Titanium Tetrachloride-mediatd Reaction of Authraquinone and Anthrone with Amines or Thiols

Abstract

Reactions of anthraquinone and anthrone with primary amines or thiols in the presence of titanium tetrachloride were studied. Anthraquinone reacted with primary amines to give N, N'-disubstituted anthraquinone diimines, while the reaction with thiols afforded 9, 10-bis(alkylthio or phenylthio)anthracene. Anthrone gave 9-(alkylamino)anthracene and 9-(alkylthio or phenylthio)anthracene by the reactions with amines and thiols, respectively. It was suggested that these 9-substituted anthracenes may be produced by dehydration of 9-substituted tetrahydro-9-antrol intermediates.