Conclusions
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1.
The cleavage of tetrahydrofuran (THF) by acetyl bromide does not require catalysis using hydrogen bromide or other acid.
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2.
Acetic anhydride is capable of cleaving certain compounds of the THF series under the catalytic influence not only of mineral acids, but also of weaker donors of protons, namely organic acids.
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3.
The cleavage of the tetrahydrofuran ring in 2-phenyl-tetrahydrofuran using acetyl bromide goes with the formation of only one structural isomer. The action of acid halides on tetrahydrofurfuryl acetate and tetrahydrofurfuryl halides leads to a mixture of isomers.
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This paper is published on the basis of the decision made by the editorial board of the journals of the Academy of Sciences of the USSR on July 12, 1962, as the dissertational work of R. M. Ispiryan.
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2513–2522, November, 1967.
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Ispiryan, R.M., Belen'kii, L.I. & Gol'dfarb, Y.L. Cleavage of the tetrahydrofuran ring by acid halides and acid anhydrides. Russ Chem Bull 16, 2391–2398 (1967). https://doi.org/10.1007/BF00911851
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DOI: https://doi.org/10.1007/BF00911851