Solvent-Dependent Substrate Reduction by (Sm[N(SiMe3)2]2(THF)2}. An Alternative Approach for Accelerating the Rate of Substrate Reduction by Sm(II)

被引：13

作者：

Chciuk, Tesia V. ^{[1
]}

Hilmersson, Goran ^{[2
]}

Flowers, Robert A., II ^{[1
]}

机构：

[1] Lehigh Univ, Dept Chem, Bethlehem, PA 18015 USA

[2] Univ Gothenburg, Dept Chem, SE-41296 Gothenburg, Sweden

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 20期

基金：

美国国家科学基金会;

关键词：

SAMARIUM(II) IODIDE; ELECTRON-TRANSFER; REDUCING POWER; SMI2; KETONES; SPHERE; HMPA;

D O I：

10.1021/jo501819z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The impact of solvent on electron transfer from Sm(II) to substrates was measured by determining the rate of reduction of 1-bromo-, 1-chlorododecane, and 3-pentanone in THF and hexanes using the highly soluble reductant {Sm[N(SiMe3)(2)](2)(THF)(2)}. Rates were found to be 3 orders of magnitude faster in hexanes than THF, and reductions of alkyl halides were inverse first order in THF. These findings show the solvent milieu significantly impacts the rate of substrate reduction, a consideration that may prove useful in synthesis.

引用

页码：9441 / 9443

页数：3

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