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Issue 8, 2010
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Synthesis and structure of stable base-free dialkylsilanimines

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Abstract

Four isolable dialkylsilanimines RH2Si[double bond, length as m-dash]NR (R = CH2Ph (5a), Ph (5b), 1-adamantyl (5c) and SiMe3 (5d), where RH2 = 1,1,4,4-tetrakis(trimethylsilyl)butane-1,4-diyl) were synthesized as air-sensitive crystals by the reaction of isolable dialkylsilylene 4 with the corresponding azides. X-ray analysis shows that 5a–5d are base-free silanimines and 5a and 5b have a remarkable bent Si[double bond, length as m-dash]N–R structure, while 5c and 5d have an almost linear structure. Distinct π(Si[double bond, length as m-dash]N)  π*(Si[double bond, length as m-dash]N) and n(N)  π*(Si[double bond, length as m-dash]N) transition bands of siliconnitrogen double bonds were observed for 5a–5d in hexane. A mechanism for the formation of silanimine from the reaction of silylene and azide is discussed using theoretical calculations with the GRRM method for model reactions.

Graphical abstract: Synthesis and structure of stable base-free dialkylsilanimines

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Publication details

The article was received on 15 Feb 2010, accepted on 18 Mar 2010 and first published on 26 Apr 2010


Article type: Paper
DOI: 10.1039/C0NJ00121J
Citation: New J. Chem., 2010,34, 1637-1645
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    Synthesis and structure of stable base-free dialkylsilanimines

    T. Iwamoto, N. Ohnishi, Z. Gui, S. Ishida, H. Isobe, S. Maeda, K. Ohno and M. Kira, New J. Chem., 2010, 34, 1637
    DOI: 10.1039/C0NJ00121J

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