NDLI: Synthesis and structure of the first clathrochelate iron(II) tris-dioximates with inherent nitrile substituent(s) and new dehalogenation – reduction reaction at a quasi-aromatic macrobicyclic framework

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Synthesis and structure of the first clathrochelate iron(II) tris-dioximates with inherent nitrile substituent(s) and new dehalogenation – reduction reaction at a quasi-aromatic macrobicyclic framework

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Synthesis and structure of the first clathrochelate iron(II) tris-dioximates with inherent nitrile substituent(s) and new dehalogenation – reduction reaction at a quasi-aromatic macrobicyclic framework

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Lebed, Ekaterina G. Bubnov, Yurii N. Stuzhin, Pavel A. Varzatskii, Oleg A. Shul'ga, Sergey V. Belov, Alexander S. Voloshin, Yan Z. Starikova, Zoya A.
Description	Author Affiliation: Voloshin YZ ( A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, 119991, Moscow, Russian Federation. voloshin@ineos.ac.ru)
Abstract	Monoribbed-substituted mono- and dicyano-functionalized iron(II) macrobicycles were obtained for the first time by the reaction of iron(II) diiodoclathrochelate precursor with copper( I) cyanide –triphenylphosphine complex under mild conditions. The target dinitrile clathrochelate is a minor product of this reaction, whereas the major product contains only one cyano group . The clathrochelates obtained were characterized using elemental analysis , $^{1}H$ and $^{13}C\{^{1}H\}$ NMR , IR and UV-vis spectroscopy , MALDI-TOF spectrometry and X-ray diffraction crystallography . The geometry of their $FeN_{6}-coordination$ polyhedra is intermediate between a trigonal prism (TP) and a trigonal antiprism (TAP); the distortion angles, φ, are 22.6–24.7°. In the molecule of the precursor, the Fe–N distances are close, whereas in the mononitrile macrobicycles those for their functionalized chelate fragments are substantially smaller than the corresponding distances in the α-benzyldioximate moieties. The heights, h, of the TP–TAP coordination polyhedra and the average bite angles, α, (2.33 Å and 39°, respectively) are the same for the X-rayed clathrochelates. The UV-vis spectra indicate a dramatic redistribution of the electron density in the π-conjugated clathrochelate framework caused by functionalization with inherent nitrile substituents. The proposed mechanism of the dehalogenation–reduction reaction of iron(II) diiodoclathrochelate resulting in substitution of their iodine atoms by a cyano group and hydrogen atom includes the anion-radical hydrodehalogenation of this precursor with acetonitrile as a source of hydrogen atom. Then, the monomethinemonoiodine macrobicyclic product underwent a substitution with a cyano group only. The copper( I) cyanide – triphenylphosphine –acetonitrile system is proposed as a tool for the synthesis of nitrile derivatives of electron-withdrawing heterocycles starting from their halogen-containing precursors.
ISSN	14779226
Issue Number	3
Journal	Dalton Trans.
Volume Number	41
e-ISSN	13645447
Language	English
Publisher	Royal Society of Chemistry
Publisher Date	2012-01-21
Publisher Place	Great Britain (UK)
Access Restriction	Subscribed
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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