Lewis-Säure- und photochemisch induzierte Dimroth-Umlagerung von 3H,6H-2,5-Bis-(p-N,N-dimethylaminophenyl)-1,2-thiazolino[5,4-d]1,2-thiazolin-3,6-dithion

✍ Scribed by Prof. Dr. E. Fanghänel; Dipl.-Chem. B. Kordts; Dr. A. M. Richter; Dipl.-Chem. K. Dutschmann

• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: English
• Weight: 424 KB
• Volume: 332
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/prac.19903320317

✦ Synopsis

Lewis‐acid and Photochemically Induced Dimroth Rearrangement of 3H,6H‐2,5‐Bis‐(p‐N,N‐dimethylaminophenyl) ‐1,2‐thiazolino[5,4‐d]1,2‐thiazoline‐3,6‐dithione

The reaction of 3H,6H‐1,2‐dithiolo[4,3‐c]1,2‐dithiole‐3,6‐dithione (5) with N,N‐dimethyl‐p‐phenylendiamin gives, depending on the conditions of the reaction, 3H,6H‐3‐(p‐N,N‐dimethylaminophenyl‐imino)‐1,2‐dithiolo[4,3‐c]1,2‐dithiole‐6‐thione (7), and 3H,6H‐2,5‐Bis‐(p‐N,N‐dimethylaminophenyl) ‐1,2‐thiazolino[5,4‐d]1,2‐thiazoline‐3,6‐dithione (3d). Catalyzed by Lewis acids the compound 3d rearranges reversibly into the isomeric 3H,6H‐3,6‐bis‐(p‐N,N‐dimethylaminophenyl‐imino) ‐1,2‐dithiolo[4,3‐c]1,2‐dithiole (4d). The Dimroth type rearrangement of 3d into 4d occurs also on irradiation.