Heterocycles p. 2619 - 2634 (2005)
Update date:2022-08-03
Topics: Characterization Cross-Coupling Reaction Purification and Isolation Synthesis of 1,4-dithiin ring Functionalization of the pyridine rings
Morak, Beata
Pluta, Krystian
Suwinska, Kinga
Grymel, Miroslawa
Besnard, Celine
Schiltz, Marc
Kloc, Christian
Siegrist, Theo
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.
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