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学科主题: 氟化学
题名: beta-(Trifluoromethyl)vinyl Sulfonium Salts: Preparation and Reactions with Active Methylene and Methenyl Compounds
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
作者: LIN HAO ; Shen QL(沈其龙) ; Lv L(吕龙)
通讯作者: 吕龙
刊名: J. Org. Chem.
发表日期: 2011
卷: 76, 期:18, 页:7359-7369
收录类别: SCI
部门归属: 中科院上海有机化学研究所
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.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000294702000008
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/19253
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:
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.
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