Regiospecific formation of the nitromethyl-substituted 3-phenyl-4,5-dihydroisoxazole via [3 + 2] cycloaddition
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Date
2018
Journal Title
Journal ISSN
Volume Title
Publisher
Springer Nature
Abstract
5-(Nitromethyl)-3-phenyl-4,5-dihydroisoxazole was obtained as a product of a high-yielding [3 + 2] cycloaddition reaction of in situ-generated benzonitrile N-oxide and 3-nitroprop-1-ene. For the first time, the regiochemistry of this reaction was unambiguously proven by X-ray structural analysis. The quantum-chemical calculation performed at the M06-2X/6-31G(d) (PCM) theoretical level affords a basis for explaining the course of reaction as well as the nature of transition states. Next, further DFT calculations together with spectral data shed light on structural aspects of the product.
Description
Keywords
Isoxazole, Nitrocompounds, 3-Nitroprop-1-ene, DFT calculations, [3 + 2] Cycloaddition
Citation
"Monatshefte für Chemie - Chemical Monthly", 2018, Vol. 149, nr 10, s. 1877-1884