ChemInform Abstract: Pyrolysis of Quinoline-3,4-dicarboxylic Anhydrides Bearing 2-Phenyl, 2- Benzyl and 2-o-Tolyl Substituents: Formation of Products of Carbene Insertion and Addition

Autor: K. J. Coulston, Roger F. C. Brown, M. R. Moffat, Frank W. Eastwood
Rok vydání: 2010
Předmět:
Zdroj: ChemInform. 23
ISSN: 0931-7597
DOI: 10.1002/chin.199252082
Popis: Flash vacuum pyrolysis of 2-phenylquinoline-3,4-dicarboxylic anhydride at 800°/0.06 mm gave indeno[1,2- b ]indole (30–40%), which readily added nucleophiles Y − at C-10 to give 5,10-dihydro derivatives (Y  H, Me, Ph, NEt 2 , OMe, CH(COOMe) 2 and CMe 2 NO 2 ). Similar pyrolysis of the 2-benzylquinoline anhydride gave a 1:2 mixture of the (expected) linear 5 H -benzo[ b ]carbazole and the (unexpected) angular 7 H -benzo[ c ]carbazole. The isomeric 2- o -tolylquinoline anhydride on similar pyrolysis gave mainly 11 H -benzo[ a ]carbazole (85%), isomeric benzocarbazoles (4%) and 11 H -indeno[1,2- b ]quinoline (2.6%). Most of these products are probably derived from exocyclic carbenes formed by aryne - carbene equilibration, but the last compound may be formed by direct aryne - methyl interaction.
Databáze: OpenAIRE
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