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Atranes

XLVIII. Kinetics and mechanism of the hydrolysis of 1-(α-chloroalkyl)silatranes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The kinetics of the hydrolysis of 1-(α-chloroalkyl)silatranes

(where R=ClCH2 Cl2CH, and CH3ClCH, and n=1–3) at 25°C in neutral and acidic aqueous and aqueous alcoholic media with H2O,2H2O, and H2 18O were studied. The rate of hydrolysis in acidic media is considerably higher than in neutral media. The introduction of methyl groups in the 3, 7, and 10 position of the atrane ring and an increase in the electronegativity of the substituent attached to the silicon atom lower the rate of hydrolysis. According to the mass spectrometric data, the triethanolamine formed during hydrolysis in H2 18O does not contain18O, which indicates hydrolytic cleavage of the Si-O bond rather than the O-C bond.

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Literature cited

  1. M. G. Voronkov, G. I. Zelchan, V. I. Savushkina, B. M. Tabenko, and E. A Chernyshev, Khim. Geterotsikl. Soedin., No. 6, 772 (1976).

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Authors and Affiliations

  1. Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, USSR

    M. G. Voronkov, I. S. Emel'yanov, V. M. D'yakov, V. Yu. Vitkovskii, L. V. Kapranova & V. T. Baryshok

Authors
  1. M. G. Voronkov
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  2. I. S. Emel'yanov
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  3. V. M. D'yakov
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  4. V. Yu. Vitkovskii
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  5. L. V. Kapranova
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  6. V. T. Baryshok
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Additional information

See [1] for communication LXVII.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1344–1346, October, 1976.

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Voronkov, M.G., Emel'yanov, I.S., D'yakov, V.M. et al. Atranes. Chem Heterocycl Compd 12, 1114–1116 (1976). https://doi.org/10.1007/BF00945592

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  • DOI: https://doi.org/10.1007/BF00945592

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