Polyhalogenoaromatic compounds. Part XXXIV. Reactions of pentachloropyridine and 3,5-dichlorotrifluoropyridine with aliphatic diamines

Abstract

The reactions of pentachloropyridine or 3,5-dichlorotrifluoropyridine with aliphatic diamines gave N-mono- and/or NN′-bis-(tetrahalogeno-4-pyridyl)diamines, depending on the reagents and the conditions. None of the N-monosubstituted compounds underwent cyclisation by intramolecular nucleophilic substitution at the 3-position of the pyridine ring, but the N-(dichlorotrifluoro-4-pyridyl) derivatives of nonane-1,9-diamine and dodecane-1,12-diamine cyclised via intramolecular attack at the 2-position.