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Arene-Alkene Cycloaddition.
Type of publication
Peer-reviewed
Publikationsform
Review article (peer-reviewed)
Publication date
2016
Author
Remy Richard, Bochet Christian G,
Project
Photons in organic synthesis
Show all
Review article (peer-reviewed)
Journal
Chemical reviews
Volume (Issue)
.(.)
Page(s)
. - .
Title of proceedings
Chemical reviews
DOI
10.1021/acs.chemrev.6b00005
Abstract
Cycloadditions are among the most efficient chemical processes, combining atom economy, stereospecificity, and the ability to generate molecular complexity in a single step. Aromatic rings would in principle be ideal reaction partners, as they contain, at least from the topological point of view, both olefinic and diene subunits; however, the stability of the conjugated aromatic system would be broken by cycloaddition reactions, which are therefore rarely applied, because kinetics and thermodynamics hinder the process. From that aspect, photochemical activation opens interesting perspectives, as one can selectively provide excess energy to one of the reactants but not to the product, thus preventing thermal back reaction. Indeed, aromatic rings show a rich photochemistry, ranging from isomerizations, substitutions, and additions to cycloadditions. In this review, we will focus on cycloadditions, covering literature from early observations up to the present.
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