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Isomerization of tetrahydrofurfuryl ethers of 1,2-glycols

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The catalytic rearrangements of tetrahydrofurfuryl 1,2-glycol ethers on Pt/C at 270‡ have been studied. Under these conditions the following initial reactions occur: isomerization of the tetrahydrofuran ring, hydrogenolysis of the ether bond in the side chain, and decarbonylation of the initial hydroxyl group.

  2. 2.

    During isomerization of the tetrahydrofuran ring at the 1,5 C-O bond, 1,5-ketoalcohols, which are changed by cyclodehydrogenation and hydrogenation reactions into homologs of 1,4-dioxene and 1,4-dioxane (16–25%), are formed.

  3. 3.

    Hydrogenolysis of the ether bond in the side chain leads to the formation of α-methyltetrahydrofuran (8–22%) and 2-pentanone (10–35%).

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Literature cited

  1. I. F. Bel'skii, S. N. Khar'kov, and N. I. Shuikin, Dokl. AN SSSR,165, 921 (1965).

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  2. N. I. Shuikin and I. F. Bel'skii, Dokl. AN SSSR,120, 548 (1958).

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  3. N. I. Shuikin, I. F. Bel'skii, and R. A. Karakhanov, Dokl. AN SSSR,127, 815 (1959).

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  4. N. I. Shuikin, I. F. Bel'skii, and Z. K. Vol'nova, Izv. AN SSSR, Ser. Khim.,1964, 1128.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    N. I. Shuikin, S. N. Khar'kov & I. F. Bel'skii

Authors
  1. N. I. Shuikin
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  2. S. N. Khar'kov
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  3. I. F. Bel'skii
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2548–2550, November, 1967.

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Shuikin, N.I., Khar'kov, S.N. & Bel'skii, I.F. Isomerization of tetrahydrofurfuryl ethers of 1,2-glycols. Russ Chem Bull 16, 2424–2426 (1967). https://doi.org/10.1007/BF00911858

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  • DOI: https://doi.org/10.1007/BF00911858

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