Synthesis of sulfonyl chlorides and thiosulfonates from H2O2–TiCl4

A new method is described for the oxidative chlorination of thiols to sulfonyl chlorides using titanium tetrachloride in combination with the oxidant hydrogen peroxide. Direct conversion of thiols into their corresponding thiosulfonates is also reported. Good to excellent yields, short reaction time...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 53; no. 3; pp. 354 - 358
Main Authors: Bahrami, Kiumars, Khodaei, Mohammad M., Khaledian, Donya
Format: Journal Article
Language:English
Published: OXFORD Elsevier 18.01.2012
Subjects:
Chemistry
Chemistry, Organic
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Physical Sciences
Reactivity and mechanisms
Science & Technology
THIOSULFINIC S-ESTERS
SELECTIVE OXIDATION
ALPHA-DISULFOXIDE
Hydrogen peroxide
SULFONAMIDES
DISULFIDES
Sulfonyl chlorides
THIOLS
SELENOESTERS
Titanium tetrachloride
CHARCOAL N2O4/CHARCOAL
INTERMEDIATE
Thiosulfonates
Oxidative chlorination
DERIVATIVES
Thiol
Chlorination
Sulfone
Thiosulfonate
Oxidant
Organic chlorine compounds
Titanium IV Chlorides
Reaction mechanism
Oxidation
Chemical synthesis
ISSN:0040-4039
Online Access:Get full text
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Summary:A new method is described for the oxidative chlorination of thiols to sulfonyl chlorides using titanium tetrachloride in combination with the oxidant hydrogen peroxide. Direct conversion of thiols into their corresponding thiosulfonates is also reported. Good to excellent yields, short reaction times, high efficiencies, cost-effectiveness, and, facile isolation of the desired products make the present methodology a practical alternative. (C) 2011 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2011.11.052