73880-29-2Relevant academic research and scientific papers
Trichlorovinylketene Imines from Perchlorobutenyne and Cycloaddition of Trichloroacetyl Isocyanate to 4H-1,3-Oxazin-4-ones
Roedig, Alfred,Ritschel, Werner,Foure, Michel
, p. 811 - 818 (2007/10/02)
The reaction of perchlorobutenyne(1) with primary aliphatic amines leads to the ketene imines 3.The stability of 3 increases with spatial requirement of amino groups.Therefore only 3e-g may be isolated in pure form.Hydrolysis of 3 yields the carboxamides 4. 4e is furthermore hydrolyzed to the known acid 5. - The cycloaddition reaction of 3 with trichloroacetyl isocyanate is followed by tautomerization to the 4H-1,3-oxazin-4-ones 8 in good yield.When treated with aqueous ethanol or absolute methanol ring opening of 8 occurs with formation of substituted malonamides 7 and 10 , respectively.The structure of 8 is confirmed by further degradation of 7 to 4.
