Dicyclopentadienoxidation. I,Unkatalysierte Flüssigphasenoxidation von Dicyclopentadien

Dicyclopentadiene Oxidation I. Uncatalyzed Liquid-Phase Oxidation of Dicyclopentadiene Dicyclopentadiene is oxidized by molecular oxygen to a mixture of the monoepoxides 2 and 3 . The identification of the epoxides 2 , 3 and 4 was executed with authentic samples prepared by epoxidation with peracetic acid or with tert-butylhydroperoxide in the presence of MoO₂(acac)₂

1 acac — Acetylacetonat

The main product is the substituted norbornene oxide 2 . Allylic oxidation is also observed. Remarkable amounts of hydroperoxides can be determined iodometrically. The formation of allylic oxidation products 7 , 8 , 9 and 10 was proved by GC-MS-analysis. It is shown that in the uncatalyzed liquid phase oxidation of dicyclopentadiene no more than 50% of epoxides are formed. The bisepoxide 4 was found in small amounts only at higher conversions of the dicyclopentadiene.