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Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene

Nitrostyrene derivatives are widely used in organic syntheses as a substrate for Michael addition, photoisomerization and cycloaddition. In contrast, ortho-hydroxy derivatives exhibit unusual behaviors in these reactions. Conjugate addition proceeded upon treatment of the ortho-hydroxy-β-nitrostyren...

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Detalles Bibliográficos
Autores principales: Iwai, Kento, Wada, Khimiya, Nishiwaki, Nagatoshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9369901/
https://www.ncbi.nlm.nih.gov/pubmed/35956754
http://dx.doi.org/10.3390/molecules27154804
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author Iwai, Kento
Wada, Khimiya
Nishiwaki, Nagatoshi
author_facet Iwai, Kento
Wada, Khimiya
Nishiwaki, Nagatoshi
author_sort Iwai, Kento
collection PubMed
description Nitrostyrene derivatives are widely used in organic syntheses as a substrate for Michael addition, photoisomerization and cycloaddition. In contrast, ortho-hydroxy derivatives exhibit unusual behaviors in these reactions. Conjugate addition proceeded upon treatment of the ortho-hydroxy-β-nitrostyrene with an amine; however, subsequent C–C bond cleavage readily occurred to afford the corresponding imine. Moreover, conversion of the trans-isomer to a cis-isomer did not occur efficiently, even when UV light was irradiated. We studied these unusual behaviors of β-nitrostyrene, focusing on the role of the ortho-hydroxy group.
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spelling pubmed-93699012022-08-12 Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene Iwai, Kento Wada, Khimiya Nishiwaki, Nagatoshi Molecules Article Nitrostyrene derivatives are widely used in organic syntheses as a substrate for Michael addition, photoisomerization and cycloaddition. In contrast, ortho-hydroxy derivatives exhibit unusual behaviors in these reactions. Conjugate addition proceeded upon treatment of the ortho-hydroxy-β-nitrostyrene with an amine; however, subsequent C–C bond cleavage readily occurred to afford the corresponding imine. Moreover, conversion of the trans-isomer to a cis-isomer did not occur efficiently, even when UV light was irradiated. We studied these unusual behaviors of β-nitrostyrene, focusing on the role of the ortho-hydroxy group. MDPI 2022-07-27 /pmc/articles/PMC9369901/ /pubmed/35956754 http://dx.doi.org/10.3390/molecules27154804 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Iwai, Kento
Wada, Khimiya
Nishiwaki, Nagatoshi
Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene
title Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene
title_full Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene
title_fullStr Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene
title_full_unstemmed Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene
title_short Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene
title_sort unusual reactivities of ortho-hydroxy-β-nitrostyrene
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9369901/
https://www.ncbi.nlm.nih.gov/pubmed/35956754
http://dx.doi.org/10.3390/molecules27154804
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