期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 3, 页码 1139-1153出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b03144
关键词
-
资金
- European Research Council under the European Union's Horizon 2020 research and innovation programme [665951-ELICOS]
- Alexander von Humboldt Foundation
- Carl Friedrich von Siemens Foundation
Upon irradiation at lambda = 366 nm, tertiary N-alkoxycarbonyl-N-aryl-beta-enaminones furnished exclusively the trans-hexahydrocarbazol-4-ones by a conrotatory [6 pi] photocyclization but epimerized on silica to cis-hexahydrocarbazol-4-ones (14 examples, 44-98% yield). The acceptor substitution on the nitrogen atom enhanced the stability of the cyclized products compared to N-alkyl-N-aryl-beta-enaminones reported previously. The mechanism of the [6 pi] photocyclization was investigated by quenching experiments, deuterium-labeling experiments, and DFT calculations, suggesting a triplet pathway for the conrotatory ring closure followed by a suprafacial [1,4] hydrogen migration.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据