2005
DOI: 10.1002/jhet.5570420313
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Nitropyridines, their synthesis and reactions

Abstract: Reaction of pyridine and substituted pyridines with N2O5 in an organic solvent gives the N‐nitropyridinium ion. When this is reacted with SO2/HSO3‐ in water, 3‐nitropyridine is obtained (77 % yield). With substituted pyridines the method gives good yields for 4‐substituted and moderate yields for 3‐substituted pyridines. The reaction mechanism is not an electrophilic aromatic substitution but one in which the nitro group migrates from the 1‐position to the 3‐position by a [1,5] sigmatropic shift. From 3‐nitrop… Show more

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Cited by 16 publications
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References 35 publications
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