Intramolecular nucleophilic carbonyl trapping of alpha-ketenyl radicals by an amino group |
| |
Authors: | Tojino Mami Uenoyama Yoshitaka Fukuyama Takahide Ryu Ilhyong |
| |
Institution: | Department of Chemistry, Faculty of Arts and Sciences, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan. |
| |
Abstract: | Free-radical carbonylation of omega-alkynylamines with tributyltin hydride gives a mixture of alpha-methylene lactams and alpha-stannylmethylene lactams. Nucleophilic addition of an internal amino group to the carbonyl group of alpha-ketenyl radicals is proposed as the cyclization step. The subsequent unusual 1,4-H shift from the resulting 1-hydroxyallyl radical, followed by elimination of the beta-tributyltin radical leads to the formation of alpha-methylene lactams. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|