2886-87-5Relevant articles and documents
Oxidative dihydroxylation of alicyclic unsaturated hydrocarbons with vinyl- and norbornene fragments in pseudohomogenic system
Alimardanov, Kh. M.,Garibov,Abdullaeva, M. Ya.,Sadygov,Kuliev,Ismailov
, p. 63 - 71 (2013/04/10)
Oxidation of alicyclic unsaturated hydrocarbons (4-vinylcyclohexene, 5-vinylnorbornene, 5-cyclohexenylnorbornene, and 5-vinylbicyclooctene) with 30% hydrogen peroxide solutions and percarbamide is studied. Reaction was carried out at 40-70 C in the presence of heterogenized peroxocomplex compounds of molybdenum and tungsten formed "in situ" in the reaction of metal oxohalides with H3PO4, nano-dimensional particles of carbon material, and hydrogen peroxide. Main oxidation products of alicyclic diene hydro-carbons are the corresponding unsaturated epoxides and diols. Depending on the reaction condition their ratio varies in a wide range.
Manganese(III) porphyrin catalysts for the oxidation of terpene derivatives: A comparative study
Maraval, Valerie,Ancel, Jean-Erick,Meunier, Bernard
, p. 349 - 357 (2007/10/03)
A comparative study involving four manganese(III) porphyrin catalysts combined with two different oxidants (sodium hypochlorite and potassium monopersulfate) has been performed in the epoxidation of three terpene derivatives. The catalytic oxidation of α-pinene produces selectively 100% of the epoxide or 65% of allylic oxidation products, only by modification of the substituents on the meso-positions of the metalloporphyrin catalyst. The catalytic oxidation of the 5-vinyl-2-norbornene is regio- and stereoselective, producing only the exo-2,3-epoxy-5-vinylnorbornane. With α-terpinene, a conjugated di-olefin, an oxidative dehydrogenation reaction was surprisingly observed, producing p-cymene as a major compound.
Diastereoselective epoxidation of olefins by organo sulfonic peracids, II
Kluge,Schulz,Liebsch
, p. 2957 - 2976 (2007/10/03)
We have investigated the behaviour of sulfonic peracids 2 in situ generated towards olefins 7a, 7b, 9, 11, 14, 16, 18, allylic acid and homoallylic alcohols 20, 22, 24, 26, 28, 30, 33 and α,β-unsaturated ketones 35, 37, 39. Generally, the epoxidation proceeds in a peracid-like manner with greater diastereoselectivity than those by common oxidants. In particular, the epoxidation of Δ4 3-ketosteroids 39a-i led to 4α,5α-epoxides 40a-i with remarkable high de-values. Enhanced α-selectivity was also found in the epoxidation of cholesterol 28b. Due to the mild reaction conditions, even acid sensitive epoxides 8a, 8b, 10, 12, 13, 15, 17, 19 were obtained in good yields.