Mechanochemical Halogenations and Rearrangement of Sydnones: Insight into Reaction Conditions and Mechanism
Abstract New mechanochemical methods for sydnone halogenation and insights into an efficient ring rearrangement yielding 1,3,4‐oxadiazolin‐2‐ones by heated ball‐milling are reported herein. Using equimolar amounts of N‐chlorosuccinimide (NCS), oxone and sodium chloride, 3‐phenylsydnone was quantitat...
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2025-01-01
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| Series: | ChemistryEurope |
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| Online Access: | https://doi.org/10.1002/ceur.202400054 |
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| author | Dr. Florian Luttringer Dr. Nicolas Pétry Dr. Eric Clot Prof. Dr. Xavier Bantreil Dr. Frédéric Lamaty |
| author_facet | Dr. Florian Luttringer Dr. Nicolas Pétry Dr. Eric Clot Prof. Dr. Xavier Bantreil Dr. Frédéric Lamaty |
| author_sort | Dr. Florian Luttringer |
| collection | DOAJ |
| description | Abstract New mechanochemical methods for sydnone halogenation and insights into an efficient ring rearrangement yielding 1,3,4‐oxadiazolin‐2‐ones by heated ball‐milling are reported herein. Using equimolar amounts of N‐chlorosuccinimide (NCS), oxone and sodium chloride, 3‐phenylsydnone was quantitatively chlorinated in short reaction time and high yields. Moreover, an efficient method for the bromination of sydnones was developed by mixing equimolar amount of N‐bromosuccinimide (NBS), Ac2O and a sydnone in a vibratory ball‐mill, in the absence of solvent, with excellent yields and a reduced environmental impact. When the reaction was heated while milling, a fast and efficient ring rearrangement into 1,3,4‐oxadiazolin‐2‐ones was observed. Insights concerning the mechanism of the reaction under solvent‐less conditions, supported by DFT calculations, are discussed. The scope of this reaction, including solid anhydrides, is presented. |
| format | Article |
| id | doaj-art-a711a29b5d22453aa9b75b4ed0ec7b7a |
| institution | Kabale University |
| issn | 2751-4765 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryEurope |
| spelling | doaj-art-a711a29b5d22453aa9b75b4ed0ec7b7a2025-01-13T07:31:32ZengWiley-VCHChemistryEurope2751-47652025-01-0131n/an/a10.1002/ceur.202400054Mechanochemical Halogenations and Rearrangement of Sydnones: Insight into Reaction Conditions and MechanismDr. Florian Luttringer0Dr. Nicolas Pétry1Dr. Eric Clot2Prof. Dr. Xavier Bantreil3Dr. Frédéric Lamaty4IBMM, Univ Montpellier CNRS ENSCM Montpellier FranceIBMM, Univ Montpellier CNRS ENSCM Montpellier FranceICGM, Univ Montpellier CNRS ENSCM Montpellier FranceIBMM, Univ Montpellier CNRS ENSCM Montpellier FranceIBMM, Univ Montpellier CNRS ENSCM Montpellier FranceAbstract New mechanochemical methods for sydnone halogenation and insights into an efficient ring rearrangement yielding 1,3,4‐oxadiazolin‐2‐ones by heated ball‐milling are reported herein. Using equimolar amounts of N‐chlorosuccinimide (NCS), oxone and sodium chloride, 3‐phenylsydnone was quantitatively chlorinated in short reaction time and high yields. Moreover, an efficient method for the bromination of sydnones was developed by mixing equimolar amount of N‐bromosuccinimide (NBS), Ac2O and a sydnone in a vibratory ball‐mill, in the absence of solvent, with excellent yields and a reduced environmental impact. When the reaction was heated while milling, a fast and efficient ring rearrangement into 1,3,4‐oxadiazolin‐2‐ones was observed. Insights concerning the mechanism of the reaction under solvent‐less conditions, supported by DFT calculations, are discussed. The scope of this reaction, including solid anhydrides, is presented.https://doi.org/10.1002/ceur.202400054sydnonesmechanochemistryball-millingrearrangementDFT calculations |
| spellingShingle | Dr. Florian Luttringer Dr. Nicolas Pétry Dr. Eric Clot Prof. Dr. Xavier Bantreil Dr. Frédéric Lamaty Mechanochemical Halogenations and Rearrangement of Sydnones: Insight into Reaction Conditions and Mechanism ChemistryEurope sydnones mechanochemistry ball-milling rearrangement DFT calculations |
| title | Mechanochemical Halogenations and Rearrangement of Sydnones: Insight into Reaction Conditions and Mechanism |
| title_full | Mechanochemical Halogenations and Rearrangement of Sydnones: Insight into Reaction Conditions and Mechanism |
| title_fullStr | Mechanochemical Halogenations and Rearrangement of Sydnones: Insight into Reaction Conditions and Mechanism |
| title_full_unstemmed | Mechanochemical Halogenations and Rearrangement of Sydnones: Insight into Reaction Conditions and Mechanism |
| title_short | Mechanochemical Halogenations and Rearrangement of Sydnones: Insight into Reaction Conditions and Mechanism |
| title_sort | mechanochemical halogenations and rearrangement of sydnones insight into reaction conditions and mechanism |
| topic | sydnones mechanochemistry ball-milling rearrangement DFT calculations |
| url | https://doi.org/10.1002/ceur.202400054 |
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