School of Chemistry and Chemical Engineering, State Key Lab of Urban Water Resource and Environment, Harbin Institute of Technology , Harbin 150080, China.
J Org Chem. 2017 Feb 3;82(3):1389-1402. doi: 10.1021/acs.joc.6b02547. Epub 2017 Jan 19.
A novel and efficient method for the synthesis of highly substituted benzobicyclo[2.2.2]octane skeletons has been explored. Under UV-light irradiation, o-divinylbenzenes underwent a pericyclic reaction to form the cyclic o-quinodimethane intermediates which were subsequently reacted with olefins through [4+2] addition to construct the benzobicyclo[2.2.2]octane skeletons in mild conditions. Gram scale reactions demonstrated the synthetic potential application of this protocol.
探索了一种新颖高效的合成高取代苯并双环[2.2.2]辛烷骨架的方法。在紫外光照射下，邻二乙烯基苯经历周环反应形成环状 o-醌二亚甲基中间体，随后通过[4+2]加成与烯烃反应，在温和条件下构建苯并双环[2.2.2]辛烷骨架。克级反应证明了该方案的潜在合成应用。
