Facile synthesis and bridgehead-functionalization of bicyclo[3.3.3]pentasiloxanes
Yuki Yokouchi1, Shintaro Ishida, Tsunenobu Onodera
1Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan. iwamoto@m.tohoku.ac.jp.
Abstract:
A fascinating but still rare bicyclic siloxane, bicyclo[3.3.3]pentasiloxane, was synthesized by the oxidation of a bicyclic silicon cluster and characterized using a combination of NMR spectroscopy and X-ray diffraction analysis. The bridgehead OSiMe3 groups of the siloxane were selectively and efficiently converted to O-K+ (siloxide) by treating with tBuOK in the presence of 18-crown-6-ether. The resulting siloxides provided various bridgehead-functionalized bicyclo[3.3.3]pentasiloxanes after treatment with electrophiles.
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