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- W1969075103 abstract "Sydnone lassen sich in 4-Position nach VILSMEIER-HAAK formylieren. N(3)-Methyl- und N(3)-(p-Anisyl)-sydnon-(4)-carbaldehyd werden mit Äthoxycarbonylmethan-phosphonsäurediäthylester nach HORNER und mit verschiedenen Arylmethylphosphoniumsalzen nach WITTIG in Gegenwart starker Basen stereoselektiv olefiniert. Im letzteren Fall tritt besonders in Abwesenheit von Lithiumkationen eine Z-Selektivität auf, die auf eine elektronische Wechselwirkung zwischen dem Sydnonring und dem aromatischen Substituenten des Phosphin-ylids im ersten Reaktionsschritt zurückgeführt wird. Die Konfigurationsbestimmung der resultierenden Z- und E-Sydnonäthylene erfolgt an Hand der 1H-NMR- und IR-Spektren. Sydnone Ethylenes. I Stereoselective Synthesis of Sydnone Ethylenes from Sydnone Aldehydes Sydnones are formylated in 4-position by the VILSMEIER-HAAK reaction. N(3)-Methyl- and N(3)-(p-Anisyl)-sydnone-(4)-carboxaldehyde react stereoselectively to sydnone ethylenes with diethyl ethoxycarbonylmethanephosphonate by HORNER reaction and with arylmethylphosphonium salts by WITTIG reaction in the presence of strong bases. In the latter case, especially in the absence of lithium cations, Z-selectivity is observed which is explained by electronic interaction between the sydnone cyclus and the aromatic substituent of the phosphine ylid in the first step of the reaction. The configuration of the obtained Z- and E-sydnone ethylenes is determined by means of 1H-NMR- and IR-spectra." @default.
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- W1969075103 date "1976-01-01" @default.
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- W1969075103 title "Sydnon-äthylene. I Stereoselektive Darstellung von Sydnon-äthylenen aus Sydnon-aldehyden" @default.
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- W1969075103 doi "https://doi.org/10.1002/prac.19763180514" @default.
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