Photocyclisations of <i>o</i> -iodobenzyl-indanones and tetralones infer the intermediacy of triplet aryl cations

Photocyclisations of aryl iodides to 2-indanones and 2-tetralones give different outcomes to analogous radical reactions implicating the intermediacy of triplet aryl cations. Additions to 2-indanones generally give dibenzoisochromenones by sequential cyclisation, CO extrusion and electrocyclisation. By contrast, 2-tetralones produce benzo[<i>a</i>]phenalenones by <i>ortho</i>-cyclisation.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc05185a
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Photocyclisations of o -iodobenzyl-indanones and tetralones infer the intermediacy of triplet aryl cations

Marian Powderly, Julien Legros, Toby Lindup
Chemical Communications
Radical Photochemical Reactions
article

Photocyclisations of o -iodobenzyl-indanones and tetralones infer the intermediacy of triplet aryl cations

Marian Powderly, Julien Legros, Toby Lindup
article en

Abstract

Photocyclisations of aryl iodides to 2-indanones and 2-tetralones give different outcomes to analogous radical reactions implicating the intermediacy of triplet aryl cations. Additions to 2-indanones generally give dibenzoisochromenones by sequential cyclisation, CO extrusion and electrocyclisation. By contrast, 2-tetralones produce benzo[<i>a</i>]phenalenones by <i>ortho</i>-cyclisation.

Chemical CommunicationsVol. 61(97)
Centre National de la Recherche Scientifique (FR), Sorbonne Université (FR), Laboratoire de Chimie Théorique (FR), Normandie Université (FR), University of Southampton (GB), Université de Rouen Normandie (FR), Institut National des Sciences Appliquées Rouen Normandie (FR)
Openalex Percentile: Top 75%
Radical Photochemical Reactions
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