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

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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
	Shen X(沈晓) ; Ni CF(倪传法) ; Hu JB(胡金波)
刊名	Helv. Chim. Acta
	2012
卷号	95 期号:10 页码:2043-2051
ISSN号	0018-019X
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
通讯作者	胡金波
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.
学科主题	氟化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1002/hlca.201200445
语种	英语
WOS记录号	WOS:000310321600030
公开日期	2013-08-23
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/28337]
专题	上海有机化学研究所_中科院有机氟化学重点实验室
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.