Oxidations

Oxidation reactions are powerful tools to convert a position that is protected in a lower oxidation state to the desired functionality, and for the activation of otherwise unfunctionalized positions. This chapter is organized by the oxidized functionality for ease in looking up specific transformations. It focuses on the oxidative cleavage of carbon‐carbon double and single bonds, and on the oxidation of double and triple bonds to the corresponding ketones or diketones. Oxidative loss of alkyl groups from phenyl ethers can be accomplished via oxidation to the quinone oxidation state, followed by loss of an alkyl cation. The oxidative conversion of arylacetonitriles into the corresponding acetophenone is accomplished by deprotonation followed by trapping with oxygen and expulsion of cyanide anion. Hydrogen peroxide‐mediated oxidation can be utilized to effect oxidative cleavage in some cases.