Acid-catalyzed decomposition and stability of diazofuranones: Experimental and mechanistic study

Dmitrii Semenok, Andrey S. Mereshchenko, Jury Medvedev, Giorgio Visentin

Результат исследований: Научные публикации в периодических изданияхстатья

Аннотация

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 оригиналаанглийский
Номер статьиe4038
ЖурналJournal of Physical Organic Chemistry
Том33
Номер выпуска3
Ранняя дата в режиме онлайн2 дек 2019
DOI
СостояниеОпубликовано - мар 2020

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Предметные области Scopus

  • Физическая и теоретическая химия
  • Органическая химия

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