Flavin hydroperoxide, alkene epoxidation

The flavin coenzyme reacts with molecular oxygen to form an intermediate species called flavin hydroperoxide. The oxygen of flavin hydroperoxide can be attacked by the % electrons of an alkene group. The subsequent nucleophilic attack of oxygen to the carbocation generates the epoxide ring (Figure 1.42). Epoxides are found as intermediate products in some biosynthetic pathways. The compound... 

Oxirans.— Epoxides are readily available from the catalytic oxidation of alkenes with 2-hydroperoxyhexafluoropropan-2-ol (HPHI) (1), which itself is easily prepared from hexafluoroacetone hydrate (2) and hydrogen peroxide (Scheme 1). HPHI is claimed to have similarities to the natural flavin hydroperoxides which are implicated in epoxidations and hydroxylations by external flavoprotein mono-oxygenases. Yields are typically in the range 77—92%. 

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