Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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.
Язык оригинала | английский |
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Номер статьи | e4038 |
Число страниц | 10 |
Журнал | Journal of Physical Organic Chemistry |
Том | 33 |
Номер выпуска | 3 |
Дата раннего онлайн-доступа | 2 дек 2019 |
DOI | |
Состояние | Опубликовано - 1 мар 2020 |
ID: 51276851