✍ Scribed by Árpád Molnár; Mihály Bartók
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The transformations of 13 alcohols and 13 diols in the presence of a small amount dimethylsulfoxide (1/16 mol) were studied. Relationships were found between the type of the hydroxy compound and the selectivity of the transformation, and conclusions were drawn regarding the transformation mechanism. The ether formation observed with certain alcohols proceeds via a carbenium cation. The reaction conditions applied were found suitable for inducing water elimination from the ditertiary 1,2‐ and 1,3‐diols (pinacol rearrangement, 1,2‐elimination). From the 1,4‐ and 1,5‐diols the corresponding oxacycloalkanes can be obtained in good yield. Cyclodehydration occurs by intramolecular nucleophilic substitution, via a concerted mechanism. The effect of DMSO is exerted directly, and protoncatalysis occurs simultaneously.
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## Abstract For Abstract see ChemInform Abstract in Full Text.
Sodium hypochlorite in acetic acid solution selectively oxidizes secondary alcohols to ketones in the presence of primary alcohols and converts aldehydes to methyl esters in the added presence of methanol. Recently, we reported a convenient and inexpensive procedure for the oxidation of secondary