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有机化学
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有机化学 ›› 1989, Vol. 9 ›› Issue (3): 221-226. 上一篇    下一篇

研究论文

含硫碳负离子的反应及其应用的研究 II: 固-液相转移催化共轭加成作用

刘广鉴;张正;许从应   

  1. 南京大学化学系
  • 发布日期:1989-06-25

Studies on some reactions of sulfur-containing carbanions and their synthetic applications II: Solid-liquid phase transfer catalyzed conjugate addition

LIU GUANGJIAN;ZHANG ZHENG;XU CONGYING   

  • Published:1989-06-25

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本文报道在固-液相转移催化条件下用碳酸钾处理α-苯亚磺酰基乙酸甲酯, 生成碳负离子, 与适当的α,β-不饱和酯的共轭加成作用, 合成了8个新化合物, 并通过元素分析, IR, ^1H NMR, MS鉴定, 证明了它们和预期的共轭加成产物的结构完全一致.

关键词: 乙酸酯, 反应机理, 质谱法, 共轭, 相转移催化, 质子磁共振谱法, 阴离子, 加成反应, 苯磺酸 P, 亚磺酰基

The sulfur-contg. carbanion PhS(O)CH-CO2Me (I) was generated from Me 2-phenylsulfinylacetate with potassium carbonate under solid-liq. phase transfer conditions and then allowed to react in situ with a,b-unsatd. esters at the temps. of 20-40? The conjugate addition of the anion (I) to acrylates, a-alkylacrylates, crotonates, and maleates proceeded smoothly.

Key words: ACETIC ACID ESTER, REACTION MECHANISM, MASS SPECTROGRAPHY, CONJUGATION, PHASE TRANSFER CATALYSIS, PROTON MAGNETIC RESONANCE SPECTROMETRY, ANION, ADDITION REACTION, BENZENESULFONIC ACID P, SULFINYL GROUP

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