ChemInform Abstract: Bis[1,2]dithiolo[3,4-b][4′,3′-e][1,4]thiazine-3,5-dione, a Planar 1,4-Thiazine.

✍ Scribed by Carlos F. Marcos; Oleg A. Rakitin; Charles W. Rees; Tomas Torroba; Andrew J. P. White; David J. Williams

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 32 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199917164

✦ Synopsis

Bis [1,2]dithiolo [3,4-b][4',3'-e][1,4]thiazine-3,5-dione, a Planar 1,4-Thiazine.

-Reaction of N-benzyldiisopropylamine (I) with S 2 Cl 2 gives N-benzyl-bisthiolothiazine (II) with typically folded structure. Debenzylation of (II) results in a dramatic flattening of the molecule structure giving the title compound (IV) having atypically a rare near planar 1,4-thiazine ring. Compound (IV) forms a blue anion with Li-or NaHMDS and does not extrude sulfur thermally to furnish the expected product (VII). An alternative route to bisdithiolopyrrole (VII) is given. -(MARCOS, CARLOS F.; RAKITIN,