In 2022,Fadeev, Alexander A.; Makarov, Anton S.; Ivanova, Olga A.; Uchuskin, Maxim G.; Trushkov, Igor V. published an article in Organic Chemistry Frontiers. The title of the article was 《Extended Corey-Chaykovsky reactions: transformation of 2-hydroxychalcones to benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans》.Product Details of 1774-47-6 The author mentioned the following in the article:
The divergent synthesis of benzannulated 2,8-dioxabicyclo[3.2.1]octanes I [R1 = H, 4-NO2, 4-Cl, etc.; R2 = Ph, 4-MeC6H4, 4-FC6H4, etc.] and 2,3-dihydrobenzofurans II [X= H, 4-NO2, 4-Cl, etc.; R1 = Ph, 4-MeC6H4, 4-FC6H4, etc.] using the concept of extended Corey-Chaykovsky reactions was reported. With this concept, 2-hydroxychalcones were treated with the Corey ylide providing highly reactive donor-acceptor cyclopropanes that were introduced in a one pot manner for further transformations. We demonstrated that the nucleophilic three-membered ring opening followed by cyclization under mild reaction conditions afforded the 2,8-dioxabicyclo[3.2.1]octane scaffold. On the other hand, heating the intermediates with a strong Bronsted acid furnished 2-phenacyl-2,3-dihydrobenzofurans. These transformations, resulting in products with crucially different heterocyclic skeletons from the same starting compounds, demonstrate the enormous potential of the extended Corey-Chaykovsky reaction.Trimethylsulfoxonium iodide(cas: 1774-47-6Product Details of 1774-47-6) was used in this study.
Trimethylsulfoxonium iodide(cas: 1774-47-6) reacts with sodium hydride to prepare dimethyloxosulfonium methylide, which is used as a methylene-transfer reagent in synthetic chemistry. It is used to prepare ylide, which reacts with carbonyl compounds to get epoxides. Further, it reacts with alfa,beta-unsaturated esters to get cyclopropyl esters.Product Details of 1774-47-6
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com