Oxidation cascade with oxone: cleavage of olefins to carboxylic acids

• DOI: 10.1016/j.tet.2014.01.042
• Publication Date: 2014-01-25T21:45:21Z
• Authors: Keshaba Nanda Parida; Jarugu Narasimha ...
• Keywords: 01 natural sciences; 0104 chemical sciences

A variety of olefins is shown to be cleaved oxidatively to the corresponding acids with oxone as the reagent. The simple methodology that works well for a range of alkenes, i.e., styrenes, nitrostyrenes, stilbenes, cinnamic acids, chalcones, etc., involves heating of the reactant with oxone in acetonitrile–water mixture (1:1, v/v) at reflux. The oxidation cascade involves initial dihydroxylation followed by oxidative cleavage and oxidation of the resultant aldehydes to acids.