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

Reutskaya, ElenaInstitute of Chemistry, Saint Petersburg State University, Saint Petersburg 199034, Russia (författare)

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.

Sapegin, AlexanderInstitute of Chemistry, Saint Petersburg State University, Saint Petersburg 199034, Russia (författare)
Peintner, Stefan,1991-Uppsala universitet,Organisk kemi(Swepub:uu)stepe841 (författare)
Erdélyi, Máté,1975-Uppsala universitet,Organisk kemi(Swepub:uu)mateerde (författare)
Krasavin, MikhailInstitute of Chemistry, Saint Petersburg State University, Saint Petersburg 199034, Russia (författare)
Institute of Chemistry, Saint Petersburg State University, Saint Petersburg 199034, RussiaOrganisk kemi (creator_code:org_t)

Ingår i:Journal of Organic Chemistry: American Chemical Society (ACS)86:8, s. 5778-57910022-32631520-6904

Av författaren/redakt...: Reutskaya, Elena; Sapegin, Alexand ...; Peintner, Stefan ...; Erdélyi, Máté, 1 ...; Krasavin, Mikhai ...

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