Facile preparation of bis(thiocarbonyl)disulfides via elimination

A robust facile synthetic preparation of bis(thiocarbonyl)disulfides is presented. The route follows an elimination mechanism rather than the more common oxidation. Addition of p-tosyl chloride to a thiocarbonyl thiolate results in the elimination of the chloride by the trithiocarbonate anion and su...

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Bibliographic Details
Published in:Tetrahedron Letters
Main Authors: Weber W.G., McLeary J.B., Sanderson R.D.
Format: Article in Journal/Newspaper
Language:unknown
Published: 2006
Subjects:
anion
bis(4 methylphenyl)disulfone
carbonic acid derivative
carbonyl derivative
chloride
disulfide
sulfone derivative
thiocarbonyl thiolate
toluenesulfonic acid derivative
trithiocarbonate
unclassified drug
article
elimination reaction
oxidation
Carbonic acid
Online Access:http://hdl.handle.net/10019.1/12543
https://doi.org/10.1016/j.tetlet.2006.04.031
Description
Summary:A robust facile synthetic preparation of bis(thiocarbonyl)disulfides is presented. The route follows an elimination mechanism rather than the more common oxidation. Addition of p-tosyl chloride to a thiocarbonyl thiolate results in the elimination of the chloride by the trithiocarbonate anion and subsequent elimination of the tosyl leaving group (by a second thiocarbonyl thiolate). The side products of the reaction are bis(4-methylphenyl)disulfone and tosylate salts/acids. © 2006 Elsevier Ltd. All rights reserved. Article

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