From alpha-carbamoyl-alpha-cyanooxiranes to 3-halogenopyruvamides

The crystal structures of the first stable alpha-diol from the alpha-haloge nopyruvamide series, 3-chloro-2,2-dihydroxy-3-phenylpropanamide, C9H10ClNO3 , and three products [3-(4-chlorophenyl)-2-cyano-2,3-epoxypropanamide, C10H 7ClN2O2, 3-bromo-2-cyano-2-hydroxy-3-p-tolylpropanamide, C11H11BrN2O2, 3-br omo-2-oxo-3-p-tolylpropanamide, C10H10BrNO2] obtained during the systematic synthesis of alpha-halogenopyruvamides are reported. The crystal structure s are dominated by hydrogen bonds involving an amide group. The stability o f the geminal diol could be ascribed to hydrogen bonds which involve both h ydroxyl groups.