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锡-铟促进和微波辐射辅助下醛和炔丙基溴的炔丙基化反应
引用本文:李前荣,顾承志,尹浩.锡-铟促进和微波辐射辅助下醛和炔丙基溴的炔丙基化反应[J].中国化学,2006,24(1):72-78.
作者姓名:李前荣  顾承志  尹浩
作者单位:[1]Structure Research Laboratory, University of Science and Technology of China, Hefei, Anhui 230026, China [2]Department of Chemistry, Shihezi Univeristry, Shihezi, Xinjiang 832003, China
基金项目:Project supported by the Natural Science Foundation of Anhui Province (No. 03045305).
摘    要:A rapid and regioselective preparation of homopropargyl alcohols was reported. In the presence of SnCl2C6HsMe3NBr and microwave irradiation, the mixture of tin-indium and propargyl bromide reacted quickly with aldehydes in aqueous media to produce the homopropargyl alcohols exclusively in high yields. For benzaldehydes bearing different substituents, electronic effect of the substituents affected the reaction, the electron-withdrawing groups promoting the reaction and the electron-donating groups impeding the reaction. The reactions of benzaldehydes bearing an ortho substituent group on the phenyl ring with propargyl bromide may yield a mixture of regioisomers (homopropargyl and homoallenyl alcohols) or a single homoallenic alcohol due to the steric effect.

关 键 词:溴化物  炔丙基    微波  有机化学  合成方法
收稿时间:2005-04-31
修稿时间:2005-04-312005-09-05

Tin-Indium Mediated and Microwave Assisted Propargylation of Aldehydes with Propargyl Bromide
Li QianRong;Gu ChengZhi;Yin Hao.Tin-Indium Mediated and Microwave Assisted Propargylation of Aldehydes with Propargyl Bromide[J].Chinese Journal of Chemistry,2006,24(1):72-78.
Authors:Li QianRong;Gu ChengZhi;Yin Hao
Abstract:A rapid and regioselective preparation of homopropargyl alcohols was reported. In the presence of SnCl2‐C6H5Me3NBr and microwave irradiation, the mixture of tin‐indium and propargyl bromide reacted quickly with aldehydes in aqueous media to produce the homopropargyl alcohols exclusively in high yields. For benzaldehydes bearing different substituents, electronic effect of the substituents affected the reaction, the electron‐withdrawing groups promoting the reaction and the electron‐donating groups impeding the reaction. The reactions of benzaldehydes bearing an orthosubstituent group on the phenyl ring with propargyl bromide may yield a mixture of regioisomers (homopropargyl and homoallenyl alcohols) or a single homoallenic alcohol due to the steric effect.
Keywords:aldehyde  propargylation  tin-indium  regioselectivity  microwave
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