Unexpected Dual Acylation of Naphtho[2,1-b]furan at the Aryl and Hetaryl Ring: Experimental and Theoretical Study
- Авторлар: Rybalkin V.1, Zmeyeva S.2, Tkachev V.3, Kletskii M.4, Burov O.4, Popova L.2, Dubonosov A.1, Bren V.2, Aldoshin S.3, Minkin V.2
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Мекемелер:
- 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
- Шығарылым: Том 89, № 7 (2019)
- Беттер: 1377-1383
- Бөлім: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/222980
- DOI: https://doi.org/10.1134/S1070363219070041
- ID: 222980
Дәйексөз келтіру
Аннотация
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).
Негізгі сөздер
Авторлар туралы
V. Rybalkin
Federal Research Centre the Southern Scientific Centre of the Russian Academy of Sciences
Email: aled@ipoc.sfedu.ru
Ресей, ul. Chekhova 41, Rostov-on-Don, 344006
S. Zmeyeva
Institute of Physical and Organic Chemistry
Email: aled@ipoc.sfedu.ru
Ресей, Rostov-on-Don
V. Tkachev
Institute of Problems of Chemical Physics of the Russian Academy of Sciences
Email: aled@ipoc.sfedu.ru
Ресей, Chernogolovka
M. Kletskii
Chemistry Department of the Southern Federal University
Email: aled@ipoc.sfedu.ru
Ресей, Rostov-on-Don
O. Burov
Chemistry Department of the Southern Federal University
Email: aled@ipoc.sfedu.ru
Ресей, Rostov-on-Don
L. Popova
Institute of Physical and Organic Chemistry
Email: aled@ipoc.sfedu.ru
Ресей, Rostov-on-Don
A. Dubonosov
Federal Research Centre the Southern Scientific Centre of the Russian Academy of Sciences
Хат алмасуға жауапты Автор.
Email: aled@ipoc.sfedu.ru
Ресей, ul. Chekhova 41, Rostov-on-Don, 344006
V. Bren
Institute of Physical and Organic Chemistry
Email: aled@ipoc.sfedu.ru
Ресей, Rostov-on-Don
S. Aldoshin
Institute of Problems of Chemical Physics of the Russian Academy of Sciences
Email: aled@ipoc.sfedu.ru
Ресей, Chernogolovka
V. Minkin
Institute of Physical and Organic Chemistry
Email: aled@ipoc.sfedu.ru
Ресей, Rostov-on-Don