Control of extremely fast competitive consecutive reactions using micromixing. Selective Friedel-Crafts aminoalkylation

A Nagaki, M Togai, S Suga, N Aoki…

Index: Nagaki, Aiichiro; Togai, Manabu; Suga, Seiji; Aoki, Nobuaki; Mae, Kazuhiro; Yoshida, Jun-Ichi Journal of the American Chemical Society, 2005 , vol. 127, # 33 p. 11666 - 11675

Full Text: HTML

Citation Number: 168

Abstract

Friedel-Crafts reactions of aromatic and heteroaromatic compounds with an N-acyliminium ion pool were studied. The reaction of 1, 3, 5-trimethylbenzene in a batch reactor gave rise to the selective formation of a monoalkylation product (69%). Presumably, the second alkylation is slower than the first alkylation because of the protonation of the monoalkylation product that decreases its reactivity. The reaction of 1, 3, 5-trimethoxybenzene, however, ...