Unexpected Dual Acylation of Naphtho[2,1-b]furan at the Aryl and Hetaryl Ring: Experimental and Theoretical Study
- Authors: Rybalkin V.P.1, Zmeyeva S.Y.2, Tkachev V.V.3, Kletskii M.E.4, Burov O.N.4, Popova L.L.2, Dubonosov A.D.1, Bren V.V.2, Aldoshin S.M.3, Minkin V.I.2
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Affiliations:
- Federal Research Centre the Southern Scientific Centre of the Russian Academy of Sciences
- Institute of Physical and Organic Chemistry
- Institute of Problems of Chemical Physics of the Russian Academy of Sciences
- Chemistry Department of the Southern Federal University
- Issue: Vol 89, No 7 (2019)
- Pages: 1377-1383
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/222980
- DOI: https://doi.org/10.1134/S1070363219070041
- ID: 222980
Cite item
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).
Keywords
About the authors
V. P. Rybalkin
Federal Research Centre the Southern Scientific Centre of the Russian Academy of Sciences
Email: aled@ipoc.sfedu.ru
Russian Federation, ul. Chekhova 41, Rostov-on-Don, 344006
S. Yu. Zmeyeva
Institute of Physical and Organic Chemistry
Email: aled@ipoc.sfedu.ru
Russian Federation, Rostov-on-Don
V. V. Tkachev
Institute of Problems of Chemical Physics of the Russian Academy of Sciences
Email: aled@ipoc.sfedu.ru
Russian Federation, Chernogolovka
M. E. Kletskii
Chemistry Department of the Southern Federal University
Email: aled@ipoc.sfedu.ru
Russian Federation, Rostov-on-Don
O. N. Burov
Chemistry Department of the Southern Federal University
Email: aled@ipoc.sfedu.ru
Russian Federation, Rostov-on-Don
L. L. Popova
Institute of Physical and Organic Chemistry
Email: aled@ipoc.sfedu.ru
Russian Federation, Rostov-on-Don
A. D. Dubonosov
Federal Research Centre the Southern Scientific Centre of the Russian Academy of Sciences
Author for correspondence.
Email: aled@ipoc.sfedu.ru
Russian Federation, ul. Chekhova 41, Rostov-on-Don, 344006
V. V. Bren
Institute of Physical and Organic Chemistry
Email: aled@ipoc.sfedu.ru
Russian Federation, Rostov-on-Don
S. M. Aldoshin
Institute of Problems of Chemical Physics of the Russian Academy of Sciences
Email: aled@ipoc.sfedu.ru
Russian Federation, Chernogolovka
V. I. Minkin
Institute of Physical and Organic Chemistry
Email: aled@ipoc.sfedu.ru
Russian Federation, Rostov-on-Don