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PREPARATIVE AND SPECTROSCOPIC STUDIES ON VOLATILE SILYLHYDROXYLAMINES AND ALKYLHYDROXYLAMINES

Norbert W. Mitzel,H. Schmidbaur-1994-01-01-PUB – Publications at Bielefeld University (Bielefeld University)
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TL;DRAbstract

(Hydridosilyl)hydroxylamines have been prepared from the corresponding chloro- and bromosilanes and alkylated hydroxylamines in the presence of an auxiliary base (NEt3, TMEDA). Dimethylsilyl groups were introduced in order to obtain open chain silylhydroxylamines, while alpha,omega-disilylalkane groups were employed for cyclic species. In mass spectral studies a nitrene extrusion was found to be one of the main fragmentation processes. N-15, O-17 (and H-1, C-13, Si-29) heteronuclear NMR studies were carried out for a larger series of silylated and alkylated hydroxylamines. The O-17 and N-15 chemical shifts are clearly distinguished from those of other compounds containing saturated nitrogen and oxygen centers. The one bond coupling constants 1J((NSi)-N-15-Si-29) indicate a pyramidal coordination of nitrogen in silylhydroxylamines.

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(Hydridosilyl)hydroxylamines have been prepared from the corresponding chloro- and bromosilanes and alkylated hydroxylamines in the presence of an auxiliary base (NEt3, TMEDA). Dimethylsilyl groups were introduced in order to obtain open chain silylhydroxylamines, while alpha,omega-disilylalkane groups were employed for cyclic species. In mass spectral studies a nitrene extrusion was found to be one of the main fragmentation processes. N-15, O-17 (and H-1, C-13, Si-29) heteronuclear NMR studies were carried out for a larger series of silylated and alkylated hydroxylamines. The O-17 and N-15 chemical shifts are clearly distinguished from those of other compounds containing saturated nitrogen and oxygen centers. The one bond coupling constants 1J((NSi)-N-15-Si-29) indicate a pyramidal coordination of nitrogen in silylhydroxylamines.

Keywords

Heteronuclear moleculeNitreneChemistryFragmentation (computing)NitrogenAlkylationChemical shiftMedicinal chemistry

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