Reaction of Ketenimine with Various Schiff's Bases

Abstract

The reaction of diphenylketene N-p-tolylimine with various Schiff's bases was carried out by heating in toluene or xylene under reflux.
Schiff's bases in which R1=(CI-10)2N or CH₃O, H, CH₃O, or Cl, and R3=H gave four-membered-ring compounds (azetidine derivatives). Their reactivities and yield S varied over a wide range with the change in the substituent R1. When R. and R2 were both H and R3 was C8H₅, no product was obtained.
The mass spectra were discussed and a reaction mechanism has been suggested.