Dicyclopentadiene Oxidation. II. Catalyzed Liquid-Phase Oxidation of Dicyclopentadiene
The liquid-phase oxidation of dicyclopentadiene 1 by molecular oxygen was studied in the presence of MoO2(acac)2 as a typical epoxidation catalyst.The yield of the mono-epoxides 2 and 3 is increased to 56.4 percent (uncatalyzed reaction: 43.6 percent).The ratio of the two mono-epoxides is decreased to 2/3 = 2.6 in relation to the uncatalyzed reaction 2/3 = 7.1).The influence of temperature, conversion and solvents is described.The bisepoxide 4 is formed at lower conversions than in the uncatalyzed reaction.But also at higher conversion of 1 not more than 10 percent of the bisepoxide 4 is formed.
Schnurpfeil, D.
p. 842 - 847
(2007/10/02)
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.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 percent of epoxides are formed.The bisepoxide 4 was found in small amounts only at higher conversions of the dicyclopentadiene.
Schnurpfeil, D.
p. 481 - 488
(2007/10/02)
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