O-BENZENEDISULFONIMIDE AND ITS DERIVATIVES

o-Benzenedisulfonimide is a strong acid, completely ionized in water, implying that the sulfonimide anion (Z:-) is highly stabilized. Several N-substituted derivatives of o-benzenedisulfonimide (Z-H) were made to examine the activity of Z:- as a leaving group in these compounds, which include Z-Cl, Z-Br, Z-OH, Z-OCH3, and Z-R; several other derivatives could not be prepared. The halides, Z-Cl and Z-Br, are very active sources of ionic positive halogen and halogenate aromatic rings with ease. The other derivatives were found not to have striking reactivity as reagents, and the leaving group activity of Z:- is inferred to be low. © 1969, American Chemical Society. All rights reserved.