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Zincke Disulfide Cleavage

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr697

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Zincke Disulfide Cleavage. Comprehensive Organic Name Reactions and Reagents. 697:3163–3167.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The preparation of arylsulfenyl halides from aryl disulfides through the oxidation of corresponding disulfides with halogens, and such method of arylsulfenyl halide formation is generally known as the Zincke disulfide cleavage. The study finds that the arylsulfenyl halides can be easily prepared from aryldisulfides, with decreasing reactivity from chlorine to iodine. To minimize possible aromatic halogenation, the Zincke disulfide cleavage is usually performed at low temperature without light and in an anhydrous solvent. Besides reacting with halogens to form sulfenyl halides, sulfinyl halides and sulfonyl halides, aryldisulfides can also react with phenols and cyclic esters of phosphoramidous acid (i.e., phosphoramidite). It has also been noticed that the reaction between phosphoramidite and disulfides proceeds by two routes. This reaction has been used for the preparation of thioethers with an adjacent halogen because sulfenyl halide can easily add to olefins. Additionally, arylsulfenyl chloride has been applied in the quantification of tryptophan and cysteine residues in protein, which are difficult to measure by traditional hydrolysis methods.

Keywords:

  • cysteine residues;
  • thioethers;
  • sulfonyl chloride;
  • 4-arylthiophenols