Understanding the Molecular Mechanism of Thermal and LA-Catalysed Diels–Alder Reactions between Cyclopentadiene and Isopropyl 3-Nitroprop-2-Enate

Autor:	Ewa Dresler, Aneta Wróblewska, Radomir Jasiński
Jazyk:	angličtina
Rok vydání:	2023
Předmět:	Diels–Alder reaction nitroalkene molecular mechanism molecular electron density theory DFT calculations Organic chemistry QD241-441
Zdroj:	Molecules, Vol 28, Iss 14, p 5289 (2023)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules28145289
Popis:	The molecular mechanism of the Diels–Alder reaction with the participation of cyclopentadiene and isopropyl 3-nitroprop-2-enate was examined based on wb97xd/6-311+G(d) (PCM) quantum chemical calculations. It was found that the type of mechanism for the conversion of addends depends significantly on the reaction conditions. In less-polar environments, a one-step polar mechanism is realised. In more polar solvents, the formation of “extended”-type zwitterionic intermediates is possible. In contrast, in the presence of an LA-type catalyst, the one-step mechanisms are replaced by respective stepwise mechanisms with zwitterionic or heterocyclic intermediates.
Databáze:	Directory of Open Access Journals
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