Regioselective geminal dichloride reactivity of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine: Access to 4,4-dioxo- and dithio-ketals

Abstract

Treatment of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine (2) with selected alkanols, arenols and thiols led to regiospecific substitution of both geminal C-4 chlorines resulting in the formation of ketal or thioketal 3,5-dichloro-4H-1,2,6-thiadiazines 8a-h in 31-97% yields. © 2015 Elsevier Ltd.