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Issue 3, 2018
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Facile synthesis and bridgehead-functionalization of bicyclo[3.3.3]pentasiloxanes

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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 OK+ (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.

Graphical abstract: Facile synthesis and bridgehead-functionalization of bicyclo[3.3.3]pentasiloxanes

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Publication details

The article was received on 15 Nov 2017, accepted on 04 Dec 2017 and first published on 12 Dec 2017


Article type: Communication
DOI: 10.1039/C7CC08790J
Citation: Chem. Commun., 2018,54, 268-270
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    Facile synthesis and bridgehead-functionalization of bicyclo[3.3.3]pentasiloxanes

    Y. Yokouchi, S. Ishida, T. Onodera, H. Oikawa and T. Iwamoto, Chem. Commun., 2018, 54, 268
    DOI: 10.1039/C7CC08790J

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