Pentakis(dimethylamido)tantalum

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Pentakis(dimethylamido)tantalum
Ta(NMe2)5.png
Names
IUPAC name
dimethylazanide;tantalum(5+)
Other names
Pentakis(dimethylamino)tantalum(V), Tantalum dimethylamide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/5C2H6N.Ta/c5*1-3-2;/h5*1-2H3;/q5*-1;+5
    Key: VSLPMIMVDUOYFW-UHFFFAOYSA-N
  • C[N-]C.C[N-]C.C[N-]C.C[N-]C.C[N-]C.[Ta+5]
Properties
C10H30N5Ta
Molar mass 401.333 g·mol−1
Appearance white solid
Melting point 100 ºC
Hazards
GHS labelling:
GHS02: FlammableGHS05: Corrosive
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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[edit]

Ta(NMe2)5 is prepared by treating TaCl5 with lithium dimethylamide.[1] The preparation is similar to that for tetrakis(dimethylamido)titanium.

The compound has idealized D3h symmetry (ignoring the organic substituents).

Tantalumamidocomplexes.tif

Applications to organic synthesis[edit]

The complex effects C-alkylation of secondary amines with 1-alkenes [2] and hydroaminoalkylation of olefins to form alkylamines.[3]

Hydroaminoalkylation Reaction Scheme

References[edit]

  1. ^ Bradley, D. C.; Thomas, I. M. (1962-07-01). "Metallo-Organic Compounds Containing Metal–Nitrogen Bonds: Part Iii. Dialkylamino Compounds of Tantalum". Canadian Journal of Chemistry. 40 (7): 1355–1360. doi:10.1139/v62-207. ISSN 0008-4042.
  2. ^ Clerici, Mario G.; Maspero, Federico (1980-01-01). "CatalyticC-Alkylation of Secondary Amines with Alkenes". Synthesis. 1980 (4): 305–306. doi:10.1055/s-1980-29002. ISSN 0039-7881.
  3. ^ Herzon, Seth B.; Hartwig, John F. (2007-05-01). "Direct, Catalytic Hydroaminoalkylation of Unactivated Olefins with N-Alkyl Arylamines". Journal of the American Chemical Society. 129 (21): 6690–6691. doi:10.1021/ja0718366. ISSN 0002-7863. PMC 2590937. PMID 17474747.