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Transfer of an alkyl group from one molecule to another
Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical,
Alkylation
Component of a petroleum refinery
An alkylation unit (alky) is one of the conversion processes used in petroleum refineries. It is used to convert isobutane and low-molecular-weight alkenes
Alkylation_unit
Set of reactions to attach substituents to an aromatic ring
to an aromatic ring. Friedel–Crafts reactions are of two main types: alkylation reactions and acylation reactions. Both proceed by electrophilic aromatic
Friedel–Crafts_reaction
the Fráter–Seebach alkylation (also known as Seebach–Fráter alkylation or Fráter–Seebach reaction) is a diastereoselective alkylation of chiral beta-hydroxy
Fráter–Seebach_alkylation
Organic reaction between amine and alkyl halide
Amine alkylation (amino-dehalogenation) is a type of organic reaction between an alkyl halide and ammonia or an amine. The reaction is called nucleophilic
Amine_alkylation
Stereogenic group placed on a molecule to encourage stereoselectivity in reactions
selectively furnishes the (Z)-enolate, which can undergo stereoselective alkylation. Alkylation of an oxazolidinone imide with benzyl bromide Activated electrophiles
Chiral_auxiliary
Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R')
In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part
Ether
Chemical reaction
The Enders SAMP/RAMP hydrazone alkylation reaction is an asymmetric carbon-carbon bond formation reaction facilitated by pyrrolidine chiral auxiliaries
Enders SAMP/RAMP hydrazone-alkylation reaction
Enders_SAMP/RAMP_hydrazone-alkylation_reaction
Reaction sequence in organic chemistry
The Stork enamine alkylation involves the addition of an enamine to a Michael acceptor (e.g., an α,β -unsaturated carbonyl compound) or other electrophile
Stork_enamine_alkylation
Organic reaction used to convert arenes to cyclohexadienes
salts are necessary to colocate the reactants via complexation. In Birch alkylation the anion formed in the Birch reduction is trapped by a suitable electrophile
Birch_reduction
Palladium-catalysed substitution reaction
The Tsuji–Trost reaction (also called the Trost allylic alkylation or allylic alkylation) is a palladium-catalysed substitution reaction involving a substrate
Tsuji–Trost_reaction
Industrial process
well as the phenol. Cumene is formed in the gas-phase Friedel–Crafts alkylation of benzene by propene. Benzene and propene are compressed together to
Cumene_process
Chemical compound
group is also known as benzhydryl. It is prepared by the Friedel–Crafts alkylation of benzyl chloride with benzene in the presence of a Lewis acid such as
Diphenylmethane
Tar distillation byproduct used as wood preservative
effects. This diagram shows an o-alkylation between phenol and methanol. Unlike the c-alkylation, the o-alkylation replaces the hydrogen atom on the
Creosote
Any chemical reaction with ammonia as a reactant
"Haloalkanes and ammonia". www.chemguide.co.uk. Ashenhurst, James (2017-05-26). "Alkylation of Amines". Master Organic Chemistry. Werner, Emil Alphonse (1918-01-01)
Ammonolysis
Protein-coding gene in the species Homo sapiens
that excises alkylation-damaged purine bases in human cells. DNA bases are subject to a large number of anomalies: spontaneous alkylation or oxidative
DNA-3-methyladenine glycosylase
DNA-3-methyladenine_glycosylase
Hydrofluoric acid spill and industrial fire
Pennsylvania. A release of hydrocarbons and hydrofluoric acid in the refinery's alkylation unit caused a ground-hugging vapor cloud which rapidly ignited, leading
2019 Philadelphia refinery explosion
2019_Philadelphia_refinery_explosion
Salt, anion or ester of a sulfonic acid
H2O Classically, alkylsulfonates can prepared by the Strecker sulfite alkylation, in which sulfite displaces a halide: RBr + Na2SO3 → RSO3Na + NaBr Arylsulfonates
Sulfonate
which is synthesized by syn-selective carbocupration of acetylene and alkylation of the resulting organocuprate in the presence of added phosphite. (15)
Reactions of organocopper reagents
Reactions_of_organocopper_reagents
Type of a chemical reaction
A salt metathesis reaction (also called a double displacement reaction, double replacement reaction, or double decomposition) is a type of chemical reaction
Salt_metathesis_reaction
Class of chemical compounds
aldehyde counterparts. Compared to their enolate counterparts, their alkylations often proceed with fewer side reactions. Cyclic ketone enamines follow
Enamine
Chemical compound
Friedel-Crafts alkylation and related reactions. AlCl3 is a common Lewis-acid catalyst for Friedel-Crafts reactions, both acylations and alkylations. These types
Aluminium_chloride
Facility that processes crude oil
the acid used, the unit is called a sulfuric acid alkylation unit (SAAU) or hydrofluoric acid alkylation unit (HFAU). In short, the alky produces a high-quality
Oil_refinery
Chemical compound
alkylation agents, such as iodoacetamide, acrylamide, and N-ethylmaleimide, 4-VP is less reactive, meaning the completion rate of cysteine alkylation
4-Vinylpyridine
Class of chemical compounds
methodology can be useful in the preparation of unusual Wittig reagents. Alkylation of Ph3P=CH2 with a primary alkyl halide R−CH2−X, produces substituted
Wittig_reagents
Chemical compounds and groups containing nitrogen with a lone pair (:N)
effects. Industrially significant alkyl amines are prepared from ammonia by alkylation with alcohols: ROH + NH 3 ⟶ RNH 2 + H 2 O {\displaystyle {\ce {ROH + NH3
Amine
Chemical compound
DIPEA is commercially available. It is traditionally prepared by the alkylation of diisopropylamine with diethyl sulfate. Pure DIPEA exists as a colorless
N,N-Diisopropylethylamine
Chemical compound
thiophenolate is highly nucleophilic, which translates to a high rate of alkylation. Thus, treatment of C6H5SH with methyl iodide in the presence of a base
Thiophenol
Organic compound
cumene is by Friedel–Crafts alkylation of benzene with propylene. The original route for manufacturing of cumene was by alkylation of benzene in the liquid
Cumene
Chemical compound
acetylpiperazine. The acetyl group is cleaved with diluted sulfuric acid. An N-alkylation of the piperazine ring with 3-methylbenzylchloride completes the synthesis
Meclizine
Chemical compound
(p-) position of phenol. The compound, a white solid, is produced by the alkylation of phenol with propylene and is relevant to the production of the commodity
4-Isopropylphenol
Chemical reaction which attaches an electrophile to an aromatic ring
nitration, aromatic halogenation, aromatic sulfonation, and Friedel-Crafts alkylation and acylation. The most widely practised example of this reaction is the
Electrophilic aromatic substitution
Electrophilic_aromatic_substitution
Chemical compound
excellent yields of α-alkylated (Z)-oximes. α,α-Dialkylation by further alkylation in similar way has been achieved. It is generally known that ketone oximes
Acetaldoxime
Organic compound (C6H5NH2); simplest aromatic amine
aniline. The largest scale industrial reaction of aniline involves its alkylation with formaldehyde. An idealized equation is shown: 2 C6H5NH2 + CH2O →
Aniline
Chemical compound
Chloro(pyridine)cobaloxime is a coordination compound containing a CoIII center with octahedral coordination. It has been considered as a model compound
Chloro(pyridine)cobaloxime
halides. The primary difficulty for alkylation reactions employing nitrile anions is over-alkylation. In the alkylation of acetonitrile, for instance, yields
Nitrile_anion
Chemical compound
scale in the petroleum industry by alkylation of isobutene with isobutane. This process is conducted in alkylation units in the presence of acid catalysts
2,2,4-Trimethylpentane
Any molecule with a cyano group (C≡N)
In chemistry, a cyanide (from Greek kyanos 'dark blue') is an inorganic chemical compound that contains a C≡N functional group. This group, known as the
Cyanide
Chemical compound
1951 and came into medical use in 1960. Carbocisteine is produced by the alkylation of cysteine with chloroacetic acid. Acetylcysteine Carbocisteine. drugbank
Carbocisteine
Series of chemical reactions
undergoes the actual alkylation reaction. Conversion of the primary amine to an imine (Schiff base) using an aldehyde. Alkylation of the imine using an
Forster–Decker_method
Russian oil company
refining, hydrotreatment, reforming and iso-reforming, sulphuric acid alkylation, thermocracking and visbreaking, coking and gas fractionation, solvent
Bashneft-Novoil
Method for the synthesis of primary amines
include the alkylation of sulfonamides and imides, followed by deprotection, to obtain amines (see Alternative Gabriel reagents). The alkylation of ammonia
Gabriel_synthesis
Chemical compound
HOC6H5 → Al(OC6H5)3 + 1.5 H2 The compound is used as a catalyst for the alkylation of phenols with various alkenes. For example, the ethylphenols are generated
Aluminium_phenolate
Hydrocarbon compound containing one or more C≡C bonds
methylacetylene (propyne using IUPAC nomenclature). They are often prepared by alkylation of monosodium acetylide. Terminal alkynes, like acetylene itself, are
Alkyne
Hydrocarbon compound (H2C=CH2)
polymerization, 2) oxidation, 3) halogenation and hydrohalogenation, 4) alkylation, 5) hydration, 6) oligomerization, and 7) hydroformylation. In the United
Ethylene
Organometallic compounds used in organic synthesis
reaction schemes. The most common application of Grignard reagents is the alkylation of aldehydes and ketones, i.e. the Grignard reaction: Note that the acetal
Grignard_reagent
Chemical process
introducing olefin metathesis, alkylation, C–H arylation, C–C, C–S, and C–N cross-coupling reactions. Rh-catalyzed Trp and Cys alkylation Using in situ generated
Bioconjugation
Reaction in organic chemistry
persulfate to form 2-tert-butylpyridine. The reaction resembles Friedel-Crafts alkylation but with opposite reactivity and selectivity. The Minisci reaction often
Minisci_reaction
Chemical compound
Markovnikov's student Nikolay Kirsanov (1874–1921). He used a Friedel–Crafts alkylation of benzene with cyclohexyl chloride using a catalyst such as aluminum
Cyclohexylbenzene
Chemical compounds in which hydroxyl group is attached directly to an aromatic ring
elaboration of phenol or cresols. They are typically produced by the alkylation of benzene/toluene with propylene to form cumene then O 2 is added with
Phenols
Sterically hindered organic base
bases are bulky, such that protons can attach to the basic center but alkylation and complexation is inhibited. A variety of amines and nitrogen heterocycles
Non-nucleophilic_base
Chemical compound
derivatization of Meldrum's acid at this position, through reactions such as alkylation and acylation. For example, deprotonation and reaction with a simple alkyl
Meldrum's_acid
Chemical reaction
Perhaps the single most important reaction of enolate ions is their alkylation by treatment with an alkyl halide or tosylate, thereby forming a new C-C
Carbonyl α-substitution reaction
Carbonyl_α-substitution_reaction
Chemical compound
are typically prepared by one of three methods: amide bond formation, N-alkylation and C-acylation. Most commonly 2,5-diketopiperazines are generated by
2,5-Diketopiperazine
Type of chemical reaction
acetic acid. A major drawback of malonic ester synthesis is that the alkylation stage can also produce dialkylated structures. This makes separation of
Malonic_ester_synthesis
Aromatic organochlorine compound
such as the benzalkonium chlorides used as surfactants, are produced by alkylation of tertiary amines with benzyl chloride. Benzyl chloride is more electrophilic
Benzyl_chloride
Chemical compound
tumors. It is thought that acylfulvene compounds kill cancer cells by DNA alkylation (see DNA methylation). Anchel, M.; Hervey, A.; Robbins, W. J. Proc. Natl
Acylfulvene
Chemical compound
general scheme for phosphetane synthesis from dienes is given below: Alkylation and cyclization pathways have been developed for both phosphines and phosphine
Phosphetane
Chemical compound
exhibits reactions typical of other simple alkyl amines, i.e. protonation, alkylation, acylation, condensation with carbonyls. Like other simple aliphatic amines
Pentylamine
Chemical process in which a methyl (CH3) group is covalently attached to a molecule
substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These terms are commonly
Methylation
Sulfur-containing aromatic compound
seen for conventional sulfides. For example, the sulfur atom resists alkylation and oxidation. Oxidation can occur both at sulfur, giving a thiophene
Thiophene
Reaction in organic chemistry
reaction is a three-component organic reaction that involves the amino alkylation of the α-position of a ketone or aldehyde with an aldehyde and a nullary
Mannich_reaction
Protein in E. coli
AlkB (Alkylation B) is a protein found in E. coli, induced during an adaptive response and involved in the direct reversal of alkylation damage. AlkB specifically
AlkB
Isomer/derivative of butane
isomerization of butane.[citation needed] Isobutane is the principal feedstock in alkylation units of refineries. Using isobutane, gasoline-grade "blendstocks" are
Isobutane
Chemical compound
v t e Grignard reaction Basic principles Alkylation Carbanion Cram's rule Nucleophilic addition Single electron transfer Grignard reagents CH3MgCl C2H5MgBr
N-Propylmagnesium_bromide
Chemical compound
is a ligand in coordination chemistry. The ligand is prepared by the alkylation of 2-picolylamine by picolyl chloride: 2 C5H4NCH2Cl + C5H4NCH2NH2 → (C5H4NCH2)3N
Tris(2-pyridylmethyl)amine
Chemical compound
nucleophile. In 2008, simultaneous publications described the allylic C-H alkylation of allylarene substrates. These reactions were catalyzed by the White
White_catalyst
Compound with carbon to copper bonds
provided by a hydrosilane. Generally, the alkylation reaction of organocopper reagents proceed via gamma- alkylation. Cis- gamma attack occurs better in cyclohexyl
Organocopper_chemistry
Chemical compound
is produced in large quantities in oil refineries. It results from the alkylation of isobutane by propylene. Often referred to as "alkylate", it is blended
2,4-Dimethylpentane
Compound derived from an acid
2 H2O Silicotungstic acid is used to manufacture ethyl acetate by the alkylation of acetic acid by ethylene: H2C=CH2 + CH3CO2H → CH3CO2CH2CH3 The Tishchenko
Ester
Chemical compound
industry. Silicotungstic acid is used to manufacture ethyl acetate by the alkylation of acetic acid by ethylene: C2H4 + CH3CO2H → CH3CO2C2H5 It's also been
Silicotungstic_acid
Organomercury chemical compound
halides: Hg + 2 Na + 2 CH3I → Hg(CH3)2 + 2 NaI It can also be obtained by alkylation of mercuric chloride with methyllithium: HgCl2 + 2 LiCH3 → Hg(CH3)2 +
Dimethylmercury
Organic chemist
work on enamine chemistry, leading to development of the Stork enamine alkylation. It is believed he was responsible for the first planned stereocontrolled
Gilbert_Stork
American chemist
was an American chemist, mostly known for developing the Friedel–Crafts alkylation and acylation reactions with Charles Friedel in 1876. A research chemist
James_Crafts
Sustainable fuel used to power aircraft
(company), TotalEnergies SPK/A Synthesized kerosene with aromatics derived by alkylation of light aromatics from non-petroleum sources Coal, Natural Gas, Biomass
Aviation_biofuel
Chemical compound
protected form of ammonia in the synthesis of primary amines. After N-alkylation, C6H5CH2OC(O) group is removable with Lewis acids. Meyer, Hartmut; Beck
Benzyl_carbamate
Antifungal medication
corresponding alcohol (4). Alkylation of the alkoxide from that alcohol with p-chlorobenzyl chloride leads to econazole (5); alkylation with o,p-dichlorobenzyl
Econazole
Class of organometallic compounds
6-5-6 A/B/C ring system was constructed using a tandem rhodium-catalyzed alkylation/cycloisomerization. The mechanism of this cascade sequence, starts with
Transition metal vinylidene complex
Transition_metal_vinylidene_complex
Chemical compound
undergoes O-alkylation to give mono- and diethers. Similarly, hydroquinone is highly susceptible to ring substitution via Friedel–Crafts alkylation. This reaction
Hydroquinone
Any salt of an organic base and hydrochloric acid
Gleason, James L. (1999). "Asymmetric Synthesis of α-Amino Acids by the Alkylation of Pseudoephedrine Glycinamide: L-Allylglycine and N-BOC-l-Allylglycine"
Hydrochloride
Brand name for a chemical product
organic synthesis. Studies have demonstrated catalytic properties in alkylation, isomerization, oligomerization, acylation, ketalization, esterification
Nafion
Discontinued steroid for heart treatment
tablet form. The drug has a high oral bioavailability, due to a C17α alkylation which allows the hormone to survive first-pass liver metabolism when ingested
Stanozolol
Large Industrial Site in Sarnia Canada
Hydrotreating 5,975 ULSD Hydrotreating 43,588 Other Hydrotreating 6,743 Alkylation 5,503 Aromatics Extraction 13,209 Hydrogen Production in mmscf/d 41
Suncor_Sarnia_Refinery
Chemical compound
Its main uses are in the production of high-octane gasoline (petrol) on alkylation units and butadiene, although some 2-butene is also used to produce the
2-Butene
Hydrocarbon compound with the formula C8H18
particular boiling fractions. A common route to such fractions is the alkylation reaction between iso-butane and 1-butene, which forms iso-octane. Octane
Octane
Chemical compound
v t e Grignard reaction Basic principles Alkylation Carbanion Cram's rule Nucleophilic addition Single electron transfer Grignard reagents CH3MgCl C2H5MgBr
Ethylmagnesium_bromide
Chemical compound
its high octane rating (112–113 RON, 101 MON) triptane was produced on alkylation units starting from 1943 for use as an anti-knock additive in gasoline
Triptane
Gas desulfurization process
sour water stripper (SWS) gas Off-gas from Rectisol Spent acid from an alkylation unit Claus process tail gas Heavy residue or petcoke-fired utility boiler
Wet_sulfuric_acid_process
Oil refinery in Essex, England
started on an extension to the refinery including a hydrogen fluoride alkylation unit to produce more gasoline. In 1978, about 1.5 million tonnes of oil
Coryton_Refinery
Organic compound with at least one covalent carbon–phosphorus bond
dialkylthiophosphinate ester. Phosphorus selenides are susceptible to further alkylation on the selenium atom. Compounds with the formula [PR4+]X− comprise the
Organophosphorus_chemistry
Conversion of a carbonyl to an amine
Reductive amination (also known as reductive alkylation) is a form of amination that converts a carbonyl group to an amine via an intermediate imine. The
Reductive_amination
Canadian diesel refinery
000 barrels per day (2,900 m3/d) No. of employees 230 Refining units alkylation, isomerisation, distillation of crude oil, hydrocracking, reforming catalytic
Come_By_Chance_Refinery
Chemical reaction
charged organic residue R attacking the aniline ring in a Friedel–Crafts alkylation. In one study this rearrangement was applied to a 3-N(CH3)(C6H5)-2-oxindole:
Hofmann–Martius_rearrangement
Chemical reaction
lithiated 1,3-dithianes serves as an acyl anion equivalent, undergoing alkylation with electrophiles. The reaction is named in honor of its discoverers
Corey–Seebach_reaction
Oil refinery in Quebec, Canada
fluid cat cracking and hydrocracking units for gasoil conversion. The alkylation unit plus a high ratio of naphtha reforming relative to total crude capacity
Montreal_Refinery
Chemical compound
compound with the formula C2H4S2CS. This yellow solid is prepared by alkylation of trithiocarbonate with 1,2-dibromoethane. Ethylene trithiocarbonate
Ethylene_trithiocarbonate
Family of sugars with a six-carbon ring
Elimination reaction Nucleophilic substitution of carbonyl group Friedel-Crafts alkylation Nucleophilic conjugate addition Transesterification Category
Cyclohexane-1,2,3,4,5,6-hexol
Chemical compound
diphosphine used in the palladium-catalyzed Trost asymmetric allylic alkylation. Other C2-symmetric ligands derived from trans-1,2-diaminocyclohexane
Trost_ligand
Chemical compound
for medical use in 1983. It is a thermosalient material. Two successive alkylation reactions convert a natural product, norscopolamine (1), into oxitropium
Oxitropium_bromide
Antiemetic and antivertigo drug
synthesized, but they have not yet been the subject of clinical trials. Alkylation of 1-Bromo-3-chloropropane [109-70-6] (1) with piperidine (2) gives 3-Piperidinopropyl
Diphenidol
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