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The reaction of bis(2-pyridyl)amine with nitric acid (50% molar excess) in sulfuric acid results in complete conversion of the substrate into mono-, di-, and trinitro derivatives which were identified by IR, NMR, and mass spectra and X-ray analysis. A mechanism was proposed for easy nitration of such a fairly basic substrate in strongly acidic medium.
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Reference：
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics