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2023-04-27Zeitschriftenartikel DOI: 10.18452/27164
(3+2)‐Cyclization Reactions of Unsaturated Phosphonites with Aldehydes and Thioketones
dc.contributor.authorMunasinghe, Don S.
dc.contributor.authorKasper, Marc-André
dc.contributor.authorJasiński, Radomir
dc.contributor.authorKula, Karolina
dc.contributor.authorPalusiak, Marcin
dc.contributor.authorCeleda, Małgorzata
dc.contributor.authorMlostoń, Grzegorz
dc.contributor.authorHackenberger, Christian
dc.date.accessioned2023-08-25T10:31:19Z
dc.date.available2023-08-25T10:31:19Z
dc.date.issued2023-04-27none
dc.date.updated2023-07-11T23:00:57Z
dc.identifier.issn0947-6539
dc.identifier.issn1521-3765
dc.identifier.urihttp://edoc.hu-berlin.de/18452/27827
dc.description.abstractBy exploiting the unique reactivity of ethynyl‐phosphonites we obtain novel P(V)‐containing five‐membered heterocycles via (3+2)‐cyclization reactions with aldehydes or cycloaliphatic thioketones in satisfactory to excellent yields. Whereas reactions with thioketones to yield 1,3‐thiaphospholes‐3‐oxides occur smoothly at room temperature with equimolar amounts of the starting materials in absence of any catalyst, the analogous conversions with aldehydes to generate 3‐oxides of 1,3‐oxaphospholes require addition of triethylamine as a base. We postulate a step‐wise (3+2)‐cyclization mechanism for the formation of the 1,3‐thiaphosphole ring based on DFT quantum chemical calculations. With this study, we introduce new cyclization reactions originating from unsaturated phosphonites as central synthetic building blocks to yield previously inaccessible stable phosphorus‐containing heterocycles with unexplored potential for the molecular sciences.eng
dc.description.sponsorshipDeutsche Forschungsgemeinschaft http://dx.doi.org/10.13039/501100001659
dc.description.sponsorshipAlexander von Humboldt-Stiftung http://dx.doi.org/10.13039/100005156
dc.language.isoengnone
dc.publisherHumboldt-Universität zu Berlin
dc.rights(CC BY-NC 4.0) Attribution-NonCommercial 4.0 Internationalger
dc.rights.urihttps://creativecommons.org/licenses/by-nc/4.0/
dc.subjectaldehydeseng
dc.subjectcyclization reactionseng
dc.subjectphosphoniteseng
dc.subjectphosphorus heterocycleseng
dc.subjectthioketoneseng
dc.subject.ddc540 Chemie und zugeordnete Wissenschaftennone
dc.title(3+2)‐Cyclization Reactions of Unsaturated Phosphonites with Aldehydes and Thioketonesnone
dc.typearticle
dc.identifier.urnurn:nbn:de:kobv:11-110-18452/27827-6
dc.identifier.doihttp://dx.doi.org/10.18452/27164
dc.type.versionpublishedVersionnone
local.edoc.pages10none
local.edoc.type-nameZeitschriftenartikel
local.edoc.container-typeperiodical
local.edoc.container-type-nameZeitschrift
dc.description.versionPeer Reviewednone
dcterms.bibliographicCitation.doi10.1002/chem.202300806none
dcterms.bibliographicCitation.journaltitleChemistrynone
dcterms.bibliographicCitation.volume29none
dcterms.bibliographicCitation.issue33none
dcterms.bibliographicCitation.articlenumbere202300806none
dcterms.bibliographicCitation.originalpublishernameWiley-VCHnone
dcterms.bibliographicCitation.originalpublisherplaceWeinheimnone
bua.departmentMathematisch-Naturwissenschaftliche Fakultätnone

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