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

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dc.contributor.authorDemchuk, Oleg M.
dc.contributor.authorMirosław, Barbara
dc.contributor.authorBabyuk, Dmytro
dc.contributor.authorŁapczuk-Krygier, Agnieszka
dc.contributor.authorKącka-Zych, Agnieszka
dc.contributor.authorJasiński, Radomir
dc.date.accessioned2022-06-23T09:04:17Z
dc.date.available2022-06-23T09:04:17Z
dc.date.issued2018
dc.description.abstract5-(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.pl
dc.description.sponsorshipThe research was carried out with the equipment purchased thanks to the financial support of the European Regional Development Fund in the framework of the Operational Program Development of Eastern Poland 2007–2013 (Contract no. UDA-POIG.02.01.00-06-212/09-03, ECOTECH Complex—Man, Environment, Production). The authors also thank the Polish Ministry of Science and High Education for financial support (Grant no. C-2/171/2017/DS).pl
dc.identifier.citation"Monatshefte für Chemie - Chemical Monthly", 2018, Vol. 149, nr 10, s. 1877-1884pl
dc.identifier.doi10.1007/s00706-018-2227-6
dc.identifier.urihttp://hdl.handle.net/20.500.12153/3229
dc.language.isoenpl
dc.publisherSpringer Naturepl
dc.rightsUznanie autorstwa-Użycie niekomercyjne-Bez utworów zależnych 3.0 Polska*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/pl/*
dc.subjectIsoxazolepl
dc.subjectNitrocompoundspl
dc.subject3-Nitroprop-1-enepl
dc.subjectDFT calculationspl
dc.subject[3 + 2] Cycloadditionpl
dc.titleRegiospecific formation of the nitromethyl-substituted 3-phenyl-4,5-dihydroisoxazole via [3 + 2] cycloadditionpl
dc.typeinfo:eu-repo/semantics/articlepl
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