1850-15-3Relevant articles and documents
Formation of acyldisulfide ions from the reaction of sulfur with thiocarboxylate ions, and reactivity towards acyl chlorides in N,N-dimethylacetamide
Robert, Julie,Anouti, Meriem,Paris, Jacky
, p. 473 - 478 (1997)
The reactivity of sulfur towards thiocarboxylate ions RC(O)S- a (R = Ph 1, Me 2, Bu′ 3) has been studied by spectroelectrochemistry in N,N-dimethylacetamide. For 2a-3a, two parallel and partial reactions, for which equilibrium constants have been determined, led to: (i) [RC(O)]2S2- b species and S3·-/S82- polysulfide ions and (ii) RC(O)S2 ions c; only traces of 1c were detected by voltammetry. As previously observed with thiolate ions, our results are consistent with an initial monoelectronic transfer between RC(O)S- ions and S2 molecules in equilibrium with S8, followed by concurrent couplings of RC(O)S· and S2·- radicals. On a preparative scale, when sulfur was added to RC(O)S- ions 1a,3a the enhanced reactivity of RC(O)S2- ions towards acyl chlorides RC(O)Cl (R = C6H5 and Bu′, respectively) only yielded diacyl disulfides 1b,3b.
Silver(I) catalyzed oxidation of thiocarboxylic acids into the corresponding disulfides and synthesis of some new Ag(I) complexes of thiophene-2-thiocarboxylate
Singh, Suryabhan,Chaturvedi, Jyotsna,Bhattacharya, Subrato,N?th, Heinrich
, p. 93 - 97 (2011)
Aromatic thiocarboxylic acids in presence of a base on treatment with silver nitrate under ambient conditions were oxidized to the corresponding disulfides. The reactions were found to be catalyzed by Ag+ ions. The catalytic oxidation is paralleled by the Ag(SCOAr) complex formation reaction which could be considerably subsided by adjustment of the reaction conditions. Attempts to use [Ag(PPh3)2]+ or [Ag(PPh 3)]+ ion as the catalyst were unsuccessful as these resulted in the formation of the corresponding thiocarboxylate complexes. The products, ArCOSSCOAr (1, 2), [Ag(SCOAr)(PPh3)2] (3, 4) and [Ag(SCOAr)(PPh3)]4 (5) (Ar = C6H5, C4H3S) were characterized by single crystal X-ray analysis. Compounds 3 and 4 are monomeric while 5 is a cyclic tetramer in the crystalline phase.
Nucleophilic substitution of acyl chlorides by electrogenerated polysulfide ions in N,N-dimethylacetamide
Robert, Julie,Anouti, Meriem,Abarbri, Mohamed,Paris, Jacky
, p. 1759 - 1764 (1997)
The reactions between acyl chlorides RC(O)Cl (a) [R = Me (1), Pri (2), Bui (3), Ph(4)] and electrogenerated S3._(? S62-) ions have been investigated in N,N-dimethylacetamide by spectroelectrochemistry. With R = alkyl, thiocarboxylate ions and sulfur resulting from the fast initial substitutions cause partial formation of both acyl disulfide ions and diacyl disulfides (b) at a y ratio [RC(O)C1]/[S3._] of 0.5; the second step stoichiometrically (y = 1) affords diacyl disulfides 1b-4b as the presumed products. The formation of these species only is confirmed on a preparative scale from two sets of experiments: (i) direction addition of acyl chlorides (1a-4a) to chemically generated S1/3- solutions; (ii) electrolysis of sulfur in the presence of acyl chlorides 2a-4a.
Asymmetric benzoic acid thio anhydride derivative and its preparation method and application (by machine translation)
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Paragraph 0023; 0024; 0028, (2018/09/21)
Asymmetric benzoic acid thio anhydride derivatives, through the substituted 2' - bromo acetophenone, thiourea and substituted benzoyl chloride in the micelles in water solvent, in the presence of a catalyst reaction. The invention asymmetric benzoic acid thio anhydride derivatives preparation method, reaction using inexpensive, easy, low-toxicity bromo acetophenone, benzoyl chloride as the raw material, low toxicity and tasteless thiourea as the sulfur source, for preparing alkyl organic sulfide synthesis provides a green, high-efficiency, low-cost, low-toxicity method. The invention asymmetric benzoic acid thio anhydride derivatives having anticancer and antibacterial function, low toxicity, good specificity, in the preparation of anti-tumor and antibacterial drugs has broad application prospects. (by machine translation)
Exploration of an imide capture/N,N-acyl shift sequence for asparagine native peptide bond formation
Mhidia, Reda,Boll, Emmanuelle,Fécourt, Fabien,Ermolenko, Mikhail,Ollivier, Nathalie,Sasaki, Kaname,Crich, David,Delpech, Bernard,Melnyk, Oleg
supporting information, p. 3479 - 3485 (2013/07/05)
Imide capture of a C-terminal peptidylazide with a side-chain thioacid derivative of an N-terminally protected aspartyl peptide leads to the formation of an imide bond bringing the two peptide ends into close proximity. Unmasking of the Nα protecting group and intramolecular acyl migration results in the formation of a native peptide bond to asparagine.
A convenient synthesis of diacyl sulfides using a novel sulfur transfer reagent
Koketsu, Mamoru,Sekiya, Yoji,Ishihara, Hideharu
, p. 633 - 635 (2007/10/03)
Various diacyl sulfides were synthesized by reaction of acyl chlorides with LiAlHSH. Reaction of glutaryl chloride with LiAlHSH afforded glutaric thioanhydride.
BIS(BROMOMAGNESIUM) SULFIDE - A REAGENT FOR THE SYNTHESIS OF DIORGANIC SULFIDES
Nedugov, A. N.,Pavlova, N. N.
, p. 1103 - 1104 (2007/10/02)
Bis(bromomagnesium) sulfide was obtained by the reaction of ethylmagnesium bromide with hydrogen sulfide. In reaction with electrophilic reagents in THF or diethyl ether it gives good yields of symmetrical sulfides with a high degree of purity.
An efficient approach toward the synthesis of phosphorothioate diesters via the Schonberg reaction
Kamer,Roelen,Van den Elst,Van der Marel,Van Boom
, p. 6757 - 6760 (2007/10/02)
Easily accessible phenacetyl or benzoyl disulfide proved to be very conventional ragents for a rapid P-sulfurization of phosphite-triesters and H-phosphonate diesters, respectively.
Bis(tributyltin) Sulfide: An Effective and General Sulfur-Transfer Reagent
Harpp, David N.,Gingras, Marc,Aida, T.,Chan, T. H.
, p. 1122 - 1124 (2007/10/02)
Bis(tributyltin) sulfide acts efficiently to transfer the sulfur atom as S(2-) to a variety of halide substrates to afford the corresponding symmetrical sulfides in good overall yield.
