Studies on the reactions of fluoroalkanesulfonyl azide with aromatic compounds

The thermal decomposition reactions of fluoroalkanesulfonyl azides RfSO2N3 () in the presence of various substituted benzene XnC6H6−n [X: CH3 (n=1, 2, 4, 6), OCH3 (n=1, 2), C6H5CH2 (n=1), F, Cl, Br] were studied in detail. The N-aryl fluoroalkanesulfonyl amides [RfSO2NHC6H5−nXn] were produced as the major products. The ortho/para ratio resembled that of an electrophilic aromatic substituted reaction. An ionic π- or σ-complex was postulated as the intermediate for these reactions.