Abstract
Several ketone allylhydrazones were electrochemically oxidized in methanol in the presence of sodium methoxide and potassium iodide to afford the corresponding azines. The electro-oxidation involves formation of a new carbon–nitrogen double bond between an allylic carbon atom and the nitrogen atom of a hydrazone to afford a conjugated system. Optimal yields were obtained when 0.5 equivalents of sodium methoxide and a catalytic amount of potassium iodide were used as the supporting electrolyte at room temperature. Presumably, the electro-oxidation involves a two-electron oxidation process where the iodide ion functions as electron carrier.
Notes
a Substrate 1a: 10 mmol, MeOH: 40 mL, constant current: 0.3 A, current passed: 2.2 F mol−1, rt: ca. 15 °C.
b Determined by GC analysis.
a Substrate 1: 10 mmol, KI: 2 mmol, NaOMe: 5 mmol, MeOH: 40 mL, constant current: 0.3 A, rt: ca. 15 °C.
b Isolated yield.