Dodecasubstituted metallochlorins (metallodihydroporphyrins)

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Kalyn M. Shea and Laurent Jaquinod


Abstract

Regioselective bromination of 2-nitro-5,10,15,20-tetraphenylporphyrin, cyclopropa[b]chlorins, or trans-bis(dicyanomethyl)chlorins occurs in the pyrrole subunit opposite the substituted ring; exhaustive bromination of functionalized tetraphenylchlorins provides a route to dodecasubstitued dihydroporphyrins for the first time.


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