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Stability of the silicon-carbon bond in alkoxy(alkyl)silanes. Containing ether or ester groupings toward 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.

    The following compounds were synthesized for the first time: dibutoxy(methoxymethyl)methylsilane, triethoxy(methoxymethyl)silane, [acetyl(ethoxycarbonyl)methyl]diethoxymethylsilane, and (bisethoxycarbonylmethyl) diethoxyethylsilane.

  2. 2.

    It was shown that, in the hydrolysis of diethoxy(ethoxycarbonylmethyl)ethylsilane and diethoxy(ethoxycarbonylmethyl)phenylsilane in alkaline and acid media, elimination of the ethoxycarbonylmethyl group occurs.

  3. 3.

    It was shown that, in the hydrolysis of diethoxy(ethoxymethyl)rnethylsilane, hydrolysis of siliconattached ethoxy groups is accompanied by partial elimination of the ethoxymethyl group, the extent of the elimination being greater in an acid medium than in an alkaline medium.

  4. 4.

    In the hydrolysis of diacetoxy(acetoxymethyl)methylsilane, rupture of the silicon-carbon link in the grouping Si- CH2OCOCH3 does not occur to any appreciable extent either in alkaline or in acid media.

  5. 5.

    Alkaline hydrolysis of [acetyl(ethoxycarbonyl)methyl]diethoxymethylsilane does not result in rupture of the link between silicon and the carbon of the ester grouping.Such rupture does occur in acid hydrolysis.

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Literature cited

  1. K: A. Andrianov and L. I. Makarova, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1956, 7O2.

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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. I. Makarova

Authors
  1. K. A. Andrianov
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  2. L. I. Makarova
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Andrianov, K.A., Makarova, L.I. Stability of the silicon-carbon bond in alkoxy(alkyl)silanes. Containing ether or ester groupings toward nucleophilic and electrophilic reagents. Russ Chem Bull 6, 583–589 (1957). https://doi.org/10.1007/BF01169274

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  • DOI: https://doi.org/10.1007/BF01169274

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