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Title: Regiospecific formation of the nitromethyl-substituted 3-phenyl-4,5-dihydroisoxazole via [3 + 2] cycloaddition
Authors: Demchuk, Oleg M.
Mirosław, Barbara
Babyuk, Dmytro
Łapczuk-Krygier, Agnieszka
Kącka-Zych, Agnieszka
Jasiński, Radomir
Keywords: Isoxazole; Nitrocompounds; 3-Nitroprop-1-ene; DFT calculations; [3 + 2] Cycloaddition
Issue Date: 2018
Publisher: Springer Nature
Citation: "Monatshefte für Chemie - Chemical Monthly", 2018, Vol. 149, nr 10, s. 1877-1884
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.
DOI: 10.1007/s00706-018-2227-6
Appears in Collections:Artykuły naukowe (WNŚiNoZ)

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