Premium
Electrochemical Reduction of Cyclohex‐2‐enones
Author(s) -
Tissot Paul,
Margaretha Paul
Publication year - 1977
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19770600503
Subject(s) - chemistry , coulometry , polarography , protonation , electrochemistry , cyclic voltammetry , electron transfer , halide , ion , allylic rearrangement , medicinal chemistry , photochemistry , dropping mercury electrode , inorganic chemistry , electrode , organic chemistry , catalysis
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 ).