Über die Si3-N-bindung: XXXV. Darstellung von N-β-halogenäthyl-N,N-bis(trimethylsilyl)aminen |
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Authors: | F Piper K Rühlmann |
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Institution: | Sektion Chemie der Humboldt-Universität zu Berlin D.D.R.;Sektion Chemie der Technischen Universität Dresden D.D.R. |
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Abstract: | N-β-Haloethyl-N,N-bis(trimethylsilyl)amines, which can be used for the introduction of aminoethyl groups into organic or organosilicon compounds, are prepared in good yields from N-trimethylsilylaziridine and trimethylhalosilanes. This reaction is spontaneous with trimethylbromo- and -iodosilane, whereas it is necessary to run the reactions with trimethylchlorosilane in the presence of dipolar aprotic solvents and at higher temperatures.N-β-Bromoethyl-N,N-bis(trimethylsilyl)amine (II) is also obtained by silylation of N-β-bromoethylamine hydrobromide with trimethylsilyldiethylamine or with N-trimethylsilyl-N-methyl acetamide. Furthermore N-β-iodoethyl-N,N- bis(trimethylsilyl)amine is prepared by the reaction of II with MgI2 or of aziridine and N-trimethylsilylaziridine respectively, with trimethylchlorosilane and MgI2.From the silylation of N-β-bromoethylamine hydrobromide with trimethylsilyldiethylamine N,N-bis(trimethylsilyl)-N′,N′-diethylethylenediamine is isolated as a side product or, at higher temperatures, as the main product. |
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