Reactivity of N-arylsulfonyl-1,4-benzoquinone imines. Reaction with hydrazoic acid

N-Arylsulfonyl-2-halo-1,4-benzoquinone imines react with hydrazoic acid in boiling acetic acid via two pathways: the 1,4-addition and nucleophilic replacement of the halogen atom by an azido group, followed by the 1,4-addition of HN₃. In the reaction of N-arylsulfonyl-2,6-dihalo-1,4-benzoquinone imines with hydrazoic acid, both halogen atoms are replaced by azido groups, while N-p-tolylsulfonyl-2-methyl-1,4-benzoquinone imine takes up HN₃ molecule according to the 1,4-addition pattern.