Pentakis(dimethylamido)tantalum

Pentakis(dimethylamido)tantalum
Names
	IUPAC name dimethylazanide;tantalum(5+)
	Other names Pentakis(dimethylamino)tantalum(V), Tantalum dimethylamide
Identifiers
CAS Number	19824-59-0;
3D model (JSmol)	Interactive image;
ChemSpider	124019;
PubChem CID	140614;
	InChI InChI=1S/5C2H6N.Ta/c51-3-2;/h51-2H3;/q5*-1;+5 Key: VSLPMIMVDUOYFW-UHFFFAOYSA-N;
	SMILES C[N-]C.C[N-]C.C[N-]C.C[N-]C.C[N-]C.[Ta+5];
Properties
Chemical formula	C10H30N5Ta
Molar mass	401.333 g·mol−1
Appearance	white solid
Melting point	100 ºC
Hazards
GHS pictograms
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

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.[1] The preparation is similar to that for tetrakis(dimethylamido)titanium.

The compound has idealized D_3h symmetry (ignoring the organic substituents).

Applications to organic synthesis

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

Hydroaminoalkylation Reaction Scheme

References

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.
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.
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.

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[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.