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6. Les énergies renouvelables

Author

Satge, J., Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), and Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Published
2006

33. An eight-membered cyclic C,N-bis(germadiyl) bis(ketenimine)

Author

UCL, Lee, VY, Declercq, Jean-Paul, Ranaivonjatovo, H., Escudie, J., Satge, J., Dubourg, A., Egorov, MP, Nefedov, OM, UCL, Lee, VY, Declercq, Jean-Paul, Ranaivonjatovo, H., Escudie, J., Satge, J., Dubourg, A., Egorov, MP, and Nefedov, OM

Abstract

The reaction of tert-butyllithium with (fluorodimesitylgermyl)- and (chlorodimesitylgermyl)phenylacetonitrile (4a,b) leads to the lithium salts 5a (X = F) and 5b (X = Cl), which exhibit an ambident character: [> C--C=N <----> > C=C=N-]Li+. Quenching of 5a with triphenylbromomethane affords the germylketenimine 8, Mes(2)FGeC(Ph)=C=NCPh3. H-1 dynamic NMR spectroscopy allows the determination of the activation energy of the nitrogen inversion Delta G* = 9.9 +/- 0.2 kcal/mol. In the absence of a trapping reagent, 5 undergoes an elimination of lithium halide with formation of the eight-membered cyclic C,N-bis(germadiyl) bis(ketenimine) 1, which is the first ring containing two ketenimine moieties. 1 has been characterized by IR (nu(C=C=N) 2015 cm(-1)) and C-13 NMR spectroscopy (170.87 ppm for the sp carbon) and by an X-ray structure determination, which displays a "cyclohexane" type structure in a chair conformation.

Published
1998

34. Unsaturated Germanium and Phosphorus-compounds - Reactions of Germaphosphenes With Alpha-ethylene Aldehydes and Ketones

Author

UCL, Ranaivonjatovo, H., Escudie, J., Couret, C., Declercq, Jean-Paul, Dubourg, A., Satge, J., UCL, Ranaivonjatovo, H., Escudie, J., Couret, C., Declercq, Jean-Paul, Dubourg, A., and Satge, J.

Abstract

Germaphosphenes MeS2Ge=PR (R: 2,4,6-triisopropylphenyl (Is), 1; 2,4,6-tri-tert-butylphenyl (Ar), 2) react with a-ethylene aldehydes and ketones to give [2 + 2] and [2 + 4] cycloadditions (for aldehydes) and [2 + 4] cycloadditions and 1,2-additions (for ketones). Four- and six-membered ring derivatives can be easily differentiated by P-31 NMR chemical shifts which are, respectively, +36 to +89 ppm and -33 to -77 ppm. 5a', obtained from 2 and crotonaldehyde, has been structurally characterized by X-ray diffraction: the six-membered ring (germaoxaphosphorinene) conformation is a sofa form, with large folding along the Ge-C axis. A NMR study at various temperatures for 3a, 3a', and 5a' displays dynamic phenomenon including phosphorus and ring inversion. The low DELTAG* values (respectively 18.2,13.7, and 13.2 kcal/mol) seem mainly due to substitution of phosphorus by the electropositive germanium and particularly to large steric effects; the 2,4,6-tri-tert-butylphenyl group lowers the inversion barrier by 5 kcal/mol when compared with the 2,4,6-triisopropylphenyl group.

Published
1993

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