Dimephosphone analogs: II. Dialkyl(diaryl)-(2-methyl-4-oxopent-2-yl)phosphine oxide oximes: Synthesis, structure, and generation of iminoxyl radicals

Татаринов, Д. А.; Миронов, В. Ф.; Kostin, A. A.; Миронова, Е. В.; Krivolapov, Dmitry B.; Морозов, В. И.; Набиуллин, В. Н.; Il'yasov, A. V.; Бузыкин, Б. И.

doi:10.1134/s107036321405020x

Cited by 4 publications

(1 citation statement)

References 14 publications

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“…Meanwhile, the “P–C analogues” of the γ‐ketophosphonates, that is, γ‐ketophosphine oxides as well as –phosphine sulfides and selenides, are much less studied. Although these compounds, due to the combination of the C=O and P=X functions in a one molecule, are rare functionalized reactive intermediates and efficient extractants of lanthanides and actinides . Thus, development of general and efficient synthetic approaches to γ‐ketophosphine chalcogenides starting from easily accessible compounds is a challenging task.…”

Section: Introductionmentioning

confidence: 99%

An Expedient Access to γ‐Ketophosphine Chalcogenides via the Chemo‐ and Regioselective Addition of Secondary Phosphine Chalcogenides to β,γ‐Ethylenic Ketones

Artem’ev

Малышева

Белогорлова

et al. 2015

Heteroatom Chemistry

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γ‐Ketophosphine chalcogenides, precursors for plethora of novel functionalized phosphine chalcogenides and phosphines, are synthesized by chemo‐ and regioselective addition of secondary phosphine chalcogenides to β,γ‐ethylenic ketones under catalyst‐ and solvent‐free conditions (80–100°C, 8–70 h) in excellent yields. The straightforward superbase‐catalyzed synthesis of starting β,γ‐ethylenic ketones from ketones and acetylenes insures the expedient access to the target γ‐ketophosphine chalcogenides.

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Section: Introductionmentioning

confidence: 99%

An Expedient Access to γ‐Ketophosphine Chalcogenides via the Chemo‐ and Regioselective Addition of Secondary Phosphine Chalcogenides to β,γ‐Ethylenic Ketones

Artem’ev

Малышева

Белогорлова

et al. 2015

Heteroatom Chemistry

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α‐Oxo‐Iminoxyls of Isoxazolones, Pyrazolones and 1,2,3‐Triazolone

et al. 2015

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A series of α‐oxo‐iminoxyls was obtained by PbO2 oxidation of 4‐oximinoisoxazol‐5(4H)‐ones, 4‐oximinopyrazol‐5(4H)‐ones, and 1‐phenyl‐4‐oximino‐1,2,3‐triazol‐5(4H)‐one and characterized by electron spin resonance spectroscopy in conjunction with DFT calculations of structures, energies, and hyperfine coupling constants. The iminoxyls are σ‐radicals existing largely in the Z configuration with respect to the C=O group, but minor amounts of the E isomers were observable in several cases. Couplings of the free‐radical electron with N1, N2, N3, C4 and C5 ring nuclei as well as the imine nitrogen N6 were observed, and some isomers were also observed to couple with a CH3 group in position 3 and with the ortho‐H atoms of an aryl group in position 3. The lower energies of the Z isomers relative to the E isomers can be ascribed to a stabilizing interaction between a singly occupied orbital on the oxime oxygen and a lone pair orbital on the carbonyl oxygen.

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Spectroelectrochemical Investigation of Nuclease Active Pt(II) Complexes Containing Pyrrole Oxime†

Erdogan

Kayı

Özalp-Yaman

2015

Electrochimica Acta

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Dimephosphone analogs: II. Dialkyl(diaryl)-(2-methyl-4-oxopent-2-yl)phosphine oxide oximes: Synthesis, structure, and generation of iminoxyl radicals

Cited by 4 publications

References 14 publications

An Expedient Access to γ‐Ketophosphine Chalcogenides via the Chemo‐ and Regioselective Addition of Secondary Phosphine Chalcogenides to β,γ‐Ethylenic Ketones

An Expedient Access to γ‐Ketophosphine Chalcogenides via the Chemo‐ and Regioselective Addition of Secondary Phosphine Chalcogenides to β,γ‐Ethylenic Ketones

α‐Oxo‐Iminoxyls of Isoxazolones, Pyrazolones and 1,2,3‐Triazolone

Spectroelectrochemical Investigation of Nuclease Active Pt(II) Complexes Containing Pyrrole Oxime†

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Dimephosphone analogs: II. Dialkyl(diaryl)-(2-methyl-4-oxopent-2-yl)phosphine oxide oximes: Synthesis, structure, and generation of iminoxyl radicals

Cited by 4 publications

References 14 publications

An Expedient Access to γ‐Ketophosphine Chalcogenides via the Chemo‐ and Regioselective Addition of Secondary Phosphine Chalcogenides to β,γ‐Ethylenic Ketones

An Expedient Access to γ‐Ketophosphine Chalcogenides via the Chemo‐ and Regioselective Addition of Secondary Phosphine Chalcogenides to β,γ‐Ethylenic Ketones

α‐Oxo‐Iminoxyls of Isoxazolones, Pyrazol­ones and 1,2,3‐Triazolone

Spectroelectrochemical Investigation of Nuclease Active Pt(II) Complexes Containing Pyrrole Oxime†

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α‐Oxo‐Iminoxyls of Isoxazolones, Pyrazolones and 1,2,3‐Triazolone