Baeyer oxidation

Baeyer-Villiger Oxidation- oxidation of ketones to esters and lactones via oxygen insertion... 

The reaction of ketones with peroxy acids is both novel and synthetically useful An oxygen from the peroxy acid is inserted between the carbonyl group and one of the attached car bons of the ketone to give an ester Reactions of this type were first described by Adolf von Baeyer and Victor Vilhger m 1899 and are known as Baeyer—Villiger oxidations... 

Using Figure 17 15 as a guide write a mechanism for the ] Baeyer-Villiger oxidation of cyclohexyl methyl ketone by peroxybenzoic acid J... 

The product (6 hexanohde) is a cyclic ester or lactone (Section 19 15) Like the Baeyer-Vilhger oxidation an oxygen atom is inserted between the carbonyl group and a carbon attached to it But peroxy acids are not involved m any way the oxidation of cyclohexanone is catalyzed by an enzyme called cyclohexanone monooxygenase with the aid of certain coenzymes... 

Section 17 16 The oxidation of ketones with peroxy acids is called the Baeyer-Vilhger oxidation and is a useful method for preparing esters... 

Compounds known as lactones which are cyclic esters are formed on Baeyer—Vilhger oxi dation of cyclic ketones Suggest a mechanism for the Baeyer—Vilhger oxidation shown... 

Baeyer-Villiger oxidation (Section 17 16) Oxidation of an aldehyde or more commonly a ketone with a peroxy acid The product of Baeyer-Vilhger oxidation of a ketone is an ester... 

Oxidation. Maleic and fumaric acids are oxidized in aqueous solution by ozone [10028-15-6] (qv) (85). Products of the reaction include glyoxyhc acid [298-12-4], oxalic acid [144-62-7], and formic acid [64-18-6], Catalytic oxidation of aqueous maleic acid occurs with hydrogen peroxide [7722-84-1] in the presence of sodium tungstate(VI) [13472-45-2] (86) and sodium molybdate(VI) [7631-95-0] (87). Both catalyst systems avoid formation of tartaric acid [133-37-9] and produce i j -epoxysuccinic acid [16533-72-5] at pH values above 5. The reaction of maleic anhydride and hydrogen peroxide in an inert solvent (methylene chloride [75-09-2]) gives permaleic acid [4565-24-6], HOOC—CH=CH—CO H (88) which is useful in Baeyer-ViUiger reactions. Both maleate and fumarate [142-42-7] are hydroxylated to tartaric acid using an osmium tetroxide [20816-12-0]/io 2LX.e [15454-31 -6] catalyst system (89). 

Obsolete uses of urea peroxohydrate, as a convenient source of aqueous hydrogen peroxide, include the chemical deburring of metals, as a topical disinfectant and mouth wash, and as a hairdresser s bleach. In the 1990s the compound has been studied as a laboratory oxidant in organic chemistry (99,100). It effects epoxidation, the Baeyer-Villiger reaction, oxidation of aromatic amines to nitro compounds, and the conversion of sodium and nitrogen compounds to S—O and N—O compounds. 

Analysis. Butenes are best characterized by their property of decolorizing both a solution of bromine in carbon tetrachloride and a cold, dilute, neutral permanganate solution (the Baeyer test). A solution of bromine in carbon tetrachloride is red the dihaUde, like the butenes, are colorless. Decoloration of the bromine solution is rapid. In the Baeyer test, a purple color is replaced by brown manganese oxide (a precipitate) and a colorless diol. These tests apply to all alkenes. 

Hsynthesis from, 3, 767 Indenobenzazepines pharmacological properties, 7, 546 Indenone oxide, 2,3-diphenyl-photochromic compound, 1, 385 In deno[ 1,2-c][ 1,2,4]triazines synthesis, 3, 434 Indicated hydrogen nomenclature, 1, 33 Indigo, I, 317, 318-319, 4, 370 Baeyer synthesis, 1, 319 colour and constitution, 1, 344-345 molecular structure, 4, 162 photochromic compound, 1, 386 synthesis, 4, 247 Indigoid dyes... 

BAEYER VILLIQER Ketone Oxidation Synthesis of esters or lactones trom ketones with retention of configuration... 

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