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学科主题: 氟化学
题名: Nucleophilic Fluoroalkylation of alpha,beta-Unsaturated Carbonyl Compounds with alpha-Fluorinated Sulfones: Investigation of the Reversibility of 1,2-Additions and the Formation of 1,4-Adducts
其他题名: a-氟化的砜对a,b-不饱和羰基化合物的亲核氟烷基化: 1,2-加成产物的可逆性和1,4-加成产物的形成研究
作者: Shen X(沈晓) ; Ni CF(倪传法) ; Hu JB(胡金波)
通讯作者: 胡金波
刊名: Helv. Chim. Acta
发表日期: 2012
卷: 95, 期:10, 页:2043-2051
收录类别: SCI
部门归属: 中科院上海有机化学研究所; 先正达集团Jealotts Hill研究中心
英文摘要: A detailed investigation of the reactions of PhSO2CF2H and PhSO2CH2F with (E)-chalcone (=(E)-1,3-diphenylprop-2-en-1-one) at low temperatures revealed that these two reactions were kinetically controlled, and the ratios of 1,2- vs. 1,4-adducts, which did not change much over time at these temperatures, reflect the relative rates of the two reaction pathways. The controlled experiments of converting the PhSO2CF2- and PhSO2CHF-substituted 1,2-adducts to 1,4-adducts showed that these isomerizations are not favored due to the low stability and hard-soft nature of PhSO2CF(2)(1) and PhSO2CHF- anions. Moreover, taking advantage of the remarkable stability and softness of (PhSO2)2CF- anion, an efficient thermodynamically controlled isomerization of (PhSO2)2CF-substituted 1,2-adduct to 1,4-adduct was achieved for the first time.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000310321600030
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/28337
Appears in Collections:中科院有机氟化学重点实验室_期刊论文

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Recommended Citation:
Shen X,Ni CF,Hu JB. Nucleophilic Fluoroalkylation of alpha,beta-Unsaturated Carbonyl Compounds with alpha-Fluorinated Sulfones: Investigation of the Reversibility of 1,2-Additions and the Formation of 1,4-Adducts[J]. Helv. Chim. Acta,2012,95(10):2043-2051.
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