Intramolecular interaction between ortho-azido and azoxy groups as a new way of forming a N-N bond.Synthesis of 2-alkylbenzotriazole 1-oxides

摘要

Heating of 2-(alkyl-NNO-azoxy)-l-azidobenzenes in boiling benzene gave 2-alkyl-benzotriazole 1-oxides(Alk = Me,Et,Pr~i,and Bu~t).This first-order reaction involves an earlier unknown intramolecular interaction between the azido and azoxy groups with simultaneous release of molecular nitrogen.The cyclization rate increases in the following sequence of the alkyl groups: Me < Et < Pr~i < Bu~t.Complete assignment of the signals in the ~1H,~(13)C,and ~(14)N NMR spectra of 2-alkylbenzotriazole 1-oxides was performed.