Research output: Contribution to journal › Article › peer-review
Reactions of substituted 4-diazotetrahydrofurane-3-ones with various acids (pKa < 3) irrespective of acid strength give rise to elimination of nitrogen with subsequent 1,2-nucleophilic migration of aryl (alkyl) groups from C-5 to C-4 position of heterocyclic core with quantitative formation of regioisomeric 3(2Н)furanones (yields up to 99%). Regioselectivity of this acid-catalyzed process increases with the decreasing of solvent polarity and strongly depends on the nature of substituents in the aryl groups. The suggested mechanism of this reaction via intermediate RN2 + cation was confirmed by density functional theory (DFT) calculations at the PBE0/6-31+G(d) functional due to good agreement between calculated and experimental data on the acid stability of diazoketones in different solvents.
Original language | English |
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Article number | e4038 |
Number of pages | 10 |
Journal | Journal of Physical Organic Chemistry |
Volume | 33 |
Issue number | 3 |
Early online date | 2 Dec 2019 |
DOIs | |
State | Published - 1 Mar 2020 |
ID: 51276851