Unusual Reactivities of <i>ortho</i>-Hydroxy-β-nitrostyrene
Nitrostyrene derivatives are widely used in organic syntheses as a substrate for Michael addition, photoisomerization and cycloaddition. In contrast, <i>ortho</i>-hydroxy derivatives exhibit unusual behaviors in these reactions. Conjugate addition proceeded upon treatment of the <i>...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-07-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/15/4804 |
| _version_ | 1797441321668968448 |
|---|---|
| author | Kento Iwai Khimiya Wada Nagatoshi Nishiwaki |
| author_facet | Kento Iwai Khimiya Wada Nagatoshi Nishiwaki |
| author_sort | Kento Iwai |
| collection | DOAJ |
| description | Nitrostyrene derivatives are widely used in organic syntheses as a substrate for Michael addition, photoisomerization and cycloaddition. In contrast, <i>ortho</i>-hydroxy derivatives exhibit unusual behaviors in these reactions. Conjugate addition proceeded upon treatment of the <i>ortho</i>-hydroxy-β-nitrostyrene with an amine; however, subsequent C–C bond cleavage readily occurred to afford the corresponding imine. Moreover, conversion of the <i>trans</i>-isomer to a <i>cis</i>-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 <i>ortho</i>-hydroxy group. |
| first_indexed | 2024-03-09T12:22:21Z |
| format | Article |
| id | doaj.art-f49f17020a5d40ce85c3c295f792a691 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T12:22:21Z |
| publishDate | 2022-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f49f17020a5d40ce85c3c295f792a6912023-11-30T22:40:09ZengMDPI AGMolecules1420-30492022-07-012715480410.3390/molecules27154804Unusual Reactivities of <i>ortho</i>-Hydroxy-β-nitrostyreneKento Iwai0Khimiya Wada1Nagatoshi Nishiwaki2School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, JapanSchool of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, JapanSchool of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, JapanNitrostyrene derivatives are widely used in organic syntheses as a substrate for Michael addition, photoisomerization and cycloaddition. In contrast, <i>ortho</i>-hydroxy derivatives exhibit unusual behaviors in these reactions. Conjugate addition proceeded upon treatment of the <i>ortho</i>-hydroxy-β-nitrostyrene with an amine; however, subsequent C–C bond cleavage readily occurred to afford the corresponding imine. Moreover, conversion of the <i>trans</i>-isomer to a <i>cis</i>-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 <i>ortho</i>-hydroxy group.https://www.mdpi.com/1420-3049/27/15/4804nitrostyreneconjugate additionC–C bond cleavagephotoisomerization1,3-dipolar cycloaddition |
| spellingShingle | Kento Iwai Khimiya Wada Nagatoshi Nishiwaki Unusual Reactivities of <i>ortho</i>-Hydroxy-β-nitrostyrene Molecules nitrostyrene conjugate addition C–C bond cleavage photoisomerization 1,3-dipolar cycloaddition |
| title | Unusual Reactivities of <i>ortho</i>-Hydroxy-β-nitrostyrene |
| title_full | Unusual Reactivities of <i>ortho</i>-Hydroxy-β-nitrostyrene |
| title_fullStr | Unusual Reactivities of <i>ortho</i>-Hydroxy-β-nitrostyrene |
| title_full_unstemmed | Unusual Reactivities of <i>ortho</i>-Hydroxy-β-nitrostyrene |
| title_short | Unusual Reactivities of <i>ortho</i>-Hydroxy-β-nitrostyrene |
| title_sort | unusual reactivities of i ortho i hydroxy β nitrostyrene |
| topic | nitrostyrene conjugate addition C–C bond cleavage photoisomerization 1,3-dipolar cycloaddition |
| url | https://www.mdpi.com/1420-3049/27/15/4804 |
| work_keys_str_mv | AT kentoiwai unusualreactivitiesofiorthoihydroxybnitrostyrene AT khimiyawada unusualreactivitiesofiorthoihydroxybnitrostyrene AT nagatoshinishiwaki unusualreactivitiesofiorthoihydroxybnitrostyrene |