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Title

Concerted albeit not pericyclic cycloadditions: Understanding the mechanism of the (4+3) cycloaddition between nitrones and 1,2‐diaza‐1,3‐dienes

AuthorsPedrón, Manuel; Delso, J. Ignacio; Tejero, Tomás CSIC ORCID; Merino, Pedro CSIC ORCID
KeywordsNitrones
Diazadienes
Cycloaddition
Density functional calculations
Reaction mechanisms
Issue Date2019
PublisherWiley-VCH
CitationEuropean Journal of Organic Chemistry (2-3): 391-400 (2019)
AbstractThe mechanism of (4+3) cycloaddition reactions of nitrones with 1,2‐diaza‐1,3‐dienes has been studied by using density functional theory (DFT) methods. The cycloaddition reaction takes place through an asynchronous concerted transition state that reflects a two‐stage process in which the formation of the first bond occurs close to the transition state, while the second bond forms well after the transition state. The alternative stepwise mechanism is higher in energy than the concerted process. In this mechanism, the nitrone oxygen acts as a nucleophile by attacking the more electrophilic terminal carbon of the 1,2‐diaza‐1,3‐diene to form an intermediate. The second step of the reaction is the rate‐limiting one, which is higher in energy than that observed for the concerted process. Topological analysis of the gradient field of electron localization function (ELF) provides a complete characterization of the electron density changes during the course of the reaction.
Publisher version (URL)https://doi.org/10.1002/ejoc.201800663
URIhttp://hdl.handle.net/10261/187170
DOI10.1002/ejoc.201800663
ISSN1434-193X
E-ISSN1099-0690
Appears in Collections:(ISQCH) Artículos




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