N-aryl-and N-vinyldiaza-18-crown-6: Synthesis and complexing ability |
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Authors: | P K Sazonov G A Artamkina I P Beletskaya |
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Institution: | (1) Faculty of Chemistry, Moscow State University, Vorob’evy gory 1, Moscow, 119992, Russia |
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Abstract: | The nucleophilic aromatic and vinyl substitution using diaza-18-crown-6 as nucleophile afforded a number of its N,N’-diaryl-aryl = 2,4-(NO2)2C6H3, 4-C5F4N, 4-CF3C6F4] and N,N’-dialkenyl-substituted derivatives alkenyl = PhC(O)CH=CH, MeOCOCH=CH, (EtO2C)2C=C(Ph), etc.]. Arylation of diaza-18-crown-6 with nonactivated aryl bromides, such as 4-Me2NC6H4Br, 4-MeOC6H4Br, C6H5Br, and 4-CF3C6H4Br, was effected under catalysis by palladium complexes. N,N’-Diaryldiaza-18-crowns-6 having electron-acceptor substituents in the aromatic rings turned out to be incapable of forming complexes with metal cations, while their analogs containing electron-donor para-methoxy and para-dimethylamino groups gave complexes with barium perchlorate. |
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