Wang Tongdao, Wang Long, Daniliuc Constantin G, Samigullin Kamil, Wagner Matthias, Kehr Gerald, Erker Gerhard
Organisch-Chemisches Institut , Westfälische Wilhelms-Universität Münster , Corrensstraße 40 , 48149 Münster , Germany . Email:
Institut für Anorganische und Analytische Chemie , Goethe-Universität Frankfurt , Max-von-Laue-Straße 7 , 60438 Frankfurt am Main , Germany.
Chem Sci. 2017 Mar 1;8(3):2457-2463. doi: 10.1039/c6sc04459j. Epub 2017 Jan 4.
-Allyltetramethylpiperidine is readily isomerized to the corresponding enamine by treatment with catalytic amounts of B(CF). It adds HB(CF) at the nucleophilic enamine carbon atom to form a C/B Lewis adduct. This reacts with two molar equivalents of carbon monoxide by selective head to tail coupling to give a five-membered COB heterocycle. In contrast the enamine/HB(CF) Lewis pair reacts with two molar equiv. of nitric oxide by head to head coupling. This reaction probably proceeds equilibrium with the corresponding vicinal N/B Lewis pair. Most products were characterized by X-ray diffraction.
烯丙基四甲基哌啶通过用催化量的B(CF)处理很容易异构化为相应的烯胺。它在亲核烯胺碳原子处添加HB(CF)以形成C/B路易斯加合物。该加合物通过选择性的头对尾偶联与两摩尔当量的一氧化碳反应，生成一个五元COB杂环。相比之下，烯胺/HB(CF)路易斯对通过头对头偶联与两摩尔当量的一氧化氮反应。该反应可能与相应的邻位N/B路易斯对处于平衡状态。大多数产物通过X射线衍射进行表征。
