Electrochemical oxidation of 4-substituted N,N-dimethylaniline in the presence of silyl enol ether. Effect of the substituent on the formation of Mannich bases. II

Autor:	Roger N. Renaud, Campbell J. Stephens, Gaétan Brochu
Rok vydání:	1984
Předmět:	chemistry.chemical_classification Tertiary amine Chemistry Organic Chemistry Substituent Dimethylaniline General Chemistry Silyl enol ether Mannich base Medicinal chemistry Catalysis chemistry.chemical_compound Enol ether Organic chemistry Aliphatic compound Acetophenone
Zdroj:	Canadian Journal of Chemistry. 62:565-569
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v84-094
Popis:	The formation of Mannich bases from the electrochemical oxidation of 4-substituted N,N-dimethylaniline in the presence of silyl enol ether was studied. The yield of bases obtained depended on the relative oxidation potentials of the starting amine compound and the base formed. An electron-donating substituent on the amine showed a large difference in the oxidation potentials and gave the highest yield of product. On the other hand, the oxidation potentials were very close with an electron-withdrawing substituent and the yield in base was relatively much lower. Furthermore, the main product in the case of an electron-withdrawing group in the presence of 1-trimethylsilyloxy-1-cyclohexene was 4-substituted 2-(2-oxocyclohexyl)-N,N-dimethylaniline. Some side products were also isolated and were identified as N,N-diketonic compounds.
Databáze:	OpenAIRE
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