Trifluoromethide as a Strong Base: [CF3-] Mediates Dichloromethylation of Nitrones by Proton Abstraction from the Solvent

被引：22

作者：

Behr, Jean-Bernard ^{[1
]}

Chavaria, Dani ^{[1
]}

Plantier-Royon, Richard ^{[1
]}

机构：

[1] Univ Reims, ICMR, CNRS, UFR Sci Exactes & Nat,UMR 7312, F-51687 Reims 2, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 22期

关键词：

NUCLEOPHILIC TRIFLUOROMETHYLATION; CARBONYL-COMPOUNDS; TETRAMETHYLAMMONIUM FLUORIDE; TRIFLUOROMETHYLTRIMETHYLSILANE; REAGENTS; DISULFIDES; FLUOROFORM; ALCOHOLS; HYDRATE; IMINES;

D O I：

10.1021/jo402028r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented reactivity of CF3-TMS has been revealed, which exploits the basic character of the generated [CF3-] capable of delivering dichloromethide from dichloromethane with subsequent transfer to nitrones under smooth conditions. The proton-abstraction pathway was demonstrated through isotopic labeling experiments in CD2Cl2. The same reaction was achieved in acetonitrile with the introduction of a cyanomethyl group onto the nitrones.

引用

页码：11477 / 11482

页数：6

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