2295-07-0Relevant academic research and scientific papers
Synthesis of silicon-functionalized (silylmethyl)silanes and-dichlorocarbosilanes using the TMOP (2,4,6-trimethoxyphenyl) protecting group: (TMOP)Me2SiCH2Cl and (TMOP) 2MeSiCH2Cl as reagents to introduce the ClMe 2SiCH2, MeOMe2SiCH2, or Cl2MeSiCH2 group by nucleophilic substitution at silicon
Laskowski, Nadine,Reis, Eva-Maria,Koetzner, Lisa,Baus, Johannes A.,Burschka, Christian,Tacke, Reinhold
, p. 3269 - 3278 (2013/07/27)
In this study, the synthetic potential of the 2,4,6-trimethoxyphenyl (TMOP)-substituted (chloromethyl)silanes (TMOP)Me2SiCH2Cl (1) and (TMOP)2MeSiCH2Cl (2) for the preparation of Si-functionalized (silylmethyl)silanes and α,ω-dichlorocarbosilanes (with skeletons consisting of alternate carbon and silicon atoms) was investigated. Compounds 1 and 2 were used as reagents to introduce the ClMe 2SiCH2, MeOMe2SiCH2, or Cl 2MeSiCH2 group by nucleophilic substitution at silicon. The three-step synthetic method involves the (i) transformation of 1 and 2 into (TMOP)Me2SiCH2MgCl, (TMOP)Me2SiCH 2Li, (TMOP)2MeSiCH2MgCl, and (TMOP) 2MeSiCH2Li, respectively, (ii) reaction of these nucleophiles with chloro- or methoxysilanes, and (iii) subsequent selective cleavage of the TMOP protecting group with HCl/Et2O or MeOH/[CF 3COOH]. Using this method, the following compounds were prepared: ClMe2SiCH2SiMe3 (3), ClMe2SiCH 2SiMe2Cl (4), ClMe2SiCH2SiMeCl 2 (5), ClMe2SiCH2SiCl3 (6), ClMe2SiCH2Si(OMe)3 (7), MeOMe 2SiCH2Si(OMe)3 (8), Cl2MeSiCH 2SiMe3 (9), Me2Si(CH2SiMe 2Cl)2 (10), and Me2Si(CH2SiMe 2CH2SiMe2Cl)2 (11).
