The Conversion of 5,5′-Bi(1,2,3-dithiazolylidenes) into Isothiazolo[5,4-d]isothiazoles
Date
2018Author
Konstantinova, Lidia S.Baranovsky, Ilia V.
Strunyasheva, Vlada V.
Kalogirou, Andreas S.
Popov, Vadim V.
Lyssenko, Konstantin A.
Koutentis, Panayiotis A.
Rakitin, Oleg A.
Source
MoleculesVolume
23Issue
6Google Scholar check
Metadata
Show full item recordAbstract
Thermolysis of 4,4&prime -dichloro-, 4,4&prime -diaryl-, and 4,4&prime -di(thien-2-yl)-5,5&prime -bi(1,2,3-dithiazol-ylidenes) affords the respective 3,6-dichloro-, 3,6-diaryl- and 3,6-di(thien-2-yl)isothiazolo[5,4-d]-isothiazoles in low to high yields. The transformation of the 4,4&prime -diaryl- and 4,4&prime -di(thien-2-yl)-5,5&prime -bi(1,2,3-dithiazolylidenes) occurs at lower temperatures in the presence of the thiophiles triphenylphosphine or tetraethylammonium iodide. Optimized reaction conditions and a mechanistic rationale for the thiophile-mediated ring transformation are presented.