Oxybenziporphyrins, oxypyriporphyrins, benzocarbaporphyrins, and their 23-oxa and 23-thia analogues: synthesis, spectroscopic characterization, metalation, and structural characterization of a palladium(II) organometallic derivative

The Journal of Organic Chemistry
Dachun LiuTimothy D Lash

Abstract

A series of nine porphyrin analogues have been synthesized using the "3 + 1" variant on the MacDonald condensation. Tripyrrane-type systems with a centrally unsubstituted pyrrole, furan, or thiophene ring were prepared using conventional methods, and these were condensed with indene-1,3-dicarbaldehyde, 5-formylsalicylaldehyde, or 3-hydroxy-2,6-pyridinedicarbaldehyde in the presence of TFA to generate benzocarba-, oxybenzi-, and oxypyriporphyrins, respectively. The furan-containing analogues proved to be highly basic and could only be isolated as the corresponding hydrochloride salts. All nine analogue systems showed porphyrin-like UV-vis spectra with one or two Soret absorptions near 400 nm and a series of weaker bands at longer wavelengths. These systems also showed large diatropic ring currents by proton NMR spectroscopy that were comparable to true porphyrins. In the presence of trace amounts of TFA, benzocarbaporphyrin 12 formed a monocation, and in 50% TFA a C-protonated dication was generated. The 23-oxacarbaporphyrin 14 gave a monocation in chloroform, although the free base was generated in 5% Et(3)N-chloroform. In 50% TFA-CHCl(3), 14 afforded a mixture of mono- and diprotonated species. Thiacarbaporphyrin 15 also forme...Continue Reading

References

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Citations

Sep 23, 2016·Chemical Reviews·Timothy D Lash
Nov 3, 2006·Organic Letters·Jessica A El-Beck, Timothy D Lash
Feb 1, 2014·Chemistry, an Asian Journal·Timothy D Lash
Nov 1, 2013·Organic & Biomolecular Chemistry·Alexandra M Young, Timothy D Lash
Apr 17, 2008·Journal of the American Chemical Society·Ewa Pacholska-DudziakLechosław Latos-Grazyński
Nov 11, 2008·The Journal of Organic Chemistry·Timothy D Lash, Amber L Von Ruden
Jun 18, 2021·Inorganic Chemistry·Timothy D LashGregory M Ferrence
May 4, 2011·Journal of the American Chemical Society·Christian BrücknerGerhard Bringmann
May 25, 2011·The Journal of Organic Chemistry·Timothy D LashGregory M Ferrence
Oct 17, 2014·The Journal of Organic Chemistry·Stacy C FosuTimothy D Lash
Jul 8, 2014·The Journal of Organic Chemistry·Daming Li, Timothy D Lash
Apr 25, 2013·The Journal of Organic Chemistry·Bartosz SzyszkoLechosław Latos-Grażyński
Apr 18, 2014·Journal of the American Chemical Society·Deyaa I AbuSalimTimothy D Lash
Nov 5, 2016·Chemical Reviews·Tamal ChatterjeeMangalampalli Ravikanth
Sep 8, 2018·The Journal of Organic Chemistry·Rima SenguptaMangalampalli Ravikanth
Sep 6, 2017·Inorganic Chemistry·Timothy D Lash, Gregory M Ferrence
Sep 7, 2006·Journal of the American Chemical Society·Yoshihiro MatanoShigeyoshi Sakaki

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