4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide
1,2,5-Oxadiazole oxides (furoxans) are well known nitric oxide donors; among them, 4-fluorofuroxans have recently been found to be important photoinduced nitric oxide donors. In this research, it was shown that the reaction of 4,4′-dinitro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-dioxide with fluoro-contain...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-02-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2023/1/M1596 |
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| author | Natalia V. Obruchnikova Oleg A. Rakitin |
| author_facet | Natalia V. Obruchnikova Oleg A. Rakitin |
| author_sort | Natalia V. Obruchnikova |
| collection | DOAJ |
| description | 1,2,5-Oxadiazole oxides (furoxans) are well known nitric oxide donors; among them, 4-fluorofuroxans have recently been found to be important photoinduced nitric oxide donors. In this research, it was shown that the reaction of 4,4′-dinitro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-dioxide with fluoro-containing reagents (tetrabutylammonium fluoride or cesium fluoride) selectively gave the bis-substitution product 4,4′-difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-dioxide. The structure of the synthesized compound was established by elemental analysis, <sup>13</sup>C, <sup>19</sup>F-NMR and IR spectroscopy, and mass-spectrometry. |
| first_indexed | 2024-03-11T06:08:36Z |
| format | Article |
| id | doaj.art-b1e1cb29218f40a3b4d568a29d6525c8 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-11T06:08:36Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-b1e1cb29218f40a3b4d568a29d6525c82023-11-17T12:49:55ZengMDPI AGMolbank1422-85992023-02-0120231M159610.3390/M15964,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-DioxideNatalia V. Obruchnikova0Oleg A. Rakitin1N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russia1,2,5-Oxadiazole oxides (furoxans) are well known nitric oxide donors; among them, 4-fluorofuroxans have recently been found to be important photoinduced nitric oxide donors. In this research, it was shown that the reaction of 4,4′-dinitro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-dioxide with fluoro-containing reagents (tetrabutylammonium fluoride or cesium fluoride) selectively gave the bis-substitution product 4,4′-difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-dioxide. The structure of the synthesized compound was established by elemental analysis, <sup>13</sup>C, <sup>19</sup>F-NMR and IR spectroscopy, and mass-spectrometry.https://www.mdpi.com/1422-8599/2023/1/M15961,2,5-oxadiazole oxides4-fluorofuroxansnucleophilic substitutioncesium fluoridetetrabutylammonium fluoride |
| spellingShingle | Natalia V. Obruchnikova Oleg A. Rakitin 4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide Molbank 1,2,5-oxadiazole oxides 4-fluorofuroxans nucleophilic substitution cesium fluoride tetrabutylammonium fluoride |
| title | 4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide |
| title_full | 4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide |
| title_fullStr | 4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide |
| title_full_unstemmed | 4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide |
| title_short | 4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide |
| title_sort | 4 4 difluoro 3 3 bi 1 2 5 oxadiazole 2 2 dioxide |
| topic | 1,2,5-oxadiazole oxides 4-fluorofuroxans nucleophilic substitution cesium fluoride tetrabutylammonium fluoride |
| url | https://www.mdpi.com/1422-8599/2023/1/M1596 |
| work_keys_str_mv | AT nataliavobruchnikova 44difluoro33bi125oxadiazole22dioxide AT olegarakitin 44difluoro33bi125oxadiazole22dioxide |