| Autor: |
Thomas Böhme, Mari Egeland, Marianne Lorentzen, Mohamed F. Mady, Michelle F. Solbakk, Krister S. Sæbø, Kåre B. Jørgensen |
| Jazyk: |
angličtina |
| Rok vydání: |
2022 |
| Předmět: |
|
| Zdroj: |
Molecules, Vol 28, Iss 1, p 237 (2022) |
| Druh dokumentu: |
article |
| ISSN: |
1420-3049 |
| DOI: |
10.3390/molecules28010237 |
| Popis: |
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. |
| Databáze: |
Directory of Open Access Journals |
| Externí odkaz: |
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