Sm. Bonesi et R. Errabalsells, ON THE SYNTHESIS AND ISOLATION OF CHLOROCARBAZOLES OBTAINED BY CHLORINATION OF N-SUBSTITUTED CARBAZOLES, Journal of heterocyclic chemistry, 34(3), 1997, pp. 891-900
Chloro derivatives of N-methylcarbazole (1), N-phenylcarbazole (2), N-
acetylcarbazole (3), N-benzoylcarbazole (4) and 2-methoxy-N-methylcarb
azole are synthesized. They are compounds 1a, 1b, 1c, 1d, 1e, 2a, 2b,
3a, 3b, 3c, 3d, 4a, 4b, 5a, 5b, 5c, 5d and 5e. Some of them are descri
bed for the first time. By using semiempirical PM3 method theoretical
substituent effects on the chlorinating reaction are calculated. A chl
orination mechanism of carbazoles and N-substituted carbazoles are com
pared.