Synthesis and chemistry of new benzoporphyrins
Benzoporphyrins 5 and 6 are the major products obtained from the cycloaddition reactions of β-fused metallopyrroloporphyrins 1 and 2 with dimethyl acetylenedicarboxylate. In the presence of excess dienophile a bis- adduct is also obtained which undergoes retro-Diels-Alder reaction to produce 5. Benzoporphyrin 5 was converted into the first reported β-fused benzochlorins 9-11, and the free-base benzoporphyrin 12 was regioselectively brominated to afford 13. Exhaustive bromination also yields hexabromobenzoporphyrin 14.
Publication Source (Journal or Book title)
Vicente, M., Jaquinod, L., Khoury, R., Madrona, A., & Smith, K. (1999). Synthesis and chemistry of new benzoporphyrins. Tetrahedron Letters, 40 (50), 8763-8766. https://doi.org/10.1016/S0040-4039(99)01825-0