Abstract
The most probable mechanism for the opening of the oxirane ring in propynyloxirane (3-ethynyl-1,2-epoxypropane) is presented. Due to the rearrangement, a mixture of the Z and E isomers of enyne alcohols is formed. The 1H NMR data and quantum-chemical calculations revealed intramolecular interactions between the π-electrons of the triple bond and the OH proton in the six-membered ring of the Z isomer.
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The work was financially supported by the Ministry of Economy and Trade of the Republic of Tajikistan (project GR no. 0116 EO 00547).
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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 11, pp. 1614–1623 https://doi.org/10.31857/S0514749221110070.
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Isobaev, M.D., Fayzilov, I.U., Abdullaev, T.K. et al. On the Mechanism of Propynyloxirane Rearrangement. Russ J Org Chem 57, 1853–1860 (2021). https://doi.org/10.1134/S1070428021110075
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DOI: https://doi.org/10.1134/S1070428021110075