New construction of p-tolylsulfonyl-substituted naphthalenes by thermal and photochemical cyclization of 1-aryl-4-(methylthio)-2-(p-tolylsulfonyl)-1,3-butadienes

✍ Scribed by Shoji Matsumoto; Shinjiro Takahashi; Katsuyuki Ogura

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 124 KB
• Volume: 12
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.1058

✦ Synopsis

Abstract

Transformation of 4‐(methylthio)‐1‐phenyl‐2‐(p‐tolylsulfonyl)‐1,3‐butadiene 1a was found to give 2‐(p‐tolylsulfonyl)naphthalene 3a either by the action of I~2~ in refluxing acetonitrile or by irradiation with a high‐pressure Hg lamp. An electron‐withdrawing group (p‐F or p‐CO~2~Me) on the phenyl ring retarded the thermal reaction, but the corresponding naphthalene derivative was efficiently produced by the photolysis in the presence of I~2~. The substituent effect of an electron‐donating methoxyl group is also reported. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:385–391, 2001