First Examples of Oxidizing Aldehydes to Carboxylic Acids in the Presence of a Tertiary Disulfide Functional Group: Synthesis of Novel Diacid-disulfides

Abstract

The disulfide functionality exists in numerous organic compounds of interest in both chemistry and biology. In view of the fact that the disulfide function is highly susceptible to further oxidation by a broad range of agents, conducting a chemoselective oxidation without further oxidizing the disulfide group poses a synthetic challenge. Disclosed herein are the first examples of such an oxidation in which a series of aldehyde disulfides (1a-e) were converted to the corresponding symmetrical carboxylic acid disulfides (2a-e), utilizing sodium chlorite as the oxidant, and dimethyl sulf­oxide as both a reaction solvent and an efficient hypochlorous acid scavenger.

Key words

aldehydes - carboxylic Acids - oxidation - disulfides

References

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5

(i) TsCl, DMAP, pyridine, CH₂Cl₂; (ii) DIBALH, CH₂Cl₂; (iii) Swern oxidation.

8

Dialdehyde 3 was prepared from the corresponding diol using a modified Swern oxidation procedure as described in ref. 4d.