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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
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- Reutskaya, Elena (author)
- Institute of Chemistry, Saint Petersburg State University, Saint Petersburg 199034, Russia
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- Sapegin, Alexander (author)
- Institute of Chemistry, Saint Petersburg State University, Saint Petersburg 199034, Russia
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- Peintner, Stefan, 1991- (author)
- Uppsala universitet,Organisk kemi
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- 2021-04-07
- 2021
- English.
- In: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 86:8, s. 5778-5791
- Journal article (peer-reviewed)
Abstract
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- 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.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- Chemistry with specialization in Organic Chemistry
- Kemi med inriktning mot organisk kemi
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- art (subject category)
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