APPLICATION OF TRICHLOROETHYLENE IN ORGAN IC-SYNTHESIS .8. SYNTHESIS OF 1-(9-CARBAZOLYL)-1-DIALKYLAMINO-2-CHLOROETHYLENES AND N,N-DIALKYL-ALPHA-(9-CARBAZOLYL)ACETAMIDES
Y. Pelikhovskii et D. Bogdal, APPLICATION OF TRICHLOROETHYLENE IN ORGAN IC-SYNTHESIS .8. SYNTHESIS OF 1-(9-CARBAZOLYL)-1-DIALKYLAMINO-2-CHLOROETHYLENES AND N,N-DIALKYL-ALPHA-(9-CARBAZOLYL)ACETAMIDES, Izvestia vyssih ucebnyh zavedenij. Himia i himiceskaa tehnologia, 37(2), 1994, pp. 61-67
Dichloroacetylene (DCA), which is generated ''in situ'' from trichloro
ethylene, reacts with carbazole and aliphatic amines under phase-trans
fer catalytic conditions (PTC) yielding 9-(E)-1, 2-dichlorovinyl) carb
azole (I), 1-(9-carbazolyl)-1-dialkylamino-2-chloroethylenes (II) and
N, N-dialkyl alpha-(9-carbazolyl) acetamides (II) in one-step synthesi
s. It is found that II and III are formed as the result of direct addi
tion of secondary amines to the triple bond of DCA followed by reactio
ns of an intermediate product with carbazole or hydroxyl anion.