Triazines. XX.1s‐triazine as a new co‐reactant in polymer synthesis

Abstract

AbstractTrimeric hydrogen cyanide, the structure of which has recently been established as striazine, exhibits as most characteristic phenomenon a marked readiness to undergo ring cleavage upon the action of nucleophilic reagents. This susceptibility to ring cleavage makes s‐triazine an important source for methine (CH) groups by means of which other functional groups can be linked each other. Advantage has been taken of the methinylation capability of s‐triazine to link the functional groups in diamines. While the lower members of the aliphatic diamine series, i.e., ethylenediamine and 1,3‐propanediamine, react With s‐triazine to give cyclic compounds, higher diamine homologs like 1,5‐pentanediamine and 1,6‐hexanediamine furnish exclusively open chain polymers termed polyamidines. 1,4‐Butanediamine, being on the verge of these two diamine categories, forms both the cyclic compound and the open chain polymer. In the polyamidine synthesis, the successful isolation of intermediates furnishes an informative picture of the mode of formation. In view of the fact that other functional groups, e.g., SH, NHNH2, and OH, are amenable to this reaction also, s‐triazine may be considered as a novel important starting material for new types of chain‐like polymers containing hetero atoms.