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Synthesis 2009(2): 211-216  
DOI: 10.1055/s-0028-1083265
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile Synthesis of Thioalkyl- and Di(thioalkyl)-Substituted Bipyridines

Daitao Chena, Ramkrishna Dea, Debra L. Mohler*a,b
a Department of Chemistry, Emory University, 1515 Dickey Dr., Atlanta, GA 30322, USA
b Department of Chemistry and Biochemistry, James Madison University, MSC 4501, Harrisonburg, VA 22807, USA
Fax: +1(540)5687938; e-Mail: mohlerdl@jmu.edu;
Further Information

Publication History

Received 10 July 2008
Publication Date:
19 December 2008 (online)

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Abstract

A convenient three-step synthesis has been developed to prepare a series of homologous 4,4′-di(ω-thioalkyl)-2,2′-bipyridines from 4,4′-dimethylbipyridine. The smallest member of the series, 4,4′-di(thiomethyl)-2,2′-bipyridine, has been synthesized by a slightly different route from 4,4′-bis(trimethylsilylmethyl)-2,2′-bipyridine; the monothiomethyl analogue has been obtained from the corresponding mono(trimethylsilylmethyl)bipyridine. Additionally, the chlororheniumtricarbonyl complex of each of the new thiol-substituted ligands has been prepared.

Key words

bipyridine - thiol - ligands - iodination - alkylation

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