Friedel−Crafts alkylation of vinyldichloromethylsilane to
benzene in the presence of
aluminum chloride catalyst at room temperature gave
hexakis((dichloromethylsilyl)ethyl)benzene (1) in 56% yield, along with small amounts of
less alkylated products. 1 was
easily converted to the corresponding compounds,
C6(CH2CH2SiMeR2)6;
(5 (R = OCH3), 6 (R
= H), 7 (R = CH3), 8 (R =
vinyl), 9 (R = allyl), 10 (R = ethynyl), and
11 (R = benzyl)) by
reaction with the appropriate nucleophilic reagents. The molecular
structures of hexakis((methylsilylethyl)benzene (6) and the solvent adducts of
hexakis((trimethylsilyl)ethyl)benzene (7·2CH2Cl2) and
hexakis((dibenzylmethylsilyl)ethyl)benzene
(11·2CHCl3) have been
determined by X-ray diffraction studies. Each dichloromethane and
chloroform molecule
formed C−H···aryl hydrogen bonds, one above and one below, to
the ring centroid. The
distances between the carbon and the ring centroid were 3.469 and 3.466
Å for CH2Cl2 and
CHCl3, respectively.
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