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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (11): 1468-1484. 上一篇    下一篇

综述与进展

2,3-联烯醇及其衍生物的反应

邓友前a，顾振华b，麻生明*,a,b   

  1. (a浙江大学化学系分子识别与合成实验室 杭州 310027)
    (b中国科学院上海有机化学研究所金属有机化学国家重点实验室 上海 200032 )
  • 收稿日期:2005-12-06 修回日期:1900-01-01 发布日期:2006-10-27
  • 通讯作者: 麻生明

Reactions of 2,3-Allenols and Their Derivatives

DENG You-Qiana,GU Zhen-Huab,MA Sheng-Ming*,a,b   

  1. (a Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027)
    (b State Key Laboratory of Organometallic Chemis-try, Shanghai Institute of Organic Chemistry,
    Chinese Academy of Sciences, Shanghai 200032)
  • Received:2005-12-06 Revised:1900-01-01 Published:2006-10-27
  • Contact: MA Sheng-Ming

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被引次数

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2,3-联烯醇是一类含1,2-二烯官能团和羟基的化合物, 具有很高的反应活性, 它及其衍生物是一类重要的联烯化合物. 概述了2,3-联烯醇及其衍生物的反应, 包括2,3-联烯醇在过渡金属催化下的自身异构环化反应、钯催化的偶联反应、钌催化的环羰基化反应、不同条件下不同方式的扩环反应、亲电试剂参与的反应、分子内环加成反应、自由基反应等和2,3-联烯醇衍生物在零价钯催化下基于亚甲基-π-烯丙基钯中间体生成联烯或1,3-共轭二烯的区域选择性反应, SN2'类型的加成-消除反应, 二价钯催化下的分子内环化反应以及重排反应等.

关键词: 重排, 2,3-联烯醇及其衍生物, SN2'类型加成/消除, 过渡金属, 自由基, 催化

2,3-Allenols, an important class of allenes containing a 1,2-propadiene unit and a hydroxy group, are highly reactive. The reactions of 2,3-allenols and their derivatives are reviewed. The reactions of 2,3-allenols include transition metal-catalyzed cycloisomerization reactions, Pd-catalyzed coupling reactions, ruthenium-catalyzed cyclic carbonylation reactions, ring expansion reactions, electrophilic addition reactions, cycloaddition reactions, and radical reactions. On the other hand, the reactions of the derivatives of 2,3-allenols are Pd(0)-catalyzed reactions involving methylene-π-allyl palladium intermediates forming allenes or 1,3-dienes regioselectively, SN2' type addition-elimination reactions, Pd(II)-catalyzed intramolecular cyclizations and rearrangement reactions.

Key words: transition metal, rearrangement, catalysis, radical, SN2' type addition-elimination, 2,3-allenol and derivative