- Glorination of Pyrimidines. Part 2. Mechanistic Aspects of the Reaction of Acetyl Hypofluorite with Uracil and Cytosine Derivatives
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The reaction of acetyl hypofluorite (AcOF) with uracil, cytosine, and some N-1-substituted derivatives dissolved in either acetic acid or water has been investigated.Analysis by radio-h.p.l.c., using (18)f as a tracer, and by (1)H n.m.r. revealed that a substituent at N-1 of uracil has a remarkable effect on the stability of the intermediate 6-acetoxy-5-fluoro-5,6-dihydrouracils.In addition, it was found that these cytosine adducts rapidly deaminate in water yielding their corresponding uracil analogues.
- Visser, W. M. Gerard,Herder, E. Renella,Kanter, Frans J. J. de,Herscheid D. M. Jacobus
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p. 1203 - 1208
(2007/10/02)
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