SYNTHESIS AND REACTIONS OF ANHYDROCHLORALURETHANS

The previously unreported anhydrochloralurethans (I) are obtained by dehydrochlorination of alkyl 1,2,2,2-tetrachloroethylcarbamates (III). Reaction of I with water, alcohols, and amines affords chloral O, N- and N,N-acetals. The latter compounds are also produced in the reaction of chloralurethans (II) with alkyl and aryl isocyanates. Treatment of II and III with carbonyl chloride in the presence of N,N-dimethylformamide as the catalyst gives rise to the formation of 1,2,2,2-tetrachloroethyl isocyanate (XI), which undergoes the Michalis-Arbuzov reaction with triethyl phosphite to afford diethyl 1-isocyanato-2,2,2-trichloroethylphosphonate (XII). © 1968, American Chemical Society. All rights reserved.