title: Complications from dual roles of sodium hydride as a base and as a reducing agent.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
authors.forename: Dusan
authors.initials: D
authors.lastname: Hesek
authors.forename: Mijoon
authors.initials: M
authors.lastname: Lee
authors.forename: Bruce C
authors.initials: BC
authors.lastname: Noll
authors.forename: Jed F
authors.initials: JF
authors.lastname: Fisher
authors.forename: Shahriar
authors.initials: S
authors.lastname: Mobashery
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D004126:Dimethylformamide / Q000737:chemistry; D019163:Reducing Agents / Q000737:chemistry; D017670:Sodium Compounds / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
chemical_list: D000097:Acetonitriles; D019163:Reducing Agents; D017670:Sodium Compounds; D012997:Solvents; C524957:sodium hydride; D004126:Dimethylformamide; C032159:acetonitrile