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

The synthesis and structural assignments of 9-chloro-1,1-phenanthroline-2(1 H)-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,...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 50; no. 26; pp. 3195 - 3197
Main Authors: Krapcho, A. Paul, Sparapani, Silvia, Leenstra, Amber, Seitz, Joshua D.
Format: Journal Article
Language:English
Published: Elsevier Ltd 01-07-2009
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Summary:The synthesis and structural assignments of 9-chloro-1,1-phenanthroline-2(1 H)-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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.01.138