Abstract
Abstract The uncatalyzed reactions of N-vinylcarbazole with electrophilic olefins have been studied. The products included both small molecules and polymers. N-Vinylcarbazole reacted with tricarbomethoxyethylene in inert solvents such as benzene at 110°C to form trimethyl 1-carbazol-9-ylbut-1-ene-3,4,4-tricarboxylate. Donor solvents such as acetone or acetonitrile gave trimethyl-1-carbazol-9-ylcyclobutane-2,2,3-tricarboxylate. A variety of additives in the inert solvents also diverted the product from the 3,4,4-tricarboxylate to the 2,2,3-tricarboxylate. These included oxygen, several silver salts, metallic mercury, diphenylpicrylhydrazyl, and tributyltinhydride. Polymers also formed in low yields in many of these reactions. Either homo-polyvinylcarbazole or the alternating copolymer of N-vinylcarbazole with tricarbomethoxyethylene formed, depending on the solvent. Pyridine prevented the formation of the former, and tert-butylhydroquinone the latter; thus their formation is ascribed to cationic and free r...
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