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.
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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. |
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