Reaction of aryldiazonium salts with acetone oxime

TLDR: The reaction of aryl diazonium salts containing electron-withdrawing substituents in the aromatic ring with acetone oxime leads to the formation of nitrogen-containing products instead of the expected functional derivatives of 1-alkyl-3-aryltriazene 1-oxides as discussed by the authors.

Abstract: The reaction of aryl diazonium salts containing electron-withdrawing substituents in the aromatic ring with acetone oxime leads to the formation of nitrogen-containing products instead of the expected functional derivatives of 1-alkyl-3-aryltriazene 1-oxides. The structure of these products is a function of the number and chemical nature of the substituents in the diazo component.