Electrochemical Reduction of Cyclohex‐2‐enones
1977; Wiley; Volume: 60; Issue: 5 Linguagem: Inglês
10.1002/hlca.19770600503
ISSN1522-2675
Autores Tópico(s)CO2 Reduction Techniques and Catalysts
ResumoAbstract The electrochemical reduction of the cyclohex‐2‐enones 1a–1e (mercury cathode, CH 3 CN, Bu 4 NBF 4 ) was studied by means of cyclic voltammetry, d.c. polarography, coulometry and chemical product analysis. Compounds 1a–1c give a mixture of the hydrodimers 4 and 5 via formation of the radical anion 2 by an irreversible one electron transfer, followed by protonation and dimerization of the allylic radical 3 . The 6‐halocyclohex‐2‐enones 1d and 1e exhibit two distinct reduction waves. The first corresponds to an irreversible two electron transfer with formation of the halide anion and the enolate anion 6 which gives 1b by protonation. The second wave corresponds to a quasi ‐reversible one electron transfer to 6 to afford the radical dianion 7 ( Scheme 2 ).
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