Conclusions
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1.
The reaction of HGeCl3 superacid with excess diphenyl ether leads to 1,3,5-tris(trichlorogermyl)-1-(p-phenoxyphenyl)cyclohexane, which is converted by the action of MeMgBr to 1,3,5-tris(trimethylgermyl)-1-(p-phenoxyphenyl)cyclohexane.
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2.
The structures of the indicated products constitute evidente for alkylation of di-phenyl ether in the reaction. The alkylating function of HGeCl3 as a Friedel-Crafts acid was thereby demonstrated for the first time.
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3.
The crystal and molecular structure of 1,3,5-tris(trimethylgermyl)-1-(p-phenoxyphenyl)-cyclohexane was determined by x-ray diffraction. The crystal contains independent A and B molecules that differ only with respect to inversion of the phenoxy group. The cyclohexane ring has a chair configuration with three equatorially oriented trimethylgermyl substituents.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1131–1137, May, 1984.
The authors thank E. V. Shuleshov for recording and interpreting the13C NMR spectra and I. E. Chlenov for his useful participation in the discussion of the results of our research.
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Kolesnikov, S.P., Lyudkovskaya, I.V., Nefedov, O.M. et al. Reaction of HGeCl3 superacid with aromatic compounds. Russ Chem Bull 33, 1038–1043 (1984). https://doi.org/10.1007/BF01141721
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DOI: https://doi.org/10.1007/BF01141721