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Unexpected Dual Acylation of Naphtho[2,1-b]furan at the Aryl and Hetaryl Ring: Experimental and Theoretical Study

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Abstract

Depending on the reaction conditions, the acylation of 2-ethylnaphtho[2,1-b]furan leads to the formation of a mixture of 1-acetyl-, 5-acetyl-, and 1,5-diacetyl derivatives with a widely varying ratio of components, the structure of which has been characterized by IR and NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis methods. Quantum-chemical simulations using the DFT B3LYP/6-311++G** method have reproduced the experimental geometry of isomeric acetyl[2,1-b]furans and indicated their close thermodynamic stability. However, the Fukui indices of the reactivity f− have indicated the preference of the primary attack of the electrophile at the C5 position (f− = 0.18) as compared to the C1 position (f− = 0.06).

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Funding

This study was performed in the scope of the basic part of the State Task of the Ministry of Education and Science of the Russian Federation in the field of scientific activity [no. 4.6497.2017/8.9, 4.5593.2017/6.7 (Southern Federal University), 0089-2014-0009 (Institute of Problems of Chemical Physics of Russian Academy of Sciences), and 01201354239 (Southern Scientific Center of Russian Academy of Sciences)].

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Authors and Affiliations

  1. Federal Research Centre the Southern Scientific Centre of the Russian Academy of Sciences, ul. Chekhova 41, Rostov-on-Don, 344006, Russia

    V. P. Rybalkin & A. D. Dubonosov

  2. Institute of Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don, Russia

    S. Yu. Zmeyeva, L. L. Popova, V. V. Bren & V. I. Minkin

  3. Institute of Problems of Chemical Physics of the Russian Academy of Sciences, Chernogolovka, Russia

    V. V. Tkachev & S. M. Aldoshin

  4. Chemistry Department of the Southern Federal University, Rostov-on-Don, Russia

    M. E. Kletskii & O. N. Burov

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  1. V. P. Rybalkin
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  2. S. Yu. Zmeyeva
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  3. V. V. Tkachev
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  4. M. E. Kletskii
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  6. L. L. Popova
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  7. A. D. Dubonosov
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  8. V. V. Bren
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  9. S. M. Aldoshin
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  10. V. I. Minkin
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Correspondence to A. D. Dubonosov.

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Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 7, pp. 1013–1020.

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Rybalkin, V.P., Zmeyeva, S.Y., Tkachev, V.V. et al. Unexpected Dual Acylation of Naphtho[2,1-b]furan at the Aryl and Hetaryl Ring: Experimental and Theoretical Study. Russ J Gen Chem 89, 1377–1383 (2019). https://doi.org/10.1134/S1070363219070041

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