无金属条件下炔基环丁烷的重排扩环反应研究  

Study on the Rearrangement and Ring Expansion of Alkynyl Cyclobutane Promoted by Boron Trifluoride Ether

作　　者：袁大富 张林宝 Yuan Dafu;Zhang Linbao(School of Chemistry and Molecular Engineering,Qingdao University of Science and Technology,Qingdao 266000,China)

机构地区：[1]青岛科技大学化学与分子工程学院,山东青岛266000

出　　处：《山东化工》2022年第18期52-54,共3页Shandong Chemical Industry

摘　　要：扩环是实现由小环化合物到中环化合物或者大环化合物的一种常见手段,通常扩环的实现需要过渡金属催化或者相对苛刻的条件。三氟化硼作为有机合成中重要的路易氏酸性催化剂,在有机反应中有着非常重要的作用。在此提出了一种简单的重排扩环手段,通过利用廉价易得的三氟化硼乙醚(46.5%)试剂实现炔基环丁烷由四元环到五元环的转变,并在反应过程中实现了与对二甲苯或乙酸酐的亲电反应。该反应在室温下进行,操作简单,无需任何金属催化剂或者添加剂,反应快速。Ring expansion is a common method to achieve from small ring compounds to medium ring compounds or macrocyclic compounds.Usually,the realization of ring expansion requires transition metal catalysis or relatively harsh conditions.As an important Lewis acid catalyst in organic synthesis,boron trifluoride plays a very important role in organic reactions.Herein,a simple rearrangement and ring expansion method is proposed to realize the transformation of alkynylcyclobutane from a four-membered ring to a five-membered ring by using an inexpensive and readily available boron trifluoride ether(46.5%)reagent.Electrophilic reactions with p-xylene or acetic anhydride were achieved during the process.The reaction is carried out at room temperature,the operation is simple,no metal catalyst or additive is required,and the reaction is rapid.

关 键 词：炔基环丁烷 三氟化硼乙醚 扩环 亲电反应 

分 类 号：O621.251[理学—有机化学]