed interest in pyrimidine chemistry and the discrepancies concerning the bromine reaction which have appeared in the literature, I wish to propose a mechanism for this reaction based on the experiments described below. 
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References
Cohn, W. E., Biochem. J., 64, 28P (1956).
Wheeler, H. L., and Johnson, T. B., J. Biol. Chem., 3, 183 (1907).
Levene, P. A., “Nucleic Acids”, Amer. Chem. Soc. Monograph No. 56, p. 54 (Chemical Catalog Co., Inc., New York, 1931).
Johnson, T. B., J. Amer. Chem. Soc., 62, 2269 (1940).
Wang et al., J. Amer. Chem. Soc., 78, 4180 (1956) for proof of structures.
Levene, P. A., J. Biol. Chem., 63, 683 (1925).
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WANG, S. Reaction of Bromine with Uracils. Nature 180, 91–92 (1957). https://doi.org/10.1038/180091a0
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DOI: https://doi.org/10.1038/180091a0
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