通过N,N-二烯丙基苯胺与兰开斯特公司的H2B-C6F5试剂反应制备环状胺/硼烷路易斯对。
Cyclic Amine/Borane Lewis Pairs by the Reaction of N,N-Diallylaniline with Lancaster's H2 B-C6 F5 Reagent.
作者信息
Wang Tongdao, Liu Lei, Grimme Stefan, Daniliuc Constantin G, Kehr Gerald, Erker Gerhard
机构信息
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn, Beringstraße 4, 53115, Bonn, Germany.
出版信息
Chem Asian J. 2016 May 6;11(9):1394-9. doi: 10.1002/asia.201600060. Epub 2016 Mar 24.
Twofold hydroboration of N,N-diallylaniline with the C6 F5 BH2 ⋅SMe2 reagent gave the respective hetero-bicyclo[3.3.0]octane and hetero-methylbicyclo[3.2.0]heptane compounds 4 and 5 as the major products, both showing strong internal N-B amine Lewis base/borane Lewis acid adduct formation. A DFT analysis indicated their formation (and that of a small amount of several isomeric five-membered heterocyclic products) under thermodynamic control. Compound 5 underwent fragmentation with propene liberation to form compound 7 with a formal N=B bond at 100 °C. This product was also obtained from the isomer 4 at much higher temperature (300 °C).
N,N-二烯丙基苯胺与C6F5BH2·SMe2试剂进行双重硼氢化反应，得到相应的杂双环[3.3.0]辛烷和杂甲基双环[3.2.0]庚烷化合物4和5作为主要产物，二者均显示出强烈的内部N-B胺路易斯碱/硼烷路易斯酸加合物形成。密度泛函理论（DFT）分析表明它们（以及少量几种异构五元杂环产物）是在热力学控制下形成的。化合物5在100 °C下发生断裂并释放出丙烯，形成具有形式上N=B键的化合物7。该产物在更高温度（300 °C）下也可从异构体4获得。
Zotero 插件