Add time:09/29/2019         Source:infona.pl

Depending on the reaction conditions, the acylation of 2-ethylnaphtho[2,1-b]furan (cas 232-95-1) 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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