Oxidative Addition of <Emphasis Type="Italic">N</Emphasis>-Aminophthalimide to Conjugated and Nonconjugated Alkylazoalkanes

A series of γ,δ-unsaturated azo compounds was prepared by thermal isomerization of allylalkylhydrazones obtained from the simplest carbonyl compounds. The oxidation of N-aminophthalimide with lead tetraacetate in the presence of these unsaturated compounds gave rise to mixtures of adducts at the azo group, regioisomers of phthalimidoazimines. The oxidative addition of N-aminophthalimide to 1-isopropylazocycloalkenes afforded bicyclic C-isopropylazo-N-phthalimidoaziridines, but the same reaction with 2-alkylazopropenes did not result in any adducts with these conjugated azocompounds.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 2, 2005, pp. 214–223.Original Russian Text Copyright © 2005 by Kuznetsov, Belov, Buchaka.