Abstract
The reaction of diethyl bromomalonate (1) or diethyl diazomalonate (6) with benzoyl isothiocyanate (2) proceeds via the carbene intermediates4, 7 or12 to afford the 1,3-dithiole5, the Δ2-oxazoline8 or the 1,3-oxathioles9 depending upon the catalyst employed. In contrast, the bis(ethoxycarbonyl)methylpyridinium bromides14 upon treatment with benzoyl isocyanates15 in pyridine give rise to vinylene dipyridinium dibromides18.
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Capuano, L., Bronder, M., Hell, W. et al. neue Heterocyclisierungen mit Malonestern 1,3-Dithiole; 1,3-Oxathiole; Δ2-Oxazoline und das Vinylendipyridiniumdikation. Monatshefte für Chemie 111, 899–907 (1980). https://doi.org/10.1007/BF00899255
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DOI: https://doi.org/10.1007/BF00899255