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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
Shen X(沈晓); Ni CF(倪传法); Hu JB(胡金波)
2012
发表期刊Helv. Chim. Acta
ISSN0018-019X
卷号95期号:10页码:2043-2051
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.
学科领域氟化学
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
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收录类别SCI
语种英语
WOS记录号WOS:000310321600030
引用统计
被引频次:14[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/28337
专题中科院有机氟化学重点实验室
通讯作者Hu JB(胡金波)
推荐引用方式
GB/T 7714
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.
APA 沈晓,倪传法,&胡金波.(2012).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.Helv. Chim. Acta,95(10),2043-2051.
MLA 沈晓,et al."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".Helv. Chim. Acta 95.10(2012):2043-2051.
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