The chemodivergent ring-opening of cyclobutanols is described under the carbocatalytic assistance of graphene oxide (GO). The protocol enables the synthesis of diversely functionalized dienes or indenes (26 examples) based on the amount of GO employed. Spectroscopic (XPS and ssNMR) as well as experimental investigations revealed a direct involvement of the π-domains of GO in tuning the stability of carbocationic intermediates during the reaction.
Graphene-Oxide Mediated Chemodivergent Ring-Opening of Cyclobutanols / Brunetti A.; Pintus A.; Lombardi L.; Kovtun A.; Mascietti F.; Bruno F.; Ravera E.; Melucci M.; Bertuzzi G.; Bandini M.. - In: CHINESE JOURNAL OF CHEMISTRY. - ISSN 1001-604X. - STAMPA. - 41:(2023), pp. 1333-1340. [10.1002/cjoc.202200757]
Graphene-Oxide Mediated Chemodivergent Ring-Opening of Cyclobutanols
Bruno F.;Ravera E.;
2023
Abstract
The chemodivergent ring-opening of cyclobutanols is described under the carbocatalytic assistance of graphene oxide (GO). The protocol enables the synthesis of diversely functionalized dienes or indenes (26 examples) based on the amount of GO employed. Spectroscopic (XPS and ssNMR) as well as experimental investigations revealed a direct involvement of the π-domains of GO in tuning the stability of carbocationic intermediates during the reaction.
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