DOI

The hydrated imidazoline ring expansion (HIRE-type) reaction was investigated for a series of di(hetero)arene-fused [1.4]thiazepinones in comparison with their sulfone counterparts. The sulfones were found to undergo ring expansion at a much higher rate compared to the thioethers, much in line with the current mechanistic understanding of the process. Moreover, the amide bond cis- and trans-isomers of the ring-expanded products were found, in the case of sulfones, to be stabilized through an intramolecular hydrogen bond. The latter phenomenon was studied in detail by NMR experiments and corroborated by X-ray crystallographic information.

Язык оригиналаанглийский
Страницы (с-по)5778-5791
Число страниц14
ЖурналJournal of Organic Chemistry
Том86
Номер выпуска8
Дата раннего онлайн-доступа7 апр 2021
DOI
СостояниеОпубликовано - 16 апр 2021

    Предметные области Scopus

  • Органическая химия

ID: 76894277