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Oxidation of thiols to sulphonic acids with Oxone ® /NaHCO 3 and KBrO 3
Author(s) -
Parida Keshaba Nanda,
Chandra Ajeet,
Moorthy Jarugu Narasimha
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600028
Subject(s) - chemistry , reagent , sulfonic acid , thiol , electron transfer , organic chemistry , inorganic chemistry
The reagent system Oxone ® /NaHCO 3 is shown to be very convenient for direct conversion of thiols to sulfonic acids. The simple procedure that involves stirring of thiol, Oxone ® /NaHCO 3 in CH 3 CN‐H 2 O (3:2, v/v) mixture at 20±5 °C allows access to a variety of aliphatic as well as electron rich and deficient aromatic sulfonic acids. The oxidation is also shown to occur with KBrO 3 , albeit over longer durations. The mechanism of thiol‐to‐sulfonic acid oxidation with Oxone ® is proposed to proceed via electron transfer steps, which is supported by the formation of disufide at low conversions.