ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Electosynthesis of N-Substituted DL-Arylglycineesters and 1,2-Diarylamino-1,2-diarylethanes by Cathodic Reduction of Azomethines in the Presence of Carbon DioxideThe electroreduction of the N-arylidene-arylamines 1-12 in CO2-saturated solvents of low proton availability as DMF at markedly more positive potentials than carbon dioxide end up in carboxylating the C-atom and hydrogenating the nitrogen of the double bond. The resulting N-arylsubstituted DL-arylglycines and traces of carbamates may be isolated as esters, adding ethylchloride during the electrolysis. A competing pathway of the electrocarboxylation is the C—C-hydrodimerisation and the hydrogenation of the double bond, whose importance increases with the water content of the solvent. Based on cyclic-voltametric evidence and product analysis the mechanism of the reductive electrocarboxylation reaction is discussed in terms of nucleophilic attack of the azomethine anion radical on a proton or CO2.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19823240306
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