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): Ver

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• 作者：Markus Fischer ; Christian Burschka ; Reinhold Tacke
• 刊名：Organometallics
• 出版年：2014
• 出版时间：February 24, 2014
• 年：2014
• 卷：33
• 期：4
• 页码：1020-1029
• 全文大小：399K
• 年卷期：v.33,no.4(February 24, 2014)
• ISSN：1520-6041

文摘

The 4-silacyclohexanones 1鈥?b>6 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 4鈥?b>6 by treatment with HCl/Et₂O in CH₂Cl₂ at 20 掳C gives the 4-chloro-4-silacyclohexanone 13. Reductive amination of 1鈥?b>6 with NH₃ or i-PrNH₂ yields the respective (4-silacyclohexan-1-yl)amines 7鈥?b>12. Compounds 1鈥?b>12 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鈺怌H)₂SiPh(TMOP) (27) were additionally characterized by single-crystal X-ray diffraction. Compounds 1鈥?b>12 with their Si- and C-functional groups represent versatile building blocks for synthesis.