Electrosynthesis of 1,2-dithiolane 1-oxides from substituted 1,3-dithianes

Richard S Glass, Amorn Petsom, George S. Wilson, Roberto Martínez, Eusebio Juaristi

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Abstract

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 languageEnglish (US)
Pages (from-to)4337-4342
Number of pages6
JournalJournal of Organic Chemistry
Volume51
Issue number23
Publication statusPublished - 1986

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Glass, R. S., Petsom, A., Wilson, G. S., Martínez, R., & Juaristi, E. (1986). Electrosynthesis of 1,2-dithiolane 1-oxides from substituted 1,3-dithianes. Journal of Organic Chemistry, 51(23), 4337-4342.