Novel Nucleophilic Aromatic Substitution of the Fluorine Atom Yielding a Stable Heptatrienide Structure.

ChemInform ◽  
2006 ◽  
Vol 37 (35) ◽  
Author(s):  
Yu. G. Gololobov ◽  
O. A. Linchenko ◽  
Z. A. Starikova ◽  
I. A. Garbuzova ◽  
P. V. Petrovskii
Keyword(s):  
Fluorine Atom ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution

scholarly journals From porphyrin benzylphosphoramidate conjugates to the catalytic hydrogenation of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin

2014 ◽  
Vol 10 ◽  
pp. 628-633 ◽  
Author(s):  
Marcos C de Souza ◽  
Leandro F Pedrosa ◽  
Géssica S Cazagrande ◽  
Vitor F Ferreira ◽  
Maria G P M S Neves ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Catalytic Hydrogenation ◽  
Fluorine Atom ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution

Three new porphyrin aminoalkyl dibenzylphosphoramidates were synthesized by nucleophilic aromatic substitution of onep-fluorine atom of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (TPPF20) by primary aminoalkyl dibenzylphosphoramidates. The nucleophilic aromatic substitution was promoted by microwave irradiation inN-methyl-2-pyrrolidinone. Attempts to remove the benzyl groups of the phosphoramidate moiety by hydrogenolysis with 10% Pd/C led to the cleavage of the P–N bond and the reduction of the macrocycle to hydroporphyrin-type derivatives. The extent of the effect of the catalytic hydrogenation toTPPF20with 10% Pd/C was then studied with a variety of solvents. The results showed that ethanol/DMF is the solvent of choice to produce chlorinTPCF20and an ethanol/DMF/NEt3mixture is more adequate to produce isobacteriochlorin (TPIF20).

Novel nucleophilic aromatic substitution of the fluorine atom yielding a stable heptatrienide structure

2005 ◽  
Vol 54 (10) ◽  
pp. 2471-2472 ◽  
Author(s):  
Yu. G. Gololobov ◽  
O. A. Linchenko ◽  
Z. A. Starikova ◽  
I. A. Garbuzova ◽  
P. V. Petrovskii
Keyword(s):  
Fluorine Atom ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution

scholarly journals Synthesis and nucleophilic aromatic substitution of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene

2016 ◽  
Vol 12 ◽  
pp. 192-197 ◽  
Author(s):  
Javier Ajenjo ◽  
Martin Greenhall ◽  
Camillo Zarantonello ◽  
Petr Beier
Keyword(s):  
Nucleophilic Substitution ◽  
Title Compound ◽  
Fluorine Atom ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Vicarious Nucleophilic Substitution ◽  
Direct Fluorination ◽  
Nitrogen Nucleophiles

3-Fluoro-5-nitro-1-(pentafluorosulfanyl)benzene was prepared by three different ways: as a byproduct of direct fluorination of 1,2-bis(3-nitrophenyl)disulfane, by direct fluorination of 4-nitro-1-(pentafluorosulfanyl)benzene, and by fluorodenitration of 3,5-dinitro-1-(pentafluorosulfanyl)benzene. The title compound was subjected to a nucleophilic aromatic substitution of the fluorine atom with oxygen, sulfur and nitrogen nucleophiles affording novel (pentafluorosulfanyl)benzenes with 3,5-disubstitution pattern. Vicarious nucleophilic substitution of the title compound with carbon, oxygen, and nitrogen nucleophiles provided 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzenes substituted in position four.

scholarly journals Machine learning meets mechanistic modelling for accurate prediction of experimental activation energies

2021 ◽  
Author(s):  
Kjell Jorner ◽  
Tore Brinck ◽  
Per-Ola Norrby ◽  
David Buttar
Keyword(s):  
Machine Learning ◽  
Activation Energies ◽  
Accurate Prediction ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Mechanistic Modelling

Hybrid reactivity models, combining mechanistic calculations and machine learning with descriptors, are used to predict barriers for nucleophilic aromatic substitution.

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.

Nucleophilic aromatic substitution using Et3SiH/cat. t-Bu-P4 as a system for nucleophile activation

2007 ◽  
pp. 2264 ◽  
Author(s):  
Masahiro Ueno ◽  
Misato Yonemoto ◽  
Masahiro Hashimoto ◽  
Andrew E. H. Wheatley ◽  
Hiroshi Naka ◽  
...  
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Nucleophile Activation
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