Ohno Masatomi, Noda Masashi, Yamamoto Yoshihiko, Eguchi Shoji
Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan.
J Org Chem. 1999 Feb 5;64(3):707-712. doi: 10.1021/jo980523d.
The acid-catalyzed and Rh-catalyzed (also photolyzed) decomposition of 4-hydroxycyclobutenones with a diazo group at C-4 gave 2(5H)-furanone and/or cyclopentene-1,3-dione via an alpha-carbocation intermediate and a carbenoid (carbene) intermediate, respectively. Thermal rearrangement of some of these compounds led to the formation of diazepinediones without the extrusion of nitrogen through tandem 4pi electrocyclic ring opening and 8pi electrocyclic ring closure processes.
在酸催化以及铑催化（也可光解）下，4位带有重氮基的4-羟基环丁烯酮发生分解，分别通过α-碳正离子中间体和类卡宾（卡宾）中间体生成2(5H)-呋喃酮和/或环戊烯-1,3-二酮。其中一些化合物的热重排通过串联的4π电环化开环和8π电环化闭环过程，导致形成二氮杂卓二酮，且没有氮的脱出。
