77988-87-5Relevant articles and documents
Diprotonative stabilization of ring-opened carbocationic intermediates: conversion of tetrahydroisoquinoline to triarylmethanes
Kurouchi, Hiroaki
supporting information, p. 8313 - 8316 (2020/08/17)
Superacid-promoted conversion of tetrahydroisoquinolines to triarylmethanes via tandem reactions of C-N bond scission, Friedel-Crafts alkylation, C-O bond scission, and electrophilic aromatic amidation was developed. Dication formation was important for stabilizing the ring-opened carbocationic intermediate, which is a new role for diprotonation in reaction mechanisms. This journal is
The mechanism of the Bischler-Napieralski Reaction
Nagubandi, Sreeramulu,Fodor, G.
, p. 1457 - 1463 (2007/10/02)
The Bischler-Napieralski dihydroisoquinoline synthesis was proven to occur via imidoyl chlorides and the corresponding nitrilium salt.Two-step process required much milder conditions (20 degC - 50 degC) compared to drastic classical conditions of refluxing at 100 degC - 200 degC.The Bischler-Napieralski reaction is shown to share a common intermediate with two other well-known reactions: the von Braun and the Ritter reactions