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Oxidation of Alkenes

The oxidation of alkenes is solvent dependant. Terminal alkenes can be dinitroxylated in high yield (Scheme 4).

Scheme 4  

Oxidation of Alcohols and Phenols

A secondary alcohol can be selectively oxidized to ketones in the presence of a primary alcohol. Under these conditions, 1,4-primary diols can be converted into lactones (Scheme 5). The formation of tetrahydrofuran predominates in molecules, which are favourable to d -hydrogen abstraction by an alkoxyl radical (Scheme 6). In the case of phenols, quinones are formed.

 

Scheme 5

Scheme 6

Oxidation of Cage Ketones

The CAN oxidation of aldehydes and ketones is of much of less synthetic importance compared to that with other methods. However, cage ketones can be oxidized using CAN to give lactones in good yield (Scheme 7).

Scheme 7

Oxidation of Nitroalkanes

The CAN oxidation affords an alternative method to the Nef reaction. For an example, nitromacrolide can be selectively oxidized in good yield (Scheme 8).

Scheme 8

Oxidative Cleavage of Organometallic Compounds

CAN is useful reagent for the oxidative cleavage of s- and π -complexes. For an example, chromium-carbene complex can be oxidatively cleaved to afford α -methylene-γ-butyrolactone in good yield (Scheme 9).

Scheme 9