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Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes
The Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic 1,3-dienes was investigated. A series of novel monofluorinated norbornenes was prepared in up to 97% yield. The reaction with 1,3-cyclohexadiene permits the preparation of monofluorinated bicyclo[2.2.2]oct-2-enes. The kinetic data of t...
| Autores principales: | , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2021
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7849230/ https://www.ncbi.nlm.nih.gov/pubmed/33564337 http://dx.doi.org/10.3762/bjoc.17.27 |
| _version_ | 1783645272089296896 |
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| author | Ponomarev, Savva A Larkovich, Roman V Aldoshin, Alexander S Tabolin, Andrey A Ioffe, Sema L Groß, Jonathan Opatz, Till Nenajdenko, Valentine G |
| author_facet | Ponomarev, Savva A Larkovich, Roman V Aldoshin, Alexander S Tabolin, Andrey A Ioffe, Sema L Groß, Jonathan Opatz, Till Nenajdenko, Valentine G |
| author_sort | Ponomarev, Savva A |
| collection | PubMed |
| description | The Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic 1,3-dienes was investigated. A series of novel monofluorinated norbornenes was prepared in up to 97% yield. The reaction with 1,3-cyclohexadiene permits the preparation of monofluorinated bicyclo[2.2.2]oct-2-enes. The kinetic data of the reactions with 1,3-cyclopentadiene and 1,3-cyclohexadiene were used to calculate activation parameters. Furthermore, the synthetic utility of the cycloadducts obtained was demonstrated. |
| format | Online Article Text |
| id | pubmed-7849230 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2021 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-78492302021-02-08 Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes Ponomarev, Savva A Larkovich, Roman V Aldoshin, Alexander S Tabolin, Andrey A Ioffe, Sema L Groß, Jonathan Opatz, Till Nenajdenko, Valentine G Beilstein J Org Chem Full Research Paper The Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic 1,3-dienes was investigated. A series of novel monofluorinated norbornenes was prepared in up to 97% yield. The reaction with 1,3-cyclohexadiene permits the preparation of monofluorinated bicyclo[2.2.2]oct-2-enes. The kinetic data of the reactions with 1,3-cyclopentadiene and 1,3-cyclohexadiene were used to calculate activation parameters. Furthermore, the synthetic utility of the cycloadducts obtained was demonstrated. Beilstein-Institut 2021-01-27 /pmc/articles/PMC7849230/ /pubmed/33564337 http://dx.doi.org/10.3762/bjoc.17.27 Text en Copyright © 2021, Ponomarev et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms) |
| spellingShingle | Full Research Paper Ponomarev, Savva A Larkovich, Roman V Aldoshin, Alexander S Tabolin, Andrey A Ioffe, Sema L Groß, Jonathan Opatz, Till Nenajdenko, Valentine G Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes |
| title | Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes |
| title_full | Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes |
| title_fullStr | Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes |
| title_full_unstemmed | Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes |
| title_short | Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes |
| title_sort | diels–alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes |
| topic | Full Research Paper |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7849230/ https://www.ncbi.nlm.nih.gov/pubmed/33564337 http://dx.doi.org/10.3762/bjoc.17.27 |
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