Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds.
[4] Hydroperoxides can be reduced to alcohols with lithium aluminium hydride, as described in this idealized equation: This reaction is the basis of methods for analysis of organic peroxides.
[6] The phosphite esters and tertiary phosphines also effect reduction: "The single most important synthetic application of alkyl hydroperoxides is without doubt the metal-catalysed epoxidation of alkenes."
For example, the cobalt catalyzed oxidation of cyclohexane to cyclohexanone:[9] Drying oils, as found in many paints and varnishes, function via the formation of hydroperoxides.
[11] Such reactions rely on radical initiators that reacts with oxygen to form an intermediate that abstracts a hydrogen atom from a weak C-H bond.
Specific reactions include addition of hydrogen peroxide across the C=O double bond: In some cases, these hydroperoxides convert to give cyclic diperoxides: Addition of this initial adduct to a second equivalent of the carbonyl: Further replacement of alcohol groups: Triphenylmethanol reacts with hydrogen peroxide gives the unusually stable hydroperoxide, Ph3COOH.
One example involves sodium perborate, a commercially important bleaching agent with the formula Na2[(HO)2B]2(OO)2)].