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0344073416
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note
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f ≈ 0.6, silica gel, ethanol). On the other hand, fluorination of 2a with xenon difluoride does not provide the difluoro derivative compound, but only oxidized byproducts were observed. In this way, no fluorinated compounds were detected in the reaction with other aminides, as pyridlnium N-(pyrimidin-2′-yl)aminide.
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25
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0345366836
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note
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The negative charge on the exocyclic nitrogen facilates the reaction of the pyridine nucleus toward electrophiles. This ability is decreased for compounds 2a-e due to the high electronegativity of halogen atom in the 5-position. Lower yields for fluorination in 5-haloaminides could be partially attributed to this effect. On the other hand, coordination of the xenon difluoride to the halogen in 5-position could also be an undesirable effect, but some attempts of fluorination increasing concentration of xenon difluoride did produce complex mixtures.
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27
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0028343515
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