A new method for the synthesis of dinaphtho[1,2-b;2′,1′-d]thiophenes and selenophenes

✍ Scribed by Ashraful Alam; Hidetoshi Ohta; Tatsuya Yamamoto; Satoshi Ogawa; Ryu Sato

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 316 KB
• Volume: 18
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20291

✦ Synopsis

Abstract

Naphthalene‐1‐sulfonic acid dimethylamides were treated with n‐BuLi and elemental sulfur or selenium to afford dinaphtho[1,2‐b:2′,1′‐d]thiophenes and selenophenes, respectively. This is the first example of making two CS/Se bonds and a CC bond in a single step at room temperature and also demonstrates a useful method for the synthesis of both thiophenes and selenophenes on naphthalene. In the case of the reactions of elemental selenium, diselenides were also obtained along with dinaphtho[1,2‐b:2′,1′‐d]selenophenes. The structure of dinaphtho[1,2‐b:′,1′‐d]thiophene was characterized by X‐ray crystallography as a representative molecule. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:239–248, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20291