Periodates with permanganate

Cleavage of an alkenoic acid can be carried out with permanganate, a permanganate—periodate mixture, periodate or with nitric acid, dichromate, ozone, or, if the unsaturation is first converted to a dihydroxy compound, lead tetraacetate (71,73). Oxidative ozonolysis is a process for the manufacture of azelaic acid [123-99-9] and pelargonic acid (74). 

Photolysis of J gives an isomeric compound K in 83% yield. Alkaline hydrolysis of K affords a hydroxy carboxylic acid L, C25H32O4. Treatment of K with silica gel in hexane yields M, C24H2g02. M is converted by sodium periodate-potassium permanganate to a mixture of N and O. What are the structures of K, L, and M ... 

Allylcarbazole (and 3-chloro- and 3-chloro-6-nitroanalogs) hydroxylate, normally with permanganate the diol from 9-allylcarbazole cleaved normally with periodate." ... 

Methyl-j8-naphthylselenone, C10H7.SeO2.CH3, occurs when the sodium salt of naphthalene-j8-seleninic acid in methyl alcohol is boiled with methyl iodide for a long period. After treatment with water and extraction with ether, removal of the latter and crystallisation from alcohol gives a 48 per cent, yield as golden-yellow crystals, M.pt. 136° C. The selenone may also be obtained by the oxidation of methyl-j3-naphthyl selenide with permanganate. 

The mechanism of this reaction has been found to be autocatalytic. The rate is proportional to the concentrations of Mn(II) and periodate and also increases with permanganate concentration. In perchloric acid solution a violet-colored complex of Mn(III) is formed as an intermediate. The proposed mechanism may be written... 

This characteristic component of the phytosphingolipids gives L-serine phosphate on oxidation with permanganate and hydrolysis, followed by periodate oxidation. 

The atisine and Garrya (35,36) alkaloids have been interrelated by converting both atisine (XXX) and veatchine, by a parallel sequence of degradations, to the same A-acetyl ester (XCV) (35, 36). The respective azomethine acetates (LXXXVII, LXXXVIII) derived from atisine (12,16-bond) and veatchine (13,16-bond) were converted to the A-acetyl derivatives (LXXXIX, XC) by reduction, acetylation, and saponification. Oxidation of LXXXIX and CX with permanganate/periodate under controlled conditions gave the respective carboxylic acids (XCIa,... 

Oxidation of the isoxazolidine 64 with permanganate causes complete decomposition of the isoxazolidine ring. Two moles of benzoic acid are obtained.2 Oxidation of the chloro compound 50, X = Cl, with periodic acid affords only an intractable purple resin with permanganate />,/> -dichloroazoxybenzene is obtained.166... 

For future labeling syntheses of potential biosynthetic precursors, as well as for preparation of monocyclic diketones 70, on a 100- to 1000-g scale, additional, nonbiomimetic syntheses to these important intermediates were elaborated (63) (see Scheme 14). The key step of the first synthesis was oxidative cleavage of suitably substituted dimethyl indenes 68, either directly with permanganate-periodate or via remarkably stable ozonides 69. The required indenes 68 could be prepared from esters 67, and thus from very cheap educts like methacrylic acid and... 

Introduction. Sodium periodate is widely used for the oxidation of a variety of organic substrates and as a cooxidant in other oxidation reactions (see Sodium Periodate-Osmium Tetroxide and Sodium Periodate-Potassium Permanganate) f The Nal04 oxidation is usually conducted in water however, for organic substrates that are insoluble in water, an organic cosolvent (e.g. MeOH, 95% EtOH, 1,4-dioxane, acetone, MeCN) is used. Alternatively, the oxidation can be conducted either with phase-transfer catalysis (PTC) using quaternary ammonium or phosphonium salts in a two-phase system, or in an organic solvent if the oxidant is first coated on an inert support. ... 

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