beta-(Trifluoromethyl)vinyl Sulfonium Salts: Preparation and Reactions with Active Methylene and Methenyl Compounds

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	beta-(Trifluoromethyl)vinyl Sulfonium Salts: Preparation and Reactions with Active Methylene and Methenyl Compounds
	LIN HAO ; Shen QL(沈其龙) ; Lv L(吕龙)
刊名	J. Org. Chem.
	2011
卷号	76 期号:18 页码:7359-7369
ISSN号	0022-3263
其他题名	三氟甲基烯基锍盐: 制备及其与含活泼亚甲基的化合物的反应
通讯作者	吕龙
英文摘要	Two trifluoromethyl-substituted building blocks beta-(trifluoromethyl)vinyl sulfonium salts 1 and 2 were developed. Reactions of beta-(trifluoromethyl)vinyl sulfonium salt 1 with active methylene compounds containing electron-withdrawing groups using DBU as the base in DMSO occurred to give trifluoromethyl-substituted cyclopropane derivatives 7 as the major products. In contrast, reactions of beta-(trifluoromethyl)vinyl sulfonium salt 2 with active methylene compounds occurred with the migration of one of the electron-withdrawing groups to give the products 8 as the major products when NaH was used as the base in DMSO. Moreover, when NaH was used as base in THF/CH(2)Cl(2) at -78 degrees C, reaction of beta-(trifluoromethyl)vinyl sulfonium salt 1 gave trifluoromethyl-substituted 2,3-dihydrofuran derivatives 9 as the major products. A working mechanism was proposed to explain the different behaviors of the beta-(trifluoromethyl)vinyl sulfonium salts 1 or 2 with active methylene compounds under these different conditions.
学科主题	氟化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/jo2009033
语种	英语
WOS记录号	WOS:000294702000008
公开日期	2013-02-25
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/19253]
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	LIN HAO,Shen QL,Lv L. beta-(Trifluoromethyl)vinyl Sulfonium Salts: Preparation and Reactions with Active Methylene and Methenyl Compounds[J]. J. Org. Chem.,2011,76(18):7359-7369.
APA	LIN HAO,沈其龙,&吕龙.(2011).beta-(Trifluoromethyl)vinyl Sulfonium Salts: Preparation and Reactions with Active Methylene and Methenyl Compounds.J. Org. Chem.,76(18),7359-7369.
MLA	LIN HAO,et al."beta-(Trifluoromethyl)vinyl Sulfonium Salts: Preparation and Reactions with Active Methylene and Methenyl Compounds".J. Org. Chem. 76.18(2011):7359-7369.