Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 20, Pages 9441-9443Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo501819z
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Funding
- National Science Foundation [CHE 1266333]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1266333] Funding Source: National Science Foundation
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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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