《Enantioselective Aryl-Iodide-Catalyzed Wagner-Meerwein Rearrangements》 was written by Sharma, Hayden A.; Mennie, Katrina M.; Kwan, Eugene E.; Jacobsen, Eric N.. Product Details of 31938-07-5 And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:
We report a strategy for effecting catalytic, enantioselective carbocationic rearrangements through the intermediacy of alkyl iodanes as stereodefined carbocation equivalent Asym. Wagner-Meerwein rearrangements of β-substituted styrenes are catalyzed by the C2-sym. aryl iodide 1 to provide access to enantioenriched 1,3-difluorinated mols. possessing interesting and well-defined conformational properties. Hammett and kinetic isotope effect studies, in combination with computational investigations, reveal that two different mechanisms are operative in these rearrangement reactions, with the pathway depending on the identity of the migrating group. In reactions involving alkyl-group migration, intermol. fluoride attack is product- and enantio-determining In contrast, reactions in which aryl rearrangement occurs proceed through an enantiodetermining intramol. 1,2-migration prior to fluorination. The fact that both pathways are promoted by the same chiral aryl iodide catalyst with high enantioselectivity provides a compelling illustration of generality across reaction mechanisms in asym. catalysis. In the experiment, the researchers used many compounds, for example, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Product Details of 31938-07-5)
2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione or a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands.Product Details of 31938-07-5
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts