34451-25-7Relevant articles and documents
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Dieng,S.Y.,Bertaina,B.
, p. 341 (1985)
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One-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole as oxidant: Interception of the sulfenyl chloride intermediate
Stellenboom, Nashia,Hunter, Roger,Caira, Mino R.
body text, p. 3228 - 3241 (2010/06/13)
A high-yielding and low temperature one-pot procedure is described for unsymmetrical disulfide synthesis from two different thiols using 1-chlorobenzotriazole (BtCl) as oxidant. The mechanism of the coupling involves in situ trapping of the sulfenyl chloride intermediate R1SCl by nucleophilic benzotriazole (BtH) to form R1SBt, which protects R1SCl from forming the homodimer R1SSR1. The methodology is applicable to all types of thiol (aliphatic, aromatic, heteroaromatic), with a variation developed for aliphatic-aliphatic couplings. Differentially N-protected cysteines couple to afford the unsymmetrical cystine derivatives in high yield (90%), which serves as a model for the one-pot intermolecular coupling of cysteine-containing peptides to form peptide disulfide heterodimers. Minimal exchange in aromatic-aromatic disulfide synthesis is noted on account of the mild conditions.
Synthesis of terminally perfluorinated long-chain alkanethiols, sulfides and disulfides from the corresponding halides
Naud,Calas,Blancou,Commeyras
, p. 173 - 183 (2007/10/03)
Semifluorinated n-alkanethiols, symmetrical sulfides and disulfides bearing the chain(s) F(CF2)n(CH2)m with n=4, 6, 8, 10, and m=2, 11 have been prepared by various synthetic methods, starting from the corresponding iodides or bromides. Methods based on sodium hydrogen sulfide, commonly used to accomplish this conversion, treatment of the Bunte salt obtained from sodium thiosulfate, the basic hydrolysis of isothiouronium salts, the hydrolysis under mild conditions of thiophosphorates formed from sodium thiophosphate and the basic hydrolysis of thiol acetic acid derivatives, have been investigated and compared relatively to the selective synthesis of the title compounds. The thiolacetic route yields essentially the thiols with some amounts of disulfides. Results from thiourea appears similar. Sodium thiophosphate constitutes an excellent route for the synthesis of thioethers, particularly when starting from the bromides. The two classical methods based on sodium hydrogen sulfide and sodium thiosulfate exhibit poor selectivity. It has been possible to obtain all the sulfur compounds reported in the pure state.