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AuthorBöhme, Thomas
AuthorEgeland, Mari
AuthorLorentzen, Marianne
AuthorMady, Mohamed F.
AuthorSolbakk, Michelle F.
AuthorSæbø, Krister S.
AuthorJørgensen, Kåre B.
Available date2023-08-28T11:33:37Z
Publication Date2023-01-01
Publication NameMolecules
Identifierhttp://dx.doi.org/10.3390/molecules28010237
CitationBöhme, 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.‏
URIhttps://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85145743841&origin=inward
URIhttp://hdl.handle.net/10576/46853
AbstractMethylated 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.
Languageen
PublisherMDPI
Subjecteliminative photochemical cyclization
formylation
Mallory reaction
methylated PAH
oxidation
oxidative 6π-electrocyclization
PAH metabolite
polycyclic aromatic hydrocarbon
TitleRegiospecific Photochemical Synthesis of Methylchrysenes
TypeArticle
Issue Number1
Volume Number28
dc.accessType Open Access


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