4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide

Obruchnikova, Natalia V.; Rakitin, Oleg A.

doi:10.3390/M1596

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4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide

by

Natalia V. Obruchnikova

and

Oleg A. Rakitin

^*

N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russia

^*

Author to whom correspondence should be addressed.

Molbank 2023, 2023(1), M1596; https://doi.org/10.3390/M1596

Submission received: 3 February 2023 / Revised: 16 February 2023 / Accepted: 20 February 2023 / Published: 23 February 2023

(This article belongs to the Collection Heterocycle Reactions)

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Abstract

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, ¹³C, ¹⁹F-NMR and IR spectroscopy, and mass-spectrometry.

Keywords: 1,2,5-oxadiazole oxides; 4-fluorofuroxans; nucleophilic substitution; cesium fluoride; tetrabutylammonium fluoride

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Obruchnikova, N.V.; Rakitin, O.A. 4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide. Molbank 2023, 2023, M1596. https://doi.org/10.3390/M1596

AMA Style

Obruchnikova NV, Rakitin OA. 4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide. Molbank. 2023; 2023(1):M1596. https://doi.org/10.3390/M1596

Chicago/Turabian Style

Obruchnikova, Natalia V., and Oleg A. Rakitin. 2023. "4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide" Molbank 2023, no. 1: M1596. https://doi.org/10.3390/M1596

APA Style

Obruchnikova, N. V., & Rakitin, O. A. (2023). 4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide. Molbank, 2023(1), M1596. https://doi.org/10.3390/M1596

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4,4′-Difluoro-[3,3′-bi(1,2,5-oxadiazole)] 2,2′-Dioxide

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