The acid catalyzed hydrogen exchange reaction of 1 -dimethylaminonaphthalene is greatly retarded by a chloro or nitro group in the 8 position. 1,8 -Bisdimethylaminonaphthalene exchanges hydrogen more slowly than the 1,5 isomer. These observations support a mechanism previously advanced.2. Carbazole and acridane derivatives are less reactive in hydrogen exchange than the corresponding diphenylamine derivatives. The role of steric factors is discussed.3. N-Methylacridane also exhibits a base catalyzed exchange reaction which is thought to involve the methylene hydrogen atoms.
Chicago, Illinois
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