Cathodic behaviour of p-toluenesulfonamides in organic solvents

Add time:09/10/2019    Source:sciencedirect.com

Cathodic reduction of several secondary and tertiary p-toluenesulfonamides and gem-N-disulfonamides were investigated by cyclic voltammetry and controlled potential electrolysis at mercury electrode in aprotic and protic dmf. In the cleavage of tertiary p-toluenesulfonamides two Faradays per mole were consummed, resulting in the formation of amine and the sulfinate ion. In the case of secondary p-toluenesulfonamides, electrochemically inactive sulfonamide anions were formed at the electrode surface by acid–base reaction between acidic substrate and electrogenerated bases. Sulfonamides anions were obtained also in the solution bulk with adding strong base and by cathodic cleavage of gem-N-disulfonamides in aprotic media. General reduction mechanisms are postulated and structure effects on the scope of the reduction are discussed for more complex sulfonamides.

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