Ethylenimine chemistry

2-Methyl-N-aminoethylenimine was synthesized by the classic Wenker method and by amination of 2-methylethylenimine with hydroxylamine-O-sulfonic acid in alkaline media. NMR spectroscopy indicated the formation of exclusively the trans-inverted isomer, the pyramidal stability of the heteroatom of which, as in N-aminoethylenimine 3–5], is preserved over a broad range of temperatures. The hydrazones of N-aminoethylenimine are characterized by an appreciably lower pyramidal stability of the nitrogen than that associated with participation of its unshared electron pair in p, conjugation with the electrons of the C=N bond. The inversion barrier in the hydrazones decreases symbatically with an increase in the degree of the indicated interaction. However, the decrease is insufficient to freeze free rotation about the nitrogen-nitrogen bond up to –80.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 45–48, January, 1971.See 1] for communication VI.