Functional Group Sensitivity to Jones Oxidation

Aldehydes are oxidized to carboxylic acids by Jones oxidation although, in certain cases, the oxidation of primary alcohols can be stopped at the aldehyde stage (see page 12). 

Aliphatic acetals Remain unchanged dimethyl acetal43 Hydrolysis dimethyl acetal44 

Cyclic acetals Remain unchanged ethylidene acetal45 Hydrolysis followed by oxidation 

Lactols are oxidized to lactones. Depending on substrate and the precise reaction conditions, sulfides can remain unchanged51 or be transformed into sulfoxides52 or sulfones.53 9-Alkyl cyclic hemiacetals including glycosides, both can remain unchanged54 or suffer oxidation to lactones.35 

Most epoxides resist Jones oxidation with the exception of the very acid-labile ones,55 that is the ones able to generate a very stable carbocation on opening. 

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