SYNTHESIS OF N-CYANOPORPHYRINS AND RELATED COMPOUNDS. CRYSTAL STRUCTURE OF N-CYANO-MESO-TETRATOLYLPORPHYRIN.

Article abstract of DOI:10.1016/S0040-4020(01)96011-9

N-Cyano-tetraphenylporphyrin was prepared either from N,N'-ethoxymethylene-meso-tetraphenylporphyrin and hydroxylamine-O-sulfonic acid or by direct cyanation with cyanogen bromide.Its metallation is rapid and concommitant cleavage of the N-substituent was observed.Such a reactivity can be used for rapid introduction of short-lived radionuclides into porphyrins.The crystal structure of N-cyano-meso-tetra-p-tolylporphyrin was determined.The macrocycle is ruffled, the pyrrole bearing the cyano group is tipped out of the (4N) plane by 29.3 deg.The angle of the cyanogroup with the corresponding pyrrole is 150 deg.