Syntheses, Structures and Reactivity of New Intramolecularly Coordinated Tin Alkoxides Based on an Enantiopure Ephedrine Derivative

Iovkova‐Berends, Ljuba; Berends, Thorsten; Dietz, Christina; Bradtmöller, Gerrit; Schollmeyer, Dieter; Jurkschat, Klaus

doi:10.1002/ejic.201100352

Cited by 33 publications

(35 citation statements)

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“…Especially the coordination mode about the tin atom and the strength of the intramolecular N→Sn coordination as a function of the identity of the substituents R and R′ were studied . With growing environmental awareness, nontoxic inorganic tin compounds lacking any tin–carbon bonds are in the focus of research . Amino alcoholate derivatives of tin are such inorganic compounds.…”

Section: Introductionmentioning

confidence: 99%

“…In continuation of our systematic studies on amino alcohol derivatives of tin, herein we report a combined experimental and theoretical approach to symmetrical and unsymmetrical spirocyclic tin(IV) amino alcoholates and study in detail the factors that control the coordination environment about the central tin atoms. In all spirocyclic tin compounds published so far, such as spiro ‐[MeN(CH 2 CMe 2 O) 2 ] 2 Sn, the nitrogen atoms are cis .…”

Section: Introductionmentioning

confidence: 99%

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CisversusTrans: The Coordination Environment about the Tin(IV) Atom in Spirocyclic Amino Alcohol Derivatives

Glowacki

Pallach

Lutter

et al. 2018

Chemistry A European J

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The syntheses of amino alcohols MeN(CH2CH2CMe2OH)2 (1), MeN(CMe2CH2OH)(CH2CMe2OH) (2), MeN(CH2CH2CH2OH)(CH2CMe2OH) (3), MeN(CH2CH2CMe2OH)(CH2CMe2OH) (4), MeN(CH2CH2CMe2OH)(CH2CH2OH) (5), and MeN(CH2CH2OH) (CH2CH2CH2OH) (6) as well as spirocyclic tin(IV) alkoxides spiro‐[nBuN(CH2CMe2O)2]2Sn (7), spiro‐[MeN(CH2CH2CMe2O)2]2Sn (8), spiro‐[para‐FC6H4N (CH2CMe2O)2]2Sn (9), spiro‐[MeN(CMe2CH2O)(CH2CMe2O)]2Sn (10), spiro‐[MeN(CH2CH2CH2O)(CH2CMe2O)]2Sn (11), spiro‐[MeN(CH2CH2CMe2O)(CH2CMe2O)]2Sn (12), spiro‐[MeN(CH2CH2CMe2O)(CH2CH2O)]2Sn (13) and spiro‐[MeN(CH2CH2O)(CH2CH2CH2O)]2Sn (14) are reported. The compounds were characterized by 1H, 13C (1–14) and 119Sn (7–14) NMR and IR spectroscopy, EIMS and single‐crystal XRD (2, 7–10 and 13, 14). Graph‐set analyses were performed for compounds [(MeNH(CMe2CH2OH)(CH2CMe2OH)][HC(O)O] (2 a) and 2. The coordination environment about the tin(IV) centre of the spirocyclic compounds and their possible stereoisomers were analysed by DFT calculations (spiro‐[MeN(CH2CMe2O)2]2Sn, 8–10 and 13).

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

CisversusTrans: The Coordination Environment about the Tin(IV) Atom in Spirocyclic Amino Alcohol Derivatives

Glowacki

Pallach

Lutter

et al. 2018

Chemistry A European J

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“…68.58 (7) 69.64 (6) 70.66 (7) 69.88 (12) 71.00 (13) 70.06(6) O(11)-Sn(1)-N (14) 71.49 (6) 71.43 (5) 75.68 (7) 76.22 (11) 76.30 (13) 75.01 (7) O (17)…”

Section: Resultsmentioning

confidence: 99%

“…89.39 (7) 88.47 (5) 82.79 (7) 88.66 (13) 88.70 (12) 84.01 (7) O(17)-Sn(1)-N (14) 75.10 (7) 76.22 (5) 76.26 (8) 78.47 (13) 77.48 (14) 78.11 (7) O(X)-Sn(1)-N (14) 131.70 (6) 135.05 (5) 130.40 (7) 138.14 (11) 138.99 (13) 129.42 (7) M(1)-Sn(1)-O (11) 120.51 (5) 130.43 (8) 131.83 (9) 123.15(5) M(1)-Sn(1)- O(17) 128.62 (6) 122.38 (13) 120.77 (10) 122.43 (5) …”

Section: Resultsmentioning

confidence: 99%

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Trapping Molecular SnBr₂(OH)₂ by Tin Alkoxide Coordination: Syntheses and Molecular Structures of [MeN(CH₂CMe₂O)₂SnBr₂]₂·SnBr₂(OH)₂ and RN(CH₂CMe₂O)₂SnL [R = Me, n‐Octyl; L = Lone Pair, Cr(CO)₅, W(CO)₅, Fe(CO)₄, Br₂]

et al. 2012

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The synthesis of the intramolecularly coordinated stannylenes and their transition-metal complexes of the type RN(CH 2 CMe 2 O) 2 SnL [1: L = lone pair, R = Me; 2: L = lone pair, R = n-octyl; 5: L =W(CO) 5 , R = Me; 6: L = Cr(CO) 5 , R = Me; 7: L =W(CO) 5 , R = n-octyl; 8: L = Fe(CO) 4 , R = Me], and of the tin(IV) compounds RN(CH 2 CMe 2 O) 2 SnBr 2 (9: R = Me), [a] 3463 [MeN(CH 2 CMe 2 O) 2 SnBr 2 ] 2 ·SnBr 2 (OH) 2 (10) and spiro-[RN(CH 2 CMe 2 O) 2 ] 2 Sn (3: R = Me; 4: R = n-octyl) is reported. The compounds were characterized by elemental analyses, 1 H, 13 C, 119 Sn, and 119 Sn magic-angle spinning (5, 6) NMR spectroscopy, electrospray mass spectrometry, and singlecrystal X-ray diffraction analysis. exhibit superior crystallization properties. They also enabled the isolation of an unprecedented trinuclear Sn-O cluster. www.eurjic.org 3469 119 Sn MAS Spectroscopy: The 119 Sn MAS NMR spectra were recorded with a Bruker Avance III 400 spectrometer using cross polarization and high-power proton decoupling [conditions: 3.7 μS (90°) pulse, 2 ms contact time, 10 s recycle delay]. For compounds Eur.

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Stable heterocyclic stannylene: The metal, ligand‐centered reactivity, and effective catalytic hydroboration of aldehydes

Arsenyeva

Klimashevskaya

Pashanova

et al. 2022

Applied Organom Chemis

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A stable O,N‐heterocyclic stannylene 1 bearing novel tetradentate 2,4‐di‐tert‐butyl‐6‐((2‐(1‐((pyridin‐2‐ylmethyl)imino)ethyl)phenyl)amino)phenolate ligand (RAPH2) was synthesized and characterized. Complex 1 is monomeric in crystal and solution due to two additional intramolecular N → Sn donor–acceptor interactions. The diverse reactivity of compound 1 towards various iron carbonyl compounds was studied. Oxidative addition of [Fe2(μ‐S2)(CO)6]2 to the tin center of 1 resulted in a new six‐coordinate Sn(IV) compound 2 containing two Sn–S bonds. The reaction of 1 with Fe2(CO)9 led to the formation of a stable tin(II) adduct 3 – RAPSn‐Fe(CO)4. The interaction between 1 and [(η5‐C5H5)Fe(CO)2]2 resulted in a transformation of the ligand skeleton. During this reaction, the tin center is oxidized to the tetravalent state, and the donor ═N–CH2–Py group is converted into an anionic one with the loss of the methylene hydrogen atom. The molecular structures of all obtained compounds were determined by single‐crystal X‐ray diffraction. The novel stannylene 1 demonstrates striking activity in benzaldehydes' hydroboration reactions down to 0.02 mole percent of the catalyst loading under mild conditions.

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Syntheses, Structures and Reactivity of New Intramolecularly Coordinated Tin Alkoxides Based on an Enantiopure Ephedrine Derivative

Cited by 33 publications

References 25 publications

CisversusTrans: The Coordination Environment about the Tin(IV) Atom in Spirocyclic Amino Alcohol Derivatives

CisversusTrans: The Coordination Environment about the Tin(IV) Atom in Spirocyclic Amino Alcohol Derivatives

Trapping Molecular SnBr₂(OH)₂ by Tin Alkoxide Coordination: Syntheses and Molecular Structures of [MeN(CH₂CMe₂O)₂SnBr₂]₂·SnBr₂(OH)₂ and RN(CH₂CMe₂O)₂SnL [R = Me, n‐Octyl; L = Lone Pair, Cr(CO)₅, W(CO)₅, Fe(CO)₄, Br₂]

Stable heterocyclic stannylene: The metal, ligand‐centered reactivity, and effective catalytic hydroboration of aldehydes

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Syntheses, Structures and Reactivity of New Intramolecularly Coordinated Tin Alkoxides Based on an Enantiopure Ephedrine Derivative

Cited by 33 publications

References 25 publications

CisversusTrans: The Coordination Environment about the Tin(IV) Atom in Spirocyclic Amino Alcohol Derivatives

CisversusTrans: The Coordination Environment about the Tin(IV) Atom in Spirocyclic Amino Alcohol Derivatives

Trapping Molecular SnBr2(OH)2 by Tin Alkoxide Coordination: Syntheses and Molecular Structures of [MeN(CH2CMe2O)2SnBr2]2·SnBr2(OH)2 and RN(CH2CMe2O)2SnL [R = Me, n‐Octyl; L = Lone Pair, Cr(CO)5, W(CO)5, Fe(CO)4, Br2]

Stable heterocyclic stannylene: The metal, ligand‐centered reactivity, and effective catalytic hydroboration of aldehydes

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Trapping Molecular SnBr₂(OH)₂ by Tin Alkoxide Coordination: Syntheses and Molecular Structures of [MeN(CH₂CMe₂O)₂SnBr₂]₂·SnBr₂(OH)₂ and RN(CH₂CMe₂O)₂SnL [R = Me, n‐Octyl; L = Lone Pair, Cr(CO)₅, W(CO)₅, Fe(CO)₄, Br₂]