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UBC Theses and Dissertations

Synthesis of 2:3-benzo-1, 1-dimethyl-1-silacyclohex-2-ene and derivatives Lo, Daniel Ching-Shun


The synthesis of 2:3-benzo-1,1-dimethyl-1-silacyclo-hex-2-ene has been reported. This compound was prepared by the simultaneous addition of 3-(o-bromophenyl)-propyl bromide and dichlorodimethylsilane to excess magnesium in tetra-hydrofuran. The six-membered ring organosilicon compound was readily brominated by N-bromosuccinimide to give the 4-derivative. Attempts were then made to synthesize the 4-cyano and the 4-carboxylate derivatives from this bromination product. Experimental data are also given for an attempted preparation of 2:3-benzo-4-(2-dimethylaminoethoxy)-1,1-dimethyl-1-silacyclohex-2-ene.

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