Chelating alcohols accelerate the samarium diiodide mediated reduction of 3-heptanone

被引：42

作者：

Dahlén, A ^{[1
]}

Hilmersson, G ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 32期

关键词：

D O I：

10.1016/S0040-4039(01)00958-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Initial rate studies of samarium diiodide mediated reduction of 3-heptanone to 3-heptanol are reported. The reduction of 3-heptanone with the polydentate tri(ethylene glycol) methyl ether is 16 times faster than without a proton donor, and 4.3 times faster than methanol. The primary kinetic isotope effect (KIE) was measured as k(H)/ k(D) approximate to 2, indicating a rate-determining proton transfer. Diols are superior to mono-alcohols as proton donors, the reduction of 3-heptanone is 255 times as fast with di(ethylene glycol) than in the absence of a proton donor. A mechanism of glycol accelerated samarium. diiodide reduction is discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5565 / 5569

页数：5

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