σ-Complex formation and oxidative nucleophilic aromatic substitution in 4-nitro-2,1,3-benzoxadiazoles

Régis Goumont; Emmanuel Jan; Mieczyslaw Makosza; Francois Terrier

doi:10.1039/b302036c

σ-Complex formation and oxidative nucleophilic aromatic substitution in 4-nitro-2,1,3-benzoxadiazoles

Organic & Biomolecular Chemistry ◽

10.1039/b302036c ◽

2003 ◽

Vol 1 (12) ◽

pp. 2192-2199 ◽

Cited By ~ 37

Author(s):

Régis Goumont ◽

Emmanuel Jan ◽

Mieczyslaw Makosza ◽

Francois Terrier

Keyword(s):

Complex Formation ◽

Nucleophilic Aromatic Substitution ◽

Aromatic Substitution

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ChemInform Abstract: INTERMEDIATES IN NUCLEOPHILIC AROMATIC SUBSTITUTION PART 11, SPIRO MEISENHEIMER COMPLEX OF N,N′-DIMETHYL-N-PICRYLETHYLENEDIAMINE, PARTIALLY RATE-LIMITING PROTON TRANSFER OF COMPLEX FORMATION, A TEMPERATURE-JUMP STUDY

Chemischer Informationsdienst ◽

10.1002/chin.197417108 ◽

1974 ◽

Vol 5 (17) ◽

pp. no-no

Author(s):

CLAUDE F. BERNASCONI ◽

CONSTANTIN L. GEHRIGER

Keyword(s):

Complex Formation ◽

Proton Transfer ◽

Temperature Jump ◽

Nucleophilic Aromatic Substitution ◽

Aromatic Substitution ◽

Rate Limiting

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Intermediates in nucleophilic aromatic substitution. Part 23. Kinetics of spiro meisenheimer complex formation from 3,6-dimethylcatechol 2,4,6-trinitrophenyl ether. Competition between a trapping and a preassociation mechanism

Journal of the American Chemical Society ◽

10.1021/ja00224a038 ◽

1988 ◽

Vol 110 (16) ◽

pp. 5498-5505 ◽

Cited By ~ 4

Author(s):

Claude F. Bernasconi ◽

Douglas E. Fairchild

Keyword(s):

Complex Formation ◽

Nucleophilic Aromatic Substitution ◽

Aromatic Substitution ◽

Kinetics Of

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ChemInform Abstract: Intermediates in Nucleophilic Aromatic Substitution. Part 23. Kinetics of Spiro Meisenheimer Complex Formation from 3,6-Dimethylcatechol 2,4,6-Trinitrophenyl Ether. Competition Between a Trapping and a Preassociation Mechanism.

ChemInform ◽

10.1002/chin.198847057 ◽

1988 ◽

Vol 19 (47) ◽

Author(s):

C. F. BERNASCONI ◽

D. E. FAIRCHILD

Keyword(s):

Complex Formation ◽

Nucleophilic Aromatic Substitution ◽

Aromatic Substitution ◽

Kinetics Of

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Intermediates in nucleophilic aromatic substitution. XI. Spiro Meisenheimer complex of N, N'-dimethyl-N-picrylethylenediamine. Partially rate-limiting proton transfer of complex formation. Temperature-jump study

Journal of the American Chemical Society ◽

10.1021/ja00811a025 ◽

1974 ◽

Vol 96 (4) ◽

pp. 1092-1099 ◽

Cited By ~ 19

Author(s):

Claude F. Bernasconi ◽

Cvonstantin L. Gehriger

Keyword(s):

Complex Formation ◽

Proton Transfer ◽

Temperature Jump ◽

Nucleophilic Aromatic Substitution ◽

Formation Temperature ◽

Aromatic Substitution ◽

Rate Limiting

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

Chemical Science ◽

10.1039/d0sc04896h ◽

2021 ◽

Cited By ~ 1

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.

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Radical-Cation-Accelerated Nucleophilic Aromatic Substitution of Electron-Rich Aryl Fluorides

Synfacts ◽

10.1055/s-0040-1719572 ◽

2020 ◽

Vol 16 (12) ◽

pp. 1467

Keyword(s):

Radical Cation ◽

Nucleophilic Aromatic Substitution ◽

Aromatic Substitution

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ChemInform Abstract: NUCLEOPHILIC AROMATIC SUBSTITUTION PROMOTED BY COBALT(III) TRIFLUOROACETATE

Chemischer Informationsdienst ◽

10.1002/chin.197815079 ◽

1978 ◽

Vol 9 (15) ◽

Author(s):

M. E. KURZ ◽

G. W. HAGE

Keyword(s):

Nucleophilic Aromatic Substitution ◽

Aromatic Substitution

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

Synlett ◽

10.1055/a-1323-2389 ◽

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.

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