40101-33-5Relevant academic research and scientific papers
Nitrogen heterocycles from trimethylbenzenes
Shklyaev,Ismagilov,Rozhkova,Fatykhov,Abdrakhmanov,Tolstikov,Dembitsky
, p. 471 - 476 (2004)
The reaction between 1,2,4-trimethyl-benzene 1, isobutyric aldehyde, and cyanoacetic ester afforded a mixture of three products: 3,3,5,6,8-pentamethyl-1, 2,3,4-tetraisoquinolylidene-1-acetic acid ether (2) and its 3,3,5,6,7- pentamethyl-(3)-and 3,3,6,7,8-
Synthesis of arylbromides from arenes and Nbromosuccinimide bromosuccinimide (NBS) in acetonitrile - A convenient method for aromatic bromination
Zysman-Colman, Eli,Arias, Karla,Siegel, Jay S.
experimental part, p. 440 - 447 (2009/12/01)
Regioselective and chemoselective electrophilic bromination of a wide series of activated arenes using N-bromosuccinimide (NBS) in acetonitrile occurs readily. Environmentally friendly conditions, large substrate scope, and ease of synthesis enhance the utility of this method over other electrophilic bromination conditions.
Regioisomerism in the Ritter reaction. 1. Synthesis of 3,3,5,6,7-, 3,3,6,7,8-, 3,3,5,7,8-, and 3,3,5,6,8-pentamethyl-3,4-dihydroisoquinolines from 1,2,3- and 1,2,4-trimethylbenzenes
Shklyaev, Yu. V.,Ismagilov,Rozhkova, Yu. S.,Fatykhov,Abdrakhmanov,Tolstikov
, p. 906 - 910 (2007/10/03)
Reactions of 1,2,3- or 1,2,4-trimethylbenzene with isobutyraldehyde and ethyl cyanoacetate (ECA) or reactions of the corresponding 1-aryl-2- methylpropan-1-ols with ECA afforded isomeric 3,3,5,6,7-, 3,3,6,7,8-, 3,3,5,7,8-, and 3,3,5,6,8-pentamethyl-3,4-di
Halogenation Using Quaternary Ammonium Polyhalides. XIV. Aromatic Bromination and Iodination of Arenes by Use of Benzyltrimethylammonium Polyhalides-Zinc Chloride System
Kajigaeshi, Shoji,Kakinami, Takaaki,Moriwaki, Masayuki,Tanaka, Toshio,Fujisaki, Shizuo,Okamoto, Tsuyoshi
, p. 439 - 443 (2007/10/02)
The reaction of arenes with benzyltrimethylammonium tribromide or benzyltrimethylammonium dichloroiodate in acetic acid in the presence of ZnCl2 at room temperature or at 70 deg C gave brome- or iodo-substituted arenes in good yield, respectively.
Selective Nuclear Halogenation of Polymethylbenzenes with Alumina-Supported Copper(II) Halides
Kodomari, Mitsuo,Satoh, Hiroaki,Yoshitomi, Suehiko
, p. 4149 - 4150 (2015/06/25)
The halogenation of polymethylbenzenes with alumina-supported copper(II) halides under heterogeneous conditions in nonpolar solvents gave nuclear-halogenated compounds selectively in high yields; no side-chain-halogenated compounds were formed.
Hydrocarbures arylaliphatiques. Partie VII. Orientation dans la reaction de bromation de benzocyclenes bi- et tricycliques superieurs
Gruber, Rene,Cagniant, Denise,Cagniant, Paul
, p. 96 - 104 (2007/10/02)
The bromination of 1,2,3-trimethylbenzene, and bi- and tricyclic fused ring systems (i.e. indan, tetralin, benzosuberan, 2a,3,4,5-tetrahydroacenaphthen and higher homologues) is described in this paper.This work is part of a research project studying the ring size influence of peri-fused semi-aromatic ring system on benzene reactivity.This study was started in a first step on acetylation and was continued on bromination.Forthcoming studies (now underway) concern the kinetic measurement of protodesilylation of univocal silyl derivatives.The synthesis of the starting bromo derivatives used for this latter study is described here.These bromides were used for the attribution via NMR spectroscopy of the electrophile reaction site in the direct bromination of the fused ring unsymmetrical systems (the reactive sites are obvious in symmetrical molecules). Thus, meta substitution is predominant in the case of tetraline and benzosuberan, but ortho substitution is relatively more important in tetralin.In 1,2,3-trimethylbenzene and the fused tricyclic compounds, substitution takes place in an ortho position respective to the substituent or the ring system, the meta position being totally deactivated.In the special case of a five-membered ring, the ortho position this ring is always non reactive.The reactivity differences between these compounds are explained by hyper conjugation and the stabilities of the transition states.
