1,3-Dipolar cycloaddition of 3-imidazoline-3-oxide nitroxyl radical to dipolarophiles containing carbon-carbon double bonds

Martin, Valérie; Володарский, Л. Б.; Voinov, Maxim A.; Berezina, T. A.; Lelyukh, T. F.

doi:10.1007/bf00961121

Cited by 9 publications

(6 citation statements)

References 7 publications

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“…Aside from the convenience of the direct introduction of a stable radical group into an unsaturated system, many of the synthesized paramagnetic compounds are unique and cannot be obtained by any other known methods . The present work continues this research and is focused on analysis of the products isolated from the reactions of radical 1 with cyclic aldonitrones of the imidazole series that contain either a conjugated or isolated nitrone group, compounds 2 and 4 , respectively. The latter, which also contains a nitroxyl group, is notable because when it is in a reaction both its electrophilic and nucleophilic components contain paramagnetic groups; this situation has not been described previously in the literature.…”

Section: Introductionmentioning

confidence: 97%

Reaction of Paramagnetic Synthon, Lithiated 4,4,5,5‐Tetramethyl‐4,5‐dihydro‐1H‐imidazol‐1‐oxyl 3‐oxide, with Cyclic Aldonitrones of the Imidazole Series

Толстиков

Tretyakov

Gorbunov

et al. 2016

Chemistry A European J

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It was shown that dipole-stabilized paramagnetic carbanion lithiated 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-oxyl 3-oxide can be attached in a nucleophilic manner to either isolated or conjugated aldonitrones of the 2,5-dihydroimidazole 3-oxide and 2H-imidazole 1-oxide series to afford adducts the subsequent oxidation of which leads to polyfunctional mono- and diradicals. According to XRD, at least two polymorphic modifications can be formed during crystallization of the resulting paramagnetic compounds, and for each of them, geometric parameters of the molecules are similar. An EPR spectrum of the diradical in frozen toluene has a complicated lineshape, which can be fairly well reproduced by using X-ray diffraction structural analysis and the following set of parameters: D=14.9 mT, E=1.7 mT; tensor a((14) N)=[0.260 0.260 1.625] mT, two equivalent tensors for the nitronyl nitroxide moiety a((14) N)=[0.198 0.198 0.700] mT, and g≈2.007. According to our DFT and ab initio calculations, the intramolecular exchange in the diradical is very weak and most likely ferromagnetic.

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Section: Introductionmentioning

confidence: 97%

Reaction of Paramagnetic Synthon, Lithiated 4,4,5,5‐Tetramethyl‐4,5‐dihydro‐1H‐imidazol‐1‐oxyl 3‐oxide, with Cyclic Aldonitrones of the Imidazole Series

Толстиков

Tretyakov

Gorbunov

et al. 2016

Chemistry A European J

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“…Martin and his team [7] investigated the reaction of the nitroxyl radical, 2,2,5,5tetramethyl-3-imidazolin-3-oxide-1-oxyl (1), with dipolarophiles containing a C=C group, including methyl ester of oleic acid (2). The main purpose was to explore the potential use of this paramagnetic heterocyclic nitrone in 32CA as a spin label for compounds containing a C=C bond.…”

Section: Oleic Acid and Its Esters As Components Of The [3+2] Cycload...mentioning

confidence: 99%

The Participation of Oleic Acid and its Esters in [3+2] Cycloaddition Reactions: A Mini-Review

Dresler

2024

Sci. Rad.

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This mini review presents the state of knowledge on the [3+2] cycloaddition reactions involving fatty acids and their esters with triatomic components (TAC). In general, the literature reports are quite sparse and relatively old. The reaction yield was in the range of 12-85%. The best result of 32CA was obtained from the reaction of butylonitrile N-oxide (4) and methyl oleate (2). Other tested TAC as components of title reactions were nitrylimines and ozone.

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“…The residue was chromatographed on a column. 4-( l',2"-Dimetboxyearbonyl)-2"-oxoetbylidene-2,2,5,5-tetramethylimidazolidine-l-oxyl (15). A solution of NaOH in methanol (10 mL).…”

Section: -(4"-ethynylphenacetylidene)-2255-tetramethylimidazolidimentioning

confidence: 99%

Reactions of heterocyclic paramagnetic aldonitrone, 2,2,5,5-tetramethyl-3-imidazoline-1-oxyl 3-oxide, with alkynes

et al. 1990

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The reactions of heterocyclic paramagnetic aldonitrone, viz., 2,2,5.5-tetramethyl-3-imidazoline-1-oxyl 3-oxide, with mono-and disubstituted alkynes afford unstable isoxazoline derivatives. The reactions with monosubstituted alkynes yield predominantly 5-substituted regioisomers. The resulting isoxazoline derivatives are readily (and often spontaneously) converted into enaminoketones, viz., imidazolidine-l-oxyt derivatives. In the presence of tolan, the title paramagnetic aldonitrone gives a dimer in which one imidazoline ring undergoes profound transtbrmation. The structure of the resulting dimer was established by X-ray diffraction analysis.

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1,3-Dipolar cycloaddition of 3-imidazoline-3-oxide nitroxyl radical to dipolarophiles containing carbon-carbon double bonds

Cited by 9 publications

References 7 publications

Reaction of Paramagnetic Synthon, Lithiated 4,4,5,5‐Tetramethyl‐4,5‐dihydro‐1H‐imidazol‐1‐oxyl 3‐oxide, with Cyclic Aldonitrones of the Imidazole Series

Reaction of Paramagnetic Synthon, Lithiated 4,4,5,5‐Tetramethyl‐4,5‐dihydro‐1H‐imidazol‐1‐oxyl 3‐oxide, with Cyclic Aldonitrones of the Imidazole Series

The Participation of Oleic Acid and its Esters in [3+2] Cycloaddition Reactions: A Mini-Review

Reactions of heterocyclic paramagnetic aldonitrone, 2,2,5,5-tetramethyl-3-imidazoline-1-oxyl 3-oxide, with alkynes

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