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Synthesis and Properties of the First 1-Silanaphthalene

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journal contribution
posted on 27.08.2002, 00:00 by Nobuhiro Takeda, Akihiro Shinohara, Norihiro Tokitoh
The first 1-silanaphthalene, 4, was successfully synthesized by taking advantage of an efficient steric protection group, 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (Tbt), and the aromaticity of 4 was discussed on the basis of its 1H, 13C, and 29Si NMR, Raman, and UV/vis spectra together with theoretical calculations. In contrast to the thermal stability of the Tbt-substituted 2-silanaphthalene 2, 1-Tbt-1-silanaphthalene (4) undergoes a ready [2 + 4] dimerization reaction in solution even at room temperature, despite its stability in the solid state.