Three-Membered Ring Imidoyl Halides

Three-membered ring imidoyl chlorides, such as X, have not been synthesized. However, 2,2-dichloroaziridines XI, which are in equilibrium with the corresponding iminium chlorides (XII), are well known. 

2 -Dichloroaziridines are synthesized from the corresponding C=N double-bond compounds and dichlorocarbene 1-12,19,20,21,24,25  

For example, l,3-diphenyl-2,2-dichloroaziridine (XIII), the first member of this class of compounds, was synthesized in 1959 by Fields and Sandri ( ). 

The dihalocarbenes can be generated from chloroform (7.12,19,21 hexachloroacetone ( ), and trihaloacetic acids and in addition to 

Heating with excess water results in the elimination of hydrogen chloride and formation of a-chloro-a-phenyl-p-ethoxyacetanilide, m.p. 145-146.5°C. The yield is quantitative. 

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