The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-Iodo-2-furaldehyde( cas:2689-65-8 ) is researched.Quality Control of 5-Iodo-2-furaldehyde.Ostapko, Jakub; Kelm, Anna; Kijak, Michal; Lesniewska, Barbara; Waluk, Jacek published the article 《Two Macrocycles in One Shot: Synthesis, Spectroscopy, Photophysics, and Tautomerism of 23-Oxahemiporphycene and 21-Oxacorrole-5-carbaldehyde》 about this compound( cas:2689-65-8 ) in Chemistry – A European Journal. Keywords: oxahemiporphycene preparation IR NMR photophys tautomerism; oxacorrolecarboxaldehyde preparation IR NMR photophys tautomerism; corroles; porphyrinoids; reaction mechanisms; structure elucidation; tautomerism. Let’s learn more about this compound (cas:2689-65-8).
The synthesis of 23-oxahemiporphycene, the first monooxa analog of hemiporphycene, a structural isomer of porphyrin, is reported. Its generation under McMurry reaction conditions is surprisingly accompanied by the appearance of a formyl derivative of oxacorrole, 21-oxacorrole-5-carbaldehyde. A mechanism for the formation of the latter is proposed, relying on pinacol rearrangement of titanium pinacolate. The structures of the most stable tautomeric forms are established for both compounds based on IR and NMR spectra combined with DFT calculations Spectral and photophys. characteristics are compared with those of structurally similar macrocycles. Replacement of one nitrogen by oxygen in hemiporphycene has only a minor impact. In contrast, for corrole it leads to the enhancement of stability and to strongly reduced rates of nonradiative deactivation of the lowest excited singlet state. This is explained by the planarity of oxacorroles, achieved by removing one of the inner hydrogen atoms from the inner cavity. Unusual crystal packing is observed for the protonated form of 23-oxahemiporphycene, which exhibits a π-π stacked columnar alignment of pos. charged macrocycle units.
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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem