ONE-POT SYNTHESIS OF 1,2,3-BENZODITHIAZOL-6-ONES

The reaction of p-benzoquinone-4-oximes with disulfur dichloride affor ds the red 6H-1,2,3-benzodithiazol-6-ones. Some ring chlorination occu rs, but 2,6-substituents are retained in the products except for a ter t-butyl group, which is, exceptionally, replaced by chlorine. 1,4-Naph thoquinone 4-oxime and 1,2-naphthoquinone 2-oxime similarly give the r ed 4-chloro-5H-naphtho[1,2-d][1,2,3]dithiazol-5-one and the blue 9-chl oro-4H-naphtho[2,3-d][1,2,3]dithiazol-4-one respectively. A unified se t of mechanisms is proposed for all of the reactions. (C) 1997 Elsevie r Science Ltd. All rights reserved.