Regiospecific Photochemical Synthesis of Methylchrysenes
Author | Böhme, Thomas |
Author | Egeland, Mari |
Author | Lorentzen, Marianne |
Author | Mady, Mohamed F. |
Author | Solbakk, Michelle F. |
Author | Sæbø, Krister S. |
Author | Jørgensen, Kåre B. |
Available date | 2023-08-28T11:33:37Z |
Publication Date | 2023-01-01 |
Publication Name | Molecules |
Identifier | http://dx.doi.org/10.3390/molecules28010237 |
Citation | Böhme, T., Egeland, M., Lorentzen, M., Mady, M. F., Solbakk, M. F., Sæbø, K. S., & Jørgensen, K. B. (2022). Regiospecific Photochemical Synthesis of Methylchrysenes. Molecules, 28(1), 237. |
Abstract | Methylated polycyclic aromatic hydrocarbons (PAHs) are suspected to be some of the toxic compounds in crude oil towards marine life and are needed as single compounds for environmental studies. 1-, 3- and 6-methylchrysene (3a,b,c) were prepared as single isomers by photochemical cyclization of the corresponding stilbenoids in the Mallory reaction using stoichiometric amounts of iodine in 82-88% yield. 2-methylchrysene (3d) was prepared by photochemical cyclization where the regioselectivity was controlled by elimination of an ortho-methoxy group under acidic oxygen free conditions in 72% yield. These conditions failed to form 4-methylchrysene from the corresponding stilbenoid. All stilbenoids were made from a common naphthyl Wittig salt and suitably substituted benzaldehydes. We have also demonstrated that methylchrysenes can be oxidized to the corresponding chrysenecarboxylic acids by KMnO4 in modest yields. |
Language | en |
Publisher | MDPI |
Subject | eliminative photochemical cyclization formylation Mallory reaction methylated PAH oxidation oxidative 6π-electrocyclization PAH metabolite polycyclic aromatic hydrocarbon |
Type | Article |
Issue Number | 1 |
Volume Number | 28 |
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Chemistry & Earth Sciences [556 items ]