In organosulfur chemistry, thiosulfinate is a functional group consisting of the linkage R-S(O)-S-R (R are organic substituents). The thiosulfinate functional group is rare, but these compounds are invoked as intermediates in the oxidation of thiols to sulfonic acids, which is a common transformation. They feature a S(IV) center linked to a S(II) center, the former being stereogenic. A well-known thiosulfinate is allicin, one of the active ingredients in garlic.

One example of a stable thiosulfinate is the tert-butyl derivative, (CH₃)₃CS(O)SC(CH₃)₃. This thiosulfinate can be obtained in optical purity by catalytic asymmetric oxidation of di-tertbutyldisulfide with hydrogen peroxide.^[1]

[edit] References

1. ^ Daniel J. Weix and Jonathan A. Ellman "(RS)-(+)-2-Methyl-2-Propanesulfinamide [tert-Butanesulfinamide]" Organic Syntheses, Vol. 82, p.157 (2005).