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DOI: 10.1055/s-2007-991086
tert-Butyl Hydroperoxide (TBHP): A Versatile Oxidizing Agent in Organic Synthesis
Publication History
Publication Date:
12 October 2007 (online)
Introduction
The clear colorless liquid is widely available as 70-90% aqueous solutions and anhydrous in hydrocarbon solvents. Aqueous solutions may be dried by a phase-separation procedure, followed by azeotropic distillation to remove the last vestiges of water if necessary. The reagent is used in oxidations of various substrates to give epoxides, [1-3] ketones, aldehydes, [4] allylic alcohols, [5] and nitro or imine compounds. [6] The reagent and its metal complexes have been extensively reviewed. This article describes representative applications to problems in organic synthesis. In view of the lability of the hydroxyl group in tertiary alcohols, it was early suspected that pure hydrogen peroxide in nonaqueous solution would react with tert -butyl alcohol reversibly to form tert -butyl hydroperoxide (TBHP). [7]
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