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A new process of oxidation of cycloalkanone acetals under the action of in situ generated performic acid has been found. The main products of the reaction are α, ω-dicarboxylic acids obtained with the yield up to 77% depending on the size of acetals ring. The process has been explored and optimized on the example of the dodecanedioic acid synthesis (a valuable industrial product).
Content available remote A new oxidation process. Transformation of gem-bishydroperoxides into esters
A new oxidation process has been found where α,ω-dicarboxylic acid esters and ω-hydroxycarboxylic acid esters are formed on heating gem-bishydroperoxides in alcohol in the presence of BF3·Et2O. By addition of H2O2 to this reaction α,ω-dicarboxylic acid esters are formed almost selectively.
It was found that oximes undergo deoximation in the presence of the H2O2aq-HBraq system to form ketones and bromo ketones. This reaction provided the basis for the synthesis of dibromo ketones in yields varying from 40% to 94%. This method is environmentally friendly, sustainable, and easy to perform. The results of this investigation extend the potential of the use of oximes for the protection of carbonyl group, thus offering the ability to perform not only conventional deoximation but also the subsequent bromination of ketones. The reaction is easily scaled up and dibromo ketones can be prepared in gram amounts. [...]
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