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Olefination with Sulfonyl Halides and Esters: Synthesis of Unsaturated Sulfonyl Fluorides

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dc.abstract.enMethanedisulfonyl fluoride, CH2(SO2F)2, transforms aromatic aldehydes into β-arylethenesulfonyl fluorides, useful substrates for the SuFEx "click"-type transformations. The reaction mimics mechanism of the Horner-Wadsworth-Emmons olefination, which runs via addition of the carbanion, followed by cyclization-fragmentation of the four-membered ring intermediate. In the absence of base, electron-rich aldehydes follow an alternative pathway of the Knoevenagel condensation to provide unsaturated 1,1-disulfonyl fluorides. We demonstrate also trapping of elusive ethene-1,1-disulfonyl fluoride, CH2C(SO2F)2, with 4-(dimethylamino)pyridine (DMAP) that forms zwitterionic adduct, characterized with X-ray studies.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorBarbasiewicz, Michał
dc.contributor.authorBasiak, Dariusz
dc.contributor.authorTryniszewski, Michał
dc.date.accessioned2024-01-25T15:43:52Z
dc.date.available2024-01-25T15:43:52Z
dc.date.copyright2022-06-02
dc.date.issued2022
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number23
dc.description.versionFINAL_PUBLISHED
dc.description.volume24
dc.identifier.doi10.1021/ACS.ORGLETT.2C01604
dc.identifier.issn1523-7060
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/114584
dc.identifier.weblinkhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.2c01604
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofOrganic Letters
dc.relation.pages4270-4274
dc.rightsCC-BY
dc.sciencecloudnosend
dc.titleOlefination with Sulfonyl Halides and Esters: Synthesis of Unsaturated Sulfonyl Fluorides
dc.typeJournalArticle
dspace.entity.typePublication