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Stereochemistry of heterocycles

XIV. Synthesis of some 1,3-dioxepans from substituted 1,4-diols

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Methods were developed for the synthesis of 2-ethoxy-1,4-butanediol and 2-ethoxy-1,4-pentanediol. The latter was a mixture of diastereomers. These diols were used to synthesize 5-ethoxy-1,3-dioxepan and 2,2,4-trimethyl-6-ethoxy-1,3-dioxepan. Gas-liquid chromatography was used to demonstrate that 2,2,4-trimethyl-6-ethoxy-1,3-dioxepan is a mixture of cis and trans isomers; the ratio of these isomers is similar to the ratio of diastereomers in the starting 2-ethoxy-1,4-pentanediol. The configurations of the indicated isomers were evaluated by conformational analysis.

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Authors and Affiliations

  1. I.I. Mechnikov Odessa State University, USSR

    A. V. Bogatskii, G. L. Kamalov, N. G. Luk'yanenko & E. A. Donets

Authors
  1. A. V. Bogatskii
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  2. G. L. Kamalov
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  3. N. G. Luk'yanenko
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  4. E. A. Donets
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Additional information

See [1] for communication XIII.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 3–6, January, 1972.

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Bogatskii, A.V., Kamalov, G.L., Luk'yanenko, N.G. et al. Stereochemistry of heterocycles. Chem Heterocycl Compd 8, 1–4 (1972). https://doi.org/10.1007/BF00478476

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  • DOI: https://doi.org/10.1007/BF00478476

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