有机化学 ›› 2020, Vol. 40 ›› Issue (5): 1388-1393.DOI: 10.6023/cjoc201910030 上一篇    下一篇

研究简报

一种1,1-二氯烯烃化合物的新合成方法

任新锋b, 宋小平a, 马影超b, 李亚b   

  1. a 海南师范大学 省部共建-热带药用植物化学教育部重点实验室 海口 570100;
    b 上海工程技术大学化学化工学院 上海 201620
  • 收稿日期:2019-10-25 修回日期:2019-12-08 发布日期:2020-01-03
  • 通讯作者: 任新锋, 李亚 E-mail:renxf@sues.edu.cn;ya.li@sues.edu.cn
  • 基金资助:
    海南师范大学省部共建-热带药用植物化学教育部重点实验室开放基金(No.2013-6)资助项目.

Method for the Synthesis of 1,1-Dichloroalkenes

Ren Xinfengb, Song Xiaopinga, Ma Yingchaob, Li Yab   

  1. a Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou 570100;
    b College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620
  • Received:2019-10-25 Revised:2019-12-08 Published:2020-01-03
  • Supported by:
    Project supported by the Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University (No. 2013-6).

1,1-二氯烯烃结构存在于许多天然产物中,同时也是一类重要的合成中间体,广泛应用于炔烃、卤代炔烃以及芳烃化合物的合成.报道了一个新的1,1-二氯烯烃化试剂:二氯甲基(2-吡啶基)砜.以叔丁醇钾作为碱,二氯甲基(2-吡啶基)砜与芳香醛顺利反应,以良好的产率制备得到了1,1-二氯烯烃化合物.该方法实验操作简便、试剂易得且纯化方便.

关键词: 二氯甲基砜, 1,1-二氯烯烃, 芳香醛

The 1,1-dichloroalkene structural unit is found in many natural products. 1,1-Dichloroalkenes are important intermediates, which have been widely used in the synthesis of alkynes, halogenated acetylenes and aromatic compounds. In this paper, a new dichloroolefinating reagent, dichloromethyl 2-pyridyl sulfone, was reported. 1,1-Dichloroalkenes can be conveniently obtained from the reaction of dichloromethyl 2-pyridyl sulfone with aromatic aldehydes using t-BuOK as base. This method has the advantage of operational simplicity, usage of easily available reagents and easy purification, which may find applications in organic synthesis.

Key words: dichloromethyl sulfone, 1,1-dichloroalkenes, aromatic aldehydes