ChemInform Abstract: Synthesis of Polyfunctionalized Thiophenes and Enediynes via Ring-Opening Reactions of 3-Lithiated Thieno[2,3-b](and [3,2-b])thiophenes, 3,4-Dilithiated Thieno[2,3-b]thiophenes and 3,6-Dilithiated Thieno[3,2-b]thiophenes.

✍ Scribed by L. S. FULLER; B. IDDON; K. A. SMITH

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199819112

✦ Synopsis

Synthesis of Polyfunctionalized Thiophenes and Enediynes via Ring-Opening Reactions of 3-Lithiated Thieno[2,3-b](and [3,2b])thiophenes , 3,4-Dilithiated Thieno[2,3-b]thiophenes and3,6-Dilithiated Thieno[3,2-b]thiophenes. -Solutions of title lithiated thienothiophenes are obtained from the corresponding dibromo derivatives (I) and (VII) via Br → Li exchange with BuLi and give either polyfunctionalized thiophenes, e.g. (IV), or polyfunctionalized enediynes, like (XI), by a novel tandem ring-opening process. -(FULLER, L.