Intermolecular [2+2] Photocycloaddition of β-Nitrostyrenes to Olefins upon Irradiation with Visible Light

The title compounds were found to undergo a [2+2] photocycloaddition with olefins at λ = 419 nm in CH (2) Cl (2) as the solvent. The resulting cyclobutanes were isolated in yields of 32–87% (11 examples) and showed a defined relative configuration at C1/C4 in the major dia­stereoisomer (nitro and ar...

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Autores principales: Mohr, Lisa-Marie, Bach, Thorsten
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Georg Thieme Verlag 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6376627/
http://dx.doi.org/10.1055/s-0036-1588524
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author Mohr, Lisa-Marie
Bach, Thorsten
author_facet Mohr, Lisa-Marie
Bach, Thorsten
author_sort Mohr, Lisa-Marie
collection PubMed
description The title compounds were found to undergo a [2+2] photocycloaddition with olefins at λ = 419 nm in CH (2) Cl (2) as the solvent. The resulting cyclobutanes were isolated in yields of 32–87% (11 examples) and showed a defined relative configuration at C1/C4 in the major dia­stereoisomer (nitro and aryl trans ). The analysis of side products and triplet sensitization experiments support a mechanistic scenario in which a 1,4-diradical is formed as a key intermediate.
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spelling pubmed-63766272019-02-19 Intermolecular [2+2] Photocycloaddition of β-Nitrostyrenes to Olefins upon Irradiation with Visible Light Mohr, Lisa-Marie Bach, Thorsten Synlett The title compounds were found to undergo a [2+2] photocycloaddition with olefins at λ = 419 nm in CH (2) Cl (2) as the solvent. The resulting cyclobutanes were isolated in yields of 32–87% (11 examples) and showed a defined relative configuration at C1/C4 in the major dia­stereoisomer (nitro and aryl trans ). The analysis of side products and triplet sensitization experiments support a mechanistic scenario in which a 1,4-diradical is formed as a key intermediate. Georg Thieme Verlag 2017-12-18 2017-08-31 /pmc/articles/PMC6376627/ http://dx.doi.org/10.1055/s-0036-1588524 Text en © Thieme Medical Publishers
spellingShingle Mohr, Lisa-Marie
Bach, Thorsten
Intermolecular [2+2] Photocycloaddition of β-Nitrostyrenes to Olefins upon Irradiation with Visible Light
title Intermolecular [2+2] Photocycloaddition of β-Nitrostyrenes to Olefins upon Irradiation with Visible Light
title_full Intermolecular [2+2] Photocycloaddition of β-Nitrostyrenes to Olefins upon Irradiation with Visible Light
title_fullStr Intermolecular [2+2] Photocycloaddition of β-Nitrostyrenes to Olefins upon Irradiation with Visible Light
title_full_unstemmed Intermolecular [2+2] Photocycloaddition of β-Nitrostyrenes to Olefins upon Irradiation with Visible Light
title_short Intermolecular [2+2] Photocycloaddition of β-Nitrostyrenes to Olefins upon Irradiation with Visible Light
title_sort intermolecular [2+2] photocycloaddition of β-nitrostyrenes to olefins upon irradiation with visible light
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6376627/
http://dx.doi.org/10.1055/s-0036-1588524
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