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UBC Theses and Dissertations

Synthesis of 2:3-benzo-4-hydroxy-1, 1-dimethyl-1-silacyclohex-2-ene Russell, William Ward

Abstract

Following the successful synthesis of 2:3-Benzo-l,l-dimethyl-l-silacyelohex-2-ene and its 4-bromo derivative, attempts were made to prepare further derivatives. The syntheses of 2:3-Benzo-4-cyano-l,l-dimethyl-l-silacyclohex-2-ene and 2:3-Benzo-4-hydroxy-l,l-dimethyl-l-silacyclohex-2-ene were attempted via substitution reactions under various conditions. Attempts to prepare the 4-cyano compound were in vain, while the 4-hydroxy compound was readily prepared, on the strength of infrared analyses. The 4-hydroxy compound, however, presented a problem in characterization, as attempts to produce several derivatives of the compound were unsuccessful. Attempts were also made to improve the methods of synthesis and the yields of various intermediate compounds.

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