Acid-Mediated Ring-Expansion Reaction of N-Aryl-2-vinylazetidines: Synthesis and Unanticipated Reactivity of Tetrahydrobenzazocines
详细信息 查看全文
- 作者：Tomoaki Shimizu ; Shunsuke Koya ; Ryu Yamasaki ; Yuichiro Mutoh ; Isao Azumaya ; Kosuke Katagiri ; Shinichi Saito
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：May 16, 2014
- 年：2014
- 卷：79
- 期：10
- 页码：4367-4377
- 全文大小：492K
- 年卷期：v.79,no.10(May 16, 2014)
- ISSN：1520-6904
文摘
The aza-Clasen rearrangement of N-aryl-2-vinylazetidines has been explored. N-Aryl-2-vinylazetidines were transformed to corresponding tetrahydrobenzazocines in good yields. Unexpectedly, the tetrahydrobenzazocine was unstable and readily isomerized to vinyltetrahydroquinoline in the presence of acid. The mechanism of this ring contraction was studied in detail.