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Kinetic and stereochemical data on the reaction of 5-fluorocytosine (1a) with hydroxylamine (2a) to form 5-fluoro-3,4,5,6-tetrahydro-6-hydroxyamino-4-hydroxyiminopyrimidin-2(1H)-one (3a) are presented. A mechanistic scheme involving acid catalysis and a change in the rate-limiting step with increasing hydroxylamine concentration is proposed.
D. J. Palling, P. J. Atkins and C. D. Hall, J. Chem. Soc., Perkin Trans. 2, 1980, 1460 DOI: 10.1039/P29800001460
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