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Family of chemical compounds
Cyclic(alkyl)(amino) carbenes (CAACs) are a class of stable singlet carbene ligands that feature one amino and one sp3 alkyl group adjacent to the carbene
Cyclic_alkyl_amino_carbenes
Type of carbene demonstrating particular stability
the carbene-like dimerization that some persistent carbenes undergo over the course of days. Persistent carbenes in general, and Arduengo carbenes in particular
Persistent_carbene
Class of carbon compounds
atom stabilized by two neutral carbene donors, most commonly N-heterocyclic carbenes (NHCs) or cyclic (alkyl)(amino)carbenes (CAACs). As such, they may be
Carbodicarbenes
Chemical compounds and groups containing nitrogen with a lone pair (:N)
the amino group. Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents
Amine
stabilized as Lewis base adducts, e.g. with a NHC carbene. Other strategies are the use of cyclic alkyl amino carbenes (CAACs) and other Lewis bases, and their
Borylene
Class of germanium (II) compounds
product. The cyclic(alkyl)(amino)carbenes (CAACs) has already been known as both a better donor and better acceptor than n-heterocyclic carbenes (NHCs) due
Germylene
American chemist
7236–7239 M. Melaimi, R. Jazzar, M. Soleilhavoup, G. Bertrand,, « Cyclic (Alkyl)(Amino)Carbenes (CAACs): Recent developments », Angew. Chem. Int. Ed., 2017
Guy_Bertrand_(chemist)
Chemical species with two electrons occupying degenerate molecular orbitals
(2018). "Modular Approach to Kekulé Diradicaloids Derived from Cyclic (Alkyl)(amino)carbenes". Journal of the American Chemical Society. 140: 2546. doi:10
Diradical
Topics referred to by the same term
collection created in 1990 by Italian business man Jean Pigozzi Cyclic alkyl amino carbenes, a class of chemical substances with a low valent carbon atom
CAAC
Hypothetical charge of an atom if all its bonds to different atoms were fully ionic
and Soleilhavoup, Michèle; Bertrand, Guy (2015). "Cyclic (Alkyl)(Amino)Carbenes (CAACs): Stable Carbenes on the Rise". Acc. Chem. Res. 48 (2): 256–266. doi:10
Oxidation_state
UV-B protectant used in sunscreens
N-heterocyclic carbene (NHC)- versus cyclic alkyl amino carbene (CAAC)-based ruthenium catalysts, an unanticipated influence of the carbene type on efficiency
Octyl_methoxycinnamate
Chemical element with atomic number 30 (Zn)
and Soleilhavoup, Michèle; Bertrand, Guy (2015). "Cyclic (Alkyl)(Amino)Carbenes (CAACs): Stable Carbenes on the Rise". Acc. Chem. Res. 48 (2): 256–266. doi:10
Zinc
Class of organosilicon compounds
silylones have been synthesized with cyclic alkyl amino carbenes (cAAC) and bidentate N-heterocyclic carbenes (bis-NHC). They are capable of reactions
Silylone
Compound derived from an acid
and comprising the bulk of animal fats and vegetable oils. Lactones are cyclic carboxylic esters; naturally occurring lactones are mainly 5- and 6-membered
Ester
Class of molecules
Dutton, Jason; Wilson, David; Gilliard Jr., Robert (2019). "Cyclic(alkyl)(amino) Carbene-Promoted Ring Expansion of a Carbodicarbene Beryllacycle". Inorganic
Carbones
Organic compounds of the form >C=O
names of the two alkyl groups attached to the carbonyl group, followed by "ketone" as a separate word. Traditionally the names of the alkyl groups were written
Ketone
Class of organoantimony compounds
carbene. Chloro-substituted stibinidenes have been trapped using a cyclic alkyl(amino)carbene (CAAC) ligand. The synthesis involved reduction of CAAC-coordinated
Stibinidene
Class of chemical compounds
"Isolation of Neutral Mono- and Dinuclear Gold Complexes of Cyclic (Alkyl)(amino)carbenes". Angewandte Chemie International Edition. 52 (34): 8964–8967
Gold_compounds
Class of organobismuth compounds
dibismuthene species. Cyclic alkyl amino carbenes have also been used to generate bismuthinidenes. Bismuthinidene is a carbene analogs. The structural
Bismuthinidene
Chemical reaction
stabilization of a metal-carbene intermediate. However, these carbenes can be so stable, as to not undergo rearrangement. Carbenes of rhodium, copper, and
Wolff_rearrangement
Organoberyllium Complex in Main Group Chemistry
Be(0) have been described. A number of beryllium complexes with cyclic alkyl amino carbene (CAAC) ligands have been proposed to feature low-oxidation state
Organoberyllium_chemistry
Chemical reactions
reduction of [(CAAC)BDurBr2] induces binding of dinitrogen (CAAC = cyclic alkyl amino carbenes, Dur = durenyl). The initial step is proposed to involve a borylene
Main-group element-mediated activation of dinitrogen
Main-group_element-mediated_activation_of_dinitrogen
Any organic compound having a sulfanyl group (–SH)
derivative is any organosulfur compound of the form R−SH, where R represents an alkyl or other organic substituent. The −SH functional group itself is referred
Thiol
Aromatic, boron-containing rings
characterize a cationic borepin state using N-heterocyclic carbenes (NHCs) and cyclic(alkyl)(amino)carbenes (CAACS). Due to the dative donation of NHCs and CAACs
Borepin
Radicals centered on boron atoms
triphenyltin chloride as a reducing agent. Cyclic alkyl amino carbene (CAAC) ligands are similarly strongly σ donating carbene ligands like NHCs, but are missing
Boryl_radicals
Class of organic compounds
readily, they can be opened. Cyclic anhydrides with smaller rings are only of academic interest, e.g., malonic anhydride. Cyclic anhydrides that would give
Organic_acid_anhydride
Organic compounds of the form RC(=O)NR′R″
group (−OH) replaced by an amino group (−NR′R″); or, equivalently, an acyl (alkanoyl) group (R−C(=O)−) joined to an amino group. Common amides are formamide
Amide
Group of atoms giving a molecule characteristic properties
class Group Formula Structural Formula Prefix Suffix Example Alkane Alkyl R(CH2)nH alkyl- -ane Ethane Alkene Alkenyl R2C=CR2 alkenyl- -ene Ethylene (Ethene)
Functional_group
Organic compound with an –S– group
typically prepared by alkylation of thiols. Alkylating agents include not only alkyl halides, but also epoxides, aziridines, and Michael acceptors. RBr + HSR'
Organic_sulfide
Cyclic chemical group (–C6H5)
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6H5−, and is often represented by the pseudoelement
Phenyl_group
Functional group with the chemical structure R–S–S–R′
disulfides. "Thiokol" polymers arise when sodium polysulfide is treated with an alkyl dihalide. In the converse reaction, carbanionic reagents react with elemental
Disulfide
Class of boron heterocyclic compounds
and the terminal monoadduct. It was also demonstrated that cyclic alkyl(amino) carbene (CAAC)-stabilized biradicaloid DBA can react with dioxygen, sulfur
Diboraanthracene
Class of organic compounds
α-Bisalkylation of Ketones via Complex-Induced Syn-Deprotonation of Chiral N-Amino Cyclic Carbamate Hydrazones". Journal of the American Chemical Society. 133
Hydrazone
Class of organophosphorus compounds
Ramírez, and alkyl-containing carbodiphosphoranes are generally synthesized by alkylation of methylene di(aryl) or di(alkyl)phosphines. Cyclic carbodiphosphoranes
Carbodiphosphoranes
Chemical radical
Benkő, Zoltán; Gilliard Jr., Robert J. (2019). "Isolation of Cyclic(Alkyl)(Amino) Carbene–Bismuthinidene Mediated by a Beryllium(0) Complex". Chemistry
Organobismuth_radical
Group of nucleophilic compounds
of σ-Aromatic AlB2 Ring via Borane Coupling with a Dicoordinate Cyclic (Alkyl)(Amino)Aluminyl Anion". Journal of the American Chemical Society. 142 (19):
Aluminium(I)_nucleophiles
Organic compounds that contain sulfur
with organosulfur compounds—sulfur is vital for life. Of the 20 common amino acids, two (cysteine and methionine) are organosulfur compounds, and the
Organosulfur_chemistry
Chemical reaction
Mukaiyama–Mannich addition intermediates produced β-amino silyl enol ethers as product. Esters, perfluorinated alkyl, or alkyne groups are good electrophiles, that
Ketimine_Mannich_reaction
–C(=O)N= consisting of a carbonyl adjacent to a nitrogen atom. cyclic amide or lactam, a cyclic compound with the amide group –C(=O)N– in the ring. metal amide
Amide_(functional_group)
Organic compound containing a sulfinyl group (>SO)
sulfonium-based oxidations of alcohols to aldehydes. The α-CH groups of alkyl sulfoxides are susceptible to deprotonation by strong bases, such as sodium
Sulfoxide
Chemical compound
indicating a less covalent metal interaction in silyenes as compared to carbenes. N-Heterocyclic silylenes react with a wide variety of main group compounds
N-Heterocyclic_silylene
Branch of photochemistry
components. While ground state redox potentials are easily measured by cyclic voltammetry or other electrochemical methods, measuring the redox potential
Photoredox_catalysis
Class of organic compounds
Primary alkyl halides react with aqueous NaOH or KOH to give alcohols in nucleophilic aliphatic substitution. Secondary and especially tertiary alkyl halides
Alcohol_(chemistry)
Organic compounds of the form >C=N–OH
also be obtained from rearrangement of unstable nitroso compounds. Thus alkyl nitrites react with carbon acids to give oximes: methyl ethyl ketone with
Oxime
Organic compound containing the functional group R–CH=O
various sulfoxides (e.g. the Swern oxidation), and amine oxides convert alkyl halides to aldehydes (e.g., the Ganem oxidation). Sterically-hindered nitroxyls
Aldehyde
Organic compound or functional group containing a C=N bond
which is a straightforward and commonly used approach for producing β-amino-carbonyl compounds: If nearby functional groups stabilize negative charge
Imine
Chemical reaction
benzothiophenes has been catalyzed by some ruthenium(II) complexes of N-heterocyclic carbenes (NHC). This system appears to possess superb selectivity (ee > 90%) and
Asymmetric_hydrogenation
Chemical element with atomic number 6 (C)
(three bonds, neutral), carbanions (three bonds, negative charge) and carbenes (two bonds, neutral), although these species are much more likely to be
Carbon
Heterocyclic aromatic organic compound
compliance with the chemical nomenclature, as in toluidine, to indicate a cyclic compound containing a nitrogen atom. The chemical structure of pyridine
Pyridine
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CYCLIC ALKYL-AMINO-CARBENES
CYCLIC ALKYL-AMINO-CARBENES
CYCLIC ALKYL-AMINO-CARBENES
CYCLIC ALKYL-AMINO-CARBENES
CYCLIC ALKYL-AMINO-CARBENES
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