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Nucleophile aromatic substitution

It looks as though we can get B from A (which is used in frame 247) and so the nitro group is the obvious source of the amino group. It will also allow us to hydrolyse one ether specifically by nucleophilic aromatic substitution. [Pg.132]

Indeed the order of leaving group reactivity m nucleophilic aromatic substitution is the... [Pg.976]

The Addition-Elimination Mechanism of Nucleophilic Aromatic Substitution... [Pg.977]

THE ADDITION-ELIMINATION MECHANISM OF NUCLEOPHILIC AROMATIC SUBSTITUTION... [Pg.977]

The generally accepted mechanism for nucleophilic aromatic substitution m nitro substituted aryl halides illustrated for the reaction of p fluoromtrobenzene with sodium methoxide is outlined m Figure 23 3 It is a two step addition-elimination mechanism, m which addition of the nucleophile to the aryl halide is followed by elimination of the halide leaving group Figure 23 4 shows the structure of the key intermediate The mech anism is consistent with the following experimental observations... [Pg.977]

A nitro group is a strongly activating substituent in nucleophilic aromatic substitution where it stabilizes the key cyclohexadienyl anion intermediate... [Pg.980]

A nitro group behaves the same way m both reactions it attracts electrons Reaction is retarded when electrons flow from the aromatic ring to the attacking species (electrophilic aromatic substitution) Reaction is facilitated when electrons flow from the attacking species to the aromatic ring (nucleophilic aromatic substitution) By being aware of the connection between reactivity and substituent effects you will sharpen your appreciation of how chemical reactions occur... [Pg.980]

The most common types of aryl halides m nucleophilic aromatic substitutions are those that bear o ox p nitro substituents Among other classes of reactive aryl halides a few merit special consideration One class includes highly fluormated aromatic compounds such as hexafluorobenzene which undergoes substitution of one of its fluorines on reac tion with nucleophiles such as sodium methoxide... [Pg.980]

Another type of nucleophilic aromatic substitution occurs under quite different reaction conditions from those discussed to this point and proceeds by a different and rather surprising mechanism It is described m the following section... [Pg.981]

Bromo 1 3 dimethylbenzene is inert to nucleophilic aromatic substitution on treatment with sodium amide in liquid ammonia It is recovered unchanged even after extended contact with the reagent Suggest an explanation for this lack of reactivity... [Pg.984]

Although nucleophilic aromatic substitution by the elimination-addition mecha nism IS most commonly seen with very strong amide bases it also occurs with bases such as hydroxide ion at high temperatures A labeling study revealed that hydroly SIS of chlorobenzene proceeds by way of a benzyne intermediate... [Pg.985]

Section 23 6 Nucleophilic aromatic substitutions of the type just shown follow an addition—elimination mechanism... [Pg.987]

Other aryl halides that give stabilized anions can undergo nucleophilic aromatic substitution by the addition-elimination mechanism Two exam pies are hexafluorobenzene and 2 chloropyridme... [Pg.987]

Nucleophilic aromatic substitution can also occur by an elimination-addition mechanism This pathway is followed when the nucleophile is an exceptionally strong base such as amide ion m the form of sodium amide (NaNH2) or potassium amide (KNH2) Benzyne and related arynes are intermediates m nucleophilic aromatic substitutions that pro ceed by the elimination-addition mechanism... [Pg.987]

Nucleophilic aromatic substitution by the elimination-addition mecha nism can lead to substitution on the same carbon that bore the leaving group or on an adjacent carbon... [Pg.987]

The product of this reaction as its sodium salt is called a Meisenheimer complex after the Ger man chemist Jacob Meisenheimer who reported on their formation and reactions in 1902 A Meisenheimer complex corresponds to the product of the nucleophilic addition stage in the addition-elimination mechanism for nucleophilic aromatic substitution... [Pg.991]

The reaction between an alkoxide ion and an aryl halide can be used to prepare alkyl aryl ethers only when the aryl halide is one that reacts rapidly by the addition-elim mation mechanism of nucleophilic aromatic substitution (Section 23 6)... [Pg.1008]

Attack by the halide nucleophile at the sp hybridized carbon of the alkyl group is anal ogous to what takes place in the cleavage of dialkyl ethers Attack at the sp hybridized carbon of the aromatic nng is much slower Indeed nucleophilic aromatic substitution does not occur at all under these conditions... [Pg.1011]

Several chemical methods have been devised for identifying the N terminal ammo acid They all take advantage of the fact that the N terminal ammo group is free and can act as a nucleophile The a ammo groups of all the other ammo acids are part of amide linkages are not free and are much less nucleophilic Sanger s method for N terminal residue analysis involves treating a peptide with 1 fluoro 2 4 dimtrobenzene which is very reactive toward nucleophilic aromatic substitution (Chapter 23)... [Pg.1131]

Addition-elimination mechanism (Section 23 6) Two stage mechanism for nucleophilic aromatic substitution In the addition stage the nucleophile adds to the carbon that bears... [Pg.1274]

Cycloalkene (Section 5 1) A cyclic hydrocarbon characterized by a double bond between two of the nng carbons Cycloalkyne (Section 9 4) A cyclic hydrocarbon characterized by a tnple bond between two of the nng carbons Cyclohexadienyl anion (Section 23 6) The key intermediate in nucleophilic aromatic substitution by the addition-elimination mechanism It is represented by the general structure shown where Y is the nucleophile and X is the leaving group... [Pg.1280]

Nucleophilic aromatic substitution (Chapter 23) A reaction m which a nucleophile replaces a leaving group as a sub stituent on an aromatic nng Substitution may proceed by an addition-elimination mechanism or an elimination-addition mechanism... [Pg.1289]


See other pages where Nucleophile aromatic substitution is mentioned: [Pg.2593]    [Pg.977]    [Pg.979]    [Pg.980]    [Pg.980]    [Pg.987]    [Pg.987]    [Pg.1282]    [Pg.691]   
See also in sourсe #XX -- [ Pg.217 ]




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1.2.4- Triazine aromatic nucleophilic substitution

Active hydrogen compounds aromatic nucleophilic substitution

Addition elimination mechanism of nucleophilic aromatic substitution

Addition reactions nucleophilic aromatic substitution

Addition-elimination mechanism for nucleophilic aromatic substitution

Aliphatic and Aromatic Nucleophilic Substitution

Alkoxides aromatic nucleophilic substitution

Amides nucleophilic aromatic substitution

Amines aromatic nucleophilic substitution

And nucleophilic aromatic substitution

Aromatic Polyethers by Nucleophilic Substitution

Aromatic Substitution, Nucleophilic and Organometallic

Aromatic compounds, nucleophilic substitution

Aromatic compounds, substituted nucleophilic reactions

Aromatic nucleophiles

Aromatic nucleophilic substitution (SNAr

Aromatic nucleophilic substitution synthesis

Aromatic substitution nucleophilic

Aromatic substitution nucleophilic

Aromatic substitution nucleophilic, 11-14, Table

Aryl azides nucleophilic aromatic substitution

Aryl ethers nucleophilic aromatic substitution

Aryl halides and nucleophilic aromatic substitution

Aryl halides nucleophilic aromatic substitution

Arylamines aromatic nucleophilic substitution

Arylboronic nucleophilic aromatic substitutions

Asymmetric nucleophilic aromatic substitution

Asymmetric nucleophilic aromatic substitution chiral catalyzed

Asymmetric nucleophilic aromatic substitution chiral nucleophiles

B Nucleophilic aromatic substitution

Benzene Nucleophilic aromatic substitution reactions

Benzene nucleophilic aromatic substitution

Benzene, tris aromatic nucleophilic substitution

Benzothiazoles aromatic nucleophilic substitution

Bimolecular displacement mechanism for nucleophilic aromatic substitution

Bis-annulation aromatic nucleophilic substitution

Carbanions nucleophilic aromatic substitution

Carbon nucleophiles aromatic nucleophilic substitution

Carbon nucleophilic aromatic substitution via

Catalyzed Nucleophilic Aromatic Substitution

Chlorobenzene nucleophilic aromatic substitution

Conjugate addition and nucleophilic aromatic substitution

Copper compounds Cu in aromatic nucleophilic substitution

Criteria for Nucleophilic Aromatic Substitution

Cyanides aromatic nucleophilic substitution

Cyclohexadienyl anion, intermediate nucleophilic aromatic substitution

Delocalization in nucleophilic aromatic substitution

Electron Pushing for Nucleophilic Aromatic Substitution

Electrophilic and Nucleophilic Aromatic Substitution

Electrophilic and nucleophilic substitution in aromatic

Electrophilic arenes nucleophilic aromatic substitution

Electrophilic aromatic substitution reactions arene nucleophiles

Elimination addition reactions nucleophilic aromatic substitution with

Fluoroarenes aromatic nucleophilic substitution

Formylation aromatic nucleophilic substitution and hydrolysis

Grignard reagents aromatic nucleophilic substitution

Halides aromatic nucleophilic substitution

Heterocyclic compounds nucleophilic aromatic substitution

Hydrides aromatic nucleophilic substitution

INDEX nucleophilic aromatic substitution

Imine formation nucleophilic aromatic substitution

In nucleophilic aromatic substitution

Indazolinones by Ugi-4CR with N-deprotection and Aromatic Nucleophilic Substitution

Intramolecular Reactions Nucleophilic Aromatic Substitution

Intramolecular nucleophilic aromatic substitution

Intramolecular nucleophilic aromatic substitution iodine

Ipso nucleophilic aromatic substitution

Isotopes nucleophilic aromatic substitution

Kinetic studies nucleophilic aromatic substitution

Kinetic studies of nucleophilic aromatic substitution

Leaving groups in nucleophilic aromatic substitution

Leaving groups, reactivity in nucleophilic aromatic substitution

Mechanism nucleophilic aromatic substitution

Mechanism of aromatic nucleophilic substitution

Multicomponent Synthesis of Annelated Thiopyranones by Coupling-Addition-Nucleophilic Aromatic Substitution Sequence

NASH (nucleophilic aromatic substitution

Nitro compounds aromatic, nucleophilic substitution

Nitrogen nucleophiles aromatic nucleophilic substitution

Nucleophile olefin combination, aromatic substitution reaction

Nucleophilic Aromatic Substitution An Addition-Elimination Reaction

Nucleophilic Aromatic Substitution An Update Overview

Nucleophilic Aromatic Substitution Diazonium Ions

Nucleophilic Aromatic Substitution by the Addition-Elimination Mechanism

Nucleophilic Aromatic Substitution. Benzyne

Nucleophilic Aromatic and Vinylic Substitution

Nucleophilic Substitution of Aromatic Chlorides

Nucleophilic aromatic

Nucleophilic aromatic oxidative substitution

Nucleophilic aromatic substitution (the SNAr mechanism)

Nucleophilic aromatic substitution 1,3-azoles

Nucleophilic aromatic substitution 2- nitrothiophene

Nucleophilic aromatic substitution 2-nitrofurans

Nucleophilic aromatic substitution 3- nitroaniline

Nucleophilic aromatic substitution 6-nitroquinoline

Nucleophilic aromatic substitution Meisenheimer adducts

Nucleophilic aromatic substitution Meisenheimer complexes

Nucleophilic aromatic substitution SnAt mechanism

Nucleophilic aromatic substitution activating groups, effects

Nucleophilic aromatic substitution addition-elimination mechanism

Nucleophilic aromatic substitution adducts

Nucleophilic aromatic substitution amine nucleophiles

Nucleophilic aromatic substitution amines, base catalysis

Nucleophilic aromatic substitution aniline derivatives

Nucleophilic aromatic substitution approach

Nucleophilic aromatic substitution aryl-copper complexes

Nucleophilic aromatic substitution benzyne mechanism

Nucleophilic aromatic substitution bimolecular displacement

Nucleophilic aromatic substitution by addition-elimination

Nucleophilic aromatic substitution copper

Nucleophilic aromatic substitution copper-catalyzed

Nucleophilic aromatic substitution coupling

Nucleophilic aromatic substitution diasteroselectivity

Nucleophilic aromatic substitution diphenylamines

Nucleophilic aromatic substitution elimination process

Nucleophilic aromatic substitution elimination-addition

Nucleophilic aromatic substitution enantioselectivity

Nucleophilic aromatic substitution examples

Nucleophilic aromatic substitution fluoro derivative

Nucleophilic aromatic substitution for

Nucleophilic aromatic substitution for hydrogen

Nucleophilic aromatic substitution general discussion

Nucleophilic aromatic substitution halogen exchange reactions

Nucleophilic aromatic substitution heterocyclic systems

Nucleophilic aromatic substitution homolytic

Nucleophilic aromatic substitution hydrogen

Nucleophilic aromatic substitution intermediate complexes

Nucleophilic aromatic substitution intramolecular rearrangements

Nucleophilic aromatic substitution isoquinoline

Nucleophilic aromatic substitution kinetic features

Nucleophilic aromatic substitution leaving groups

Nucleophilic aromatic substitution limitations

Nucleophilic aromatic substitution metal-catalyzed

Nucleophilic aromatic substitution nitro-group activated

Nucleophilic aromatic substitution nitro-group displacement

Nucleophilic aromatic substitution nucleophiles

Nucleophilic aromatic substitution nucleophiles

Nucleophilic aromatic substitution of hydrogen

Nucleophilic aromatic substitution of hydrogen NASH)

Nucleophilic aromatic substitution of pyridines

Nucleophilic aromatic substitution organic reaction mechanisms

Nucleophilic aromatic substitution orientation

Nucleophilic aromatic substitution ortho-selectivity

Nucleophilic aromatic substitution palladium

Nucleophilic aromatic substitution phase transfer catalysis

Nucleophilic aromatic substitution photochemical

Nucleophilic aromatic substitution polymerization

Nucleophilic aromatic substitution quinoline

Nucleophilic aromatic substitution radical

Nucleophilic aromatic substitution radical chain mechanism

Nucleophilic aromatic substitution reaction characteristics

Nucleophilic aromatic substitution reactions diazonium ions

Nucleophilic aromatic substitution reactivity

Nucleophilic aromatic substitution rearrangements

Nucleophilic aromatic substitution reviews

Nucleophilic aromatic substitution solid-state

Nucleophilic aromatic substitution solvent effects

Nucleophilic aromatic substitution substituent effects

Nucleophilic aromatic substitution synthetic applications

Nucleophilic aromatic substitution systems

Nucleophilic aromatic substitution water

Nucleophilic aromatic substitution, quinoxaline

Nucleophilic substitution aromaticity

Nucleophilic substitution aromatics

Nucleophilic substitution reaction aromatic compounds

Nucleophilic substitution, aromatic activated aryl halides

Nucleophilic substitution, aromatic anionic intermediates

Nucleophilic substitution, aromatic aryne intermediates

Nucleophilic substitution, aromatic deuterium exchange

Nucleophilic substitution, aromatic diazonium salts

Nucleophilic substitution, aromatic nitrobenzene

Nucleophilic substitution, aromatic pyridine

Nucleophilic substitution, aromatic rates

Nucleophilic substitution—continued mechanisms for aromatic compounds

Organolithium compounds aromatic nucleophilic substitution

Organolithium reagents aromatic nucleophilic substitution

Organometallic compounds aromatic nucleophilic substitution

Orientation in nucleophilic aromatic substitution

Oxygen nucleophiles aromatic nucleophilic substitution

P-Toluenesulfonic acid nucleophilic aromatic substitution

Peterson reagent aromatic nucleophilic substitution

Phenols and Aryl Halides Nucleophilic Aromatic Substitution

Phenols nucleophilic aromatic substitution

Phosphorus nucleophiles aromatic nucleophilic substitution

Photochemical Nucleophile-Olefin Combination, Aromatic Substitution

Photochemical reactions aromatic nucleophilic substitution

Photoinduced radical reactions nucleophilic aromatic substitution

Polyglymes aromatic nucleophilic substitution

Preparation of Phenols Nucleophilic Aromatic Substitution

Pyridazines, nucleophilic aromatic substitution

Pyridines derivatives, nucleophilic aromatic substitution

Quinolines, nucleophilic aromatic substitution

Quinone methides, generation water, nucleophilic aromatic substitution

Radical-nucleophilic aromatic substitution carbanions

Radical-nucleophilic aromatic substitution electron transfer

Radical-nucleophilic aromatic substitution experiments

Radical-nucleophilic aromatic substitution halides

Radical-nucleophilic aromatic substitution heterocyclic synthesis

Radical-nucleophilic aromatic substitution initiation step

Radical-nucleophilic aromatic substitution intermolecular

Radical-nucleophilic aromatic substitution intramolecular

Radical-nucleophilic aromatic substitution propagation steps

Reaction mechanisms nucleophilic aromatic substitution

Reactions of Arenes Electrophilic and Nucleophilic Aromatic Substitution

Reactivity in nucleophilic aromatic substitution

Regioselectivity nucleophilic aromatic substitution

Related Nucleophilic Aromatic Substitution Reactions

Related Nucleophilic Aromatic Substitutions

Resonance nucleophilic aromatic substitution

SNAr reaction nucleophilic aromatic substitution

Selenium nucleophiles aromatic nucleophilic substitution

Solvent effects in aromatic nucleophilic substitution

Substituent effects of nucleophilic aromatic substitution

Substituent effects on nucleophilic aromatic substitution

Substitution reactions aromatic nucleophilic (addition-elimination

Substitution reactions nucleophilic aromatic

Substitution, allylic nucleophilic aromatic

Sulfites aromatic nucleophilic substitution

Sulfur nucleophiles aromatic nucleophilic substitution

Synthesis continued) nucleophilic aromatic substitution

Tellurium nucleophiles aromatic nucleophilic substitution

The Addition-Elimination Mechanism of Nucleophilic Aromatic Substitution

The Elimination-Addition Mechanism of Nucleophilic Aromatic Substitution Benzyne

Thio anions aromatic nucleophilic substitution

Thioalkoxides aromatic nucleophilic substitution

Thiocyanates aromatic nucleophilic substitution

Thioiminium salts aromatic nucleophilic substitution

Ugi-4CR and Nucleophilic Aromatic Substitution

Vicarious nucleophilic aromatic substitution

Vicarious nucleophilic substitutions , aromatic hydrogens

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