Reaction ofN-arylsulfonyl-p-quinonimines and semiquinoid compounds derived therefrom with arylsulfinic acids

N-Arylsulfonyl-2,3,5,6-tetrachloro-l,4-benzoquinonimines and 4-arylsulfonylimino-2,3,5,6,6-pentachloro-2-cyclohexen-l-ones react with arylsulfinic acids regioselectively along 6,1-addition. With 4-arylsulfonylimino-2,3,5,6,6-pentachloro-2-cyclohexen-l-ones the 6,1 addition is preceded by nucleophilic substitution of chlorine in position 2. WithN-arylsulfonyl-2,3-dichloro-l,4-naphthoquinonimines, 4-arylsulfonyl-2,2,3-trichloro-l,2,3,4-tetrahydronaphthalen-l-ones and 4-arylsulfonyl-2,2,3,3-tetrachloro-1,2,3.4-tetrahydronaphthalen-l-ones occurred nucleophilic substitution of chlorine in position 2 followed by 6,1-addition of arylsulfinic acid molecule.