Regiospecific formation of the nitromethyl-substituted 3-phenyl-4,5-dihydroisoxazole via [3 + 2] cycloaddition

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 an...

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Detalles Bibliográficos
Autores principales: Mirosław, Barbara, Babyuk, Dmytro, Łapczuk-Krygier, Agnieszka, Kącka-Zych, Agnieszka, Demchuk, Oleg M., Jasiński, Radomir
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2018
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6133101/
https://www.ncbi.nlm.nih.gov/pubmed/30237620
http://dx.doi.org/10.1007/s00706-018-2227-6
Descripción
Sumario: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. GRAPHICAL ABSTRACT: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s00706-018-2227-6) contains supplementary material, which is available to authorized users.

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