Structural Organozinc Chemistry

Jastrzebski, Johann T. B. H.; Boersma, J.; Koten, Gerard van

doi:10.1002/9780470093399.ch2

Cited by 18 publications

(26 citation statements)

References 201 publications

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“…The mixed dialkyl(iminoaryl)tin(IV) chlorides, R′SnR 2 Cl [R′ = (E)-2-(2′,6′-i Pr 2 C 6 H 3 N=CH)C 6 H 4 ; R = Me (1), Bu 3] were obtained by reacting the in situ prepared Grignard reagent (E)-2-(2′,6′i Pr 2 C 6 H 3 N=CH)C 6 H 4 MgBr with R 2 SnCl 2 , in anhydrous THF. Halogen exchange reactions between 1 and 3 and excess of KX, carried out in CH 2 Cl 2 /H 2 O mixture, afforded the isolation of the corresponding R′SnR 2 X [R = Me, X = I (2); R = Bu, X = F (4), Br (5)] (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…Crystallographic data for the structural analysis of compounds 1-5 have been deposited with the Cambridge Crystallographic Data Centre [CCDC no. 871118 (1), 871120 (2), 871121 3, 871124 (4) and 871122 (5)]. Copies of the information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-1223-336033; e-mail: deposit@ccdc.cam.ac.uk or www: http:// www.ccdc.cam.ac.uk).…”

Section: Supplementary Materialsmentioning

confidence: 99%

“…Aromatic ligands with one or two pendant arms containing sp 3 nitrogen as donor atom, were extensively used in last years in the organotin chemistry. Such ligands include 2-(R 2 NCH 2 )C 6 H 4 (R = Me, 1 Et 2 ), 2-(Et 2 NCH 2 )-4,6-t Bu 2 C 6 H 2 , 3 2-[Me 2 NCH(R)]C 6 H 4 (R = Me, 4 t Bu 5 ) and 2,6-(Me 2 NCH 2 ) 2 C 6 H 3 . 6 In addition to stabilization of unusual, low-valent species which are important from fundamental point of view, some of the organotin compounds bearing such organic substituents were reported to exhibit biological 7 and catalytic properties.…”

Section: Introduction *mentioning

confidence: 99%

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Hypercoordinated organotin(IV) compounds containing (imino)aryl ligands - [(E)-2-(2′,6′-iPr2C6H3N=CH)C6H4]SnR2X (R = Me; X = Cl, I; R = nBu, X = Cl, F, Br). Molecular structures and supramolecular aspects

Comşa¹,

Varga²,

Soran³

et al. 2020

Rev.Roum.Chim.

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Five new dialkyl(iminoaryl)tin(IV) halides, [(E)-2-(2′,6′i Pr 2 C 6 H 3 N=CH)C 6 H 4 ]SnR 2 X [R = Me, X = Cl (1), I (2); R = n Bu, X = Cl (3), F (4), Br (5)], were prepared by reacting either [(E)-2-(2′,6′-i Pr 2 C 6 H 3 N=CH)C 6 H 4 ]MgBr with R 2 SnCl 2 for 1 and 3, or by halogen exchange reaction between the chlorides [(E)-2-(2′,6′-i Pr 2 C 6 H 3 N=CH)C 6 H 4 ]SnR 2 Cl with KX (X = I, F, Br) for 2, 4 and 5, respectively. The compounds were characterized by solution multinuclear (1 H, 13 C, 119 Sn) NMR spectroscopy and mass spectrometry. The crystal and molecular structure of all five compounds was established by single-crystal X-ray diffraction. The NMR data for 1-5 are consistent with the presence of an intramolecular N→Sn coordination which results in a trigonal bipyramidal (C,N)SnC 2 X core, similar with that observed in solid state. In the crystal of 1-5 different supramolecular architectures, based on intermolecular X•••H and C-H•••π (Ar centroid) interactions, were evidenced and discussed.

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Section: Resultsmentioning

confidence: 99%

Section: Supplementary Materialsmentioning

confidence: 99%

Section: Introduction *mentioning

confidence: 99%

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Hypercoordinated organotin(IV) compounds containing (imino)aryl ligands - [(E)-2-(2′,6′-iPr2C6H3N=CH)C6H4]SnR2X (R = Me; X = Cl, I; R = nBu, X = Cl, F, Br). Molecular structures and supramolecular aspects

Comşa¹,

Varga²,

Soran³

et al. 2020

Rev.Roum.Chim.

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“…In complexes of main group elements and the Zn triad, such processes have been studied largely in complexes of C,N ligands. [43][44][45][46][47][48][49] In the heterobimetallic Li/Rh complex shown in Fig. 10 48 the two, bridging ipso carbons are chiral.…”

Section: Hemilabile Ligands Without Redundant Donor Atomsmentioning

confidence: 99%

Dynamic stereochemical rearrangements in chiral organometallic complexes

Heard

2007

Chem. Soc. Rev.

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Organometallic complexes have long been known to display a wide variety of dynamic stereochemical processes. Classic examples of such processes include the exchange of axial and equatorial environments in trigonal bipyramidal complexes, such as Fe(CO)(5), and the migration of the metal moiety round the periphery of the cyclopentadiene ring in eta(1)-bound Cp complexes. The systematic study of fluxional processes is of interest because it can not only help provide a detailed, quantitative 'picture' of the bonding between the metals and ligands involved, but it can also help to rationalise chemical reactivity patterns. The introduction of chirality into organometallic complexes, usually in the form of a non-racemic chiral ligand, has led to an explosion in the importance such species, particularly with regard to their applications in organic functional group transformations. The presence of a chiral centre can also provide an excellent spectroscopic handle on the complex in question, enabling both novel fluxional processes to be observed and new light to be shed on old (unresolved) problems. In this critical review (101 references) the literature on metal-centred fluxional rearrangements in chiral transition and main group organometallic complexes is reviewed, complementing the recent review by Faller (see reference 8).

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“…[2-(Me 2 NCH 2 CH 2 NvCH)C 6 H 4 ] 4 Sn,4, Sn, which were obtained in excellent yield using a new and green synthetic procedure for the preparation of such organometallic species, i.e. condensation reactions of [2-(OvCH)C 6 H 4 ] 4 Sn and the corresponding primary amines in the absence of a solvent.…”

Section: Introductionmentioning

confidence: 99%

Di(imino)aryltin(iv) dichlorides as tectons for heterometallic coordination compounds

et al. 2013

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Hydrolysis of [2-{(CH2O)2CH}C6H4]2SnCl2 (1) [prepared from 2-[(CH2O)2CH]C6H4MgBr and SnCl4, in 2 : 1 molar ratio] gave [2-(O=CH)C6H4]2SnCl2 (2). Treatment of with the appropriate amine, in the absence of a solvent or catalyst, resulted in the isolation in high yields of [2-(RN[double bond, length as m-dash]CH)C6H4]2SnCl2 [R = 2'-C10H7 (3), 2',4',6'-Me3C6H2 (4), PhCH2 (5), Me2NCH2CH2 (6), 2'-PyCH2 (7)]. The reaction of with [Pd(COD)Cl2] provided the heterometallic species [Cl2Pd{2-(2'-PyCH2N[double bond, length as m-dash]CH)C6H4}2SnCl2] (8). The compounds were characterised by multinuclear NMR spectroscopy in solution, and mass spectrometry and IR spectroscopy in the solid state. The molecular structures of 1, 2, 4-7 and 8·CH3CN were established by single-crystal X-ray diffraction. For all diorganotin(IV) dichlorides intramolecular O→Sn or Nimine→Sn coordination results in hypercoordinated species with a distorted octahedral (C,E)2SnCl2 core (E = O, N). The presence of intramolecular N→Sn interactions in solution, responsible for the restriction of free rotation of mesityl groups around the C-N(=C) single bonds, is suggested by (1)H and (13)C NMR data. In the heterometallic dinuclear complex 8 the octahedral coordination around tin is preserved as in 7 and the nitrogen atoms from the pyridyl groups in the pendant arms are coordinated to palladium, leading to a trans-square planar PdCl2N2 core.

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Structural Organozinc Chemistry

Cited by 18 publications

References 201 publications

Hypercoordinated organotin(IV) compounds containing (imino)aryl ligands - [(E)-2-(2′,6′-iPr2C6H3N=CH)C6H4]SnR2X (R = Me; X = Cl, I; R = nBu, X = Cl, F, Br). Molecular structures and supramolecular aspects

Hypercoordinated organotin(IV) compounds containing (imino)aryl ligands - [(E)-2-(2′,6′-iPr2C6H3N=CH)C6H4]SnR2X (R = Me; X = Cl, I; R = nBu, X = Cl, F, Br). Molecular structures and supramolecular aspects

Dynamic stereochemical rearrangements in chiral organometallic complexes

Di(imino)aryltin(iv) dichlorides as tectons for heterometallic coordination compounds

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