SYNTHESIS AND REACTIONS OF ANHYDROCHLORALURETHANS

被引:68
作者
ULRICH, H
TUCKER, B
SAYIGH, AAR
机构
[1] Upjohn Company, Donald S. Gilmore Research Laboratories, North Haven, Connecticut
关键词
D O I
10.1021/jo01271a061
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
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页码:2887 / &
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