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Arylamination

Arylamines are generally prepared by the reduction of nitro compounds. When only small quantities are to be reduced and the time element is important and cost is a secondary consideration, tin and hydrochloric acid may be employed, for example ... [Pg.559]

Aryl and alkenyl phenyl sulfides are prepared by the reaction of aryl and alkenyl halides and inflates with tributylstannyl phenyl sulfide. 2-Chloropyrimidine (737) is used for the coupling[606,607]. The diaryl or divinyl sulfide 739 is prepared by the reaction of distannyl sulfide (738)[548], N,N-Diethylaminotributyltin (740) reacts with aryl halides to give arylamines[608]. [Pg.238]

Alkylthiothiazo one (184) reacts with ammonia, al-kylamines. and arylamines to give the corresponding 2-iminothiazolidin-... [Pg.424]

Arylamino-2-chloroprop-2- enoic esters (72) obtained from 2-chloroaceto acetic ester (71) and arylamines, react with thiourea to yidd substituted 2-aminothiazoles (73), probably by initial nucleophilic substitution of the chloro atom of 72, followed by cyclization with loss of aniline (Scheme 33) (729). [Pg.205]

Arylamines Aniline like alkylamines has a pyramidal arrangement of bonds around nitrogen but its pyramid is somewhat shallower One measure of the extent of this flat tenmg is given by the angle between the carbon-nitrogen bond and the bisector of the H—N—H angle... [Pg.916]

The orbital and resonance models for bonding in arylamines are simply alternative ways of describing the same phenomenon Delocalization of the nitrogen lone pair decreases the electron density at nitrogen while increasing it m the rr system of the aro matic ring We ve already seen one chemical consequence of this m the high level of reactivity of aniline m electrophilic aromatic substitution reactions (Section 12 12) Other ways m which electron delocalization affects the properties of arylamines are described m later sections of this chapter... [Pg.918]

The simplest arylamme aniline is a liquid at room temperature and has a boiling point of 184°C Almost all other arylamines have higher boiling points Aniline is only... [Pg.918]

Arylamines are about 1 million times (6 pK units) weaker bases than ammonia and alkylammes... [Pg.920]

Nitro groups are readily reduced to primary amines by a variety of methods Cat alytic hydrogenation over platinum palladium or nickel is often used as is reduction by iron or tin m hydrochloric acid The ease with which nitro groups are reduced is especially useful m the preparation of arylamines where the sequence ArH ArN02 ArNH2 IS the standard route to these compounds... [Pg.932]

Outline syntheses of each of the following arylamines from... [Pg.932]

Both alkylamines and arylamines undergo these reactions... [Pg.936]

Arylamines contain two functional groups the amine group and the aromatic ring they are difunctional compounds The reactivity of the amine group is affected by its aryl substituent and the reactivity of the ring is affected by its amine substituent The same electron delocalization that reduces the basicity and the nucleophilicity of an arylamme nitrogen increases the electron density in the aromatic ring and makes arylamines extremely reactive toward electrophilic aromatic substitution... [Pg.939]

The reactivity of arylamines was noted m Section 12 12 where it was pointed out that —NH2 —NHR and —NR2 are ortho para directing and exceedingly powerful... [Pg.939]

Direct nitration of aniline and other arylamines fails because oxidation leads to the formation of dark colored tars As a solution to this problem it is standaid practice to first protect the ammo group by acylation with either acetyl chloride or acetic anhydride... [Pg.940]

Protecting the amino group of an arylamine in this way moderates its reactivity and per mits nitration of the ring to be achieved The acetamido group is activating toward elec trophilic aromatic substitution and is ortho para directing... [Pg.941]

Unprotected arylamines are so reactive toward halogenation that it is difficult to limit the reaction to monosubstitution Generally halogenation proceeds rapidly to replace all the available hydrogens that are ortho or para to the ammo group... [Pg.942]

Aryl diazonium ions prepared by nitrous acid diazotization of primary arylamines are substantially more stable than alkyl diazonium ions and are of enormous synthetic value Their use m the synthesis of substituted aromatic compounds is described m the following two sections... [Pg.945]

We learned m the preceding section that different reactions are observed when the var lous classes of alkylammes—primary secondary and tertiary—react with mtrosatmg agents Although no useful chemistry attends the nitrosation of tertiary alkylammes elec trophilic aromatic substitution by mtrosyl cation ( N=0 ) takes place with A A dialkyl arylamines... [Pg.945]

Primary arylamines like primary alkylammes form diazonium ion salts on nitro sation Aryl diazonium 10ns are considerably more stable than their alkyl counterparts Whereas alkyl diazonium 10ns decompose under the conditions of their formation aryl diazonium salts are stable enough to be stored m aqueous solution at 0-5°C for a rea sonable time Loss of nitrogen from an aryl diazonium ion generates an unstable aryl cation and is much slower than loss of nitrogen from an alkyl diazonium ion... [Pg.945]

A reaction of aryl diazonium salts that does not involve loss of nitrogen takes place when they react with phenols and arylamines Aryl diazonium ions are relatively weak elec trophiles but have sufficient reactivity to attack strongly activated aromatic rings The reaction is known as azo coupling two aryl groups are joined together by an azo (—N=N—) function... [Pg.950]

Reduction of aryl nitro compounds (Sec tion 22 9) The standard method for the preparation of an arylamine is by nitra tion of an aromatic ring followed by reduction of the nitro group Typical re ducing agents include iron or tin in hydro chloric acid or catalytic hydro genation... [Pg.957]

Electrophilic aromatic substitution (Sec tion 22 14) Arylamines are very reac tive toward electrophilic aromatic sub stitution It IS customary to protect arylamines as their N acyl derivatives before carrying out ring nitration chio rination bromination sulfonation or Friedel-Crafts reactions... [Pg.959]

Secondary alkylamines and secondary arylamines y e d N nitroso amines... [Pg.959]

Arylamine Electrophile Product of electrophilic aromatic substitution... [Pg.959]

Sandmeyer reaction using cop per(l) bromide is applicable to the conversion of primary arylamines to aryl bromides... [Pg.961]

Reductive deamination of primary arylamines The ammo substituent of an arylamine can be replaced by hydrogen by treatment of its de rived diazonium salt with ethanol or with hypophosphorous acid... [Pg.961]

Diazotization of an arylamine followed by treatment with fluoroboric acid gives an aryl diazonium fluoroborate salt Heating this salt converts it to an aryl fluoride... [Pg.973]

Diazotization of a primary arylamine followed by treatment of the diazo mum salt with copper(l) bromide or copper(l) chloride yields the corre spending aryl bromide or aryl chloride... [Pg.973]


See other pages where Arylamination is mentioned: [Pg.1049]    [Pg.8]    [Pg.913]    [Pg.913]    [Pg.920]    [Pg.939]    [Pg.939]    [Pg.940]    [Pg.940]    [Pg.941]    [Pg.941]    [Pg.945]    [Pg.945]    [Pg.950]    [Pg.956]    [Pg.957]    [Pg.960]    [Pg.960]    [Pg.960]    [Pg.961]    [Pg.961]    [Pg.961]    [Pg.961]   
See also in sourсe #XX -- [ Pg.9 , Pg.24 , Pg.206 , Pg.215 , Pg.224 ]

See also in sourсe #XX -- [ Pg.43 ]

See also in sourсe #XX -- [ Pg.1054 ]




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A- -arylamines

Acetic acid with arylamines

Acetic anhydride with arylamines

Acetyl chloride with arylamines

Alkenylation arylamines

Amination arylamination

Amines arylamine

Amines arylamines

Amines primary arylamines with nitrous

Aminoalkylation arylamines

Antioxidants arylamine

Arenediazonium salt from arylamines

Arenediazonium salt reaction with arylamines

Aryl bromides arylamine synthesis

Aryl derivatives arylamines

Aryl derivatives primary arylamines

Aryl halides arylamine synthesis

Arylamin

Arylamin

Arylamination olefins

Arylamine

Arylamine

Arylamine Mixtures

Arylamine NATs

Arylamine basicity

Arylamine diazotization

Arylamine dye

Arylamine electrophilic aromatic substitution

Arylamine formation

Arylamine from nitroarenes

Arylamine hydrochloride

Arylamine material

Arylamine moiety

Arylamine reaction with arenediazonium

Arylamine reactions

Arylamine reactions dimerization

Arylamine resonance

Arylamine salts

Arylamine sulfonamides

Arylamine synthesis

Arylamines

Arylamines

Arylamines (oxidative dealkylation)

Arylamines Aniline Diazonium salts)

Arylamines DNA adducts

Arylamines Diazonium salts

Arylamines Mannich reaction

Arylamines acylation

Arylamines alkylation

Arylamines aromatic nucleophilic substitution

Arylamines basicity

Arylamines bioactivation

Arylamines charge transport of molecular glasses, hole

Arylamines conjugates

Arylamines copper-catalyzed

Arylamines copper-catalyzed coupling

Arylamines derivatives

Arylamines electrophilic aromatic substitution

Arylamines in reductive amination

Arylamines mobilities

Arylamines molecular glasses, fluorescence quantum

Arylamines mutations

Arylamines nitrosation

Arylamines nomenclature

Arylamines on Phenolic Compounds

Arylamines oxidation potential

Arylamines oxidation products

Arylamines palladium complexes

Arylamines palladium-catalyzed

Arylamines photochemical

Arylamines preparation

Arylamines reaction with nitrous acid

Arylamines reactions

Arylamines s. Amines

Arylamines structure and bonding

Arylamines synthesis

Arylamines via SrnI reaction

Arylamines vinylation

Arylamines yield

Arylamines, color reactions

Arylamines, color reactions diazotization

Arylamines, hetero

Arylamines, oxidation

Arylamines, oxidative dimerization

Arylamines, reaction with sulfur

Arylamines, sulfation

Arylamines, tertiary

Arylation of Primary Arylamines

Arylation of arylamines

Azo compounds via primary arylamines

BINAP ligand primary arylamines

Basicity of Arylamines

Basicity of Substituted Arylamines

Basicity, alkylamines arylamines

Catalyzed Coupling of Arylamines

Charge transport arylamines

Chemicals arylamine

Diazonium formation from arylamines

Diazonium salts, from arylamines, reactions

Electrophilic Aromatic Substitution in Arylamines

Electrophilic aromatic substitution arylamines and

Fluorescence quantum yield arylamines

Friedel-Crafts acylation reaction arylamines and

Friedel-Crafts alkylation reaction arylamines and

From Arylamines

Heterocyclic arylamines , substituted

How Are Arylamines Synthesized

Imine Arylations-Synthesis of Arylamines

Manganese dioxide primary arylamines

Mitosane via selenoamination of allylic arylamines

N-Acetoxy arylamines

N-Hydroxy arylamines

N-Sulfonyloxy arylamines

N-arylamine

Nickel peroxide primary arylamines

Nitroarene, arylamines from

Nitroarene, arylamines from reduction

Nitrosation of Arylamines

Nitroso-arylamine

Nitrous acid primary arylamines

Oxidation of Arylamines

Oxidation of arylamines, arylhydroxylamines and other derivatives

Oxidative Carbonylation of Arylamines

Oxidative arylamines

Oxidative carbonylation arylamines

Phenols from arylamines

Polymeric arylamine

Preparation of Arylamines

Protecting groups for arylamines

Protonated N-hydroxy arylamines

Quinolines from arylamines

Reactions arylamination

Reactions of Arylamines

Resonance arylamines and

Silver permanganate, bispyridineoxidation primary arylamines

Sodium hypochlorite primary arylamines

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