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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)

Journal article
Authors T. V. Chciuk
Göran Hilmersson
R. A. Flowers
Published in Journal of Organic Chemistry
Volume 79
Issue 20
Pages 9441-9443
ISSN 0022-3263
Publication year 2014
Published at Department of Chemistry and Molecular Biology
Pages 9441-9443
Language en
Links dx.doi.org/10.1021/jo501819z
Keywords SAMARIUM(II) IODIDE, ELECTRON-TRANSFER, REDUCING POWER, SMI2, COSOLVENT, ADDITIVES, KETONES, SML(2), SPHERE, HMPA
Subject categories Inorganic Chemistry

Abstract

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.

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