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searching for Carbanion 87 found (185 total)

alternate case: carbanion

Orotidine 5'-phosphate decarboxylase (1,182 words) [view diff] exact match in snippet view article find links to article

Current consensus suggests that the mechanism proceeds through a stabilized carbanion at the C6 after loss of carbon dioxide. This mechanism was suggested from

Organomercury chemistry (1,125 words) [view diff] no match in snippet view article find links to article

Organomercury chemistry refers to the study of organometallic compounds that contain mercury. Typically the Hg–C bond is stable toward air and moisture

Corey–Winter olefin synthesis (376 words) [view diff] exact match in snippet view article find links to article

the carbanion by a second molecule of trimethylphosphite with concomitant cleavage of the sulfur-carbon bond. The phosphorus stabilized carbanion then

Ethynyl group (126 words) [view diff] exact match in snippet view article find links to article

interstellar medium, and transiently on earth during chemical reactions. Ethynyl carbanion acetylide (HC≡C−) Ethynylation Propynyl ( H3C–C≡C–R, 1-propynyl group;

Krapcho decarboxylation (792 words) [view diff] exact match in snippet view article find links to article

by decarboxylation, followed by hydrolysis of the resulting stabilized carbanion. ZCH2CO2CH3 + I− + H2O → ZCH3 + CH3I + CO2 + OH− The reaction is carried

Mannich base (223 words) [view diff] exact match in snippet view article find links to article

resonance stabilized imine (iminium ion or imine salt). The addition of a carbanion from a CH acidic compound (any enolizable carbonyl compound, amide, carbamate

Corey–House synthesis (1,517 words) [view diff] exact match in snippet view article find links to article

byproducts. Li+[R–Cu–R]− + R′–X → R–R′ + "R–Cu" + LiX In principle, a carbanion equivalent such as an organolithium or Grignard reagent can react directly

Metal–halogen exchange (1,200 words) [view diff] exact match in snippet view article find links to article

the rate of exchange is primarily influenced by the stabilities of the carbanion intermediates (sp > sp2 > sp3) of the organolithium reagents. Two mechanisms

Peterson olefination (727 words) [view diff] exact match in snippet view article find links to article

(also called the Peterson reaction) is the chemical reaction of α-silyl carbanions (1 in diagram below) with ketones (or aldehydes) to form a β-hydroxysilane

Darzens reaction (717 words) [view diff] exact match in snippet view article find links to article

at the halogenated position. Because of the ester substituents, this carbanion is a resonance-stabilized enolate. This nucleophile next attacks the carbonyl

Irina Beletskaya (1,039 words) [view diff] exact match in snippet view article find links to article

known for her studies on aromatic reaction mechanisms, as well as work on carbanion acidity and reactivity. She developed some of the first methods for carbon-carbon

Enolase (3,252 words) [view diff] exact match in snippet view article find links to article

2-PG to PEP is proposed to be an E1cB elimination reaction involving a carbanion intermediate. The following detailed mechanism is based on studies of

Adamantanone (188 words) [view diff] exact match in snippet view article find links to article

reluctant to form enolates. This barrier arises because the resulting carbanion cannot exist in conjugation with the carbonyl pi-bond. Geluk, H. W.; Keizer

Transition metal pincer complex (1,768 words) [view diff] exact match in snippet view article find links to article

examples of pincer ligands (not called such originally) were anionic with a carbanion as the central donor site and flanking phosphine donors; these compounds

Epoxide (2,319 words) [view diff] exact match in snippet view article find links to article

performs a nucleophilic conjugate addition to give a stabilized carbanion. This carbanion then attacks the same oxygen atom, displacing a leaving group

Epoxide (2,319 words) [view diff] exact match in snippet view article find links to article

performs a nucleophilic conjugate addition to give a stabilized carbanion. This carbanion then attacks the same oxygen atom, displacing a leaving group

Electrophilic amination (2,074 words) [view diff] exact match in snippet view article find links to article

formation of a carbon–nitrogen bond through the reaction of a nucleophilic carbanion with an electrophilic source of nitrogen. Electrophilic amination reactions

Alanine racemase (1,382 words) [view diff] exact match in snippet view article find links to article

racemase reaction is that of a two-base mechanism with a PLP-stabilized carbanion intermediate. PLP is used as an electron sink stabilize the negative charge

Organolithium reagent (5,971 words) [view diff] exact match in snippet view article find links to article

In aryllithium complexes, the lithium cation coordinates to a single carbanion center through a Li−C σ type bond. Like other species consisting of polar

W. Clark Still (2,031 words) [view diff] exact match in snippet view article find links to article

of this reaction is the difficulty in forming the alkoxy-substituted carbanion which initiates the 2,3-sigmatropic rearrangement. Traditionally, this

Möbius–Hückel concept (1,651 words) [view diff] exact match in snippet view article find links to article

the first organic correlation diagrams were in a 1961 publication on carbanion rearrangements. It had been noted that when an occupied molecular orbital

Malonic ester synthesis (315 words) [view diff] exact match in snippet view article find links to article

carbons alpha to carbonyl groups can be deprotonated by a strong base. The carbanion formed can undergo nucleophilic substitution on the alkyl halide, to give

Methitural (163 words) [view diff] exact match in snippet view article find links to article

somewhat more complex side chain is incorporated by alkylation of the carbanion of the substituted cyanoacetate (1) with 2-chloroethylmethyl sulfide (2)

Reimer–Tiemann reaction (796 words) [view diff] exact match in snippet view article find links to article

deprotonated by a strong base (normally hydroxide) to form the chloroform carbanion (2) which will quickly alpha-eliminate to give dichlorocarbene (3); this

Seyferth–Gilbert homologation (529 words) [view diff] exact match in snippet view article find links to article

2-migration forms the desired alkyne H. The dimethyl (diazomethyl)phosphonate carbanion can be generated in situ from dimethyl-1-diazo-2-oxopropylphosphonate

Decarboxylation (1,200 words) [view diff] exact match in snippet view article find links to article

distillation. Overall, decarboxylation depends upon stability of the carbanion synthon R− , although the anion may not be a true chemical intermediate

Ronald Breslow (2,040 words) [view diff] exact match in snippet view article find links to article

bond, and one p orbital for the π framework. It had been suggested that carbanion-sulfone double bonds will not show aromatic character-primarily as a result

Barbituric acid (1,142 words) [view diff] exact match in snippet view article find links to article

with pKa 8.95) because of the additional aromatic stabilization of the carbanion. Using the Knoevenagel condensation reaction, barbituric acid can form

SCH-5472 (194 words) [view diff] exact match in snippet view article find links to article

reaction of potassium metal with liquid ammonia. The coupling between the carbanion created from diphenylmethane [101-81-5] (1) and ethyl 2-furoate [614-99-3]

Hydrazone (1,169 words) [view diff] exact match in snippet view article find links to article

2024 (link) Wang, H; Dai, X.-J.; Li, C.-J. (2017). "Aldehydes as alkyl carbanion equivalents for additions to carbonyl compounds". Nature Chemistry. 9

Glycolysis (8,782 words) [view diff] exact match in snippet view article find links to article

associate with the alcohol group. The resulting carbanion is stabilized by the structure of the carbanion itself via resonance charge distribution and by

Julia olefination (1,302 words) [view diff] exact match in snippet view article find links to article

olefination.[5] The reaction involves the addition of a sulfonyl-stabilized carbanion to a carbonyl compound, followed by elimination to form an alkene. In

Uridine monophosphate synthase (3,560 words) [view diff] exact match in snippet view article find links to article

going through a carbanion state has been proposed. Finally, catalysis might take place by simple electrostatic attraction. C6 carbanion formation would

Wittig reagents (714 words) [view diff] exact match in snippet view article find links to article

Treatment of Me3PCH2 with butyl lithium affords Me2P(CH2)2Li. Having carbanion-like properties, lithiated ylides function as ligands. Thus Me2P(CH2)2Li

Fumarase (1,474 words) [view diff] exact match in snippet view article find links to article

Figure 1: Conversion of fumarate to S-malate by fumarase through a carbanion intermediate.

Paul G. Gassman (670 words) [view diff] exact match in snippet view article find links to article

cyclo-addition reactions, enzyme mechanisms, organoelectro-chemistry, carbanion chemistry, synthesis of heterocyclic molecules, oxidation of hydrocarbons

Methylmagnesium chloride (302 words) [view diff] exact match in snippet view article find links to article

center. Like methyllithium, it is the synthetic equivalent to the methyl carbanion synthon. It reacts with water and other protic reagents to give methane

Cyclononatetraene (485 words) [view diff] exact match in snippet view article find links to article

ISBN 0521215803. OCLC 3033135. Cram, Donald J. (1965). Fundamentals of Carbanion Chemistry. Burlington: Elsevier Science. ISBN 9780323162449. OCLC 843200178

Chao-Jun Li (1,308 words) [view diff] exact match in snippet view article find links to article

Hydrazones as organo-metallic equivalent (HOME Chemistry): Carbonyls as alkyl carbanion equivalents for 1,2-nucleophilic additions, conjugate additions, and cross-couplings

Transition-metal allyl complex (1,344 words) [view diff] exact match in snippet view article find links to article

allylmagnesium bromide or related allyl lithium reagent. However, the carbanion salt precursors require careful synthesis, as allyl halides readily undergo

Ethane-1,2-dithiol (277 words) [view diff] exact match in snippet view article find links to article

aldehydes is that the methyne group can be deprotonated and the resulting carbanion alkylated. 1,2-Ethanedithiol is commonly used as a scavenger in peptide

Ethyl acetoacetate (506 words) [view diff] exact match in snippet view article find links to article

since the protons alpha to carbonyl groups are acidic, and the resulting carbanion undergoes nucleophilic substitution. Ethyl acetoacetate is often used

Donald J. Cram (1,320 words) [view diff] exact match in snippet view article find links to article

McGraw-Hill. pp. 444pp. LCCN 66024479. Cram, Donald J. (1965). Fundamentals of Carbanion Chemistry. New York: Academic Press. pp. 289pp. Cram, Donald J.; George

Pyruvate dehydrogenase (1,279 words) [view diff] exact match in snippet view article find links to article

contacts and conformations of TPP leads to formation of the reactive C2-carbanion, eventually. After the cofactor TPP decarboxylates pyruvate, the acetyl

Georg Wittig (738 words) [view diff] exact match in snippet view article find links to article

Staudinger's highly criticized theory of macromolecules. The foundations of carbanion chemistry were laid during Wittig's time in Freiburg. In 1944 he succeeded

Rick L. Danheiser (1,258 words) [view diff] exact match in snippet view article find links to article

stereoselective [4 + 1] cyclopentene annulations based on oxyanion and carbanion-accelerated vinylcyclopropane rearrangements; the application of organosilanes

Bropirimine (243 words) [view diff] exact match in snippet view article find links to article

butyllithium. Acylation of the anion with benzoyl chloride proceeds at the carbanion, which is more nucleophilic (because of the higher charge density). This

Oxoglutarate dehydrogenase complex (1,893 words) [view diff] exact match in snippet view article find links to article

The OGDH E1-TPP mechanism involves the formation of a stabilized carbanion intermediate.

Time resolved crystallography (660 words) [view diff] exact match in snippet view article find links to article

intermediate in enzymatic thiamin catalysis: Crystal structure of the α-carbanion of (α,β-dihydroxyethyl)-thiamin diphosphate in the active site of transketolase

Pagoclone (756 words) [view diff] exact match in snippet view article find links to article

imide carbonyl groups give the corresponding alcohol. Reaction with the carbanion from Ethyl 5-methyl-3-oxohexanoate leads to the product from the displacement

Trifluoromethyltrimethylsilane (506 words) [view diff] exact match in snippet view article find links to article

"Anion-Initiated Trifluoromethylation by TMSCF3: Deconvolution of the Siliconate–Carbanion Dichotomy by Stopped-Flow NMR/IR". Journal of the American Chemical Society

Carboxyglutamic acid (646 words) [view diff] exact match in snippet view article find links to article

CO2 is subsequently added. The reaction intermediate is a γ-glutamyl carbanion. This reaction is catalyzed by a carboxylase that requires vitamin K as

Rogletimide (285 words) [view diff] exact match in snippet view article find links to article

2-(4-pyridyl)butyrate [76766-56-8] (2). Base catalyzed conjugate addition of the carbanion to acrylamide (3) gives (4). The last step is an intramolecular cyclization

Imine (2,621 words) [view diff] exact match in snippet view article find links to article

to ketones and aldehydes, primary imines are susceptible to attack by carbanion equivalents. The method allow for the synthesis of secondary amines: R2C=NR'

Sodium amide (1,618 words) [view diff] exact match in snippet view article find links to article

"amides". doi:10.1351/goldbook.A00266 Buncel, E.; Menon, B. (1977). "Carbanion mechanisms: VII. Metallation of hydrocarbon acids by potassium amide and

Ring expansion and contraction (1,704 words) [view diff] exact match in snippet view article find links to article

rearrangement is a classic anionic ring contraction. It proceeds through a carbanion that attacks an endocyclic carbon and expels a leaving group (a halide)

Catechol 1,2-dioxygenase (1,856 words) [view diff] exact match in snippet view article find links to article

C3 hydroxyl group to ketonize and increases the carbanion character of C4. The newly formed C4 carbanion attacks O2, thus binding it to the substrate. Another

Oxidative decarboxylation (1,564 words) [view diff] exact match in snippet view article find links to article

the left-hand side, the thiazolium form of the TPP cofactor, which is a carbanion resulting from loss of H+ from the unusually acidic C2 of the thiazole

Magnesium anthracene (198 words) [view diff] exact match in snippet view article find links to article

the two benzo groups is 72.6°. The compound behaves as a source of the carbanion [C14H10]2- as well as a source of highly reactive Mg. With electrophiles

Sodium methylsulfinylmethylide (507 words) [view diff] exact match in snippet view article find links to article

Solvents: Look Out". Corey, E. J.; Chaykovsky, M. (1965). "Methylsulfinyl Carbanion (CH3-SO-CH2−). Formation and Applications to Organic Synthesis". J. Am

Argininosuccinate lyase (1,497 words) [view diff] exact match in snippet view article find links to article

water molecule. Lysine 289 is thought to stabilize the negatively charged carbanion intermediate. Although there is no consensus of the catalytic acid that

Methionine (2,980 words) [view diff] exact match in snippet view article find links to article

the cofactor PLP (pyridoxal phosphate), which functions by stabilising carbanion intermediates. If it reacts with cysteine, it produces cystathionine,

Bicyclomycin (839 words) [view diff] exact match in snippet view article find links to article

the key olefin proceeded in good overall yield followed by bridgehead carbanion oxidation with molecular oxygen gave the single hydroxylation product

Nitrile anion (999 words) [view diff] exact match in snippet view article find links to article

S. (1984). "Addition and Substitution Reactions of Nitrile-Stabilized Carbanions". Org. React. 31: 1–71. doi:10.1002/0471264180.or031.01. ISBN 0471264180

Organoiron chemistry (2,670 words) [view diff] exact match in snippet view article find links to article

organolithium compounds: ArLi + Fe(CO)5 → LiFe(CO)4C(O)R In this case, the carbanion attacks a CO ligand. In a complementary reaction, Collman's reagent can

4-Chlorobutyronitrile (364 words) [view diff] case mismatch in snippet view article find links to article

doi:10.1039/C7OB00442G. "N-VINYLPYRROLIDIN-2-ONE AS A 3-AMINOPROPYL CARBANION EQUIVALENT IN THE SYNTHESIS OF SUBSTITUTED 1-PYRROLINES: 2-PHENYL-1-PYRROLINE"

Prodigiosin (1,405 words) [view diff] exact match in snippet view article find links to article

the enzyme pigJ. This fragment is then able to react with the masked carbanion formed from the pyridoxal phosphate (PLP) mediated decarboxylation of

Nitroalkane oxidase (287 words) [view diff] exact match in snippet view article find links to article

Fitzpatrick PF, Orville AM, Nagpal A, Valley MP (2005). "Nitroalkane oxidase, a carbanion-forming flavoprotein homologous to acyl-CoA dehydrogenase". Arch. Biochem

Perfluorocycloalkene (628 words) [view diff] exact match in snippet view article find links to article

presence of a base. Attack of the nucleophile on the PFCA ring generates a carbanion which can eliminate a fluoride ion, resulting in vinyl substituted and

Pyrrole (3,142 words) [view diff] exact match in snippet view article find links to article

Claisen condensation. This fragment is then able to react with the masked carbanion formed from the PLP mediated decarboxylation of L-serine, which cyclizes

Cys/Met metabolism PLP-dependent enzyme family (610 words) [view diff] exact match in snippet view article find links to article

cofactor. PLP is employed as it binds to amino groups and stabilises carbanion intermediates. PLP enzymes exist in their resting state as a Schiff base

Aryne (2,936 words) [view diff] exact match in snippet view article find links to article

substituents, e.g. CF3, will direct the nucleophile addition to place carbanion as close as possible to EWG. However, electron donating (EDG) substituents

Mescaline (4,905 words) [view diff] exact match in snippet view article find links to article

tricarbonyl-(η6-1,2,3-trimethoxybenzene) chromium complex with acetonitrile carbanion in THF and iodine, followed by reduction of the nitrile with lithium aluminum

Andrew Streitwieser (415 words) [view diff] exact match in snippet view article find links to article

1021/ja01542a075. ISSN 0002-7863. J., Cram, Donald (1965). Fundamentals of Carbanion Chemistry. Burlington: Elsevier Science. ISBN 9780323162449. OCLC 843200178

Fischer carbene (1,435 words) [view diff] exact match in snippet view article find links to article

deprotonation of Fischer carbene, could be alkylated. However, because the carbanion is highly stabilized, a reactive alkylating reagent, such as methyl fluorosulfonate

Electrophilic substitution of unsaturated silanes (1,477 words) [view diff] exact match in snippet view article find links to article

stereospecifically anti, nucleophilic addition to either face of the silyl-stabilized carbanion leads to the formation of mixtures of double bond isomers. Diastereomeric

Organozinc chemistry (3,394 words) [view diff] exact match in snippet view article find links to article

thiolactone: The Barbier reaction involves nucleophilic addition of a carbanion equivalent to a carbonyl. The conversion is similar to the Grignard reaction

Alkenylaluminium compounds (1,660 words) [view diff] exact match in snippet view article find links to article

electron-withdrawing group). Coordination of aluminium to the resulting trans vinyl carbanion leads to the observed trans configuration of the product. (3) Neutral

Ketoacyl synthase (2,238 words) [view diff] exact match in snippet view article find links to article

primer substrate. The donor substrate is then decarboxylated, forming a carbanion internmediate, which will attack C1 of the primer substrate, and create

Scott E. Denmark (1,085 words) [view diff] exact match in snippet view article find links to article

ISSN 0002-7863. Denmark, S. E.; Harmata, M. A. (September 1, 1982). "Carbanion-accelerated Claisen rearrangements". Journal of the American Chemical

Superelectrophilic anion (4,212 words) [view diff] exact match in snippet view article find links to article

of the C–H bond occurs, which formally leads to a carbanion [CH3]– and a proton H+. The carbanion binds to the electrophilic boron atom of [B12X11]–

Woodward–Hoffmann rules (11,923 words) [view diff] exact match in snippet view article find links to article

bonds is 2n (or 2n + 2, if a (formal) lone pair from a heteroatom or carbanion is conjugated thereto). The electron count of a σ bond is 2. The bond

Cyclopentadienylcobalt dinitrosyl (3,688 words) [view diff] exact match in snippet view article find links to article

source. The fluoride source desilylated the substrate and produced the carbanion which could serve as the nucleophile in reaction with the Michael acceptor

Borylation (3,976 words) [view diff] exact match in snippet view article find links to article

(E)-γ-(dimethylphenylsilyl)allylboronate, a chiral allylic alcohol β-carbanion equivalent for the enantioselective synthesis of 2-butene-1,4-diols from

Jirō Tsuji (1,032 words) [view diff] case mismatch in snippet view article find links to article

REDUCTION OF α,β-UNSATURATED KETONES. II. FORMATION AND ALKYLATION OF A β-CARBANION INTERMEDIATE". Journal of the American Chemical Society. 83 (12): 2783–2784

Non steroidal aromatase inhibitors (3,675 words) [view diff] exact match in snippet view article find links to article

4-cyanobenzyl bromide followed by alkylation of triazole. The latter step is carbanion generation and nucleophilic aromatic substitution. In general NSAIs have

Hydrogen isotope biogeochemistry (30,904 words) [view diff] exact match in snippet view article find links to article

donate electrons to the positive charge. The opposite trend is seen in carbanion stability. In isotopes, a tertiary bound hydrogen is more likely to be