Synthesis of Fluorine-Containing Imidazolidin-2-Ones, Glycolurils, and Hydantoins Based on Perfluorodiacetyl and Ureas*

The reactions of perfluorodiacetyl with urea, N,N'-dimethyl- and N,N'-diethylureas produced the cis and trans isomers of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones in 60-90% yields. The reaction of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one with urea gave 1,5-bis-(trifluoro-methyl)-2,4,6,8-tetraazobicyclo[3.3.0]octane-3,7-dione in 88% yield. The analogous reaction of 1,3-di-methyl- and 1,3-diethylimidazolidin-2-ones with urea, N,N'-dimethyl- and N,N'-diethylureas led to the formation of 5-hydroxy-1,3-dimethyl(diethyl)-5-trifluoromethylimidazolidine-2,4-diones (hydantoins) in 60-87% yields. The molecular structures of cis-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one, trans-4,5-dihydroxy-1,3-dimethyl-4,5-bis(trifluoromethyl)imidazolidin-2-one, and 5-hydroxy-1,3-di-methyl-5-trifluoromethylimidazolidine-2,4-dione were studied by X-ray structural analysis.