Micellar catalysis of organic reactions. IX. The reaction of sodium azide with activated aromatic halides and the subsequent decomposition of the initially formed aryl azide

1982 ◽  
Vol 35 (12) ◽  
pp. 2557 ◽  
Author(s):  
TJ Broxton ◽  
AC Jakovljevic
Keyword(s):  
Sodium Azide ◽  
Substitution Reaction ◽  
Cetyltrimethylammonium Bromide ◽  
Micellar Catalysis ◽  
Organic Reactions ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Aryl Azide ◽  
Snar Reaction ◽  
Subsequent Decomposition

The effect of micelles of cetyltrimethylammonium bromide on the SNAr reaction of azide ions with 1-halogeno-2,4-dinitrobenzenes and on the subsequent decomposition of the aryl azide product has been measured. The nucleophilic aromatic substitution reaction is shown to be subject to significant micellar catalysis whereas the subsequent decomposition of the aryl azide is not.

One-Pot Approach for SNAr Reaction of Fluoroaromatic Compounds with Cyclopropanol

Synlett ◽  
2019 ◽  
Vol 30 (08) ◽  
pp. 982-986
Author(s):  
Hao Jin ◽  
Zhuo Gao ◽  
Shaodong Zhou ◽  
Chao Qian
Keyword(s):  
Aromatic Compounds ◽  
Substitution Reaction ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
One Pot ◽  
Mild Conditions ◽  
Snar Reaction ◽  
Novel Method ◽  
The One ◽  
Application Scope

A novel method for preparing aromatic compounds containing cyclopropoxy via nucleophilic aromatic substitution reaction (SNAr) of fluoroaromatic compounds with cyclopropanol under relatively mild conditions is presented. As compared to the approaches reported previously for preparing 1-(cyclopropyloxy)-2-nitrobenzene, the one proposed in this work is simplified without sacrificing the yields: When the reaction was performed at 75 °C with Cs2CO3 as the base and DMF as solvent, after 6 h the yield was up to 90%. Finally, various fluoroaromatic compounds were employed as substrates for a test that proves a wide application scope of the method.

Micellar Catalysis of Organic Reactions. XXXVIII A Study of the Catalytic Effect of Micelles of 3-Hydroxymethyl-1-tetradecylpyridinium Bromide on Amide Hydrolysis and Nucleophilic Aromatic Substitution

1998 ◽  
Vol 51 (7) ◽  
pp. 541 ◽  
Author(s):  
Trevor J. Broxton
Keyword(s):  
Catalytic Effect ◽  
Micellar Catalysis ◽  
Aryl Halides ◽  
Organic Reactions ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Rate Determining Step ◽  
Amide Hydrolysis

The preparation of 3-hydroxymethyl-1-tetradecylpyridinium bromide and its use as a catalyst of nucleophilic aromatic substitution and also amide hydrolysis are reported. It was found that the hydroxydehalogenation of nitro-activated aryl halides was much faster in these micelles than in the presence of cetyl(2-hydroxyethyl)dimethylammonium bromide. It was concluded that the increased catalysis of nucleophilic aromatic substitution by this micelle was due to a faster decomposition of the aryl micellar ether which must occur before the phenolate product is released. No such difference in the two micelles was found for amide or thioamide hydrolysis since in these reactions the product amine is produced in the first step of the reaction and decomposition of the acylated micelle is not required in the rate-determining step of the reaction.

One-pot Microwave-assisted Tandem Deprotection of Arylmethanesulfonates / SNAr Reaction for K2CO3-mediated C(Aryl)–O Bond Formation

2007 ◽  
Vol 62 (9) ◽  
pp. 1183-1186 ◽  
Author(s):  
Hui Xu ◽  
Hong-Feng Li
Keyword(s):  
Substitution Reaction ◽  
Bond Formation ◽  
Aryl Halides ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
One Pot ◽  
Diaryl Ethers ◽  
Microwave Assisted ◽  
Snar Reaction

One-pot microwave-assisted tandem deprotection of arylmethanesulfonates / nucleophilic aromatic substitution reaction (SNAr) with activated aryl halides to synthesize asymmetrical diaryl ethers is described.

Dynamics of a gas-phase SNAr reaction: non-concerted mechanism despite the Meisenheimer complex being a transition state

2020 ◽  
Vol 22 (45) ◽  
pp. 26562-26567
Author(s):  
Nishant Sharma ◽  
Rupayan Biswas ◽  
Upakarasamy Lourderaj
Keyword(s):  
Transition State ◽  
Gas Phase ◽  
Substitution Reaction ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Concerted Mechanism ◽  
Snar Reaction

Multi-step roaming pathway in the nucleophilic aromatic substitution reaction involving a Meisenheimer transition state.

Enantioselective Nucleophilic Aromatic Substitution Reaction of Azlactones to Synthesize Quaternary α-Amino Acid Derivatives

Synlett ◽  
2020 ◽  
Author(s):  
Xiaohua Liu ◽  
Yi Li ◽  
Hao Pan ◽  
Wang-Yuren Li ◽  
Xiaoming Feng
Keyword(s):  
Hydrogen Bonding ◽  
Charge Transfer ◽  
Amino Acid ◽  
Substitution Reaction ◽  
Nucleophilic Aromatic Substitution ◽  
Amino Acid Derivatives ◽  
Amino Acid Esters ◽  
Aromatic Substitution ◽  
Charge Transfer Interaction ◽  
Acid Esters

AbstractAn asymmetric organocatalytic nucleophilic aromatic substitution reaction of azlactones with electron-deficient aryls was established. A variety of α-aryl α-alkyl α-amino acid esters and peptides were obtained in decent yields and stereoselectivities. A new bifunctional catalytic mode involving charge-transfer interaction and hydrogen bonding is proposed to explain the enantioselectivity.

Studies on the Regioselective Nucleophilic Aromatic Substitution (SNAr) Reaction of 2-Substituted 3,5-Dichloropyrazines

2013 ◽  
Vol 15 (9) ◽  
pp. 2156-2159 ◽  
Author(s):  
Stephanie Scales ◽  
Sarah Johnson ◽  
Qiyue Hu ◽  
Quyen-Quyen Do ◽  
Paul Richardson ◽  
...  
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Snar Reaction

New Highly Stable Metallabenzenes via Nucleophilic Aromatic Substitution Reaction

2011 ◽  
Vol 17 (15) ◽  
pp. 4223-4231 ◽  
Author(s):  
Ran Lin ◽  
Hong Zhang ◽  
Shunhua Li ◽  
Jiani Wang ◽  
Haiping Xia
Keyword(s):  
Substitution Reaction ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution
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