Comparison of Birch with electrochemical reduction of 2,3-diphenyl-1,4-diazaspiro[4.5]deca-1,3-diene

Reduction of 2,3-diphenyl-1,4-diazaspiro[4.5]deca-1,3-diene is investigated both voltammetrically (glassy-carbon electrode, 20 °C, non-aqueous-solvents) and using dissolving-metals (sodium, −78 °C, tetrahydrofuran (THF)/NH3(l)). Remarkably, electro-reduction furnishes two two-electron processes, whilst only a four-electron product results from Birch synthesis.