Displacement reactions of 2-chloro- and 2,9-dichloro-1,10-phenanthroline: synthesis of a sulfur-bridged bis-1,10-phenanthroline macrocycle and a 2,2′-amino-substituted-bis-1,10-phenanthroline |
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Authors: | A Paul Krapcho Silvia Sparapani Amber Leenstra Joshua D Seitz |
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Institution: | Department of Chemistry, University of Vermont, Burlington, VT 05405, United States |
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Abstract: | The synthesis and structural assignments of 9-chloro-1,1-phenanthroline-2(1H)-thione and 1,10-dihydro-1,10-phenanthroline-2,9-dithione have been accomplished. The sulfur-bridged bis-1,10-phenanthroline macrocycle was readily prepared by heating the thione or equimolar amounts of the dithione and 2,9-dichloro-1,10-phenanthroline in diphenyl ether. Displacements of 2-chloro- or 2,9-dichloro-1,10-phenanthroline with N,N-dimethylethylenediamine afforded the corresponding amine and diamino analogues. An amino-substituted-2,2′-bis-1,10-phenanthroline has been prepared. |
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Keywords: | 9-Chloro-1 10-phenanthroline-2(1H)-thione 1 10-Dihydro-1 10-phenanthro-line-2 9-dithione Sulfur-bridged bis-1 1-phenanthroline macrocycle 2-Amino- and 2 9-diamino-substituted 1 10-phenanthrolines Amino-substituted-2 2&prime -bis-1 10-phenanthroline |
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