Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 2-3, Pages 267-282Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800916
Keywords
Cycloaddition; Bond theory; Electron Localization Function; Molecular Electron Density Theory; Molecular mechanisms
Categories
Funding
- Ministry of Economy and Competitiveness (MINECO) of the Spanish Government [CTQ2016-78669-P]
- European Social Fund [BES-2014-068258]
- MINECO
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After Huisgen's and Firestone's mechanistic proposals made in the 1960s based on experiments, several theories were proposed during the last century to explain [3+2] cycloaddition (32CA) reactions, most of them still prevailing today. Recent molecular electron density theory (MEDT) studies of 32CA reactions involving representative three-atom components have allowed characterising at least four different electronic structures, which experience a dissimilar chemical reactivity. In this review, the four simplest reactivity models are presented, providing a modern rationalisation of 32CA reactions based on MEDT.
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