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Synthesis of 4‑Silacyclohexan-1-ones and (4-Silacyclohexan-1-yl)amines Containing the Silicon Protecting Groups MOP (4-Methoxyphenyl), DMOP (2,4-Dimethoxyphenyl), or TMOP (2,4,6-Trimethoxyphenyl): Versatile Si- and C‑Functional Building Blocks for Synthesis

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posted on 24.02.2014, 00:00 authored by Markus Fischer, Christian Burschka, Reinhold Tacke
The 4-silacyclohexanones 16 were prepared in convenient multistep syntheses, starting from MeSi­(OMe)3 and PhSi­(OMe)3, respectively. Cleavage of the 4-methoxyphenyl (MOP), 2,6-dimethoxyphenyl (DMOP), and 2,4,6-trimethoxyphenyl (TMOP) protecting groups of 46 by treatment with HCl/Et2O in CH2Cl2 at 20 °C gives the 4-chloro-4-silacyclohexanone 13. Reductive amination of 16 with NH3 or i-PrNH2 yields the respective (4-silacyclohexan-1-yl)­amines 712. Compounds 112 and all new precursors synthesized were characterized by elemental analyses (C, H, N) or mass spectrometric investigations (ESI-HRMS) and by NMR spectroscopic studies (1H, 13C, 29Si). Compounds 1, 3, 5, and 6 and the precursors (MeO)2SiPh­(TMOP) (21) and (CH2CH)2SiPh­(TMOP) (27) were additionally characterized by single-crystal X-ray diffraction. Compounds 112 with their Si- and C-functional groups represent versatile building blocks for synthesis.