Clathrochelate monoribbed-functionalized iron(ii) α-dioximates: synthetic pathways and structural and electrochemical features

Voloshin, Yan Z.; Zavodnik, V. E.; Varzatskii, Оleg А.; Belsky, V. K.; Palchik, Aleksei V.; Strizhakova, Nataly G.; Vorontsov, Ivan I.; Antipin, M. Yu.

doi:10.1039/b107021p

Cited by 81 publications

(44 citation statements)

References 30 publications

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“…The monotetrahydrofuryl substituted clathrochelate FeBd 2 (Cl(THF)Gm)(BF) 2 was obtained in a good yield by the reflux of the macrobicyclic precursor in tetrahydrofuran in the presence of tert-butylhydroperoxide as a radical initiator. The benzoyl peroxide and 1,1'-azo-bis(cyclohexane-1-carbnitrile) (VAZO catalyst 88) also can be used as the radical initiators (Table 2).…”

Section: Resultsmentioning

confidence: 99%

“…The reaction studied has a high regioselectivity; the total yield of the clathrochelate complexes isolated after this reaction (the sum of the precursor FeBd 2 (Cl 2 Gm)(BF) 2 and the only resulting macrobicycle FeBd 2 (Cl(THF)Gm)(BF) 2 ) is approximately 95-98% (100% corresponds to the initial amount of the dichloroclathrochelate precursor). This result was explained by the stabilization of the tetrahydrofur-2-yl radical by the adjacent oxygen atom.…”

Section: Discussionmentioning

confidence: 99%

“…The clathrochelate precursor FeBd 2 (Cl 2 Gm)(BF) 2 was obtained as described in [2] . 3,6,10,13,16,19-hexaaza-4,5,11,12-tetraphenyl-17-chloro-18-(2-tetrahydrofuryl)bicyclo [6.6.6]eicosa -3,5,10,12,16,18-hexaen(2-) iron(2+), FeBd 2 (Cl(THF)Gm)(BF) 2 (a typical procedure).…”

Section: Methodsmentioning

confidence: 99%

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Free-radical Reaction of the Iron(II) Dichloroclathrochelate with Tetrahydrofurane Radical Derivatives: Synthesis and Structure of the Monotetrahydrofuryl-Containing Cage Complex

Vershinin¹,

Бурдуков²,

Первухина³

et al. 2012

MHC

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Free-radical substitution of the chlorine atoms in the fluoroboron-capped iron(II) dichloroclathrochelate with tetrahydrofuran radical derivatives was studied. The reaction proceeds with high regioselectivity and yields the monofunctionalized macrobicyclic product. The molecular structure of this complex was determined both in solution and in the solid state using multinuclear NMR and the single-crystal X-ray diffraction.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Free-radical Reaction of the Iron(II) Dichloroclathrochelate with Tetrahydrofurane Radical Derivatives: Synthesis and Structure of the Monotetrahydrofuryl-Containing Cage Complex

Vershinin¹,

Бурдуков²,

Первухина³

et al. 2012

MHC

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“…The iron(II) mono-and bis-clathrochelates under study were obtained as described previously. [4,32,[37][38][39][40][41][42] ESI-MS were obtained on a Bruker MicrOTOF-Q spectrometer equipped with an Apollo II electrospray ionization source with an ion funnel. The instrumental parameters were .…”

Section: Methodsmentioning

confidence: 99%

“…[29][30][31] We thus aimed on studying cation-receptor properties of halogen-containing iron(II) mono-and bis-clathrochelates (Scheme 1) having from two (FeBd 2 (Cl 2 Gm)(BF) 2 , FeBd 2 (Br 2 Gm)(BF) 2 , FeBd 2 (I 2 Gm) (BF) 2 , {FeBd 2 (BrGm)(BF) 2 } 2 and {FeBd 2 (IGm)(BF) 2 } 2 ) to six (Fe(Cl 2 Gm) 3 (Bn-C 4 H 9 ) 2 ) chlorine atoms in their chelate α-dioximate fragments. Note that these reactive compounds have been earlier recognized as convenient macrobicyclic precursors for their further functionalization with N,O,C,Snucleophiles [3,24,27,[29][30][31][32][33][34][35][36][37][38] (including those with ionophoric, pharmacophoric and fluorophoric groups), and for the design of hybride and multicentered compounds. [24,27,28] Here we also describe the cation-receptor properties of their dimethyl-and diamine-containing clathrochelate analogs FeBd 2 Dm(BF) 2 …”

Section: Introductionmentioning

confidence: 99%

ESI-MS Study of Ionization Pathways and Cation-Receptor Properties of the Iron(II) Mono- and Bis-Clathrochelates

Varzatskii¹,

Shul’ga²,

Kozłowski³

et al. 2014

MHC

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Ionization pathways of iron(II) di-and hexachloromonoclathrochelates, bis-clathrochelates and their oximehydrazonate, dimethyl-and diamine-containing macrobicyclic analogs, and the cation-receptor properties of such cage compounds towards alkali metal cations (as individual ions or their mixtures) as well as the competitive complexation in the presence of 18-crown-6 were studied by ESI-MS method. Ionization of iron(II) mono-and bis-clathrochelates under the conditions of ESI-MS experiments was found to proceed via different pathways. The macrobicyclic iron(II

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Iron: Inorganic & Coordination ChemistryBased in part on the article Iron: Inorganic & Coordination Chemistry by Pelham N. Hawker & Martyn V. Twigg which appeared in theEncyclopedia of Inorganic Chemistry, First Edition.

Burgess

Twigg

2005

Encyclopedia of Inorganic Chemistry

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Iron, the most abundant transition element in the biosphere, is essential in higher forms of life and its compounds have numerous industrial applications. The element has catalytic properties. Several simple iron compounds are industrially important, for example, large amounts of iron oxides are produced for pigment and magnetic recording media applications. Oxidation states ranging from −2 to +6 are known, the most familiar are +2 (ferrous iron) and +3 (ferric iron). Most common complexes are octahedral, although examples of higher (e.g. seven coordinate) and lower (e.g. tetrahedral and square planar) geometries are well known, as are a variety of mixed oxidation state compounds. Depending on ligands involved high‐ and low‐spin complexes can be formed, and temperature‐dependent spin‐state crossover complexes are well documented. The thermodynamics and kinetics of reactions of low‐spin iron(II) complexes with ligands such as 1,4‐diimines and CN − have been extensively studied. While low‐spin iron(II) is present in biological systems such as oxygenated heme centered oxygen carriers and thiolate clusters, iron(III) is more common. Thiolate‐containing iron clusters form readily, and here mixed oxidation states are a prominent feature that is exploited in some important electron transfer proteins. Microorganism iron uptake is facilitated by tris‐catecholate and tris‐hydroxamate ligands like enterobactin that have an extraordinarily high affinity for iron(III) that results in a dramatic enhancement of the 3+ relative to the 2+ state in terms of redox potential.

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Clathrochelate monoribbed-functionalized iron(ii) α-dioximates: synthetic pathways and structural and electrochemical features

Cited by 81 publications

References 30 publications

Free-radical Reaction of the Iron(II) Dichloroclathrochelate with Tetrahydrofurane Radical Derivatives: Synthesis and Structure of the Monotetrahydrofuryl-Containing Cage Complex

Free-radical Reaction of the Iron(II) Dichloroclathrochelate with Tetrahydrofurane Radical Derivatives: Synthesis and Structure of the Monotetrahydrofuryl-Containing Cage Complex

ESI-MS Study of Ionization Pathways and Cation-Receptor Properties of the Iron(II) Mono- and Bis-Clathrochelates

Iron: Inorganic & Coordination ChemistryBased in part on the article Iron: Inorganic & Coordination Chemistry by Pelham N. Hawker & Martyn V. Twigg which appeared in theEncyclopedia of Inorganic Chemistry, First Edition.

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