Über den Zerfall von Pentazadienen in protischen Medien

Abstract

1,5-diaryl-3-alkylpentaza-1,4-dienes (3) were prepared by coupling primary aliphatic amines with aryldiazonium ions at pH > 9. In protic solvents they decompose into the same mixture of products as found by nitrous acid deamination of the original primary amine. – Product analysis and kinetic measurements show that this degradation is initiated by a slow heterolytic scission of 3 to give an alkyl-aryltriazene; its prototropic form further solvolyses to an aromatic amine and an alkyldiazonium cation, the decomposition of which, giving rise to an unsolvated carboniumion, may be studied under different solvent- and pH-conditions.