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Paper | Regular issue | Vol 65, No. 11, 2005, pp.2619-2634
Published online, 13th September, 2005
DOI: 10.3987/COM-05-10491
Synthesis and Structure of Dipyrido-1,4-dithiins

Beata Morak, Krystian Pluta,* Kinga Suwinska, Miroslawa Grymel, Céline Besnard, Marc Schiltz, Christian Kloc, and Theo Siegrist

*Department of Organic Chemistry, The Medical University of Silesia, Jagielloñska 4, 41-200 Sosnowiec, Poland

Abstract

Synthesis, properties and reactions of two isomeric dipyrido-1,4-dithiins of the C2h and C2v symmetry are described. Their structure determination and identification are based on spectroscopic methods (1H and 13C NMR, HETCOR, gHMBC and MS), physical properties (mp and Rf), the 1,4-dithiin ring opening reactions and finally X-Ray analysis. A very unusual type of the Smiles rearrangement (S→S, the pyridyl group migrates from one sulfur atom to another) during the 1,4-dithiin ring opening with sodium methanethiolate enabling isomerization of dithiin with the C2h symmetry to dithiin with the C2v symmetry is found.