89787-30-4Relevant academic research and scientific papers
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.
Renaud, Roger N.,Stephens, Campbell J.,Brochu, Gaetan
, p. 565 - 569 (2007/10/02)
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.
