Bis(2-methoxyethyl)aminosulfur trifluoride: A new broad-spectrum deoxofluorinating agent with enhanced thermal stability

被引：422

作者：

Lal, GS ^{[1
]}

Pez, GP ^{[1
]}

Pesaresi, RJ ^{[1
]}

Prozonic, FM ^{[1
]}

Cheng, HS ^{[1
]}

机构：

[1] Air Prod & Chem Inc, Allentown, PA 18195 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 19期

关键词：

D O I：

10.1021/jo990566+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bis(2-methoxyethyl)aminosulfur trifluoride, (CH3OCH2CH2)(2)NSF3 (Deoxo-Fluor reagent), is a new deoxofluorinating agent that is much more thermally stable than DAST (C2H5)(2)NSF3 and its congeners. It is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gem-difluorides, and carboxylic acids to the trifluoromethyl derivatives with, in some cases, superior performance compared to DAST. The enhanced stability is rationalized on the basis of conformational rigidity imposed by a coordination of the alkoxy groups with the electron-deficient sulfur atom of the trifluoride.

引用

页码：7048 / 7054

页数：7

共 38 条

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