Naphtho[2,3- b]carbaporphyrins

The Journal of Organic Chemistry
Eric Y GrabowskiTimothy D Lash

Abstract

Acid-catalyzed condensation of a benzo[ f]indane dialdehyde with a tripyrrane, followed by an oxidation step, afforded the first example of a naphtho[2,3- b]-21-carbaporphyrin. This π-extended porphyrinoid system is strongly aromatic and gave a porphyrin-like UV-vis spectrum with a Soret band at 432 nm. Protonation with TFA gave a monocation, but under highly acidic conditions a C-protonated dication was generated. Reaction of the naphthoporphyrin with ferric chloride produced a 21-chloro derivative. Alkylation with methyl iodide and potassium carbonate gave a 22-methyl derivative, and this reacted with palladium(II) acetate to afford a palladium(II) complex in which the internal methyl group had migrated from a nitrogen to a carbon atom. Treatment of the naphthocarbaporphyrin with silver(I) acetate generated the corresponding silver(III) complex. In naphtho[2,3- b]-21-carbaporphyrin and many of its derivatives, the aromatic conjugation pathways appear to bypass the naphthalene unit, and for this reason the UV-vis spectra were little affected. However, the diprotonated dication and the palladium(II) complex have aromatic pathways that pass through the naphthalene moiety, and this leads to large bathochromic shifts for these spe...Continue Reading

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Citations

Aug 21, 2019·The Journal of Organic Chemistry·Mario A NoboaTimothy D Lash
Jan 3, 2019·Inorganic Chemistry·Kamil KupietzLechosław Latos-Grażyński
Sep 18, 2020·The Journal of Organic Chemistry·Alissa N Latham, Timothy D Lash
Sep 25, 2021·Organic Letters·Takeo NakanoKensuke Naka

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