Bis(2-methoxyethyl)aminosulfur trifluoride: A new broad-spectrum deoxofluorinating agent with enhanced thermal stability
Bis(2-methoxyethyl)aminosulfur trifluoride: A new broad-spectrum deoxofluorinating agent with enhanced thermal stability
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DOI：
10.1021/jo990566
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发表时间：
1999-09-17
影响因子：
3.6
通讯作者：
Cheng, HS
中科院分区：
文献类型：
--
作者：
Lal, GS;Pez, GP;Cheng, HS
双（2-甲氧基乙基）氨基三氟化硫（CH 3 OCH 2CH 2）（2）NSF 3（Deoxo-Fluor reagent）是一种新型的脱氧氟化剂，其热稳定性远高于DAST（C2 H5）（2）NSF 3及其同类物。它可有效地将醇转化为烷基氟化物，将醛/酮转化为相应的偕-二氟化物，以及将羧酸转化为三氟甲基衍生物，在某些情况下，与DAST相比具有上级性能。增强的稳定性是合理化的基础上的构象刚性所施加的烷氧基与缺电子的硫原子的三氟化物的协调。
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.