APPLICATION OF TRICHLOROETHYLENE IN ORGANIC-SYNTHESIS .8. COMPETITIVEREACTIONS OF DICHLOROACETYLENE WITH SECONDARY-AMINES AND CARBAZOLE - NEW EVIDENCE FOR THE REACTION-MECHANISM

Dichloroacetylene (DCA), which is generated in situ from trichloroethy lene, reacts with carbazole and secondary aliphatic amines under phase -transfer catalytic conditions to yield 9-((E)-1,2-dichlorovinyl)carba zole 4, 1-(9-carbazolyl)-1-dialkylamino-2-chloroethylenes 5 and N,N-di alkyl-2-(9-carbazolyl) acetamides 6 in a one-pot synthesis. The compou nds 5 and 6 are formed as the result of direct addition of secondary a mines to the triple bond of DCA followed by the reactions of intermedi ate products with either carbaxole or hydroxyl anions.