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Photochemical reactions of aromatic compounds and the concept of the photon as a traceless reagent

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Abstract

Electronic excitation significantly changes the reactivity of chemical compounds. Compared to ground state reactions, photochemical reactions considerably enlarge the application spectrum of a particular functional group in organic synthesis. Multistep syntheses may be simplified and perspectives for target oriented synthesis (TOS) and diversity oriented synthesis (DOS) are developed. New compound families become available or may be obtained more easily. In contrast to common chemical reagents, photons don’t generate side products resulting from the transformation of a chemical reagent. Therefore, they are considered as a traceless reagent. Consequently, photochemical reactions play a central role in the methodology of sustainable chemistry. This aspect has been recognized since the beginning of the 20th century. As with many other photochemical transformations, photochemical reactions of aromatic, benzene-like compounds illustrate well the advantages in this context. Photochemical cycloadditions of aromatic compounds have been investigated for a long time. Currently, they are applied in various fields of organic synthesis. They are also studied in supramolecular structures. The phenomena of reactivity and stereoselectivity are investigated. During recent years, photochemical electron transfer mediated reactions are particularly focused. Such transformations have likewise been performed with aromatic compounds. Reactivity and selectivity as well as application to organic synthesis are studied.

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  1. Institut de Chimie Moléculaire de Reims, UMR 7312 CNRS et Université de Reims Champagne-Ardenne, Equipe de Photochimie, UFR Sciences, B.P. 1039, F-51687, Reims, cedex 02, France

    Norbert Hoffmann

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This article is published as part of a themed issue in honour of Jean-Pierre Desvergne on the occasion of his 65th birthday.

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Hoffmann, N. Photochemical reactions of aromatic compounds and the concept of the photon as a traceless reagent. Photochem Photobiol Sci 11, 1613–1641 (2012). https://doi.org/10.1039/c2pp25074h

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