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New Routes to Functionalized Polyhedral Oligomeric Silsesquioxanes via Friedel-Crafts Alkylation and Dichlorocarbene Addition to Octavinylsilsesquioxane

Dare E., Olatunji G., Ogunniyi D., Lasisi A.

Polish Journal of Chemistry

2005

Vol. 79 / nr 1

109-114

Selective functionalization of (CH2=CH)8Si8O12 1 by the addition of dichlorocarbene to vinyl double bonds giving (C3H3)8Si8O12 2 or (C2H3)4(C3H3Cl2)4Si8O12 3 respectively is described. The dichlorocarbene was generated from CHCl3 in phase transfer catalytic system (PTC). Furthermore, (PhCH2CH2)8Si8O12 4 has been synthesized by Friedel-Crafts alkylation reaction of benzene with 1 using AlCl3 as catalyst.

Phase Transfer Catalyzed Reactions of Chloroform with Methacrylic Esters

Fedoryński M., Błażejczyk A., Mąkosza M.

Polish Journal of Chemistry

2003

Vol. 77 / nr 5

709-717

Chloroform reacts with an excess of methyl methacrylate in the presence of 50% aq NaOH and benzyltriethylammonium chloride (TEBA) as a catalyst (phase transfer catalysis, PTC) to give a mixture of dichlorocarbene and trichloromethyl anion adducts, 1 and 2, respectively. These additions proceed as parallel processes, there is a slow conversion of 2_ 1, which proceeds as an intramolecular process.