Complications from Dual Roles of Sodium Hydride as a Base and as a Reducing Agent

Sodium hydride is a common reagent for substrate activation in nucleophilic substitution reactions. Sodium hydride can behave both as a base and as a source of hydride. This dual ability in the presence of an electrophile such as benzyl bromide results in the formation of byproducts when dimethylfor...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-03, Vol.74 (6), p.2567-2570
Main Authors: Hesek, Dusan, Lee, Mijoon, Noll, Bruce C., Fisher, Jed F., Mobashery, Shahriar
Format: Article
Language:English
Subjects:
Acetonitriles - chemistry
Chemical reactivity
Chemistry
Dimethylformamide - chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
Reducing Agents - chemistry
Sodium Compounds - chemistry
Solvents - chemistry
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Summary:Sodium hydride is a common reagent for substrate activation in nucleophilic substitution reactions. Sodium hydride can behave both as a base and as a source of hydride. This dual ability in the presence of an electrophile such as benzyl bromide results in the formation of byproducts when dimethylformamide or acetonitrile are used as solvents for these reactions. The structural nature of these byproducts is revealed in this report.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo802706d