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Synthesis of organosilicon compounds containing amine nitrogen and their reactions with nucleophilic and electrophilic reagents

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    A study was made of the replacement of the halogen of silicon-attached chloromethyl by an amino group. New organosilicon compounds obtained were: 4-[(diethoxymethylsilyl)methyl]morpholine, 4-[(ethoxydimethylsilyl)methyl]morpholine, o-chloro-N-[(ethoxydimethylsilyl)methyl]aniline, o-chloro-N-[(diethoxy methylsilyl)methyl]aniline,N-[(diethoxymethylsilyl)methyl]diethylamine, 2-(trimethylsiloxy)ethylamine, 2-[(trimethylsilyl)methyl amino]ethanol, and 2,2,8,8-tetramethyl-3-oxa-6-aza-2,8-disilanonane.

  2. 2.

    An investigation was made of the stability of the silicon-carbon bond in N-[(diethoxymethylsilyl)methyl] aniline in acid, alkaline, and neutral aqueous media at 40° and 90°, and it was shown that the Si- C bond is not broken in alkaline and neutral media under these conditions. In an acid medium rupture of the Si-C bond occurs to a slight extent with elimination of the anilinomethyl group, and the extent to which this occurs increases with increase in the acidity of the medium.

  3. 3.

    In the course of the study of the hydrolysis of N-[(diethoxymethylsilyl)methyl ]aniline in an alkaline medium, a crystalline substance was isolated and found to be 1,3,5-trisanilinomethyl-1,3,5-trim ethyl- 1,5-trisiloxanediol.

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds of the Academy of Sciences of the USSR, USSR

    K. A. Andrianov & L. M. Volkova

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  1. K. A. Andrianov
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  2. L. M. Volkova
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Andrianov, K.A., Volkova, L.M. Synthesis of organosilicon compounds containing amine nitrogen and their reactions with nucleophilic and electrophilic reagents. Russ Chem Bull 6, 591–598 (1957). https://doi.org/10.1007/BF01169275

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  • DOI: https://doi.org/10.1007/BF01169275

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