per-Hydroxylated Prism[ n]arenes: Supramolecularly Assisted Demethylation of Methoxy-Prism[5]arene

Rocco Del Regno; Paolo Della Sala; Davide Picariello; Carmen Talotta; Aldo Spinella; Placido Neri; Carmine Gaeta

doi:10.1021/acs.orglett.1c02800

per-Hydroxylated Prism[ n]arenes: Supramolecularly Assisted Demethylation of Methoxy-Prism[5]arene

Org Lett. 2021 Nov 5;23(21):8143-8146. doi: 10.1021/acs.orglett.1c02800. Epub 2021 Oct 11.

Authors

Rocco Del Regno¹, Paolo Della Sala¹, Davide Picariello¹, Carmen Talotta¹, Aldo Spinella¹, Placido Neri¹, Carmine Gaeta¹

Affiliation

¹ Dipartimento di Chimica e Biologia "A. Zambelli", Università di Salerno, Via Giovanni Paolo II 132, I-84084 Fisciano (Salerno), Italy.

Abstract

Methoxy-prism[5]arene PrS[5]^Me is demethylated by a supramolecularly assisted reaction. In the presence of a tetramethylammonium cation, PrS[5]^Me is demethylated by BBr₃ in high yield, while in its absence a 55/40 mixture of PrS[5]^OH/PrS[6]^OH is formed. The dealkylation of prismarenes, such as PrS[6]^R (R = Et, nPr) and c-PrS[5]^Me, can be easily obtained in high yields in the presence of BBr₃.