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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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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. |
format | Online Article Text |
id | pubmed-9369901 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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