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Nitrogen-based molecule
In chemistry, a nitrene or imene (R−:Ṅ·) is the nitrogen analogue of a carbene. The nitrogen atom is uncharged and monovalent, so it has only 6 electrons
Nitrene
Chemical reaction
was a two-step processes, with the loss of nitrogen gas forming an acyl nitrene, followed by migration of the R-group to give the isocyanate. However,
Curtius_rearrangement
Chemical compound used in organic synthesis
valued for its ability to transfer diazo groups and generate reactive nitrene intermediates. Although it is one of the more stable sulfonyl azides, it
Tosyl_azide
nitrene is a chemical compound with generic formula RSO2N. Known sulfonyl nitrenes include methyl sulfonyl nitrene, trifluoromethyl sulfonyl nitrene,
Sulfonyl_nitrene
Chemical reaction
Nitrene C–H insertion is a chemical reaction in which a nitrene, a monovalent nitrogen, inserts across a C–H bonds and yields an amine or amide C–N bond
Nitrene_C–H_insertion
sulfinyl nitrene is a chemical compound with generic formula R-S(O)N, with oxygen and nitrogen both bonded to the sulfur atom. Sulfinyl nitrenes can be
Sulfinyl_nitrene
Chemical compound
from R2N–NMX (M = Na, K; X = SO2Ar). Treatment of secondary amines with nitrene sources including electrophilic amination reagents; Angeli's salt;[page needed]
Isodiazene
Functional group made of a carbon-carbon-nitrogen heterocycle
reaction of certain oximes with Grignard reagents, which affords aziridines: Nitrene addition to alkenes is a well-established method for the synthesis of aziridines
Aziridines
Organic compounds of the form >C=O
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Ketone
Class of hypervalent organoiodine compounds
(PhINTs). Iminoiodinanes are electrophilies and are often used as a source of nitrene in organic synthesis. An iminoiodinane may be represented by its alternate
Iminoiodinane
Latin letter N with diaeresis
letter), Jersey Dutch, and Ocaina language. In chemistry, N̈ represents a nitrene. "N̈" and "n̈" appear in very few languages, so they are not represented
N̈
Chemical compounds and groups containing nitrogen with a lone pair (:N)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Amine
Chemical compounds with the structure R–O–O–R'
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Peroxide
Cyclic chemical group (–C6H5)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Phenyl_group
Hydrocarbon compound containing one or more C=C bonds
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Alkene
Compound derived from an acid
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Ester
Chemical group (–CH3) derived from methane
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Methyl_group
Functional group (C=O)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Carbonyl_group
Organic compound of the form >C=C=O
U. W.; Orru, R. V. A. (2022). "Transition metal-catalysed carbene- and nitrene transfer to carbon monoxide and isocyanides". Chemical Society Reviews
Ketene
German-Australian chemist (born 1970)
preparation of reactive and functional molecules including the first stable nitrene. Beckmann was born in December 1970 in Arnsberg, Westphalia, Germany, and
Jens_Beckmann
Class of organic compounds
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Alcohol_(chemistry)
Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R')
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Ether
Organic compound
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Urea
Chemical group (–C(=O)C6H5
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Benzoyl_group
Group of atoms giving a molecule characteristic properties
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Functional_group
Functional group with the chemical structure R–S–S–R′
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Disulfide
Class of chemical compounds
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Hydroperoxide
Any organic compound having a sulfanyl group (–SH)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Thiol
Class of organic compounds
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Chlorofluorocarbon
Chemical compound
method is a variation on nitrogen expulsion in azides with formation of a nitrene. The synthesis of the diphosphorus precursor consists of reacting a terminal
Diphosphorus
Type of chemical reaction
amide into an intermediate isocyanate. The formation of an intermediate nitrene is not possible because it implies also the formation of a hydroxamic acid
Hofmann_rearrangement
Organic compounds with the structure R–S(=O)2–OH
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Sulfonic_acid
Chemical group (R–O)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Alkoxy_group
Chemical group (–N=C=O)
necessary to avoid side-reactions of the nitrene intermediate. Three rearrangement reactions involving nitrenes give isocyanates: Schmidt reaction, a reaction
Isocyanate
Salt that is a metal-thioate/O-esters of dithiocarbonate
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Xanthate
Locally acting nonsteroidal anti-inflammatory drug
carbonyl azide. On heating, nitrogen is evolved and a separatable mixture of nitrene insertion product and the desired ketoindazole # results. The latter reaction
Benzydamine
Class of organic compounds
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Hydrazone
Organic compound containing an –NO2 group
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Nitro_compound
Organic compound containing the functional group R–CH=O
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Aldehyde
Organic compound containing a –C(=O)OH group
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Carboxylic_acid
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Reductone
Class of organic compounds
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Organic_acid_anhydride
Organic compounds of the form RC(=O)NR′R″
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Amide
Type of organosulfur compound
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Sulfinylamine
Chemical group, –C(=O)CH3
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Acetyl_group
Chemical compound
sodium hypochlorite (NaOCl). Upon treatment with base, this undergoes a nitrene insertion reaction (4) to produce tiabendazole (5). An alternative synthesis
Tiabendazole
Organic compounds of the form R–O–O–R′
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Organic_peroxides
Organic ring compounds with the formula C2H3N
often obtained by the thermolysis of vinyl azides. During this reaction, a nitrene is formed as an intermediate. Alternatively, they can be obtained by oxidation
Azirine
Chemical group (–OCH3)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Methoxy_group
Organic compounds with a carbon-carbon-oxygen ring
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Epoxide
Chemical group (–CH2–CH3)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Ethyl_group
Chemical group (–OH)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Hydroxy_group
Halogen compounds derived from methane
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Halomethane
Molecular entity formed as an elementary step in a multi-step chemical reaction
carbon chain or an alkyl halide. Carbenoid Ion-neutral complex Keto anions Nitrenes Oxocarbenium ions Phosphinidenes Phosphoryl nitride Tetrahedral intermediates
Reaction_intermediate
Organosulfur compound and oxoacid
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Sulfenic_acid
Chemical group (R–C=O)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Acyl_group
Class of organic compounds
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Acetal
Class of chemical compounds
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Sulfite_ester
Organosulfur compound of the form >S(=O)2
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Sulfone
Chemical group derived from alkanes (one hydrogen removed)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Alkyl_group
Class of chemical compounds
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Imide
Chemical reaction
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Hydrodealkylation
Hydrocarbon compound (C6H6)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Benzene
French researcher and chemist (born 1945)
discovery of a new class of carbene and nitrene iron complexes and of one of the first catalytic systems of nitrene transfer to alkanes and alkenes. He has
Daniel_Mansuy
Chemical group (–N=C=S)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Isothiocyanate
Organic molecule with two different functional groups
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Bifunctionality
Organic compounds of the form RC≡CC(=O)R′
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Ynone
Chemical compound with the group –N+≡C–
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Isocyanide
Any part of a molecule with the chemical formula –CH2–
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Methylene_bridge
Chemical compound containing carbon and at least one halogen
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Halocarbon
Functional group consisting of sulfur double-bonded to oxygen
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Thionyl_group
Anion with formula OCN and charge –1
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Cyanate
Anion and chemical group (–N3)
converted into molecular nitrogen (N2) and a reactive radical (such as nitrene); therefore, it is also used to render organic molecules photoactivable
Azide
Organic compound or functional group containing a C=N bond
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Imine
Chemical group (>N–C(=O)–O–)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Carbamate
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Arsonic acid (functional group)
Arsonic_acid_(functional_group)
Organic molecule containing a neutral carbon with two unbound valence electrons
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Carbene
American chemist and academic (born 1956)
evolved cytochrome P450 to carry out cyclopropanation and carbene and nitrene transfer reactions. In addition to evolving individual molecules, she has
Frances_Arnold
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Amide_(functional_group)
Chemical group (–CH2–C6H5)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Benzyl_group
Class of chemical compounds
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Thiosulfonate
South Korean chemist (born 1962)
catalyzed intermolecular amidation of arenes using sulfonyl azide as a nitrene precursor. This reaction generates N2 as the single byproduct, doesn't
Sukbok_Chang
Organic compounds of the form >C=N–OH
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Oxime
Functional group
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Methylenedioxy
Divalent organolead(II) analogues of carbenes
forms a bridging ring; absent such an atom, the azide evolves N2 to form a nitrene, which then inserts into a C-H bond of an arene substituent and coordinates
Plumbylene
Class of chemical compounds
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Sulfinic_acid
Chemical group (–C4H9) derived from butane
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Butyl_group
Organic compounds that contain sulfur
sulfimides are chiral. Sulfimides form stable α-carbanions. Sulfinyl nitrenes, despite their formal resonance structure as R–S(=O)≡N, instead behave
Organosulfur_chemistry
Chemical group (–C3H7) derived from propane
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Propyl_group
Polyatomic ion (NO3, charge –1) found in explosives and fertilisers
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Nitrate
Chemical group (–CH=CH2)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Vinyl_group
Organic compound containing C–PO(OR)2 groups
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Phosphonate
Chemical compound
unpaired electrons on one of the terminal nitrogen atoms—essentially an azido-nitrene. The structure of N+ 4 has been predicted by theoretical experiments and
Tetranitrogen
Organic compounds with a diazenyl group (–N=N–)
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Azo_compound
Hydrocarbon compound containing one or more C≡C bonds
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Alkyne
Class of chemical compounds
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Seleninic_acid
Group of carbenes
group 15 elements the neutral nitrogen carbene analog (RN) is called a nitrene. The phosphorus analog is a phosphinidene. There are charged group 15 carbene
Carbene_analog
Organic chemical reaction
rearrangement or cationotropic rearrangement a free radical by homolysis a nitrene. The driving force for the actual migration of a substituent in step two
1,2-rearrangement
Organosulfur compounds of the form R–SC(=O)–R′
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Thioester
Chemical compound
oxygen (one element, not C, H or O) Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile
Glycidamide
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NITRENE
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