One pot synthesis of 1,2,3-benzodithiazol-6-ones

✍ Scribed by Cecilia Polo; Vicente Ramos; Tomás Torroba; Oleg A. Rakitin; Charles W. Rees

• Book ID: 104208266
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 777 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)10272-1

✦ Synopsis

The reaction of p-benzoquinone-4-oximes with disulfur dichloride affords the red 6H-1,2,3benzodithiazol-6-ones. Some ring chlorination occurs, but 2,6-substituents are retained in the products except for a ferr-butyl group, which is, exceptionally, replaced by chlorine. 1,4-Naphthoquinone 4-oxime and 1,2-naphthoquinone 2-oxime similarly give the red 4-chloro-SH-naphtho[ I ,2-d[ 1,2,3]dithiazol-5-one and the blue 9-chloro-4H-naphtho[2,3-d][ 1,2,3]dithiazol-4-one respectively. A unified set of mechanisms is proposed for all of the reactions.