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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 19
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Original Articles

Anodic Oxidation of Ketone Allylhydrazones into the Corresponding Azines

, , , , , & show all
Pages 3320-3328 | Received 13 Jan 2008, Published online: 12 Sep 2008
 

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.

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