Hydrogen peroxide glycol cleavage

Oxidations. Glycol cleavage by NalO can be improved using the silca gel support and microwave irradiation. The oxidation of sulfides to either sulfoxides or sulfones by the same method seems to be dependent on the duration of the irradiation. Supported titanium/tartaric acid catalyst is suitable for the conversion of sulfides to sulfoxides using hydrogen peroxide as the main oxidant." ... 

The reaction of (148) with glycol and hydrogen peroxide gave (149). Compound (19b) has been reduced with liAlH4 to the corresponding alcohol, which was converted into the aldehyde and bromomethyl and aminomethyl derivatives that are of pharmaceutical interest. A mild method for the hydrolysis and decarboxylation of various amides of methyl 3-aminothiophen-2-carboxylates has been developed. Thermal decomposition of (150) led to cleavage of the thiophen ring, with extrusion of sulphur and formation of the isothiazole (151). ... 

More powerful oxidants are almost always needed. Those commonly used for cleavage of olefins — and for other degradations — include nitric acid, hydrogen peroxide, permanganate, chromic acid, very concentrated alkali hydroxides, and in particular ozone. The products to be expected from oxidative fission of an ethylenic carbon-carbon double bond are carbonyl compounds — an aldehyde or a ketone or both according as the doubly bonded carbon atoms do or do not carry a hydrogen atom — but it often happens that 1,2-glycols are obtained as intermediates. 

Strychninonic acid must be an a-ketoamide, the diagnostic barium hydroxide-hydrogen peroxide oxidation (147) giving carbon dioxide, glycolic acid (strychninolone type of cleavage), and the amino acid Ba(OH)2 + H2O,... 

The combination of A -bromoacetamidc, silver acetate, and dry acetic acid has been shown to be superior to Woodward s procedure for the rfy-hydroxylation of olefins. Work up of the reaction mixture is simply effected by hydrolysis of the dioxolenium ion, followed by cleavage of the hydroxyacetate intermediate with lithium aluminium hydride. The use of a co-oxidant, such as sodium chlorate or hydrogen peroxide, allows the addition of catalytic quantities of osmium tetroxide to prepare c/y-diols from olefins. However the reaction is often complicated by further oxidation of the glycol to the a-ketol. The use of tertiary amine A -oxides, particularly A -methylmorpholine A -oxide, prevents this oxidation and gives higher yields of the desired product (Table 6). Another variation on this theme employs... 

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