Singlet oxygenation of triquinacene, barrelene, and homobarrelene
Özet
The singlet oxygenation of three polycyclic hydrocarbons, triquinacene, barrelene and homobarrelene was studied. Triquinacene reacted by way of a perepoxide intermediate, transferring an oxygen atom to another triquinacene molecule to give exclusively the mono epoxide. Barrelene, on the other hand, underwent a rare homo-Diels-Alder reaction with O-1(2) to give the decomposition product from the initial tetracyclic 1,2-dioxolane leading to benzofuran. The latter reacted with O-1(2) in a [2 + 2] cycloaddition to give an unstable 1,2-dioxetane which collapsed to 2-formylphenyl formate. The latter was independently synthesized via singlet oxygenation of authentic benzofuran. Homobarrelene reacted in a similar fashion to give a homo-Diels product, decomposition of which led to a keto aldehyde which was characterized spectroscopically. Computational work confirms the barrelene and homobarrelene reactions with O-1(2) as concerted [pi(2)(s)+ pi 2(s)+ pi 2(s)] cycloadditions. (C) 2020 Elsevier Ltd. All rights reserved.
Sürdürülebilir Kalkınma Amaçları
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SKA 3: Sağlıklı Bireyler
Atıf için künye
Ortega, T., Özer, G., Gronert, S., & Erden, I. (2020). Singlet oxygenation of triquinacene, barrelene, and homobarrelene. Tetrahedron Letters, 61(16). https://doi.org/10.1016/j.tetlet.2020.151779
BibTeX
@article{ortega2020-334675,
author = {Ortega, Teresa and Özer, Galip and Gronert, Scott and Erden, Ihsan},
title = {Singlet oxygenation of triquinacene, barrelene, and homobarrelene},
journal = {Tetrahedron Letters},
year = {2020},
volume = {61},
number = {16},
issn = {0040-4039},
doi = {10.1016/j.tetlet.2020.151779},
url = {https://akademik.atauni.edu.tr/yayinlar/334675-singlet-oxygenation-of-triquinacene-barrelene-and-homobarrelene}
}