pentakis(dimethylamido)tantalum
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| ImageFile = Ta(NMe2)5.png
| ImageSize =
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| IUPACName = Tantalum(V) dimethylazanide
| OtherNames = Pentakis(dimethylamino)tantalum(V), Tantalum dimethylamide
|Section1={{Chembox Identifiers
| CASNo = 19824-59-0
| PubChem = 140614
| ChemSpiderID = 124019
| InChIKey = VSLPMIMVDUOYFW-UHFFFAOYSA-N
| InChI=1S/5C2H6N.Ta/c5*1-3-2;/h5*1-2H3;/q5*-1;+5
| SMILES = C[N-]C.C[N-]C.C[N-]C.C[N-]C.C[N-]C.[Ta+5]}}
|Section2={{Chembox Properties
| Ta=1|N=5|C=10|H=30
| MolarMass =
| Appearance = orange powder (xtl)
| Density =
| MeltingPt = 100 °C
| BoilingPt =
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|Section3={{Chembox Hazards
| ExternalSDS =
| GHSPictograms = {{GHS02}}{{GHS05}}
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| FlashPt =
| AutoignitionPt = }}
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Pentakis(dimethylamido)tantalum is an organometallic compound of tantalum. It is a colorless solid that is soluble in organic solvents. It hydrolyzes readily to release dimethylamine.
Synthesis and structure
Ta(NMe2)5 is prepared by treating TaCl5 with lithium dimethylamide.{{Cite journal|last1=Bradley|first1=D. C.|last2=Thomas|first2=I. M.|date=1962-07-01|title=Metallo-Organic Compounds Containing Metal–Nitrogen Bonds: Part Iii. Dialkylamino Compounds of Tantalum|journal=Canadian Journal of Chemistry|volume=40|issue=7|pages=1355–1360|doi=10.1139/v62-207|issn=0008-4042|doi-access=free}} The preparation is similar to that for tetrakis(dimethylamido)titanium.
The compound has idealized D3h symmetry (ignoring the organic substituents).
Applications to organic synthesis
{{main|Organotantalum chemistry}}
The complex effects C-alkylation of secondary amines with 1-alkenes {{Cite journal|last1=Clerici|first1=Mario G.|last2=Maspero|first2=Federico|date=1980-01-01|title=CatalyticC-Alkylation of Secondary Amines with Alkenes|journal=Synthesis|language=en|volume=1980|issue=4|pages=305–306|doi=10.1055/s-1980-29002|s2cid=94579838 |issn=0039-7881}} and hydroaminoalkylation of olefins to form alkylamines.{{Cite journal|last1=Herzon|first1=Seth B.|last2=Hartwig|first2=John F.|date=2007-05-01|title=Direct, Catalytic Hydroaminoalkylation of Unactivated Olefins with N-Alkyl Arylamines|journal=Journal of the American Chemical Society|volume=129|issue=21|pages=6690–6691|doi=10.1021/ja0718366|issn=0002-7863|pmc=2590937|pmid=17474747}}