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Sulfur heterocycles.

12. Reactions of cyclic anhydrides of β-sulfinocarboxylic acids with nucleophiles

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    1,2-Oxathiolan-5-one-2-oxides are readily cleaved by nucleophiles (H2O, ROH, HNR2) under mild conditions at the O-CO bond only, with the formation of the β-(hydroxysulfinyl)-alkanoic acid derivatives.

  2. 2.

    2,1-Benzoxathiol-3-one-1-oxide is cleaved by alcohols at both the O-CO and the O-SO bonds to give the unstable monoesters at the carboxyl and sulfinyl groups.

  3. 3.

    Unlike 2,1-benzoxathiol-3-one-1-oxide, 1,2-oxathiolan-5-one-2-oxides on boiling with excess alcohols give β-(hydroxysulfinyl)alkanoic acid bisesters.

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Literature cited

  1. T. P. Vasil'eva, V. M. Bystrova, O. V. Kil'disheva, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 1299 (1986).

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  4. T. P. Vasil'eva, M. G. Lin'kova, O. V. Kil'disheva, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 159 (1981).

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    T. P. Vasil'eva, V. M. Bystrova & O. V. Kil'disheva

Authors
  1. T. P. Vasil'eva
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  2. V. M. Bystrova
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  3. O. V. Kil'disheva
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Additional information

For previous communication, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1633–1640, July, 1988.

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Vasil'eva, T.P., Bystrova, V.M. & Kil'disheva, O.V. Sulfur heterocycles.. Russ Chem Bull 37, 1448–1455 (1988). https://doi.org/10.1007/BF00962760

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  • DOI: https://doi.org/10.1007/BF00962760

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