N-germyl derivatives of 4-nitrophenylamine: Germylamines, stable germa-imine

Article abstract of DOI:10.1080/10426500008046615

N-germyl secondary amines of 4-nitrophenylamine were obtained by transamination from N-trialkylgermyldimethylamine, by transmetallation from the N-lithium derivative of 4-nitrophenylamine, or by intermolecular dehydrohalogenation between the corresponding halogermane and p-nitrophenylamine. Halogermylamines formed by the same methods are always obtained as a mixture with the corresponding diamine bis(4-nitrophenylamino)dimesitylgermane, and cannot be used as germa-imine precursors. However, elimination reactions from N-dimethylaminodimesitylgermyl-4-nitrophenylamine and N-dimesitylchlorogermyl-4-nitrophenylamine, formed from N-triethylgermyl N-dimesitylchlorogermyl-4-nitrophenylamine, yielded the thermally stable N-(4-nitrophenyl)dimesitylgerma-imine as a deep red amorphous powder. This germa-imine is moisture-sensitive, yielding (4-nitrophenylamino)dimesitylgermanol which adds to the germa-imine forming bis(4-nitrophenylaminodimesitylgermyl)oxide which was isolated as an orange powder. N-4-nitrophenyl)dimesitylgerma-imine adds readily to chloroform yielding N-dimesitylchlorogermyl-4-nitrophenylamine. The 3+2 addition of the germa-imine to N-t-butyl-phenylnitrone gave an adduct whose thermal decomposition began at 100°C yielding benzylidene-4-nitrophenylamine and dimesitylgermoxane. The germa-imine addition to 4,5-di-t-butyl ortho-quinone led to the corresponding dimesitylgermadioxolane through decomposition at room temperature of a transient adduct. The formation of isobutene in this reaction is constitent with a Single Electron Transfer mechanism in the first step.

Full text of DOI:10.1080/10426500008046615

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N-GERMYL DERIVATIVES
OF 4-NITROPHENYLAMINE:
GERMYLAMINES, STABLE
GERMA-IMINE
a
b
b
F. El Baz , M. Riviere-baudet , C. Chazalettte
&
b
H. Gornitzka
a
Laboratoire de Chimie Organique et
Organométallique , Université Ibnou Zohr, Faculté
des Sciences , BP 28/S, Agadir, Maroc
b
Laboratoire d'Hétérochimie Fondamentale et
Appliquée UPRES-A 5069 du CNRS , Université Paul
Sabatier , 118 route de Narbonne, 31062, Toulouse
cedex, France
Published online: 04 Oct 2006.
To cite this article: F. El Baz , M. Riviere-baudet , C. Chazalettte & H. Gornitzka
(
2000) N-GERMYL DERIVATIVES OF 4-NITROPHENYLAMINE: GERMYLAMINES, STABLE
GERMA-IMINE, Phosphorus, Sulfur, and Silicon and the Related Elements, 163:1,
21-142, DOI: 10.1080/10426500008046615
1
To link to this article: http://dx.doi.org/10.1080/10426500008046615
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