烯烃一锅法合成1-氯-2-碘化合物的新方法研究  

One-pot synthesis of 1-chloro-2-iodide compounds from olefins

作　　者：许响生[1] 祝欢欢 XU Xiangsheng;ZHU Huanhuan(College of Chemical Engineering,Zhejiang University of Technology,Hangzhou 310014,China)

机构地区：[1]浙江工业大学化学工程学院

出　　处：《浙江工业大学学报》2019年第5期490-494,共5页Journal of Zhejiang University of Technology

基　　金：863计划子课题(2013AA065005)

摘　　要：发展了一种一锅法制备1-氯-2-碘化合物的方法。以叔丁基过氧化氢为氧化剂,碘单质、1-羟基苯并三氮唑和烯烃反应,生成α-碘代-N-烷氧基苯并三氮唑中间体,中间体不经分离,与乙酰氯反应,一锅法合成了1-氯-2-碘化合物。较优反应条件为:以二氯甲烷为溶剂,第一步在40℃下反应5 h,添加乙酰氯后室温下反应16 h,(1-氯-2-碘乙烷基)苯的总收率为50%。本反应适用于芳香烯烃和脂肪烯烃,收率为13%~68%。产品及重要中间体结构经1H-NMR,13 C-NMR和HRMS表征确认。该反应具有条件温和、操作简单和区域选择性高等优点。One-pot synthesis of 1-chloro-2-iodine compounds was developed.The reaction of olefins with 1-hydroxybenzotriazole and iodine in the presence of tertiary butyl peroxide generatedα-iodide-N-alkoxyl-1H-benzo[d][1,2,3]triazole intermediates,which further directly reacted with acetyl chloride to produce 1-chloro-2-iodide compounds.Reaction of styrene with the other reagents in dichloromethane at 40℃for 5 h followed by addition of acetyl chloride at room temperature for another 16 h produced(1-chloro-2-iodoethyl)benzene with yield of 50%.Both aromatic and aliphatic alkenes can be readily employed in this reaction to obtain the desired products and the yields varied from 13%to 68%.Structures of all products and important intermediates were confirmed by 1H-NMR,13 C-NMR and HRMS.The developed one-pot synthetic protocol has advantages of mild,simple and high regioselectivity.

关 键 词：烯烃 1-氯-2-碘化合物 一锅法 区域选择性 

分 类 号：O625.2[理学—有机化学]