Applications of trisulfide radical anion S₃˙⁻ in organic synthesis

Abstract

The trisulfide radical anion is well-known as the blur chromophore in ultramarines and it has a versatile role in materials chemistry, especially in the redox chemistry of alkali-metal-sulfur batteries, electrochemistry,...

Synthesis of 2-benzyl benzoxazoles and benzothiazoles via elemental sulfur promoted cyclization of styrenes with 2-nitrophenols and N,N-dialkyl-3-nitroanilines

“…These results somewhat indicated that a mechanism involving the trisulfide radical anion should be considered. 10,11…”

CS2/KOH System-Promoted Stereoselective Synthesis of (E)-Alkenes from Diarylalkynes and a “Hidden” Zinin-Type Reduction of Nitroarenes into Arylamines

“…Initially, at room temperature, CS 3 2– is produced in situ by reacting CS 2 and KOH in DMF, resulting in a dark red solution. , As the reaction temperature reaches 120 °C, CS 2 and S 2– are produced by the thermal decomposition of CS 3 2– . Considering that DMF can act as an oxidant to produce trisulfide radical anions (S 3 •– ) from S 2– , the semireduction of alkynes initiates with the addition of S 3 •– to the C–C triple bond of 1 to give I . This vinyl radical intermediate can abstract a hydrogen atom from water to generate II , leading to the formation of vinylic sulfide A after dissociation.…”

Photocatalytic iodosulfonylation of internal alkynes under green conditions

“…Methods for creating carbon–heteroatom bonds, including C–S bonds, are in high demand in modern organic chemistry. 1–10 Sulfur-containing compounds are widely used as catalysts, 11,12 reagents and synthetic intermediates, 13–19 as well as for the preparation of biologically active compounds 20 and functional materials. 21,22…”