ChemInform Abstract: REACTIONS OF TRIETHYLGERMYLLITHIUM WITH N,N‐DIALKYLATED CARBOXAMIDES

Bravo‐Zhivotovskii, Dmitry; Pigarev, S. D.; Kalikhman, I. D.; Vyazankina, O. A.; Vyazankin, N. S.

doi:10.1002/chin.198341288

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“…Chemical shift variations of ipso aromatic carbon atoms (cf. Table ) toward low field suggest a localization of negative charge on the germanium atom. 1b, At the methoxy group, shifts to lower field are also observed, in the 1 H NMR as in the 13 C NMR spectra. The same phenomenon has already been reported for the reaction of 1-methoxynaphthalene with n -BuLi, and this has been attributed to an oxygen−lithium complexation .…”

Section: Resultsmentioning

confidence: 85%

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Synthesis and Characterization of New Lithiated Organogermanium Compounds

et al. 1996

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New (8-methoxy-1-naphthyl)arylgermanes 1a−c are synthesized. The crystal structure of 1b (aryl = mesityl), determined by X-ray diffraction, shows that an intramolecular interaction occurs between the oxygen and germanium atoms, the Ge- - -O distance being 2.75 Å. The corresponding (diarylgermyl)lithiums R2HGeLi are prepared in high yield by hydrogermolysis of tert-butyllithium in THF and are susprisingly stable. Their characterization by 1H, 13C, and 7Li NMR spectroscopy is reported. Dimetalation of the initial arylgermanes depends upon steric hindrance around the germanium atom and the nature of the organolithium compound RLi. The reaction of 1a or 1c with n-BuLi followed by MeI affords the expected dialkylation product, whereas 1b gives the unexpected iodide 5b due to steric hindrance around the germanium atom.

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Section: Resultsmentioning

confidence: 85%

“…At present, little is known about germyldilithiums. The formation of (diphenylgermyl)dilithium has been noted, without comment, in the reaction of lithium with diphenylgermane in HMPA using a method analogous to that described for Ph 2 GeK 2 8b. More recently, the preparation of Et 2 GeLi 2 by a very difficult route has been described …”

Section: Resultsmentioning

confidence: 99%