Electrochemical Sulfonylation of 4-tert-Butylcatechol

Abstract

Electrochemical oxidation of 4-tert-butylcatechol (1) has been studied in the presence of benzenesulfinic acids (2a and 2b) as nucleophiles in aqueous solution, using cyclic voltammetry and controlled-potential coulometry. The results indicate that the quinone derived from 4-tert-butylcatechol (1) participates in Michael addition reaction with 2 of form the corresponding arylsulfonylbenzenediols (3a and 3b). The electrochemical synthesis of 3a and 3b has been successfully performed at carbon rod electrodoes in an undivided cell in good yield and purity.

Keywords:

• Electrochemical oxidation
• Michael reaction
• Cyclic voltammetry
• 4-tert-Butylcatechol
• Sulfonylation