The copper-catalyzed radical cyclization (RC) of N-α-perchloroacyl cyclic ketene-N, X (X= O, NR, S)-acetals was studied. While the RC of N-acyl ketene-N, O-acetals was unsuccessful, the 5-endo cyclization of the other ketene acetals provided much better results, with the following order of cyclization efficiency: hexa-atomic cyclic ketene-N, NR-acetals