Controlled potential oxidation of a variety of 5-substituted 2-tert-butyl-1,3-dithianes in wet acetonitrile, using an undivided electrochemical cell, provide 4-substituted 1,2-dithiolane 1-oxides selectively and in good yields. Adsorption to the electrode surface of the platinum anode, rendering it passive in the electrolysis of these sulfur-containing compounds is a solvable problem. Although acid-sensitive O-trimethylsilyl ethers are cleaved under the reaction conditions, O-tert-butyldimethylsilyl ethers only suffer cleavage to a modest extent, and an ethylene ketal moiety suffers little, if any, cleavage.
|Original language||English (US)|
|Number of pages||6|
|Journal||Journal of Organic Chemistry|
|Publication status||Published - 1986|
ASJC Scopus subject areas
- Organic Chemistry