Tautomerism of 2‐amino‐2‐oxazolin‐4‐ones. II

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Abstract
The study of the tautomerism of 2‐amino‐2‐oxazolin‐4‐one (1) and its methyl derivatives has been completed. The methylation of 1 gave 2‐imino‐3‐methyloxazolidin‐4‐one (4) and 2‐methyl‐amino‐2‐oxazolin‐4‐one (7). All attempts to isolate O‐methyl derivatives failed. The uv, nmr, ir, and Raman spectra led to the definite conclusion, in agreement with the chemical evidence, that the 2‐aminooxazolinic form a, if it is theoretically possible, predominates in all compounds investigated. Otherwise the 2‐iminooxazolidinic form b predominates. The assignment of the carbonyl stretching is discussed on the basis of ir and Raman data. The nmr spectrum of compound 7 shows anomalous behaviour, most probably due to the existence of a monomer‐dimer equilibrium.