Journal of Organic Chemistry p. 4337 - 4342 (1986)
Update date:2022-07-29
Topics:
Glass, Richard S.
Petsom, Amorn
Wilson, George S.
Martinez, Roberto
Juaristi, Eusebio
Controlled potential oxidation of 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.
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