| 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. |
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