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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Stereoselective synthesis of different cyclic tetrasiloxane isomers depending on the superacid catalyst employed
Kanako Sonoda1, Norimitsu Tohnai2, Yoshiro Kaneko1
1Graduate School of Science and Engineering, Kagoshima University, 1-21-40, Korimoto, Kagoshima 890-0065, Japan. ykaneko@eng.kagoshima-u.ac.jp.
Abstract:
In this study, we investigated the hydrolytic condensation of 3-aminopropyldiethoxymethylsilane over different superacid catalysts. We found that cyclic tetrasiloxanes with different stereostructures (Am-CyTS-NNf2 and Am-CyTS-NHf2) could be selectively prepared in high yields (>95%) depending on the superacid catalyst employed (bis(nonafluorobutanesulfonyl)imide or cyclohexafluoropropane-1,3-bis(sulfonyl)imide). The single-crystal X-ray structural analyses of compounds in which amino groups of Am-CyTS-NNf2 and Am-CyTS-NHf2 were protected by the tert-butoxycarbonyl group revealed the formation of all-cis and cis-trans-cis cyclic tetrasiloxanes, respectively.
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