Pub No:
29
Title:
Electrophilic Attack at the Porphyrin Periphery
Authors:
Paine, J.B. and David Dolphin
Journal:
J. Am. Chem. Soc.
Year:
1971
Pages:
93, 4080-4081
Abstract:
Rates of D incorporation into the meso-positions of various octaalkylporphyrins were measured in refluxing deuterioacetic acid. The rates were similar for both the metal-free porphyrins, and for their complexes with Co(II), Co(III) and Fe(III), thereby showing that N-protonation is responsible for the strong deactivation in stronger acids, and that metal d-π-p-π overlap with N is not a significant feature of the transition state for meso electrophilic attack.

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