Photochemical Cycloaddition between Benzene Derivatives and Alkenes

Norbert Hoffmann

doi:10.1055/s-2004-815973

REVIEW

Photochemical Cycloaddition between Benzene Derivatives and Alkenes

Norbert Hoffmann*
Laboratoire des Réactions Sélectives et Applications, UMR CNRS et Université de Reims Champagne-Ardenne, UFR Sciences, B.P. 1039, 51687 REIMS, Cedex 2, France
Fax: +33(3)26913166; e-Mail: norbert.hoffmann@univ-reims.fr;

Abstract

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Abstract

The photochemical cycloaddition of benzene derivatives with alkenes yield polycyclic compounds, which are of great interest in organic synthesis. Three modes are observed: [2+2] (ortho), [3+2] (meta) and, less frequently, [4+2] (para) photocycloaddition. The [3+2] cycloaddition has preferentially been studied and its intramolecular version was frequently applied to the synthesis of natural products. The [2+2] photocycloaddition is observed when electron active subsituents are present on the reaction partners. This mode is often followed by photochemical or thermal rearrangements. Furthermore, the [2+2] mode occurs concomitantly with the [3+2] photocycloaddition and leads frequently to complex reaction mixtures. More recent investigations deal with this item and show how the reaction may be directed to the [2+2] mode.

1 Introduction
2 [3+2] Photocycloaddition
3 [2+2] Photocycloaddition
4 [4+2] Photocycloaddition
5 Other Related Photocycloaddtions with Benzene Derivatives
6 Concluding Remarks

Key words

cycloadditions - arenes - photochemistry - stereoselectivity - natural products

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