Synthesis and inclusion of S-aryl alkylthiosulfinates as stable allicin mimics

Stellenboom, Nashia; Hunter, Roger; Caira, Mino; Bourne, Susan; Cele, Khethiwe; Qwebani, Tozama

Synthesis and inclusion of S-aryl alkylthiosulfinates as stable allicin mimics

Journal Article

2007

Journal Title

ARKIVOC - Online Journal of Organic Chemistry

Link to Journal

https://dx.doi.org/10.7196/sajs.718

Department

Department of Chemistry

Faculty

Faculty of Science

Abstract

S-Aryl alkylthiosulfinates showing aromatic rings with varying electronic demand have been prepared by oxidation of the corresponding disulfide, the latter prepared using new one-pot methodology involving thiol oxidation with 1-chlorobenzotriazole. Whereas thiosulfinates with electron-withdrawing substituents in the aromatic ring were unstable towards isolation, those with a releasing substituent in the para-position have shown good stability as potential allicin mimics and one of them (p-OMe) has been characterised as its inclusion compound in the cyclodextrin, TRIMEB, by X-ray crystallography.