The products that may be obtained from the oxidation of thiols by perm
anganate under heterogeneous conditions have been compared with those
that are known to be produced by use of the same oxidant under homogen
eous conditions. The products obtained from the oxidation of thiols un
der homogeneous and heterogeneous conditions are distinctively differe
nt. Sulfonic acids are obtained under homogeneous conditions, while di
sulfides are the only detectable products when the reactions are carri
ed out heterogeneously. For example, a quantitative yield of dibutyl d
isulfide is obtained from the oxidation of butane-1-thiol, and oxidati
on of pentane-1,5-dithiol gives the corresponding cyclic disulfide, 1,
2-dithiepane.