Azo-coupling and reduction of cyclopropanediazonium ions in the reactions with polyhydroxyarenes and aminophenols

A reaction of cyclopropanediazonium ion, generated by decomposition of N-cyclopropyl-N-nitrosourea upon treatment with potassium or cesium carbonates, with various poly-hydroxyarenes and aminophenols has been studied. The reaction of azo-coupling proceeds with phloroglucinol, resorcinol, 3-methoxy- and 3-aminophenol giving rise to mono-, bis-, and tris(cyclopropylazo)arenes as the major products. Oxidizable phenols such as hydro-quinone, 2-methoxy-, 4-amino-, and 2-aminophenol give products of radical transformations with participation of cyclopropyl radical. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1671–1679, August, 2008.