Oxidation of Thioacetals Mercaptals and Mercaptoles

The cyclic mercaptal of acetaldehyde (2-methyl-l,3-dithiane) is oxidized by m-chloroperoXybenzoic acid or sodium periodate to a mixture of diastereomeric cis and monosulfoxides (equation 569) [323]. 

Acetone 2-chloroethylmercaptole is oxidized with potassium permanganate to the corresponding disulfone (sulfonal) (equation 570) [846]. 

Mercaptals of pentoses and hexoses are converted into sulfonals (di-sulfones), which easily undergo dehydration. The dimethylmercaptal of D-ribose or D-arabinose gives, on oxidation with peroxypropionic acid, 1,1-bis(methylsulfonyl)-D-er f/iro-pentos-l-ene (equation 571) [340.  

Under controlled conditions, thioacetals can be transformed into disulfoxides or disulfones (equation 572) [136]. 

Hexylketene diethylmercaptole is oxidized with peroxyphthalic acid to l,l-bis(ethanesulfonyl)-l-octene (equation 573) [33.  

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