33663-80-8Relevant academic research and scientific papers
Radical Substitution Provides a Unique Route to Disulfides
Wu, Zijun,Pratt, Derek A.
, p. 10284 - 10290 (2020)
Radical substitution on tetrasulfides is demonstrated to be a highly effective means to prepare unsymmetric disulfides. Alkyl and aryl radicals generated thermally or photochemically underwent substitution on readily prepared dialkyl, diaryl, and diacyl tetrasulfides to yield the corresponding disulfides in good to excellent yields. Classic and contemporary thermal and photochemical radical sources could be employed; while photoredox catalysis approaches led to either oxidation or reduction of the tetrasulfide, energy transfer photocatalysis was particularly useful. The success of the approach is driven by the thermodynamic stability of the perthiyl radicals formed upon substitution on the tetrasulfide; they simply combine under the reaction conditions to provide the starting tetrasulfide. Competition kinetic experiments reveal that alkyl radical substitution on tetrasulfides is a rapid reaction (6 × 105 M-1 s-1) that is enhanced at least 6-fold upon moving from dialkyl tetrasulfide to diacyl tetrasulfide due to favorable polar effects. This unique and versatile reaction enables introduction of disulfide moieties from a variety of radical precursors and straightforward access to hydropersulfides.
Medium Effects in Unsymmetrical Disulfides Compounds. Synthesis from Bunte Salts
Hiver, Patricia,Dicko, Amadou,Paquer, Daniel
, p. 9569 - 9572 (1994)
The present study allows us to show the influence of the polarity of the reaction medium as well as the electron-donating and withdrawing character of para substituents of α-halogeno toluenes in the preparation of unsymmetrical disulfides using the Bunte
Application of novel persulfide reagent in synthesis of asymmetric persulfides
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Paragraph 0271-0282, (2022/01/12)
The invention relates to the technical field of organic synthesis, and in particular, relates to an application of a novel persulfide reagent in synthesis of asymmetric persulfides, wherein the novel persulfide reagent is easy to synthesize, mild in reaction condition and high in practicability, the persulfide reagent and (pseudo) haloalkane are adopted for nucleophilic substitution, and the novel persulfide reagent can be used for synthesizing various asymmetric persulfides; and the novel persulfide reagent is high in practicability, wide in substrate application range and suitable for industrial production, and the problems that in existing persulfide synthesis, undesirable co-coupling byproducts exist, functional group tolerance is poor, a thiol precursor is excessively oxidized, the substrate application range is narrow, and thiol is unpleasant in smell and high in toxicity are solved.
A new electrochemical method of preparation of unsymmetrical disulfides
Do, Quang Tho,Elothmani, Driss,Le Guillanton, Georges,Simonet, Jacques
, p. 3383 - 3384 (2007/10/03)
A new method is described for the preparation of unsymmetrical disulfides by reaction of the electrogenerated sulfenium cation R1-S+ with thiols or disulfides.
A simple method to prepare unsymmetrical di- tri- and tetrasulfides
Derbesy, Gerard,Harpp, David N.
, p. 5381 - 5384 (2007/10/02)
Unsymmetrical di- tri- and tetrasulfides can be prepared in a one-pot reaction using SO2Cl2 SCl2 and S2Cl2 respectively to permit coupling of the appropriate thiols.
Sodium Tellurite as a Mild and Selective Oxidizing Agent for Thiols: Its Use in the One-Pot Synthesis of Unsymmetrical Disulfides
Suzuki, Hitomi,Kawato, Sei-ichi,Nasu, Akira
, p. 626 - 627 (2007/10/02)
Sodium tellurite acts as a mild and highly selective oxidizing agent for thiols under phase-transfer conditions at room temperature.Aromatic and benzylic thiols are rapidly converted to disulfides.Short-chain primary thiols undergo oxidation in preference to long-chain thiols.Secondary thiols are sluggish in oxidation and tertiary thiols remain intact.No overoxidation of the sulfur atom is observed.Similar results are also obtained with sodium tellurate.
