Sulfur Oxidation Increases the Rate of HIRE-Type [1.4]Thiazepinone Ring Expansion and Influences the Conformation of a Medium-Sized Heterocyclic Scaffold

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Sulfur Oxidation Increases the Rate of HIRE-Type [1.4]Thiazepinone Ring Expansion and Influences the Conformation of a Medium-Sized Heterocyclic Scaffold. / Reutskaya, Elena ; Sapegin, Alexander; Peintner, Stefan; Erdélyi, Máté; Krasavin, Mikhail.

в: Journal of Organic Chemistry, Том 86, № 8, 16.04.2021, стр. 5778-5791.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{ea284c0ff0d24004a1d7db48579a97c6,

title = "Sulfur Oxidation Increases the Rate of HIRE-Type [1.4]Thiazepinone Ring Expansion and Influences the Conformation of a Medium-Sized Heterocyclic Scaffold",

abstract = "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. ",

author = "Elena Reutskaya and Alexander Sapegin and Stefan Peintner and M{\'a}t{\'e} Erd{\'e}lyi and Mikhail Krasavin",

year = "2021",

month = apr,

day = "16",

doi = "10.1021/acs.joc.1c00236",

language = "English",

volume = "86",

pages = "5778--5791",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "8",

}

RIS

TY - JOUR

T1 - Sulfur Oxidation Increases the Rate of HIRE-Type [1.4]Thiazepinone Ring Expansion and Influences the Conformation of a Medium-Sized Heterocyclic Scaffold

AU - Reutskaya, Elena

AU - Sapegin, Alexander

AU - Peintner, Stefan

AU - Erdélyi, Máté

AU - Krasavin, Mikhail

PY - 2021/4/16

Y1 - 2021/4/16

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85105051037&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/f9d9ce8d-8c92-352d-be2f-54d63278797a/

U2 - 10.1021/acs.joc.1c00236

DO - 10.1021/acs.joc.1c00236

M3 - Article

AN - SCOPUS:85105051037

VL - 86

SP - 5778

EP - 5791

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 8

ER -

ID: 76894277