Abstract
Previously [1] we studied the anodic oxidation of symmetrical bisamides of type RCONH(CH2)nNHCOR (n = 2-4) under constant current electrolysis (CCE), in methanol. Those with 3 and 4 methylene groups as spacers undergo mostly mono- and dimethoxylation at the alpha-position to 'N' atom. However, when the spacer contains two methylene groups only, the anodic process favors fragmentation products due to CH2-CH2 bond cleavage, as shown in Eq. 1.Following the above results, for better selectivity, the anodic oxidation of symmetrical aromatic bisamides with ‘CH2CH2’ as a spacer (ArCONHCH2CH2NHCOAr), was investigated [2] in acetonitrile, and under controlled potential electrolysis (CPE). The outcome indicates that the major products involve unsymmetrical geminal bisamides (Eq. 2) that are difficult to synthesize by other methods.
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