A Qualitative Comparison of the Reactivities of 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine and 4,5-Dichloro-1,2,3-dithiazolium Chloride.
The high yielding transformations of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine into 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (up to 85%) and 2-(3,5-dichloro-4H-1,2,6-thiadiazin-4-ylidene)malononitrile (up to 83%) have been investigated and compared to the analogous transformations of the closely-related 4,5-dichloro-1,2,3-dithiazolium chloride (Appel's salt) into 4-chloro-5H-1,2,3-dithiazol-5-one and 2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)malononitrile. Furthermore, cyclocondensation of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine with 2-aminophenol and 1,2-benzenediamines gave fused 4H-1,2,6-thiadiazines in 68%-85% yields.
Department of Chemistry, University of Cyprus, P.O. Box 20537, Nicosia 1678, Cyprus. kalogirou.andreas@ucy.ac.cy.
Andreas S
AS
Kalogirou
Department of Chemistry, University of Cyprus, P.O. Box 20537, Nicosia 1678, Cyprus. koutenti@ucy.ac.cy.
Panayiotis A
PA
Koutentis
D055598:Chemical Phenomena; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry; D013829:Thiadiazines / Q000138:chemical synthesis / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry*
C570987:4,5-dichloro-1,2,3-dithiazolium chloride; D006843:Hydrocarbons, Chlorinated; D013829:Thiadiazines; D013844:Thiazoles
1,2,3-dithiazoles; 1,2,6-thiadiazines; Appel’s salt; heterocycle