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- W2969398571 abstract "Acid-catalyzed condensation of azulidipyrrane aldehydes with a dihydrodipyrrin carbaldehyde afforded the first examples of azulichlorins. These macrocyclic products were isolated in a monoprotonated form, and the free bases proved to be somewhat unstable. The monocations were strongly diatropic, and proton NMR spectroscopy showed the internal C–H at ca. −2 ppm. Addition of TFA gave the related dications, but these exhibited significantly reduced aromatic ring currents. Reaction of an azulichlorin with tert-butyl hydroperoxide and KOH in dichloromethane/methanol gave a benzocarbachlorin and two related aldehydes. The UV–vis spectrum for the benzocarbachlorin showed a split Soret band at 414 and 430 nm, together with a strong chlorin-like absorption at 684 nm. The proton NMR spectrum indicated that the carbachlorin is strongly aromatic and the internal C–H was observed at −4.64 ppm. Addition of TFA afforded a C-protonated dication with a significantly increased diatropic ring current. The proton NMR spectrum, NICS calculations, and AICD plots indicated that the system favors a 22π electron delocalization pathway that runs through the fused benzo unit. Addition of TFA to the benzocarbachlorin aldehydes primarily led to the formation of monocations, and the generation of C-protonated dications was no longer favored due to the presence of electron-withdrawing formyl moieties." @default.
- W2969398571 created "2019-08-29" @default.
- W2969398571 creator A5040106748 @default.
- W2969398571 creator A5066014054 @default.
- W2969398571 creator A5084449121 @default.
- W2969398571 date "2019-08-20" @default.
- W2969398571 modified "2023-10-01" @default.
- W2969398571 title "Azulichlorins and Benzocarbachlorins Derived Therefrom" @default.
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- W2969398571 doi "https://doi.org/10.1021/acs.joc.9b01578" @default.
- W2969398571 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/31429281" @default.
- W2969398571 hasPublicationYear "2019" @default.
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