Ylide, the Glossary
An ylide or ylid is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both atoms have full octets of electrons.[1]
Table of Contents
77 relations: Aldehyde, Allyl alcohol, Allylic rearrangement, Amino acid, Atom, Aziridines, Azomethine ylide, Betaine, Bis(diphenylphosphino)methane, Bond order, Butyllithium, Carbanion, Carbene, Carbenoid, Carbonyl group, Catalysis, Chemical Society Reviews, Chemistry, Comptes rendus de l'Académie des Sciences, Covalent bond, Diazo, Dipolar compound, Dipole, Electric charge, Electron-withdrawing group, Elimination reaction, Epoxide, Ether, Ethyl diazoacetate, Fullerene, Group 3 element, Haloalkane, Helvetica Chimica Acta, Heteroatom, Homoleptic, Ionic bonding, Isodiazene, Johnson–Corey–Chaykovsky reaction, Journal of the American Chemical Society, Ketone, Menshutkin reaction, Molecule, Nitrile ylide, Nitrogen, Onium ion, Organic chemistry, Palladium, Persistent carbene, Phenyl group, Phenylsilane, ... Expand index (27 more) »
Aldehyde
In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure. Ylide and aldehyde are functional groups.
Allyl alcohol
Allyl alcohol (IUPAC name: prop-2-en-1-ol) is an organic compound with the structural formula.
Allylic rearrangement
An allylic rearrangement or allylic shift is an organic chemical reaction in which reaction at a center vicinal to a double bond causes the double bond to shift to an adjacent pair of atoms: It is encountered in both nucleophilic and electrophilic substitution, although it is usually suppressed relative to non-allylic substitution.
See Ylide and Allylic rearrangement
Amino acid
Amino acids are organic compounds that contain both amino and carboxylic acid functional groups.
Atom
Atoms are the basic particles of the chemical elements.
See Ylide and Atom
Aziridines
doi-access. Ylide and Aziridines are functional groups.
Azomethine ylide
Azomethine ylides are nitrogen-based 1,3-dipoles, consisting of an iminium ion next to a carbanion.
See Ylide and Azomethine ylide
Betaine
A betaine in chemistry is any neutral chemical compound with a positively charged cationic functional group that bears no hydrogen atom, such as a quaternary ammonium or phosphonium cation (generally: onium ions), and with a negatively charged functional group, such as a carboxylate group that may not be adjacent to the cationic site.
Bis(diphenylphosphino)methane
1,1-Bis(diphenylphosphino)methane (dppm), is an organophosphorus compound with the formula CH2(PPh2)2.
See Ylide and Bis(diphenylphosphino)methane
Bond order
In chemistry, bond order is a formal measure of the multiplicity of a covalent bond between two atoms.
Butyllithium
Butyllithium may refer to one of 5 isomeric organolithium reagents of which 3 are commonly used in chemical synthesis.
Carbanion
In organic chemistry, a carbanion is an anion in which carbon is negatively charged.
Carbene
In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. Ylide and carbene are functional groups.
Carbenoid
In chemistry a carbenoid is a reactive intermediate that shares reaction characteristics with a carbene.
Carbonyl group
For organic chemistry, a carbonyl group is a functional group with the formula, composed of a carbon atom double-bonded to an oxygen atom, and it is divalent at the C atom. Ylide and carbonyl group are functional groups.
Catalysis
Catalysis is the increase in rate of a chemical reaction due to an added substance known as a catalyst.
Chemical Society Reviews
Chemical Society Reviews is a biweekly peer-reviewed scientific journal published by the Royal Society of Chemistry, for review articles on topics of current interest in chemistry.
See Ylide and Chemical Society Reviews
Chemistry
Chemistry is the scientific study of the properties and behavior of matter.
Comptes rendus de l'Académie des Sciences
(English: Proceedings of the Academy of Sciences), or simply Comptes rendus, is a French scientific journal published since 1835.
See Ylide and Comptes rendus de l'Académie des Sciences
Covalent bond
A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms.
Diazo
In organic chemistry, the diazo group is an organic moiety consisting of two linked nitrogen atoms at the terminal position. Ylide and diazo are functional groups.
See Ylide and Diazo
Dipolar compound
In organic chemistry, a dipolar compound or simply dipole is an electrically neutral molecule carrying a positive and a negative charge in at least one canonical description.
See Ylide and Dipolar compound
Dipole
In physics, a dipole is an electromagnetic phenomenon which occurs in two ways.
See Ylide and Dipole
Electric charge
Electric charge (symbol q, sometimes Q) is the physical property of matter that causes it to experience a force when placed in an electromagnetic field.
Electron-withdrawing group
An electron-withdrawing group (EWG) is a group or atom that has the ability to draw electron density toward itself and away from other adjacent atoms.
See Ylide and Electron-withdrawing group
Elimination reaction
An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism.
See Ylide and Elimination reaction
Epoxide
In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. Ylide and epoxide are functional groups.
Ether
In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom bonded to two organyl groups (e.g., alkyl or aryl). Ylide and ether are functional groups.
See Ylide and Ether
Ethyl diazoacetate
Ethyl diazoacetate (N.
See Ylide and Ethyl diazoacetate
Fullerene
A fullerene is an allotrope of carbon whose molecules consist of carbon atoms connected by single and double bonds so as to form a closed or partially closed mesh, with fused rings of five to seven atoms.
Group 3 element
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Haloalkane
The haloalkanes (also known as halogenoalkanes or alkyl halides) are alkanes containing one or more halogen substituents. Ylide and haloalkane are functional groups.
Helvetica Chimica Acta
Helvetica Chimica Acta is a peer-reviewed scientific journal of chemistry established by the Swiss Chemical Society.
See Ylide and Helvetica Chimica Acta
Heteroatom
In chemistry, a heteroatom is, strictly, any atom that is not carbon or hydrogen.
Homoleptic
In inorganic chemistry, a homoleptic chemical compound is a metal compound with all ligands identical.
Ionic bonding
Ionic bonding is a type of chemical bonding that involves the electrostatic attraction between oppositely charged ions, or between two atoms with sharply different electronegativities, and is the primary interaction occurring in ionic compounds.
Isodiazene
In organic chemistry, an isodiazene, also known by the incorrectly constructed (but commonly used) name 1,1-diazene or systematic name diazanylidene, is an organic derivative of the parent isodiazene (H2N+. Ylide and isodiazene are functional groups.
Johnson–Corey–Chaykovsky reaction
The Johnson–Corey–Chaykovsky reaction (sometimes referred to as the Corey–Chaykovsky reaction or CCR) is a chemical reaction used in organic chemistry for the synthesis of epoxides, aziridines, and cyclopropanes.
See Ylide and Johnson–Corey–Chaykovsky reaction
Journal of the American Chemical Society
The Journal of the American Chemical Society (also known as JACS) is a weekly peer-reviewed scientific journal that was established in 1879 by the American Chemical Society.
See Ylide and Journal of the American Chemical Society
Ketone
In organic chemistry, a ketone is an organic compound with the structure, where R and R' can be a variety of carbon-containing substituents. Ylide and ketone are functional groups.
See Ylide and Ketone
Menshutkin reaction
In organic chemistry, the Menshutkin reaction converts a tertiary amine into a quaternary ammonium salt by reaction with an alkyl halide.
See Ylide and Menshutkin reaction
Molecule
A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion.
Nitrile ylide
Nitrile ylides also known as nitrilium ylides or nitrilium methylides, are generally reactive intermediates formally consisting of a carbanion of an alkyl or similar group bonded to the nitrogen atom of a cyanide unit. Ylide and nitrile ylide are functional groups.
Nitrogen
Nitrogen is a chemical element; it has symbol N and atomic number 7.
Onium ion
In chemistry, an onium ion is a cation formally obtained by the protonation of mononuclear parent hydride of a pnictogen (group 15 of the periodic table), chalcogen (group 16), or halogen (group 17). Ylide and onium ion are chemical nomenclature.
Organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.
See Ylide and Organic chemistry
Palladium
Palladium is a chemical element; it has symbol Pd and atomic number 46.
Persistent carbene
A persistent carbene (also known as stable carbene) is an organic molecule whose natural resonance structure has a carbon atom with incomplete octet (a carbene), but does not exhibit the tremendous instability typically associated with such moieties. Ylide and persistent carbene are functional groups.
See Ylide and Persistent carbene
Phenyl group
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula, and is often represented by the symbol Ph (archaically φ).
Phenylsilane
Phenylsilane, also known as silylbenzene, a colorless liquid, is one of the simplest organosilanes with the formula C6H5SiH3.
Phosphine
Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula PH3, classed as a pnictogen hydride. Ylide and Phosphine are functional groups.
Phosphite ester
The general structure of a phosphite ester showing the lone pairs on the P In organic chemistry, a phosphite ester or organophosphite usually refers to an organophosphorous compound with the formula P(OR)3. Ylide and phosphite ester are functional groups.
Phosphonate
In organic chemistry, phosphonates or phosphonic acids are organophosphorus compounds containing groups, where R is an organic group (alkyl, aryl). Ylide and phosphonate are functional groups.
Phosphonium
In chemistry, the term phosphonium (more obscurely: phosphinium) describes polyatomic cations with the chemical formula (where R is a hydrogen or an alkyl, aryl, or halide group). Ylide and phosphonium are functional groups.
Phosphorus
Phosphorus is a chemical element; it has symbol P and atomic number 15.
Platinum
Platinum is a chemical element; it has symbol Pt and atomic number 78.
Porphyrin
Porphyrins are a group of heterocyclic macrocycle organic compounds, composed of four modified pyrrole subunits interconnected at their α carbon atoms via methine bridges (.
Prato reaction
The Prato reaction is a particular example of the well-known 1,3-dipolar cycloaddition of azomethine ylides to olefins.
In chemistry, a reactive intermediate or an intermediate is a short-lived, high-energy, highly reactive molecule.
See Ylide and Reactive intermediate
Reagent
In chemistry, a reagent or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs.
Resonance (chemistry)
In chemistry, resonance, also called mesomerism, is a way of describing bonding in certain molecules or polyatomic ions by the combination of several contributing structures (or forms, also variously known as resonance structures or canonical structures) into a resonance hybrid (or hybrid structure) in valence bond theory.
See Ylide and Resonance (chemistry)
Sigmatropic reaction
A sigmatropic reaction in organic chemistry is a pericyclic reaction wherein the net result is one σ-bond is changed to another σ-bond in an uncatalyzed intramolecular reaction.
See Ylide and Sigmatropic reaction
SN2 reaction
Bimolecular nucleophilic substitution (SN2) is a type of reaction mechanism that is common in organic chemistry.
Sommelet–Hauser rearrangement
The Sommelet–Hauser rearrangement (named after M. Sommelet and Charles R. HauserRearrangements of Benzyltrimethylammonium Ion and Related Quaternary Ammonium Ions by Sodium Amide Involving Migration into the Ring Simon W. Kantor, Charles R. Hauser J. Am. Chem. Soc., 1951, 73 (9), pp 4122–4131) is a rearrangement reaction of certain benzyl quaternary ammonium salts.
See Ylide and Sommelet–Hauser rearrangement
Stevens rearrangement
The Stevens rearrangement in organic chemistry is an organic reaction converting quaternary ammonium salts and sulfonium salts to the corresponding amines or sulfides in presence of a strong base in a 1,2-rearrangement.
See Ylide and Stevens rearrangement
Substituent
In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. Ylide and substituent are chemical nomenclature.
Suffix
In linguistics, a suffix is an affix which is placed after the stem of a word.
See Ylide and Suffix
Tebbe's reagent
Tebbe's reagent is the organometallic compound with the formula (C5H5)2TiCH2ClAl(CH3)2.
Tert-Butyl bromide
tert-Butyl bromide (also referred to as 2-bromo-2-methylpropane) is an organic compound with the formula Me3CBr (Me.
See Ylide and Tert-Butyl bromide
The Journal of Organic Chemistry
The Journal of Organic Chemistry, colloquially known as JOC, is a peer-reviewed scientific journal for original contributions of fundamental research in all branches of theory and practice in organic and bioorganic chemistry.
See Ylide and The Journal of Organic Chemistry
A transition metal carbene complex is an organometallic compound featuring a divalent carbon ligand, itself also called a carbene.
See Ylide and Transition metal carbene complex
Triphenylphosphine
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P.
See Ylide and Triphenylphosphine
Wittig reaction
The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent.
Zwitterion
In chemistry, a zwitterion, also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively and negatively charged functional groups.
1,2-Bis(diphenylphosphino)ethane
1,2-Bis(diphenylphosphino)ethane (dppe) is an organophosphorus compound with the formula (PhPCH) (Ph.
See Ylide and 1,2-Bis(diphenylphosphino)ethane
1,3-Dipolar cycloaddition
The 1,3-dipolar cycloaddition is a chemical reaction between a 1,3-dipole and a dipolarophile to form a five-membered ring.
See Ylide and 1,3-Dipolar cycloaddition
1,3-dipole
In organic chemistry, a 1,3-dipolar compound or 1,3-dipole is a dipolar compound with delocalized electrons and a separation of charge over three atoms.
References
[1] https://en.wikipedia.org/wiki/Ylide
Also known as 1,2-dipole, Phosphazide, Sulfonium ylide, Thiocarbonyl ylide, Ylid, Ylides, Ylidic.
, Phosphine, Phosphite ester, Phosphonate, Phosphonium, Phosphorus, Platinum, Porphyrin, Prato reaction, Reactive intermediate, Reagent, Resonance (chemistry), Sigmatropic reaction, SN2 reaction, Sommelet–Hauser rearrangement, Stevens rearrangement, Substituent, Suffix, Tebbe's reagent, Tert-Butyl bromide, The Journal of Organic Chemistry, Transition metal carbene complex, Triphenylphosphine, Wittig reaction, Zwitterion, 1,2-Bis(diphenylphosphino)ethane, 1,3-Dipolar cycloaddition, 1,3-dipole.