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Synthesis 2004(4): 481-495
DOI: 10.1055/s-2004-815973
DOI: 10.1055/s-2004-815973
REVIEW
© Georg Thieme Verlag Stuttgart · New YorkPhotochemical Cycloaddition between Benzene Derivatives and Alkenes
Weitere Informationen
Received
23 December 2003
Publikationsdatum:
12. Februar 2004 (online)
Publikationsverlauf
Publikationsdatum:
12. Februar 2004 (online)
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.
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1 Introduction
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2 [3+2] Photocycloaddition
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3 [2+2] Photocycloaddition
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4 [4+2] Photocycloaddition
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5 Other Related Photocycloaddtions with Benzene Derivatives
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6 Concluding Remarks
Key words
cycloadditions - arenes - photochemistry - stereoselectivity - natural products
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