Oxidation of Thiols and Other Sulfur Compounds

PROBLEM 16.27 Starting from inorganic reagents, tosyl chloride, formaldehyde, acetaldehyde, acetone, and butyl alcohol, devise syntheses of the following molecules  

Like alcohols, thiols (mercaptans) can be oxidized, but oxidation usually takes place not at carbon, as with alcohols, but on sulfur to give sulfonic acids (Fig. 16.76). 

FIGURE 16.76 Oxidation of thiols (mercaptans) with nitric acid gives sulfonic acids. 

Milder oxidation, using halogens (F or Br2) in base, is a general source of disulfides. This reaction probably involves a sequence of displacement reactions (Fig. 16.77). 

FIGURE 16.77 Mild oxidation with bromine (or iodine) in base gives disulfides. 

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Oxidation of Thiols and Other Sulfur Compounds to Sulfonic Acids Thiol-sulfonic acid oxidation... 

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