Issue 12, 2017

Synthesis, structure and thermolysis of oxazagermines and oxazasilines

Abstract

Seven new spirocyclic amido alkoxides of silicon and germanium were synthesized by the reactions of substituted 2-(aminomethyl)phenols with silicon(IV) and germanium(IV) chloride, respectively. The spirocyclic compounds 1–7 exhibit the general structural motif M[OC6H3(CH2NR1)-2-R2-4]2 [M = Si, R1 = Ph, R2 = H (1), Me (2), Br (3); M = Ge, R1 = Ph, R2 = H (4), Me (5), Br (6); M = Ge, R1 = i-Pr, R2 = H (7)]. The use of 2-(ethylamino)benzylalcohol and germanium(IV) chloride as starting materials afforded the spirocyclic compound Ge[EtNC6H4(CH2O)-2]2 (8). The structurally related germylene, germanium(II)-2-(phenylamidomethyl)phenolate (9), was prepared by the reaction of Ge[N(SiMe3)2]2 with 2-(phenylaminomethyl)phenol. The tetravalent compounds were isolated as racemates, with the exception of the spirocyclic germanium compound 8, for which the R and the S isomers crystallized separately. The compounds were characterized by single-crystal X-ray diffraction analysis, NMR spectroscopy (1H, 13C{1H}, 29Si{1H} for 1–3), IR spectroscopy, and TGA analysis. Porous Ge@C composites were observed after the carbonization of compounds 4–9 under argon. The as-prepared Ge@C materials were analyzed by elemental analysis, nitrogen physisorption measurements, powder X-ray diffraction analysis, Raman spectroscopy, and SEM/EDX analysis.

Graphical abstract: Synthesis, structure and thermolysis of oxazagermines and oxazasilines

Supplementary files

Article information

Article type
Paper
Submitted
17 Mar 2017
Accepted
09 May 2017
First published
09 May 2017

New J. Chem., 2017,41, 4990-4997

Synthesis, structure and thermolysis of oxazagermines and oxazasilines

F. Dannenberg, G. Thiele, E. Dornsiepen, S. Dehnen and M. Mehring, New J. Chem., 2017, 41, 4990 DOI: 10.1039/C7NJ00894E

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