In this study, the synthetic potential of the 2,4,6-trimethoxyphenyl (TMOP)-substituted (chloromethyl)silanes (TMOP)Me 2 SiCH 2 Cl (1) and (TMOP) 2 MeSiCH 2 Cl (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 2 SiCH 2 , MeOMe 2 SiCH 2 , or Cl 2 MeSiCH 2 group by nucleophilic substitution at silicon. The three-step synthetic method involves the (i) transformation of 1 and 2 into (TMOP)Me 2 SiCH 2 MgCl, (TMOP)-Me 2 SiCH 2 Li, (TMOP) 2 MeSiCH 2 MgCl, and (TMOP) 2 MeSiCH 2 Li, respectively, (ii) reaction of these nucleophiles with chloro-or methoxysilanes, and (iii) subsequent selective cleavage of the TMOP protecting group with HCl/Et 2 O or MeOH/[CF 3 COOH]. Using this method, the following compounds were prepared: ClMe 2 SiCH 2 SiMe 3 (3), ClMe 2 SiCH 2 SiMe 2 Cl (4), ClMe 2 SiCH 2 SiMeCl 2 (5), ClMe 2 SiCH 2 SiCl 3 (6), ClMe 2 SiCH 2 Si-(OMe) 3 (7), MeOMe 2 SiCH 2 Si(OMe) 3 (8), Cl 2 MeSiCH 2 SiMe 3 (9), Me 2 Si(CH 2 SiMe 2 Cl) 2 (10), and Me 2 Si-(CH 2 SiMe 2 CH 2 SiMe 2 Cl) 2 (11).
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