ChemInform Abstract: RK. VON PYRANYLIDENPHOSPHORANEN MIT CARBONYLVERBINDUNGEN

Krivun, S. V.; Voziyanova, O. F.; Baranov, S. N.

doi:10.1002/chin.197223303

Cited by 4 publications

(5 citation statements)

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“…[52] Chromatographic purification was performed with Silicagel 60 (0.063-0.200 µm). 2,6-diphenyl-4H-pyran-4-yl triphenylphosphonium tetrafluoroborate 1, [43] ferrocenylmethylenepyran 5, [40] and phenylmethylenepyran 8, [53] were synthesized according to published procedures. quoted against the ferrocene-ferricenium redox couple; ferrocene was added as an internal standard at the end of each experiment [54].…”

Section: General Experimental Methodsmentioning

confidence: 99%

Anisyl and ferrocenyl adducts of methylenepyran-containing β-diketone: Synthesis, spectral, structural, and redox properties

Novoa¹,

Roisnel²,

Dorcet³

et al. 2014

Journal of Organometallic Chemistry

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International audienceWittig reaction between the in situ generated [2,6-diphenyl-4H-pyran-4-yl phosphorane and methyl 4-formylbenzoate afforded the methyl 4-[(2,6-diphenyl-4H-pyran-4-ylidene)methyl]benzoate precursor 2 in 75% yield. The anisyl and ferrocenyl adducts of methylenepyran-containing β-diketones 3 and 4, respectively, were prepared from the base-catalyzed Claisen condensation reaction between precursor 2 and 4-methoxyacetophenone or acetylferrocene, using t-BuO−K+ as basic initiator. Both β-diketones 3 and 4 were isolated as an orange and dark-red crystalline solids in 50% yield, respectively. The acetyl derivative 6, 1-acetyl-1′-methylenepyranyl-ferrocene, was synthesized following a classical Friedel-Crafts acylation reaction of the parent ferrocenylmethylenepyran 5, and isolated in 61% yield as a red microcrystalline powder. The condensation reaction between the electron-rich acetyl complex 6 and acetyl acetate, using lithium diisopropylamide as the active base initiator, provided the ferrocenylmethylenepyran-containing β-diketone, 1-(1,3-dioxobutyl)-1′-[(2,6-diphenyl-4H-pyran-4-ylidene)methyl] ferrocene 7, isolated in 20% yield as an orange powder. The composition and identity of the new compounds 2-4, 6 and 7 are supported by elemental analysis, FT-IR, one- and two-dimensional 1H and 13C NMR spectral data and mass spectrometry. Additionally, the molecular structures of compounds 2, 4 and 6 were ascertained by single-crystal X-ray diffraction study. FT-IR and NMR spectral data indicate that both β-diketones 3 and 4 do solely exist as their keto-enol tautomeric form in solution and in the solid state, whereas a mixture of keto-enol and β-diketone tautomers in a 73:27 spectroscopic ratio was observed for 7. In the three cases, enolization takes place exclusively away from the anisyl or ferrocenyl group with formation of a six-membered pseudo-aromatic keto-enol ring, confirmed by the crystal structure of 4. Cyclic voltammetric measurements revealed that all the compounds undergo a single one-electron oxidation, localized presumably at the methylenepyran unit. This first oxidation generates a radical cation that undergoes an intermolecular C-C bond coupling to form the corresponding dimer. Anodically shifted to the first oxidation, cyclovoltammogram of 4 exhibits one reversible two-electron oxidation while that of 6 and 7 present two successive reversible one-electron oxidations, attributed in the three cases to the ferrocenyl fragment of the dimer

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Section: General Experimental Methodsmentioning

confidence: 99%

Anisyl and ferrocenyl adducts of methylenepyran-containing β-diketone: Synthesis, spectral, structural, and redox properties

Novoa¹,

Roisnel²,

Dorcet³

et al. 2014

Journal of Organometallic Chemistry

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“…The redox behaviour of representative compounds ferrocenyl bispyran 2, pyridyl pyran 10 and phenylpyran 13 [24] (Fig. 1, R = R 0 = Ph) was investigated by cyclic voltammetry in CH 2 Cl 2 in the presence of Bu 4 NPF 6 as supporting electrolyte, to determine parameters which lead to the formation of extended bipyran via a radical cation, as observed for compound 1.…”

Section: Electrochemical Studiesmentioning

confidence: 99%

Ferrocenyl and pyridyl methylenepyrans as potential precursors of organometallic electron-rich extended bipyrans: Synthesis, characterization and crystal structure

Guen

Cabon

et al. 2010

Journal of Organometallic Chemistry

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“…All of the molecules include a 4 H -pyran-4-ylidene as the donor moiety, a thiophene ring as part of the conjugated π-system, and four common strong organic acceptors. Despite the fact that the thiophene ring is a very common heteroaromatic unit in push–pull systems, to our knowledge, there are only two papers in which the synthesis of a 4 H -pyran-4-ylidene derivative linked to a thiophene ring , is described. Although one of these papers concerns a study of the third-order nonlinearities, the second order NLO properties of such molecules remain unexplored.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Optical Properties of 4H-Pyran-4-ylidene Donor-Based Chromophores: The Relevance of the Location of a Thiophene Ring in the Spacer

et al. 2012

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A series of new 4H-pyran-4-ylidene donor-based chromophores with a thiophene ring in the spacer has been synthesized. The linear and nonlinear optical (NLO) properties of these compounds have been determined and compared with the results of computational calculations. The position of the thiophene ring proved essential to optimize the figure of merit μβ, with the best results obtained when the heterocyclic system was closer to the donor moiety.

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ChemInform Abstract: RK. VON PYRANYLIDENPHOSPHORANEN MIT CARBONYLVERBINDUNGEN

Abstract: Zu einer Suspension von tert.‐Kaliumbutylat in Äther gibt man bei ‐30°C unter Stickstoff ein absolut trockenes Pyranyltriphenylphosphoniumsalz ( ;z.B. Perchlorat) (I).

Cited by 4 publications

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Anisyl and ferrocenyl adducts of methylenepyran-containing β-diketone: Synthesis, spectral, structural, and redox properties

Anisyl and ferrocenyl adducts of methylenepyran-containing β-diketone: Synthesis, spectral, structural, and redox properties

Ferrocenyl and pyridyl methylenepyrans as potential precursors of organometallic electron-rich extended bipyrans: Synthesis, characterization and crystal structure

Synthesis, Characterization, and Optical Properties of 4H-Pyran-4-ylidene Donor-Based Chromophores: The Relevance of the Location of a Thiophene Ring in the Spacer

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