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The new bulky organosilicon compound HC(Me 2 SiCH 2 CH 2 CH 2 OCH 2 CycloCHCH 2 O) 3 was synthesized by hydrosilylation of tris(dimethylsilyl)methane (HMe 2 Si) 3 CH and allyl glycidyl ether (AGE) in the presence of H 2 PtCl 6 as a catalyst. Polysiloxanes containing 3-(2,3-epoxypropoxy)propyl and chloromethylphenethyl groups were synthesized by hydrosilylation of AGE and chloromethyl styrene (CMS) with hydrogen-containing polymethylsiloxane (PMHS). Both types of polymers could be modified by incorporation of the highly sterically-demanding tris(trimethylsilyl)methyl [trisyl = (Me 3 Si) 3 C] substituent. The trisyl (Tsi) groups were attached to the obtained polymers as side chains by reacting excess trisyl lithium with benzyl chloride and epoxy groups. The epoxy groups possess a higher reactivity for TsiLi than the chloromethyl groups. The ring opening reaction between the epoxy groups and TsiLi is fast. The modification increases the rigidity of the polymers as shown by differential scanning calorimetry analysis. The incorporation of the Tsi groups into the polymer structure creates macromolecules of novel architecture with potential use as membranes for fluid separation. All the resulting polymers were characterized by FT-IR and 1 H NMR spectroscopy.

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Tris(dimethylsilyl)methane, (HMe2Si) 3 −CH, reacts with n‐propyl, iso‐propyl, n‐butyl, s‐butyl, iso‐butyl, n‐pentyl, s‐pentyl, n‐hexyl alcohol, and phenol in the presence of chloroplatinic acid (H2PtCl6ċ6H2O) in air to give products (ROMe2Si)3CH (where R is n‐propyl, iso‐propyl, n‐butyl, s‐butyl, iso‐butyl, n‐pentyl, s‐pentyl, n‐hexyl, phenyl). Similar reactions with benzyl alcohol and acetic acid lead to the unexpected products, (PhCH2)2O and HC(Me2SiOSiMe2)3CH, respectively. The compound (n‐BuOMe2Si)3CSiMe2H was made from (n‐BuOMe2Si)3CH by treatment with lithium diisopropylamide, followed by quenching with HMe2SiCl. The homopolymer poly{(4‐chloromethyl)styrene} and copolymers with styrene (in 1:1 and 1:3 mol ratio) were synthesized by free radical polymerization, and (HMe2Si)3C groups were linked to them by nucleophilic substitution reactions between (HMe2Si)3CLi and the chloromethyl groups of the polymer side chains. The resulting functional polymers containing Si—H bonds reacted with various alcohols in the presence of chloroplatinic acid under heterogeneous conditions. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:365–376, 2008; Published online in Wiley InterScience (http://www.interscience.wiley.com). DOI 10.1002/hc.20440

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