126395-03-7Relevant articles and documents
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
, p. 5778 - 5791 (2021)
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.
Iron-catalyzed cross-coupling of imidoyl chlorides with Grignard reagents
Ottesen, Lars K.,Ek, Fredrik,Olsson, Roger
, p. 1771 - 1773 (2007/10/03)
A general, high yielding rapid iron-catalyzed cross-coupling reaction between Grignard reagents and imidoyl chlorides is described. These reactions are typically completed within 5 min, resulting in high yields of 71-96% using 5% iron catalyst in a THF-NM
