Synthesis and structure of dipyrido-1,4-dithiins

Synthesis, properties and reactions of two isomeric dipyrido-1,4-dithiins of the C-2h and C-2v symmetry are described. Their structure detennination and identification are based on spectroscopic methods (H-1 and C-13 NMR, HETCOR, gHMBC and MS), physical properties (mp and R-f), 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 C-2h symmetry to dithiin with the C-2v symmetry is found.


Publié dans:
Heterocycles, 65, 11, 2619-2634
Année
2005
Autres identifiants:
Laboratoires:




 Notice créée le 2006-03-29, modifiée le 2019-12-05


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