Synthesis and Reactivity of meso‐(3‐Carbamoylpyridinio)‐porphyrins

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Abstract
The redox systems of porphyrins and nicotinamide have been combined in synthetic meso‐(3‐carbamoylpyridinio)porphyrins and related compounds. 5‐(3‐carbamoylpyridinio)octaethyl‐porphyrin chloride (1c) forms stable, hydrogen bridged dimers in chloroform solution. The electrophilic reactivity of the nicotinamide substituent resembles the reactivity of other N‐alkylated 3‐carbamoylpyridinium salts. In the porphyrin derivative the substituent is, however, sensitized to visible light and additions to C‐4 of the pyridine ring are extraordinarily favored above attack on C‐2 and C‐6. Pyridination of deuteroporphyrinato zinc dimethyl ester (3b) in the presence of thallium(III) salts occurred only at the methine bridges. The 3,8‐β‐pyrrolic sites did not react.

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