Stable ?-adducts of 4,6-dinitrotetrazolo[1,5-a]pyridine with alkoxide anions

The reaction of 2-chloro-3,5-dinitropyridine with two equivalents of KN3 in the presence of ROH results in stable Meisenheimer-type σ-adducts of 4,6-dinitrotetra-zolo[1,5-a]pyridine with RO− anions (R = H, Alk, Ph). The mechanism of σ-complex formation was suggested. The structure of the σ-adduct with R = Me was established by IR and NMR spectroscopy and by X-ray diffraction analysis.