Sulfonyl Chloride Formation from Thiol Derivatives by N-Chlorosuccinimide Mediated Oxidation

Abstract

Oxidation of several thiol derivatives by a combination of N-chlorosuccinimide and dilute hydrochloric acid proceeded smoothly, affording the corresponding sulfonyl chlorides in good yield.

Key words

thiol derivatives - oxidation - solvent effects - NCS - chlorosulfonation

References

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13

Oxidation of 3e with 5; the procedure was the same as the general procedure for NCS. This reaction required 2 equiv of 5.

14

Oxidation of 3e with 6; the procedure was the same as the general procedure for NCS. This reaction required 1.3 equiv of 6. The resulting solid was filtered off and washed with IPE (3.5 v/w to NCS) before work-up.

15

Depending on the substrate properties, e.g. solubility, reactivity may somewhat differ from these results. Especially for large-scale synthesis, appropriate hazardous safety evaluations should be undertaken.