87353-59-1Relevant academic research and scientific papers
N-(α-ALKOXYALKYL)AMINES. SYNTHESIS OF 9-CARBAZOLYLETHOXYPHENYLMETHANES AND THE MECHANISM OF THEIR ACID HYDROLYSIS
Anfinogenov, V. A.,Filimonov, V. D.,Zamyatina, Z. N.,Kroneval'd, G. V.
, p. 1355 - 1361 (2007/10/02)
It was shown that the acid-catalyzed reaction of benzaldehydes with carbazoles in the presence of ethanol and ethyl orthoformate leads to the formation of 9-carbazolylethoxyphenylmethanes and not acetals or aminals.The kinetics of the acid hydrolysis of the synthesized compounds were studied, and the effect of substituents in the benzene and carbazole rings on the hydrolysis rate was assessed.In conjunction with data on the kinetic isotope effect of the solvent and the entropies of activation, the results are interpreted in terms of a mechanism close to the A-1 mechanism of hydrolysis of acetals with preferential cleavage of the C-O bond and the intermediate formation of a carbenium-immonium ion.
