The use of 1, 2-shifts in carbenes and nitrenes in the generation of novel heterocumulenes

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Abstract

Ethenedithione, S=C=C=S, has been generated in flash vacuum pyrolysis (FVP) reactions from isoxazolone and Meldrum's acid derivatives and characterized by IR, UV and mass spectrometry. Evidence for the existence of HN=C=C=S and its isomerization to thioformyl cyanide is also presented. The preparation and characterization of iminopropadienone derivatives RN=C=C=C=X (X = 0, S, or NR') from a variety of isoxazole compounds is described. These highly reactive cumulenes are formed via vinylidene, vinylnitrene, and ketenimine intermediates. © 1995 IUPAC

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Wentrup, C., Kappe, C. O., & Wong, M. W. (1995). The use of 1, 2-shifts in carbenes and nitrenes in the generation of novel heterocumulenes. Pure and Applied Chemistry, 67(5), 749–754. https://doi.org/10.1351/pac199567050749

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