ADDITION OF DIAZOMETHANE TO 3-NITROPHTHALODINITRILE AND 4-NITROPHTHALODINITRILE

The reaction of two nitrophthalodinitriles with diazomethane is descri bed. If the nitro group is at position 3, only one of the two nitrile functions reacts giving three isomeric N-methyl 1,2,3-triazoles. In co ntrast, if the nitro group is at position 4, both nitriles react, each producing a 2-N-methyl 1,2,3-triazole. The reactivity was accounted f or in terms of electronic densities, which were determined for several nitrile compounds. Interestingly, for 4-nitrophthalodinitrile, origin al methylation of the aromatic ring at position 5 was also observed.