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Alkylation of tetrahydrofuran with alkenes and unsaturated ethers

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

Conclusions

  1. 1.

    The alkylation of tetrahydrofuran with alkenes and unsaturated ethers in presence of di-t-butyl peroxide was investigated. Alkylation goes at the 2-carbon atom of tetrahydrofuran, and alkenes and unsaturated ethers add through their terminal unsaturated carbon atom.

  2. 2.

    The effect of the proportions of the components, the length of the carbon chain of the alkene, and other factors on the yield of the monoderivative was studied. With diminution in the concentration of 1-hexene in the reaction mixture from 33 to 3.3%, the yield of hexyltetrahydrofuran rises from 13.2 to 79.2%.

  3. 3.

    Alkylation in presence of the peroxide is accompanied by the isomerization of the alkyltetrahydrofuran into the corresponding aliphatic ketone.

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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 & B. L. Lebedev

Authors
  1. N. I. Shuikin
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  2. B. L. Lebedev
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 639–644, March, 1967.

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Shuikin, N.I., Lebedev, B.L. Alkylation of tetrahydrofuran with alkenes and unsaturated ethers. Russ Chem Bull 16, 615–618 (1967). https://doi.org/10.1007/BF00906004

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  • DOI: https://doi.org/10.1007/BF00906004

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