Thallium in organic synthesis. XIV. Orientation control in an electrophilic aromatic substitution reaction

1970 ◽  
Vol 92 (7) ◽  
pp. 2175-2177 ◽  
Author(s):  
Edward Curtis. Taylor ◽  
Frank. Kienzle ◽  
Roger L. Robey ◽  
Alexander. McKillop
Keyword(s):  
Organic Synthesis ◽  
Substitution Reaction ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Orientation Control

scholarly journals Bi(NO3)3 · 5H2O mediated synthesis of 4,4′-diaminotriarylmethane leuco malachite compounds under solvent-free conditions

2009 ◽  
Vol 7 (1) ◽  
pp. 138-142 ◽  
Author(s):  
Ghasem Bardajee ◽  
Farnaz Jafarpour
Keyword(s):  
Functional Groups ◽  
Substitution Reaction ◽  
Solvent Free ◽  
Synthesis And Characterization ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Aryl Aldehydes ◽  
Solvent Free Conditions

AbstractIn this report, we described the synthesis and characterization of a variety of diaminotriarylmethane derivatives with dimethylamino functional groups. These compounds were synthesized by the tandem regio-selective electrophilic aromatic substitution reaction of N,N-dimethylaniline with aryl aldehydes to form the corresponding diaminotriarylmethane compounds. In our strategy, Bi(NO3)3 was used as a catalyst under solvent free conditions to afford the desired products in good to excellent yields.

scholarly journals Theoretical Studies on Electrophilic Aromatic Substitution Reaction for 8-Hydroxyquinoline

2016 ◽  
Vol 32 (1) ◽  
pp. 253-260 ◽  
Author(s):  
Hasan Obayes ◽  
Khalida Al.Azawi ◽  
Shaymaa Khazaal ◽  
Ghadah Alwan ◽  
Abdulnasser AL-Gebori ◽  
...  
Keyword(s):  
Substitution Reaction ◽  
Electrophilic Aromatic Substitution ◽  
Theoretical Studies ◽  
Aromatic Substitution

Synthesis of Bench-Stable N-Quaternized Ketene N,O-Acetals and Preliminary Evaluation as Reagents in Organic Synthesis

2019 ◽  
Author(s):  
Alisha M. Blades ◽  
Danielle L. McConnell ◽  
Danielle Gomes Rodrigues ◽  
Phoebe V. Keyes ◽  
Justin C. Sonberg ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Lewis Acid ◽  
Reactive Intermediates ◽  
Electrophilic Aromatic Substitution ◽  
Preliminary Evaluation ◽  
Aromatic Substitution ◽  
Triflic Acid ◽  
Synthetic Intermediates ◽  
Nucleophilic Aromatic Substitutions

<div>N-Quaternized ketene N,O-acetals are typically an unstable, transient class of compounds most commonly observed as reactive intermediates. In this report, we describe a general approach to a variety of benchstable N-quaternized ketene N,O-acetals via treatment of pyridine or aniline bases with ethoxyacetylene and an appropriate Brønsted or Lewis acid (triflic acid, triflimide, or scandium(III) triflate). The resulting pyridinium and anilinium salts may be used as reagents or synthetic intermediates in multiple reaction types. For example, N-(1-ethoxyvinyl) pyridinium or anilinium salts can thermally release highly reactive O-ethyl ketenium ions that undergo electrophilic aromatic substitution with electron rich arenes. N-(1-ethoxyvinyl)-2-halopyridinium salts can also be utilized in peptide couplings as a derivative of Mukaiyama reagents, or react with alcohol and amines in nucleophilic aromatic substitutions.</div>

scholarly journals Precise through-space control of an abiotic electrophilic aromatic substitution reaction

2017 ◽  
Vol 8 (1) ◽  
Author(s):  
Kyle E. Murphy ◽  
Jessica L. Bocanegra ◽  
Xiaoxi Liu ◽  
H.-Y. Katharine Chau ◽  
Patrick C. Lee ◽  
...  
Keyword(s):  
Substitution Reaction ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution

Removal of chlorine gas by an amine functionalized metal–organic framework via electrophilic aromatic substitution

2015 ◽  
Vol 51 (62) ◽  
pp. 12474-12477 ◽  
Author(s):  
Jared B. DeCoste ◽  
Matthew A. Browe ◽  
George W. Wagner ◽  
Joseph A. Rossin ◽  
Gregory W. Peterson
Keyword(s):  
Substitution Reaction ◽  
Metal Organic Framework ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Amine Functionalized ◽  
Chlorine Gas ◽  
Metal Organic ◽  
Organic Framework

Chlorine gas is removed from airstreams with an amine functionalized metal–organic framework via an electrophilic aromatic substitution reaction producing HCl, which is subsequently neutralized by the substrate.

AlCl3-Catalyzed Intramolecular Hydroarylation of Arenes with Alkynes

Synlett ◽  
2017 ◽  
Vol 28 (16) ◽  
pp. 2159-2162 ◽  
Author(s):  
Guangxin Gu ◽  
Hao Guo ◽  
Yang Li ◽  
Yu Wang ◽  
Dawen Xu ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Lewis Acid ◽  
Substitution Reaction ◽  
Functional Group ◽  
Catalytic Amount ◽  
Main Group ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Main Group Metal ◽  
Acid Catalyzed

Herein, we wish to report the main-group metal Lewis acid catalyzed intramolecular hydroarylation of arenes with alkynes. This cyclization proceeds efficiently in the presence of a catalytic amount of AlCl3, affording phenanthrenes in moderate to excellent yields. The catalyst is cheap and nontoxic. The functional-group tolerance is high. A plausible electrophilic aromatic substitution reaction mechanism is proposed for this transformation.

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