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有机化学 ›› 2010, Vol. 30 ›› Issue (11): 1759-1763. 上一篇    下一篇

研究简报

薄荷基氯格氏试剂与卤代烃的立体选择性反应研究

朱新强，阳年发*，任芳   

  1. (湘潭大学化学学院 环境友好化学与应用省部共建教育部重点实验室 湘潭 411105)
  • 收稿日期:2010-03-22 修回日期:2010-05-01 发布日期:2010-06-22
  • 通讯作者: 阳年发 E-mail:nfyang@xtu.edu.cn
  • 基金资助:

    国家自然科学基金;湖南省自然科学基金

Stereoselsctive Reaction of Menthyl Magnesium Chloride with Halo-hydrocarbon

ZHU Xin-Qiang, YANG Nian-Fa, REN Fang   

  1. (Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105)
  • Received:2010-03-22 Revised:2010-05-01 Published:2010-06-22
  • Supported by:

    ;Natural Science Foundation of Hunan Province

PDF

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被引次数

1

研究了薄荷基氯格氏试剂与卤代烃的立体选择性反应. 薄荷基氯格氏试剂与卤代烃反应生成两种产物: 薄荷基衍生物和新薄荷基衍生物, 主要产物是薄荷基衍生物. 其立体选择性与卤代烃的活性有关, 卤代烃的活性越差, 立体选择性越好. 活泼的苄基氯的反应产物de值为27.9%, 活性稍差的α-溴苯乙烯和2-溴丙烯的反应产物的de值在91%以上, 活性差的二氯甲烷和溴苯的反应产物的de值达到100%.

关键词: 薄荷基氯, 格氏试剂, 卤代烃, 反应活性, 立体选择性

The stereoselective reaction of the Grignard reagent derived from menthyl chloride with halohydrocarbon has been studied. The reaction yielded menthyl compound and neomenthyl compound, and the main product was menthyl compound. The stereoselectivity was relactive to the activity of halohydrocarbon. The poorer the activity of halohydrocarbon, the better the stereoselectivity. The de of the reaction of active benzyl chloride was 27.9% , that of less active α-bromostyrene and 2-bromopropene were more than 91% and that of bromobenzene and dichloromethane came to 100%.

Key words: menthyl chloride, Grignard reagent, halohydrocarbon, reactivity, stereoselectivity