We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
The First Example of the Friedel–Crafts Cyclization Leading to (10-Hydroxy-9,10-dihydroanthr-9-yl)phosphonium Salts without the Expected Bradsher Dehydration.
- Authors
Owsianik, Krzysztof; Różycka-Sokołowska, Ewa; Koprowski, Marek; Turek, Marika; Knopik, Łucja; Vivek, Vivek; Dudziński, Bogdan; Bałczewski, Piotr
- Abstract
The reaction of (ortho-acetalaryl)arylmethanols with various phosphines PR1R2R3 (R1 = R2 = R3 = Ph; R1 = R2 = Ph, R3 = Me and R1 = R2 = Me, R3 = Ph) under acidic conditions (e.g., HCl, HBF4, TsOH) unexpectedly led to the formation of (10-hydroxy-9,10-dihydroanthr-9-yl)phosphonium salts instead of the corresponding anthryl phosphonium salts. The cyclization occurred according to the Friedel–Crafts mechanism but without the usually observed Bradsher dehydration, giving cyclic products in the form of cis/trans isomers and their conformers. In case of electron-rich and less-hindered dimethylphenylphosphine, all four stereoisomers were recorded in 31P{1H} NMR spectra, while for the other phosphines, only the two most stable cis/trans stereoisomers were detected. This study was supported by DFT and NCI calculations in combination with FT-IR analysis.
- Subjects
PHOSPHONIUM compounds; RING formation (Chemistry); DEHYDRATION; STEREOISOMERS; PHOSPHINES; ISOMERS
- Publication
International Journal of Molecular Sciences, 2024, Vol 25, Issue 3, p1741
- ISSN
1661-6596
- Publication type
Article
- DOI
10.3390/ijms25031741