Oxidations of alkenes and cycloalkenes

The oxidation of alkenes and cycloalkenes may affect the double bonds, the rest of the molecule, or both. Also included in this section are aromatic hydrocarbons containing double bonds in their side chains. Compounds containing double bonds and other functional groups, such as hydroxyl, carbonyl, or carboxyl, will be discussed in the appropriate sections, such as unsaturated alcohols, aldehydes, ketones, acids, and esters. 

The oxidation of alkenes and cycloalkenes and their halogen derivatives with at least one hydrogen or halogen atom at the double bond leads to carboxylic acids. Ozonolysis usually requires the oxidative decomposition of the ozonide. The oxygen content of the ozonide is not sufficient for the formation of two molecules of acids or one dicarboxylic acid. The nonoxidative decomposition of cyclohexene ozonide gives an aldehyde-acid or its derivatives [1108]. It comes, therefore, as a surprise that carboxylic acids are claimed as products of the decomposition of ozonides by hydrogenation over the Lindlar catalyst [55] (equation 108). 

OL-Bromo ketones. The reagent in combination with triethylamine converts oxides of alkenes and oxides of five- to seven-membered cycloalkenes into a-bromo ketones in 70-80% yield, Morpholinoenamines under these conditions are also converted into a-bromo ketones. 

The same oxidizing agents and conditions used for the hydroxylation of alkenes and cycloalkenes are applied to unsaturated alcohols, ethers, aldehydes, ketones, and acids and their derivatives. 

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