Article abstract of DOI:10.1080/10426509608046364

Germyl derivatives of N-2,4,6-trifluoroaniline were synthesized either by dehydrohalogenation between halogermanes and 2,4,6-trifluoroaniline over DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or by elimination between halogermanes and 2,4,6-trifluoroanilinolithium. Dimesitylfluorogermyl N-2,4,6-trifluoroanilinolithium stabilized by THF slowly eliminated lithium fluoride leading to 2,4(2,4,6-trifluorophenyl)-1,3-tetramesitylcyclodigermazane, mainly through intermolecular elimination while in the presence of MgBr₂ or tBuMgBr the corresponding germa-imine was formed. Dimesitylchlorogermyl-2,4,6-trifluoroanilino lithium also led to cyclodigermazane while the corresponding bromogermyl lithium or magnesium compound gave mainly the stable 2,4,6-trifluorophenyl dimesitylgerma-imine by intramolecular elimination. The same stable germa-imine was also obtained by exchange reaction between dichlorodimesitylgermane and N-bis(triethylgermyl)2,4,6-trifluoroaniline. Reactivities of monomeric germa-imine and its dimer cyclodigermazane are compared. The dimer is almost inert towards water and methanol and does not react with chloroform and N-tert-butylphenyl nitrone while the germa-imine leads to the corresponding adducts. The adduct with chloroform through α-elimination of dichlorocarbene gave N-dimesitylchlorogermyl trifluoroaniline. The electron withrawing effects of the trifluorophenyl group on nitrogen stabilize the germa-imine, preventing its dimerization, but also induce a decrease in reactivity of germanium nitrogen compounds within the series.

Full text of DOI:10.1080/10426509608046364

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Phosphorus, Sulfur, and Silicon and the
Related Elements
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DERIVES N-GERMANIES DE LA 2,4,6-
TRIFLUOROANILINE: GERMYLAMINES,
GERMA-IMINE, CYCLODIGERMAZANE
Monique Riviere-baudet a , Fatima El Baz b , Jaques Satge a ,
Abdelhay Khallaayoun b & Mohamed Ahra b
a Laboratoire d'Hétérochimie Fondamentale et Appliquée , URA 477
du CNRS, Université Paul Sabatier , 118 Route de Narbone, 31062,
Toulouse-cedex, France
b Laboratoire de Chimie Organique et Organométallique, Faculté des
Sciences , Université Ibnou Zohr , B.P 28/S, Agadir, Maroc
Published online: 04 Oct 2006.
To cite this article: Monique Riviere-baudet , Fatima El Baz , Jaques Satge , Abdelhay Khallaayoun &
Mohamed Ahra (1996) DERIVES N-GERMANIES DE LA 2,4,6-TRIFLUOROANILINE: GERMYLAMINES, GERMA-
IMINE, CYCLODIGERMAZANE, Phosphorus, Sulfur, and Silicon and the Related Elements, 112:1-4,
203-217, DOI: 10.1080/10426509608046364
To link to this article: http://dx.doi.org/10.1080/10426509608046364
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