General structure of a thiosulfinate, drawn in expanded octet style[1]
In organosulfur chemistry, thiosulfinate is a functional group consisting of the linkage R-S(O)-S-R (R are organic substituents). Thiolsulfinates are also named as alkanethiosulfinic (or arenethiosulfinic) acid esters.
They are the first of the series of functional groups containing an oxidized disulfide bond. Other members of this family include thiosulfonates (R-SO2-S-R), α-disulfoxides (R-S(O)-S(O)-R), sulfinyl sulfones (R-S(O)-SO2-R), and α-disulfones (R-SO2-SO2-R), of which all (except α‑disulfoxides[2]) are known. The thiosulfinate group can occur in cyclic as well as acyclic structures.[3][4][5]
^See sulfoxide for discussion and references regarding the bonding in divalent monooxosulfur structures.
^Block, S. S.; Weidner, J. P. (1966) [1 Sept 1964]. "Vibrational behavior and structure of disulfide dioxides (thiolsulfonates)". Applied Spectroscopy. 20 (2). doi:10.1366/000370266774386272.
^Kice JL (1980). "Mechanisms and reactivity in reactions of organic oxyacids of sulfur and their anhydrides". Advances in Physical Organic Chemistry. 17: 65–181. doi:10.1016/S0065-3160(08)60128-8. ISBN 9780120335176.
^Takata, T; Endo, T (1990). "Thiosulphinic acids and esters". The Chemistry of Sulphinic Acids, Esters and Their Derivatives, S. Patai, Ed. (John Wiley, NY): 527–575. doi:10.1002/9780470772270.ch18. ISBN 9780470772270.
^Braverman, S; Cherkinsky, M.; Levinger, S. (2007). "Alkanethiosulfinic Acid Esters". Sci. Synth. 39: 229–235.
In organosulfur chemistry, thiosulfinate is a functional group consisting of the linkage R-S(O)-S-R (R are organic substituents). Thiolsulfinates are...
odor. It is a thioester of sulfenic acid. It is also known as allyl thiosulfinate. Its biological activity can be attributed to both its antioxidant activity...
compounds serve as the precursors of several thiosulfinates such as S-(2-hydroxyethyl) 2-hydroxyethane)thiosulfinate, S-(2-hydroxylethyl) phenylmethanethiosulfinate...
well as oxidation with hydrogen peroxide or peracetic acid giving the thiosulfinate methyl methanethiosulfinate (CH3S(O)SCH3). DMDS is used as a food additive...
ester through a 6-membered cyclic transition state yields the alkene. Thiosulfinates can eliminate in the manner analogous to sulfoxides. Representative...
Cl2 -> 2 ArSCl}}} More unusually, oxidation of disulfides gives first thiosulfinates and then thiosulfonates: RSSR + [O] → RS(=O)SR RS(=O)SR + [O] → RS(=O)2SR...
("sulfide oxide"), a sulfone, R−S(O)2−R, is the S,S-dioxide of a sulfide, a thiosulfinate, R−S(O)−S−R, is the S-oxide of a disulfide, and a thiosulfonate, R−S(O)2−S−R...
mainly in Japan. These efforts led to the discovery of allicin (diallyl thiosulfinate) in garlic, which became a model for medicinal chemistry efforts to...
to cleave the sulfur-containing compound alliin to release reactive thiosulfinates. These then react with each other and with amino acids found naturally...
to chemical substances. Substances such as piperine, capsaicin, and thiosulfinates can cause a burning or tingling sensation by inducing a trigeminal nerve...
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