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With alkyl halides

With Alkylating Agents 2.1.1. With Alkyl Halide.s [Pg.372]

The reaction of disodium telluride with alkyl halides is the oldest known method for the preparation of dialkyl telluriums. The required solutions of disodium telluride can be prepared from tellurium and sodium formaldehyde sulfoxylate (Rongalite C) in aqueous sodium hydroxide (Vol. IX, p. 1048), from tellurium and sodium in liquid ammonia dimethylformamide or tetrahydrofuran in the presence of naphthalene , from tellurium and hydrazine hydrate/sodium hydroxide in water or dimethylformamide °, from tellurium and thiourea dioxide in aqueous tetrahydrofuranor from tellurium and sodium borohydride in methanol, ethanol, tetrahydrofuran, or aqueous sodium hydroxide  [Pg.372]

The sodium borohydride method appears to be the most convenient and most widely applicable route to dialkyl telluriums. Sodium dithionite was also used to prepare disodium telluride, which subsequently was reacted with methyl, ethyl, propyl, and pentyl halides. Tellurium was also electrochemically reduced to the telluride anion in an ultrasonically aided reaction using tellurium powder in acetonitrile, and to the tetratelluride dianion with a tellurium rod as cathode and sodium perchlorate in dimethylformarnide as electrolyte . [Pg.372]

Diethyl TeUurium (Liquid Ammonia Method) An apparatus suitable for work with liquid ammonia is set up. 12.7 g (0.1 mol) of fine tellurium powder are suspended in liquid ammonia and then 4.6 g (0.2 mol) of sodium are added to the suspension. The mixture is stirred for 4 h. 10.9 g (0.1 mol) of ethyl bromide are added dropwise to the liquid ammonia, and the mixture is stirred for 30 min. The ammonia is evaporated. Water is added to the residue, the aqueous solution is extracted with diethyl ether, and the extract is dried with magnesium sulfate. The ether is evaporated and the residual liquid is distilled yield 7 g (38%) b.p. 138 . [Pg.372]

The limited solubility of long-chain alkyl halides in liquid ammonia makes it advantageous to evaporate the ammonia after the disodium telluride has formed and to dissolve the residue in an appropriate organic solvent. Ethanolic solutions of disodium telluride that had been prepared in liquid ammonia were used for the synthesis of the following heterocyclic tellurium compounds  [Pg.373]


NaOCHjCHa. White solid (Na in EtOH). Decomposed by water, gives ethers with alkyl halides reacts with esters. Used in organic syntheses particularly as a base to remove protons adjacent to carbonyl or sulphonyl groups to give resonance-stabilized anions. [Pg.364]

The sodio derivative, which is prepared by mixing alcoholic solutions of the ester and of sodium ethoxide, condenses with alkyl halides to yield mono-alkyl C-substituted products, for example ... [Pg.475]

Alkylation of Enolates (condensation of enolates with alkyl halides and epoxides) Comprehensive Organic Synthesis 1991, vol. 3, 1. [Pg.74]

The proton of terminal acetylenes is acidic (pKa= 25), thus they can be deprotonated to give acetylide anions which can undergo substitution reactions with alkyl halides, carbonyls, epoxides, etc. to give other acetylenes. [Pg.115]

The higher homologues of propyne, e.g. 1-decyne, can be obtained in a similar way. Starting from 1-butyne and its homologues, alkylation with alkyl halides leads to 1-alkynes with a branched substituent. [Pg.49]

A special problem arises in the preparation of secondary amines. These compounds are highly nucleophilic, and alkylation of an amine with alkyl halides cannot be expected to stop at any specifle stage. Secondary amides, however, can be monoalkylated and lydrolyzed or be reduced to secondary amines (p. 11 If.). In the elegant synthesis of phenyl- phrine an intermediate -hydroxy isocyanate (from a hydrazide and nitrous acid) cyclizes to pve an oxazolidinone which is monomethylated. Treatment with strong acid cleaves the cyclic irethan. [Pg.301]

The haloalkane dehydrogenase is believed to act by using one of its side chain carboxylates to dis place chloride by an Sn2 mechanism (Recall the reac tion of carboxylate ions with alkyl halides from Table 8 1 )... [Pg.339]

The large rate enhancements observed for bimolecular nucleophilic substitutions m polai aprotic solvents are used to advantage m synthetic applications An example can be seen m the preparation of alkyl cyanides (mtiiles) by the reaction of sodium cyanide with alkyl halides... [Pg.347]

The same cannot be said about reactions with alkyl halides as substrates The conver Sion of optically active 2 octanol to the corresponding halide does involve a bond to the chirality center and so the optical purity and absolute configuration of the alkyl halide need to be independently established... [Pg.353]

Alkylation of benzene with alkyl halides m the presence of aluminum chloride was discovered by Charles Friedel and James M Crafts m 1877 Crafts who later became president of the Massachusetts Institute of Technology collaborated with Friedel at the Sorbonne m Pans and together they developed what we now call the Friedel-Crafts reaction into one of the most useful synthetic methods m organic chemistry... [Pg.481]

The properties of organometallic compounds are much different from those of the other classes we have studied to this point Most important many organometallic com pounds are powerful sources of nucleophilic carbon something that makes them espe cially valuable to the synthetic organic chemist For example the preparation of alkynes by the reaction of sodium acetylide with alkyl halides (Section 9 6) depends on the presence of a negatively charged nucleophilic carbon m acetylide ion... [Pg.587]

Lithium dialkylcuprates react with alkyl halides to produce alkanes by carbon-carbon bond formation between the alkyl group of the alkyl halide and the alkyl group of the dialkylcuprate... [Pg.603]

The most frequently used organocuprates are those m which the alkyl group is pri mary Steric hindrance makes secondary and tertiary dialkylcuprates less reactive and they tend to decompose before they react with the alkyl halide The reaction of cuprate reagents with alkyl halides follows the usual 8 2 order CH3 > primary > secondary > tertiary and I > Br > Cl > F p Toluenesulfonates are somewhat more reactive than halides Because the alkyl halide and dialkylcuprate reagent should both be primary m order to produce satisfactory yields of coupled products the reaction is limited to the formation of RCH2—CH2R and RCH2—CH3 bonds m alkanes... [Pg.603]

Zinc reacts with alkyl halides m a manner similar to that of magnesium... [Pg.604]

Sulfur IS more nucleophilic than oxygen (Section 8 7) and sulfides react with alkyl halides much faster than do ethers The products of these reactions called sulfonium salts, are also more stable than the corresponding oxygen analogs... [Pg.686]

Section 16 17 Sulfides react with alkyl halides to give sulfonium salts... [Pg.695]

Because etiolate anions are sources of nucleophilic carbon one potential use m organic syn thesis IS their reaction with alkyl halides to give a alkyl denvahves of aldehydes and ketones... [Pg.781]

Treatment of the anion of diethyl malonate with alkyl halides leads to alkylation at C 2... [Pg.897]

Lithium dialkylamides are excellent bases for making ketone enolates as well Ketone enolates generated m this way can be alkylated with alkyl halides or as illus trated m the following equation treated with an aldehyde or a ketone... [Pg.904]

The reaction of amines with alkyl halides was seen earlier (Section 22 7) as a complicat ing factor in the preparation of amines by alkylation of ammonia... [Pg.937]

Reaction with Alkyl Halide. The active methylene group of an Al-acylamino-malonic acid ester or Ai-acylamino cyanoacetic acid ester condenses readily with primary alkyl hahdes. [Pg.277]

IV-Methylated pyridazinones can be obtained from 3,6-dialkoxypyridazines by treatment with alkyl halides or dialkyl sulfates. Methyl iodide and dimethyl sulfate are most frequently used. According to the proposed mechanism, an intermediate quaternary pyridazinium salt is formed, followed by elimination of a group R from the alkoxy group. At higher temperature, l,2-dimethylpyridazine-3,6(l//,2//)-dione is formed with dimethyl sulfate. [Pg.15]

Phthalazine forms monoquaternary salts with alkyl halides. 1-Substituted phthalazines are quaternized predominantly at position 3, and the site of quaternization of 1,4-disub-stituted phthalazines is determined by the steric hindrance of both substituents. [Pg.18]

Pyrroles do not react with alkyl halides in a simple fashion polyalkylated products are obtained from reaction with methyl iodide at elevated temperatures and also from the more reactive allyl and benzyl halides under milder conditions in the presence of weak bases. Alkylation of pyrrole Grignard reagents gives mainly 2-alkylated pyrroles whereas N-alkylated pyrroles are obtained by alkylation of pyrrole alkali-metal salts in ionizing solvents. [Pg.53]

The dianions derived from furan- and thiophene-carboxylic acids by deprotonation with LDA have been reacted with various electrophiles (Scheme 64). The oxygen dianions reacted efficiently with aldehydes and ketones but not so efficiently with alkyl halides or epoxides. The sulfur dianions reacted with allyl bromide, a reaction which failed in the case of the dianions derived from furancarboxylic acids, and are therefore judged to be the softer nucleophiles (81JCS(Pl)1125,80TL505l). [Pg.72]

Pyrrolethiols, readily obtained from the corresponding thiocyanates by reduction or treatment with alkali, rapidly oxidize to the corresponding disulfides. They are converted into thioethers by reaction with alkyl halides in the presence of base. Both furan- and thiophene-thiols exist predominantly as such rather than in tautomeric thione forms. [Pg.78]


See other pages where With alkyl halides is mentioned: [Pg.166]    [Pg.334]    [Pg.337]    [Pg.338]    [Pg.353]    [Pg.404]    [Pg.428]    [Pg.845]    [Pg.27]    [Pg.93]    [Pg.867]    [Pg.896]    [Pg.937]    [Pg.937]    [Pg.358]    [Pg.18]    [Pg.68]    [Pg.69]   
See also in sourсe #XX -- [ Pg.477 ]

See also in sourсe #XX -- [ Pg.552 , Pg.555 ]




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2.4- Diketones, alkylation at the 1position with alkyl halides

Acetoacetates reacting with alkyl halides

Acetylide anions reactions with alkyl halides

Active methylene compounds with alkyl halides

Alcohol conversion to alkyl halides with

Alcohols reaction with alkyl halides

Alkenes reaction with alkyl halides

Alkenes reductive coupling with alkyl halides

Alkoxide ions with alkyl halides

Alkyl and Acyl Halides with the Sodio-derivatives of Ethyl Cyanoacetate

Alkyl groups alcohol reactions with hydrogen halides

Alkyl halide malonic ester synthesis with

Alkyl halide reaction with Gilman reagents

Alkyl halide reaction with carboxylate ions

Alkyl halide reaction with phthalimide ion

Alkyl halide reaction with thiourea

Alkyl halide reaction with tributyltin hydride

Alkyl halide with pyrimidines

Alkyl halide, reduction with organotin

Alkyl halide, reduction with organotin hydride

Alkyl halides Compounds with halogen

Alkyl halides Compounds with halogen Table

Alkyl halides Compounds with halogen ammonia

Alkyl halides Compounds with halogen elimination reaction

Alkyl halides Compounds with halogen from alcohols

Alkyl halides Compounds with halogen nucleophilic

Alkyl halides alcohol reactions with hydrogen

Alkyl halides elimination with bases

Alkyl halides formation with phosphorus reagents

Alkyl halides reacting with

Alkyl halides reaction with acetylides

Alkyl halides reaction with water

Alkyl halides reactions with ambident

Alkyl halides reactions with organocopper reagents

Alkyl halides reactions with sulfur

Alkyl halides superacidic alkylation with

Alkyl halides synthetic reactions with

Alkyl halides treatment with alkoxide

Alkyl halides with (3-diketones

Alkyl halides with acetylide anions

Alkyl halides with alkali metals

Alkyl halides with alkynide ions

Alkyl halides with amines

Alkyl halides with ammonia

Alkyl halides with carbonyls

Alkyl halides with chlorine, reaction

Alkyl halides with coenzyme

Alkyl halides with cyanide

Alkyl halides with enamines

Alkyl halides with lithium

Alkyl halides with lithium dialkylcuprates

Alkyl halides with magnesium

Alkyl halides with metal cations

Alkyl halides with metal hydrides

Alkyl halides with nitrogen, reaction

Alkyl halides with organocopper reagents

Alkyl halides with organometallics

Alkyl halides with sodium azide

Alkyl halides with thiourea

Alkyl halides with transition metal reagents

Alkyl halides with triphenylphosphine

Alkyl halides with typical nucleophiles

Alkyl halides, from alcohols nitrile alkylation with

Alkyl halides, reaction with aluminum

Alkyl halides, reaction with indole Grignard

Alkyl halides, reaction with indole Grignard reagents

Alkyl halides, reactions with arene

Alkyl halides, reactions with arene Table

Alkyl halides, reactions with trimethylsilyl

Alkylation of Alkenes with Organic Halides

Alkylation of Pyrroles with Allyl Halides

Alkylation of Pyrroles with Propargyl Halides

Alkylation reactions phenols with alkyl halides

Alkylation with Alkyl Halides. Scope and Limitations

Alkylation with alkyl halides

Alkylation with alkyl halides

Alkylation with alkyl halides in organic solvents other than nitromethane

Alkylation with allylic halide

Alkylation with organic halides

Alkylation, mechanism with alkyl halides

Alkyne anions reaction with alkyl halides

Allylsilanes with alkyl halides

Ammonia reaction with alkyl halides

Antimony, reaction with alkyl halides

Aromatic hydrocarbons with alkyl halides

Azide ion reaction with alkyl halides

Benzene with alkyl halides

Benzylic reaction with alkyl halides

Butyrolactones, reactions with alkyl halide

By Reaction with Alkyl Halides

Carbocation alkyl halide reaction with Lewis

Catalytic asymmetric cross-coupling reactions with secondary alkyl halides

Conversion of Alcohols to Alkyl Halides with HX

Conversion of Alcohols to Alkyl Halides with SOCI2 and PBr

Copper reactions with alkyl halides

Copper with alkyl halides

Coupling of alkyl halides with organometallic compounds

Coupling with alkyl halides

Cross-coupling reactions alkyl halides with Grignard reagents

Cross-coupling reactions with alkyl halides

Cyanamide reaction with alkyl halides

Cyanides, metal, reaction with alkyl halides

Cyanocuprates, reactions with alkyl halides

Diastereoselective Alkylation of Glycine Schiff Base with Optically Enriched Alkyl Halides

Displacement with cyanide ion on an alkyl halide

Dithiane anions reaction with alkyl halides

Enolate anions reaction with alkyl halides

Enolate anions, dianions reaction with alkyl halides

Enolate anions, esters, reaction with alkyl halides

Enolates reaction with alkyl halide

Enolates with alkyl halides

Ethers reaction with alkyl halides

Ethers, vinyl with alkyl halides

Friedel Crafts alkylation with alkyl halides

Friedel-Crafts reaction with alkyl halides

Gilman cuprates, reactions with alkyl halides

Grignard reaction: alkylation with mercury halides

Grignard reagents coupling reactions with alkyl halides

Grignard reagents with alkyl halides

Grignard reagents, bonding coupling with alkyl halides

Grignard reagents, reaction with alkyl halides

Halide ions reaction with alkyl halides

Halides alkyl transfer with

Halides coupling reactions with primary alkyl Grignard

Halides palladium-catalyzed coupling with alkyl

Halides, alkyl coupling with Grignard reagents

Halides, alkyl coupling with organocuprates

Halides, alkyl diastereoselectivity with enolate

Halides, alkyl intramolecular reactions with

Halides, alkyl oxidation with DMSO

Halides, alkyl reaction with NaSH

Halides, alkyl reaction with acetoacetic ester anions

Halides, alkyl reaction with acid salts

Halides, alkyl reaction with alkoxides

Halides, alkyl reaction with alkynes

Halides, alkyl reaction with aluminum hydride reagents

Halides, alkyl reaction with amide anions

Halides, alkyl reaction with amines

Halides, alkyl reaction with aromatic compounds

Halides, alkyl reaction with carbanions

Halides, alkyl reaction with carboxylic acid salts

Halides, alkyl reaction with cyanohydrins

Halides, alkyl reaction with enamines

Halides, alkyl reaction with hexamethylenetetramine

Halides, alkyl reaction with hydrazone anions

Halides, alkyl reaction with hydrogen sulfide

Halides, alkyl reaction with hydroxide

Halides, alkyl reaction with ketone enolate anions

Halides, alkyl reaction with ketones

Halides, alkyl reaction with lithium

Halides, alkyl reaction with magnesium

Halides, alkyl reaction with malonate anions

Halides, alkyl reaction with metals

Halides, alkyl, reaction with Bu3SnH

Halides, alkyl, reaction with Lewis acids

Halides, alkyl, reaction with Subject

Halides, alkyl, reaction with acid dianions

Halides, alkyl, reaction with amino ester enolates

Halides, alkyl, reaction with amino-alcohols

Halides, alkyl, reaction with azide

Halides, alkyl, reaction with cuprates

Halides, alkyl, reaction with cyanide

Halides, alkyl, reaction with cyanoborohydride

Halides, alkyl, reaction with dimethyl sulfide

Halides, alkyl, reaction with ester dianions

Halides, alkyl, reaction with ester enolates

Halides, alkyl, reaction with ferrate

Halides, alkyl, reaction with imides

Halides, alkyl, reaction with lactone enolates

Halides, alkyl, reaction with malonate enolates

Halides, alkyl, reaction with nitrile enolates

Halides, alkyl, reaction with nitro compounds

Halides, alkyl, reaction with organocuprates

Halides, alkyl, reaction with organolithium reagents

Halides, alkyl, reaction with phthalimide

Halides, alkyl, reaction with succinimide

Halides, alkyl, reaction with sulfides

Heck alkyl halides with styrenes

Heck-type Reaction of Alkyl Halides with Styrenes

Hydroxide, potassium reaction with alkyl halides

Hydroxy halides, alkylation reaction, with alkali

Indole Grignard reagents with alkyl halides

Internal alkynes with alkyl halides

Iodide, potassium reaction rates with alkyl halides

Iodide, sodium reaction with alkyl halides

Iron, reaction with alkyl halides

Lactams, alkylation with alkyl halides

LiAlH4, reaction with alkyl halides

Lithium dialkylcopper with alkyl halides

Lithium, vinylalkylation reaction with alkyl halides

Magnesium reaction of with alkyl and aryl halide

Magnesium reaction with alkyl halides, mechanism

Magnesium, reaction with alkyl halides form Grignard reagents

Mechanism, radical with alkyl halides

Mechanisms alkyl halides with alkoxides

Metal phosphites reaction with alkyl halides

Metals, activated reactivity with alkyl halides

Metals, activated with alkyl halides

Nickel with alkyl halides

Nitrite, sodium reaction with alkyl halides

Organocopper compounds, reactions with alkyl halides

Organocuprates, addition with alkyl halides

Organolithium reagents coupling with alkyl halides

Organolithium with alkyl halides

Organometallic compound, coupling with alkyl halide

Organometallic compounds reaction with alkyl halides

Organometallic compounds with alkyl halides

Organozinc reagents cross-coupling reactions with alkyl halides

Oxazine anions, reaction with alkyl halides

Oxazine anions, reaction with alkyl halides alkylation

Palladium, phenylbis catalysis arylmagnesium halide reaction with alkyl halides

Phosphines reaction with alkyl halides

Phosphines reaction with alkyl halides, kinetics

Phosphines with alkyl halides

Phosphines, alkylation with alkyl halides

Phosphoramidic acid, N- diethyl ester reaction with alkyl halides

Phosphorane, iminovinylidenetriphenylphosphonium ylide synthesis reactions with alkyl halides

Phosphorane, oxovinylidenetriphenylreactions with alkyl halides

Phosphorane, oxovinylidenetriphenylreactions with alkyl halides cycloaddition

Phosphorane, oxovinylidenetriphenylreactions with alkyl halides synthesis

Phosphorus, reaction with alkyl halides

Primary alkyl coupling reactions with alkenyl halides

Primary alkyl coupling reactions with aromatic halides

Primary alkyl reactions with alkenyl halides

Primary conversion to alkyl halides with

REDUCTION OF ALKYL HALIDES AND TOSYLATES WITH SODIUM CYANOBOROHYDRIDE

Radical mechanism, addition with alkyl halides

Radicals, coupling reactions with alkyl halides

Reaction of Alkyl, Alkenyl, and Aryl Halides with Metals

Reaction of Amines with Alkyl Halides

Reaction of Lithiated Bis(methylthio)methane with Alkyl Halides

Reaction of alkyl halides with sulfites and sulfinic acids

Reaction of stabilized carbanions (enolates) with alkyl halides (enolate alkylation)

Reaction with Alkyl and Aryl Halides

Reaction with alkyl halides

Reaction with alkyl halides to form

Reactions with Simple Alkyl Halides

Reactions with activated alkyl halides

Reactivity, alkyl halides with

Reactivity, alkyl halides with aromatic compounds

Reactivity, alkyl halides with dioxide

Reactivity, alkyl halides with ethanol

Reactivity, alkyl halides with reactions

Reactivity, alkyl halides with solvent polarity

Reactivity, alkyl halides with variation

Secondary alcohols conversion to alkyl halides with

Secondary alkyl halides acetylide anion reactions with

Secondary conversion to alkyl halides with

Silane, a-phenylthiomethyltrimethylreaction with alkyl halides

Silane, a-phenylthiomethyltrimethylreaction with alkyl halides synthesis of aldehydes

Silver cyanide, reaction with alkyl halides in synthesis of isocyanides

Silver nitrate, reaction with alkyl halides

Silver nitrite, with alkyl halides

Silver reaction with alkyl halides

Sodium acetylide reaction with, alkyl halides

Sodium cyanate with alkyl halides

Sodium nitrite, with alkyl halides

Sodium reaction with alkyl halides

Sodium sulfide, reaction with alkyl halides

Solvolysis rates with alkyl halides

Stabilized carbanions with alkyl halides

Sulfones anions, reaction with alkyl halides

Sulfonic acid salts, alkylation with aryl halides

Superoxide, potassium, with alkyl halides

Terminal alkynes with alkyl halides

Tertiary alkyl coupling reactions with alkenyl halides

Tertiary halides, alkylation with

Tetracarbonylferrate reaction with alkyl halides

The Reaction with Alkyl Halides

Thiocyanates reaction with alkyl halides

Thioethers reaction with alkyl halides

Thioethers with alkyl halides

Thiol reaction with alkyl halides

Thiolate ions reaction with alkyl halides

Thiols reaction with alkyl halides

Thioureas reaction with alkyl halides

Triphenylphosphine reaction with alkyl halides

Tris silane with alkyl halide

With Simple Alkyl Halides

Zinc reagents cross-coupling with alkyl halides

Zinc, reaction with alkyl halides

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