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. Author manuscript; available in PMC: 2014 Nov 6.
Published in final edited form as: J Am Chem Soc. 2013 Oct 22;135(44):10.1021/ja405739m. doi: 10.1021/ja405739m

Figure 2.

Figure 2

Proposed mechanism for the selective oxidation of (1-OH) with CAN to verdoheme complex (4-X) via formation of intermediates (PIm+•)FeIV=O, isoporphyrin (2) and benzoyl-biliverdin (3). Drawings for analogs produced in the chemistry of (5-OH) are given in the Scheme S1. EPR and 2H-NMR data for complexes (1-OH; see SI), (5-OH; high-spin FeIII), (4-X; high-spin FeIII) generated in the crude reaction mixture (i.e., in situ), and for the isolated (4-X; high-spin FeIII), were also obtained (See SI).