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

摘要

The synthesis and structural assignments of 9-chloro-1,1-phenanthroline-2(1H)-thione and 1,10-dihy-dro-1,10-phenanthroline-2,9-dithione have been accomplished. The sulfur-bridged bis-1,10-phenanthro-line 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.