Collect. Czech. Chem. Commun. 1979, 44, 2982-2986

Reactions of asymmetric carbodiimides with azoimide

Jan Světlík, Igor Hrušovský and Augustin Martvoň

Department of Organic Chemistry, Slovak Institute of Technology, 880 37 Bratislava


Reaction of asymmetric aliphatic-aromatic and diaryl carbodiimides with HN3 leads to 1,5-disubstituted tetrazoles. Carbodiimides of general formula C6H5-N=C=N-R (R = alkyl) from an adduct at C=N bond exclusively at a less basic nitrogen, i.e. near phenyl whereas those with R = aryl afford a 1 : 1 mixture of products. 1H-NMR spectroscopy revealed an aminotetrazole-iminotetrazoline tautomerism of the prepared 1=phenyl-5-alkylaminotetrazoles, which undergo isomerization to 1-alkyl-5-anilinotetrazoles.