GENERATION AND REACTIONS OF TRIFLUOROACETIMIDOYL RADICALS

N-Aryltrifluoroacetimidoyl radicals have been generated by three diffe rent methods: the tin-radical promoted deiodination and photochemical homolysis of imidoyl iodides and the thermal homolysis of imidoyl azo- compounds. N-[2-(1-alkynyl)phenyl]trifluoroacetimidoyl iodides have be en converted to trifluoromethylated indoles by the tin-radical promote d homolysis of the carbon-iodine bond followed by intramolecular cycli zation. The photolysis of trifluoroacetimidoyl iodides enabled both in tra- and intermolecular cyclization to indoles and quinolines. Likewis e, thermal reactions of N-(2,2,2-trifluoro-1-tritylazoethylidene) anil ines provided trifluoromethylated quinolines and indoles.