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- W2019720424 abstract "Als cyclische Carbonyl-ylide nehmen die neuen 2-Alkylthio-5-trifluoracetyl-1,3-oxathiolylium-4-olate vom Typ 1a–d in 2,5-Stellung Acetylendicarbonsäure-dimethylester unter Bildung nicht-isolierbarer Primäraddukte auf, die unter COS-Abspaltung Furandicarbonester 3a–d liefern. Mit Propiolsäure-methylester reagiert 1a–c zu Gemischen aus den regioisomeren Furancarbonestern 4a–c und 5a–c, deren Hauptkomponenten 4a–c isolierbar sind. Dagegen vereinigen sich Phenylacetylen, 1-Diethylaminopropin bzw. (Z)-1-Methoxy-1-buten-3-in mit 1a regiospezifisch zu den Furan-Derivaten 6, 7 bzw. 8. Die beobachteten Regioselektivitäten werden qualitativ auf der Basis der MO-Störungstheorie diskutiert. A New Entry to Alkylthio(trifluoroacetyl)furans by Way of Thermal [3 + 2]Cycloaddition Reactions of New Mesoionic 1,3-Oxathiol-4-ones to Alkynes As cyclic carbonyl ylides, the novel 2-alkylthio-5-trifluoroacetyl-1,3-oxathiolylium-4-olates of type 1a–d combine with dimethyl acetylenedicarboxylate across the 2,5-position with formation of non-isolable primary adducts, which release COS to give the furandicarboxylic diesters 3a–d. Methyl propiolate reacts with 1a–c to produce mixtures of the regioisomeric furancarboxylic esters 4a–c and 5a–c, whose main components 4a–c are isolable. On the other hand, the reactions of phenylacetylene, 1-diethylaminopropyne, or (Z)-1-methoxy-1-buten-3-yne with 1a proceed with regiospecific formation of the furan derivatives 6, 7, or 8, respectively. The observed regioselectivities are qualitatively discussed on the basis of MO-perturbation theory." @default.
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- W2019720424 title "Ein neuer Zugang zu Alkylthio(trifluoracetyl)furanen durch thermische [3 + 2]‐Cycloadditionen neuer mesoionischer 1,3‐Oxathiol‐4‐one an Alkine" @default.
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- W2019720424 doi "https://doi.org/10.1002/cber.19851180237" @default.
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