Abstract
AbstractNew cyclic and spirocyclic aminosilanes were synthesised using ethylenediamine, 2-aminobenzylamine, 1,8-diaminonaphthalene, o-phenylenediamine, andtrans-cyclohexane-1,2-diamine as starting material. These diamines were converted into aminosilanes using silicon tetrachloride and dimethyldichlorosilane directly and via theN,N’-bis(trimethylsilylated) amino derivatives. 15 new compounds of the type (diamino)(SiMe3)2, (diamino)2Si, (diamino)SiMe2, and (diamino)SiCl2have been prepared. The formation of two cyclotrisilazane derivatives was observed starting from (N,N’-2-aminobenzylamino)dichlorosilane by trimerisation. All synthesised compounds have been characterised with NMR-, Raman-, or IR-spectroscopy, mass-spectrometry, and boiling or melting point. Single-crystal X-ray structure analyses of several derivatives have been performed.The degree of substitution with trimethylsilyl groups in the final compounds depends on the ring size of the spirocycles. It was shown with quantum chemical calculations on the M062X/6-31G(d) level that trimethylsilyl groups have a stabilising effect on 5-membered ring systems and a destabilising effect on 6-membered rings in these compounds.
Highlights
New cyclic and spirocyclic aminosilanes were synthesised using ethylenediamine, 2-aminobenzylamine, 1,8-diaminonaphthalene, o-phenylenediamine, and trans-cyclohexane-1,2-diamine as starting material
It was shown with quantum chemical calculations on the M062X/6-31G(d) level that trimethylsilyl groups have a stabilising effect on 5-membered ring systems and a destabilising effect on 6-membered rings in these compounds
Two different routes are pursued for the synthesis of cyclic and spirocyclic aminosilanes: The reaction of the diamines 1-5 with the chlorosilane in the presence of triethylamine as base is denoted as method A (Scheme 2)
Summary
Abstract: New cyclic and spirocyclic aminosilanes were synthesised using ethylenediamine, 2-aminobenzylamine, 1,8-diaminonaphthalene, o-phenylenediamine, and trans-cyclohexane-1,2-diamine as starting material. These diamines were converted into aminosilanes using silicon tetrachloride and dimethyldichlorosilane directly and via the N,N’-bis(trimethylsilylated) amino derivatives. The formation of two cyclotrisilazane derivatives was observed starting from (N,N’-2-aminobenzylamino)dichlorosilane by trimerisation. The degree of substitution with trimethylsilyl groups in the final compounds depends on the ring size of the spirocycles. It was shown with quantum chemical calculations on the M062X/6-31G(d) level that trimethylsilyl groups have a stabilising effect on 5-membered ring systems and a destabilising effect on 6-membered rings in these compounds
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