Electrochemical Oxidation of Iminobibenzyl and Related Compounds
نویسندگان
چکیده
Electrochemical oxidation of iminobibenzyl and several related compounds has been investigated in acetonitrile. The mechanism of the oxidation is best described by an ECE process with coupling of the product of an ini t ial oneelectron oxidation in a subsequent but very fast reaction to form a dimeric compound that is fur ther oxidized by an over-al l two-electron process at potentials more negative than those required for oxidation of the parent compounds. The electrochemistry of these compounds is complicated by the release of protons dur ing the oxidation which protonate the s tar t ing materials and the neut ra l dimerized products render ing them electrochemically inactive. Differences in the electrochemistries of the various coupled products are discussed in terms of s t ructural variations. In recent years considerable effort has been expended in elucidating the mechanisms of electrolytic oxidation of heterocyclic n i t rogen and amine compounds as well as other ni.trogen containing species. [See Ref. (1) and (2) for reviews of the work in this area.] One of the prominent characteristics of aromatic amines is oxidative coupling to form a variety of dimerized derivatives of the original parent compounds. Certain heterocyclic n i t rogen compounds such as carbazole which may be considered as being der ived from diphenylamine also undergo a similar coupling process on oxidation (3). The present invest igat ion was ini t ia l ly unde r t aken to compare the electrochemistry of imipramine hydrochloride, a widely prescribed ant idepressant drug, with the electrochemical behavior of the s t ructura l ly similar but physiologically less active iminobibenzyl and 5-methyl iminobibenzyl . We also felt it worthwhile to compare the electrochemistry of these compounds with that of the related carbazoles(I) whose p r imary s tructural difference with the above compounds is the na ture of the b iphenyl linkage. The homogeneous oxidation of most of the present compounds along with a number of carbazoles with chemical oxidants (e.g., 2,3-dichloro-5,6-dicyano-pbenzoquinone) has shown recent ly (4) that all of the compounds undergo oxidative coupling with ul t imate formation o~ the cation radical salt of the coupled product. The electrochemical coupling of the carbazoles has been previously investigated by Ambrose and Nelson (3) who showed that the neut ra l coupled products can be oxidized to corresponding cation radicals and dications at potentials negative of those for the oxidat ion of the parent compounds. The electrochemical behavior of the carbazoles was consistent with an ECE mechanism with oxidative peak heights of the potential sweep vol tammograms being twice those expected for a 1-electron process (3). Controlled potential electrolysis also gave an n value of 2. Ambrose and Nelson (3) proposed the following mechanism for the oxidative coupling of the carbazoles (3). RH. e ~ RH + [1]
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