Synthesis of β,β-Dichloro-α,β-unsaturated Ketones by Trichloro-methyl Radical Addition/Elimination of Enol Silyl Ethers

doi:10.6023/cjoc201911023

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1625-1629.DOI: 10.6023/cjoc201911023 Previous Articles Next Articles

Special Issue: 有机硅化学虚拟合辑

烯醇硅醚经三氯甲基自由基加成串联消除反应合成β,β-二氯-α,β-不饱和酮

葛浩程, 杜科莹, 盛卫坚

浙江工业大学化学工程学院杭州 310014

收稿日期:2019-11-15 修回日期:2020-03-10 发布日期:2020-03-31
通讯作者: 盛卫坚 E-mail:swj@zjut.edu.cn

Synthesis of β,β-Dichloro-α,β-unsaturated Ketones by Trichloro-methyl Radical Addition/Elimination of Enol Silyl Ethers

Ge Haochen, Du Keying, Sheng Weijian

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2019-11-15 Revised:2020-03-10 Published:2020-03-31

1. 201625S.pdf(986KB)

Abstract

Using di-tert-butyl peroxide (DTBP) as oxidant, chloroform or carbon tetrachloride as trichloromethyl radical source and reaction solvent, enol silyl ethers derived from aryl ketone was transferred to β,β-dichloro-α,β-unsaturated ketone by trichloromethyl radical addition/elimination. The conditions are mild with avoiding the use of metal catalysts, and the enol silyl ethers substrate has good universality.

Key words: trichloromethyl radical, enol silyl ethers, β,β-dichloro-α,β-unsaturated

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Ge Haochen, Du Keying, Sheng Weijian. Synthesis of β,β-Dichloro-α,β-unsaturated Ketones by Trichloro-methyl Radical Addition/Elimination of Enol Silyl Ethers[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1625-1629.

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烯醇硅醚经三氯甲基自由基加成串联消除反应合成β,β-二氯-α,β-不饱和酮

Synthesis of β,β-Dichloro-α,β-unsaturated Ketones by Trichloro-methyl Radical Addition/Elimination of Enol Silyl Ethers

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