Regioselective phosphorylation and thiophosphorylation of N-confused porphyrin: a route to hybrid carbaporphyrinoids

Abstract

N-confused porphyrin (NCP) undergoes controlled regioselective phosphorylations at the inner, outer or both carbon atoms of the inverted pyrrole ring. Reactivity centered at the internal carbon atom is enhanced in the Ag(III) NCP's whereas the preference for perimeter substitution is characteristic of free base NCP. The addition of S₈ resulted in the formation of thio-derivatives containing 21-diphenylthiophosphoryl or 21-phosphinodithioic substituents.