A mu(4)-oxide-containing a dimeric variant of a sodium dialkyl(amido)zincate reagent

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Abstract

Post-metallation derivatives of the sodium dialkyl(amido)zincate reagent (TMEDA) Na(mu-TMP)Zn(Bu-t)(2) (TMEDA is N,N,N',N'-tetramethylethylenediamine and TMP is 2,2,6,6-tetramethylpiperidide) have been of structural interest due to the insight they give into aromatic metallation mechanisms. Here, the aromatic substrate is formally replaced with [ZnO](2) to give tetra-tert-butyldi-mu(4)-oxido-bis(tetramethylethylenediamine-kappa N-2,N')bis(mu(2)-2,2,6,6-tetramethylpiperidin-1-ido-kappa N-2:N)-disodiumtetrazinc hexane 0.59-solvate, [Na2Zn4(C4H9)(4)-(C9H18N)(2)O-2(C6H16N2)(2)]center dot 0.59C(6)H(14). The crystallographically centrosymmetric complex retains many of the structural features of its parent monomer but has an unusual dimeric structure, with a central planar Zn-O-Zn-O ring joined to two orthogonal near-planar Zn-O-Na-N rings through the distorted tetrahedral geometries of the oxide ions.

LanguageEnglish
PagesM252-M254
Number of pages3
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume67
Issue number7
DOIs
Publication statusPublished - Jul 2011

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Thymidine Monophosphate
Oxides
Sodium
O rings
Hexanes
Monomers
Ions
Derivatives
Geometry
Substrates
N,N,N',N'-tetramethylethylenediamine
phenyllithium
2,2,6,6-tetramethylpiperidide

Keywords

  • structural basis
  • metalation
  • zincation
  • amide

Cite this

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title = "A mu(4)-oxide-containing a dimeric variant of a sodium dialkyl(amido)zincate reagent",
abstract = "Post-metallation derivatives of the sodium dialkyl(amido)zincate reagent (TMEDA) Na(mu-TMP)Zn(Bu-t)(2) (TMEDA is N,N,N',N'-tetramethylethylenediamine and TMP is 2,2,6,6-tetramethylpiperidide) have been of structural interest due to the insight they give into aromatic metallation mechanisms. Here, the aromatic substrate is formally replaced with [ZnO](2) to give tetra-tert-butyldi-mu(4)-oxido-bis(tetramethylethylenediamine-kappa N-2,N')bis(mu(2)-2,2,6,6-tetramethylpiperidin-1-ido-kappa N-2:N)-disodiumtetrazinc hexane 0.59-solvate, [Na2Zn4(C4H9)(4)-(C9H18N)(2)O-2(C6H16N2)(2)]center dot 0.59C(6)H(14). The crystallographically centrosymmetric complex retains many of the structural features of its parent monomer but has an unusual dimeric structure, with a central planar Zn-O-Zn-O ring joined to two orthogonal near-planar Zn-O-Na-N rings through the distorted tetrahedral geometries of the oxide ions.",
keywords = "structural basis, metalation, zincation, amide",
author = "Liam Balloch and Kennedy, {Alan R.} and Mulvey, {Robert E.} and Robertson, {Stuart D.}",
year = "2011",
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doi = "10.1107/S0108270111022645",
language = "English",
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journal = "Acta Crystallographica Section C: Crystal Structure Communications",
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T1 - A mu(4)-oxide-containing a dimeric variant of a sodium dialkyl(amido)zincate reagent

AU - Balloch, Liam

AU - Kennedy, Alan R.

AU - Mulvey, Robert E.

AU - Robertson, Stuart D.

PY - 2011/7

Y1 - 2011/7

N2 - Post-metallation derivatives of the sodium dialkyl(amido)zincate reagent (TMEDA) Na(mu-TMP)Zn(Bu-t)(2) (TMEDA is N,N,N',N'-tetramethylethylenediamine and TMP is 2,2,6,6-tetramethylpiperidide) have been of structural interest due to the insight they give into aromatic metallation mechanisms. Here, the aromatic substrate is formally replaced with [ZnO](2) to give tetra-tert-butyldi-mu(4)-oxido-bis(tetramethylethylenediamine-kappa N-2,N')bis(mu(2)-2,2,6,6-tetramethylpiperidin-1-ido-kappa N-2:N)-disodiumtetrazinc hexane 0.59-solvate, [Na2Zn4(C4H9)(4)-(C9H18N)(2)O-2(C6H16N2)(2)]center dot 0.59C(6)H(14). The crystallographically centrosymmetric complex retains many of the structural features of its parent monomer but has an unusual dimeric structure, with a central planar Zn-O-Zn-O ring joined to two orthogonal near-planar Zn-O-Na-N rings through the distorted tetrahedral geometries of the oxide ions.

AB - Post-metallation derivatives of the sodium dialkyl(amido)zincate reagent (TMEDA) Na(mu-TMP)Zn(Bu-t)(2) (TMEDA is N,N,N',N'-tetramethylethylenediamine and TMP is 2,2,6,6-tetramethylpiperidide) have been of structural interest due to the insight they give into aromatic metallation mechanisms. Here, the aromatic substrate is formally replaced with [ZnO](2) to give tetra-tert-butyldi-mu(4)-oxido-bis(tetramethylethylenediamine-kappa N-2,N')bis(mu(2)-2,2,6,6-tetramethylpiperidin-1-ido-kappa N-2:N)-disodiumtetrazinc hexane 0.59-solvate, [Na2Zn4(C4H9)(4)-(C9H18N)(2)O-2(C6H16N2)(2)]center dot 0.59C(6)H(14). The crystallographically centrosymmetric complex retains many of the structural features of its parent monomer but has an unusual dimeric structure, with a central planar Zn-O-Zn-O ring joined to two orthogonal near-planar Zn-O-Na-N rings through the distorted tetrahedral geometries of the oxide ions.

KW - structural basis

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