Peripheral Mercuration of Metalloporphyrins: Novel Syntheses of Deoxophylloerythroetioporphyrin and Deoxophylloerythrin Methyl Ester

Article abstract of DOI:10.1021/jo00198a006

Zinc(II) porphyrins bearing unsubstituted β positions can be mercurated at the β position and at an adjacent meso position.Palladium / olefin reactions with the dimercurated porphyrins produce products possessing a five-membered isocyclic ring bridging the β and meso positions and resembling that found in chlorophyll derivatives.With use of this methodology, novel syntheses of deoxophylloerythroetioporphyrin (2) and deoxophylloerythrin methyl ester (3), two degradation products of chlorophyll, are described.