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Search for "aminoxyl radical" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.
Oxime radicals: generation, properties and application in organic synthesis
- Igor B. Krylov,
- Stanislav A. Paveliev,
- Alexander S. Budnikov and
- Alexander O. Terent’ev
Beilstein J. Org. Chem. 2020, 16, 1234–1276, doi:10.3762/bjoc.16.107
- nitroimine 10 is explained by the interaction of oxime radical 8 with nitric oxide. Pivalonitrile (11) is presumably formed via β-scission of iminyl radical 12 (Scheme 3). During the decomposition of oxime radical 8 an EPR signal typical for a dialkyl aminoxyl radical (type I in Figure 1) was also observed
Graphical Abstract
Figure 1: Imine-N-oxyl radicals (IV) discussed in the present review and other classes of N-oxyl radicals (I–...
Figure 2: The products of decomposition of iminoxyl radicals generated from oximes by oxidation with Ag2O.
Scheme 1: Generation of oxime radicals and study of the kinetics of their decay by photolysis of the solution...
Scheme 2: Synthesis of di-tert-butyliminoxyl radical and its decomposition products.
Scheme 3: The proposed reaction pathway of the decomposition of di-tert-butyliminoxyl radical (experimentally...
Scheme 4: Monomolecular decomposition of the tert-butyl(triethylmethyl)oxime radical.
Scheme 5: The synthesis and stability of the most stable dialkyl oxime radicals – di-tert-butyliminoxyl and d...
Scheme 6: The formation of iminoxyl radicals from β-diketones under the action of NO2.
Scheme 7: Synthesis of the diacetyliminoxyl radical.
Scheme 8: Examples of long-living oxime radicals with electron-withdrawing groups and the conditions for thei...
Figure 3: The electronic structure iminoxyl radicals and their geometry compared to the corresponding oximes.
Figure 4: Bond dissociation enthalpies (kcal/mol) of oximes and N,N-disubstituted hydroxylamines calculated o...
Scheme 9: Examples demonstrating the low reactivity of the di-tert-butyliminoxyl radical towards the substrat...
Scheme 10: The reactions of di-tert-butyliminoxyl radical with unsaturated hydrocarbons involving hydrogen ato...
Scheme 11: Possible mechanisms of reaction of di-tert-butyliminoxyl radical with alkenes.
Scheme 12: Products of the reaction between di-tert-butyliminoxyl radical and phenol derivatives.
Scheme 13: The reaction of di-tert-butyliminoxyl radical with amines.
Scheme 14: Reaction of di-tert-butyliminoxyl radicals with organolithium reagents.
Scheme 15: Cross-dehydrogenative C–O coupling of 1,3-dicarbonyl compounds with oximes under the action of mang...
Scheme 16: Cross-dehydrogenative C–O coupling of 1,3-dicarbonyl compounds with oximes under the action of Cu(BF...
Scheme 17: Oxidative C–O coupling of benzylmalononitrile (47) with 3-(hydroxyimino)pentane-2,4-dione (19).
Scheme 18: The proposed mechanism of the oxidative coupling of benzylmalononitrile (47) with diacetyl oxime (19...
Scheme 19: Oxidative C–O coupling of pyrazolones with oximes under the action of Fe(ClO4)3.
Scheme 20: The reaction of diacetyliminoxyl radical with pyrazolones.
Scheme 21: Oxidative C–O coupling of oximes with acetonitrile, ketones, and esters.
Scheme 22: Intramolecular cyclizations of oxime radicals to form substituted isoxazolines or cyclic nitrones.
Scheme 23: TEMPO-mediated oxidative cyclization of oximes with C–H bond cleavage.
Scheme 24: Proposed reaction mechanism of oxidative cyclization of oximes with C–H bond cleavage.
Scheme 25: Selectfluor/Bu4NI-mediated C–H oxidative cyclization of oximes.
Scheme 26: Oxidative cyclization of N-benzyl amidoximes to 1,2,4-oxadiazoles.
Scheme 27: The formation of quinazolinone 73a from 5-phenyl-4,5-dihydro-1,2,4-oxadiazole 74 under air.
Scheme 28: DDQ-mediated oxidative cyclization of thiohydroximic acids.
Scheme 29: Plausible mechanism of the oxidative cyclization of thiohydroximic acids.
Scheme 30: Silver-mediated oxidative cyclization of α-halogenated ketoximes and 1,3-dicarbonyl compounds.
Scheme 31: Possible pathway of one-pot oxidative cyclization of α-halogenated ketoximes and 1,3-dicarbonyl com...
Scheme 32: T(p-F)PPT-catalyzed oxidative cyclization of oximes with the formation of 1,2,4-oxadiazolines.
Scheme 33: Intramolecular cyclization of iminoxyl radicals involving multiple C=C and N=N bonds.
Scheme 34: Oxidative cyclization of β,γ- and γ,δ-unsaturated oximes employing the DEAD or TEMPO/DEAD system wi...
Scheme 35: Cobalt-catalyzed aerobic oxidative cyclization of β,γ-unsaturated oximes.
Scheme 36: Manganese-catalyzed aerobic oxidative cyclization of β,γ-unsaturated oximes.
Scheme 37: Visible light photocatalytic oxidative cyclization of β,γ-unsaturated oximes.
Scheme 38: TBAI/TBHP-mediated radical cascade cyclization of the β,γ-unsaturated oximes.
Scheme 39: TBAI/TBHP-mediated radical cascade cyclization of vinyl isocyanides with β,γ-unsaturated oximes.
Scheme 40: tert-Butylnitrite-mediated oxidative cyclization of unsaturated oximes with the introduction of an ...
Scheme 41: Transformation of unsaturated oxime to oxyiminomethylisoxazoline via the confirmed dimeric nitroso ...
Scheme 42: tert-Butylnitrite-mediated oxidative cyclization of unsaturated oximes with the introduction of a n...
Scheme 43: Synthesis of cyano-substituted oxazolines from unsaturated oximes using the TBN/[RuCl2(p-cymene)]2 ...
Scheme 44: Synthesis of trifluoromethylthiolated isoxazolines from unsaturated oximes.
Scheme 45: Copper-сatalyzed oxidative cyclization of β,γ-unsaturated oximes with the introduction of an azido ...
Scheme 46: TBHP-mediated oxidative cascade cyclization of β,γ-unsaturated oximes and unsaturated N-arylamides.
Scheme 47: Copper-сatalyzed oxidative cyclization of unsaturated oximes with the introduction of an amino grou...
Scheme 48: TEMPO-mediated oxidative cyclization of unsaturated oximes followed by elimination.
Scheme 49: Oxidative cyclization of β,γ-unsaturated oximes with the introduction of a trifluoromethyl group.
Scheme 50: Oxidative cyclization of unsaturated oximes with the introduction of a nitrile group.
Scheme 51: Oxidative cyclization of β,γ-unsaturated oximes to isoxazolines with the introduction of a nitrile ...
Scheme 52: Oxidative cyclization of β,γ-unsaturated oximes to isoxazolines with the introduction of a sulfonyl...
Scheme 53: Oxidative cyclization of β,γ- and γ,δ-unsaturated oximes to isoxazolines with the introduction of a...
Scheme 54: Oxidative cyclization of β,γ-unsaturated oximes to isoxazolines with the introduction of a thiocyan...
Scheme 55: PhI(OAc)2-mediated oxidative cyclization of oximes with C–S and C–Se bond formation.
Scheme 56: PhI(OAc)2-mediated oxidative cyclization of unsaturated oximes accompanied by alkoxylation.
Scheme 57: PhI(OAc)2-mediated cyclization of unsaturated oximes to methylisoxazolines.
Scheme 58: Oxidative cyclization-alkynylation of unsaturated oximes.
Scheme 59: TEMPO-mediated oxidative cyclization of C-glycoside ketoximes to C-glycosylmethylisoxazoles.
Scheme 60: Silver-сatalyzed oxidative cyclization of β,γ-unsaturated oximes with formation of fluoroalkyl isox...
Scheme 61: Oxidative cyclization of β,γ-unsaturated oximes with the formation of haloalkyl isoxazolines.
Scheme 62: Cyclization of β,γ-unsaturated oximes into haloalkyl isoxazolines under the action of the halogenat...
Scheme 63: Synthesis of haloalkyl isoxazoles and cyclic nitrones via oxidative cyclization and 1,2-halogen shi...
Scheme 64: Electrochemical oxidative cyclization of diaryl oximes.
Scheme 65: Copper-сatalyzed cyclization and dioxygenation oximes containing a triple C≡C bond.
Scheme 66: Photoredox-catalyzed sulfonylation of β,γ-unsaturated oximes by sulfonyl hydrazides.
Scheme 67: Oxidative cyclization of β,γ-unsaturated oximes with introduction of sulfonate group.
Scheme 68: Ultrasound-promoted oxidative cyclization of β,γ-unsaturated oximes.
TEMPO-derived spin labels linked to the nucleobases adenine and cytosine for probing local structural perturbations in DNA by EPR spectroscopy
- Dnyaneshwar B. Gophane and
- Snorri Th. Sigurdsson
Beilstein J. Org. Chem. 2015, 11, 219–227, doi:10.3762/bjoc.11.24
- paired with A, G, C or T in a DNA duplex. UA and UC had similar mobility order for the different base pairs, with the lowest mobility when paired with C and the highest when paired with T. Keywords: aminoxyl radical; ESR spectroscopy; nitroxide; nucleic acids; site-directed spin labeling (SDSL); spin
Graphical Abstract
Figure 1: Base pairing of TC with G (A), TA with T (B), UC with G (C) and UA with T (D).
Scheme 1: Synthesis of nucleoside TA and its corresponding phosphoramidite 5. TPS = 2,4,6-triisopropylbenzene...
Scheme 2: Synthesis of nucleoside UA and its corresponding phosphoramidite 10.
Scheme 3: Synthesis of nucleoside UC and its corresponding phosphoramidite 14.
Figure 2: EPR spectra of 14-mer DNA duplexes 5′-d(GACCTCGTAATCGTG)•5′-d(CACGATYCGAGGTC), (10 mM phosphate, 10...
Figure 3: Possible base pairing of TAH+ with C (A) and G (B) at pH 5.
Figure 4: Possible base pairing of UA and UC with C.
Figure 5: EPR spectra of 14-mer DNA duplex 5′-d(GACCTCGUAATCGTG)•5′-d(CACGATYCGAGGTC) (A), and 5′-d(GACCTCGUC...
