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Synthesis of 2,6-dioxabicyclo[3.3.0]octanes and 3,8-dioxabicyclo[4.4.0]dec-1(6)-enes by electrophilic cyclization of 3,4-dimethylene-1,6-hexanediols

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Abstract

3,4-Dimethylene-1,6-hexane diols2 obtained by allylboration of ketones with 2,3-dimethylene-1,4-bis(dipropylboryl)butane1 undergo cyclization on treatment with I2/NaHCO3 to give 1,5-cis-di(iodomethyl)-2,6-dioxabicyclo[3.3.0]octanes (4) and/or 3,8-dioxabicyclo[4.4.0]dec-1(6)-enes (5). 4,4,9,9-Tetramethyl-3,8-dioxacyclodeca-1,6-dione (9) was synthesized by ozonolysis of bicyclic compound5b. The structure of compound5e was confirmed by X-ray diffraction analysis.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation

    M. E. Gurskii, S. B. Golovin, M. O. Dekaprilevich & Yu. N. Bubnov

  2. A. N. Nemeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation

    Yu. T. Struchkov

Authors
  1. M. E. Gurskii
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  2. S. B. Golovin
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  3. M. O. Dekaprilevich
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  4. Yu. T. Struchkov
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  5. Yu. N. Bubnov
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1308–1314, July, 1995.

This study was financially supported by the Russian Foundation for Basic Research (Grant No. 94-03-18193) and the International Science Foundation (Grant No. M3Y000).

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Gurskii, M.E., Golovin, S.B., Dekaprilevich, M.O. et al. Synthesis of 2,6-dioxabicyclo[3.3.0]octanes and 3,8-dioxabicyclo[4.4.0]dec-1(6)-enes by electrophilic cyclization of 3,4-dimethylene-1,6-hexanediols. Russ Chem Bull 44, 1262–1268 (1995). https://doi.org/10.1007/BF00700900

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  • DOI: https://doi.org/10.1007/BF00700900

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