NDLI: Cubic Siloxanes with Both Si−H and Si−OtBu Groups for Site-Selective Siloxane Bond Formation

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Cubic Siloxanes with Both Si−H and Si−OtBu Groups for Site-Selective Siloxane Bond Formation

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Saito, Shohei Yamasue, Nao Shimojima, Atsushi Kuroda, Kazuyuki Wada, Hiroaki
Description	Author Affiliation: Saito S ( Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University, Okubo-3, Shinjuku-ku, Tokyo, 169-8555, Japan.); Yamasue N ( Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University, Okubo-3, Shinjuku-ku, Tokyo, 169-8555, Japan.); Wada H ( Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University, Okubo-3, Shinjuku-ku, Tokyo, 169-8555, Japan.); Shimojima A ( Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University, Okubo-3, Shinjuku-ku, Tokyo, 169-8555, Japan. shimojima@waseda.jp.); Kuroda K ( Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University, Okubo-3, Shinjuku-ku, Tokyo, 169-8555, Japan. kuroda@waseda.jp.)
Abstract	Cage-type siloxanes have attracted increasing attention as building blocks for silica-based nanomaterials as their corners can be modified with various functional groups. Cubic octasiloxanes incorporating both Si−H and Si−OtBu groups $[(tBuO)_{n}H_{8−n}Si_{8}O_{12};$ n=1, 2 or 7] have been synthesized by the reaction of octa(hydridosilsesquioxane) $(H_{8}Si_{8}O_{12})$ and tert-butyl alcohol in the presence of a $Et_{2}NOH$ catalyst. The Si−H and Si−OtBu groups are useful for site-selective formation of Si−O−Si linkages without cage structure deterioration. The Si−H group can be selectively hydrolyzed to form a Si−OH group in the presence of $Et_{2}NOH,$ enabling the formation of the monosilanol compound $(tBuO)_{7}(HO)Si_{8}O_{12}.$ The Si−OH group can be used for either intermolecular condensation to form a dimeric cage compound or silylation to introduce new reaction sites. Additionally, the alkoxy groups of $(tBuO)_{7}HSi_{8}O_{12}$ can be treated with organochlorosilanes in the presence of a $BiCl_{3}$ catalyst to form Si−O−Si linkages, while the Si−H group remains intact. These results indicate that such bifunctional cage siloxanes allow for stepwise Si−O−Si bond formation to design new siloxane-based nanomaterials.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	39
Volume Number	22
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2016-09-19
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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