Aziridines-IV Catalytic decomposition of phenyldiazomethane in Schiff's bases

Catalytic decomposition of phenyldiazomethane in Schiff's bases is found to proceed via formation of trans-1,3-dipole (azomethine ylide) as an intermediate product. Depending on the size and quantity of the substituents, the ylide undergoes either cyclization in controtatory sense to cis-aziridine or cycloaddition[2+3]to the C=N bond of imine. The reactivity of double bonds to ylide decreases in the order C=C > C=O > C=N.