Stereochemistry of the Formation of 4-Alkoxyimino-5,6-dihydro-6-alkoxyaminopyrimidin-2(1H)-ones from Cytosines and Hydroxylamines
High resolution 1H and 19F n.m.r. data together with deuterium labelling studies are presented which reveal that the addition of hydroxylamines across the 5,6-double bond of cytosines is predominantly trans.The 4-alkoxyimino-5,6-dihydro-6-alkoxyaminopyrimidin-2(1H)-one products show syn/anti isomerism about the 4-alkoxyimino-group dependent on the substituent at N(3) (H or Me, respectively) and conformational changes throughout the molecules which are dependent on the substituents at N(1) (H or Me) and C(5) (H or F).
Atkins, Paul J.,Hall, C. Dennis
p. 155 - 160
(2007/10/02)
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