Gabriel Ethylenimine Method (Gabriel-Marckwald Ethylenimine Synthesis)

S. Gabriel et al., Ber. 21, 1049 (1888); W. Marckwald et al., ibid. 32, 2036 (1899); 33, 764 (1900); 34, 3544 (1901).

Formation of ethylenimines (aziridines) by elimination of hydrogen halides from aliphatic vicinal haloamines with alkali. The method can be extended to the preparation of five- and six-membered cyclic amines:



O. C. Dermer, G. E. Ham, Ethylenimine and Other Aziridines (Academic Press, New York, 1969) pp 1-59; R. Bartnik et al., Pol. J. Chem. 53, 537 (1979); K. H. Sunwoo et al., Dyes Pigments 41, 19 (1999).