Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
The reaction of trifluoroacetyl alkynes [ArC≡C(C=O)CF 3 ] with H 2 SO 4 or TfOH affords products of addition of the acids to the acetylene bond. Hydrolysis of these adducts results in the formation of the corresponding 1,3-diketones existing in form of enols [Ar(HO)C=CH(C=O)CF 3 ] in up to 98 % yield. The application of less acidic TfOH-pyridine system permits transformation of these alkynes into the corresponding vinyl triflates in up to 76 % yield. Moreover, this reaction is totally stereoselective to give only Z-configured vinyl triflates. The reaction of trifluoroacetyl alkynes with arenes in TfOH or under the action of acidic HUSY zeolites CBV-720 gives rise to 1,3-diaryl-1-CF 3 -indenes in up to 81 % yield. Electronic characteristics of initial intermediate mono- and dicationic species derived from such alkynes in the highly acidic media were studied by DFT calculations. Plausible cationic reaction mechanism was proposed.
Язык оригинала | английский |
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Страницы (с-по) | 1293-1300 |
Число страниц | 8 |
Журнал | European Journal of Organic Chemistry |
Том | 2019 |
Номер выпуска | 6 |
DOI | |
Состояние | Опубликовано - 14 фев 2019 |
ID: 44001750