Thiosulfinate
Encyclopedia
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 thiol
s to sulfonic acid
s, 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
.
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
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 thiol
Thiol
In organic chemistry, a thiol is an organosulfur compound that contains a carbon-bonded sulfhydryl group...
s to sulfonic acid
Sulfonic acid
Sulfonic acid usually refers to a member of the class of organosulfur compounds with the general formula RS2–OH, where R is an alkyl or aryl. The formal part of acid, HS2–OH, are formally derivatives of the "parent" inorganic compound with the formula HSO2.-Preparation:Sulfonic acid is...
s, 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
Garlic
Allium sativum, commonly known as garlic, is a species in the onion genus, Allium. Its close relatives include the onion, shallot, leek, chive, and rakkyo. Dating back over 6,000 years, garlic is native to central Asia, and has long been a staple in the Mediterranean region, as well as a frequent...
.
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
Hydrogen peroxide
Hydrogen peroxide is the simplest peroxide and an oxidizer. Hydrogen peroxide is a clear liquid, slightly more viscous than water. In dilute solution, it appears colorless. With its oxidizing properties, hydrogen peroxide is often used as a bleach or cleaning agent...
.