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.

Highlights

  • Methoxy-prism[5]arene PrS[5]Me is demethylated by a supramolecularly assisted reaction

  • Our group reported the prism[n]arenes8−10 (PrS[n]R, n = 5 and 6, R = Me, Et, nPr, Figure 1), a novel class of macrocyclic hosts constituted by 1,5-methylenebridged naphthalene units, obtained by one-pot condensation of 2,6-dimethoxynaphthalene and paraformaldehyde in the presence of trifluoracetic acid (TFA).11

  • Very recently12 the saucer[n]arene macrocycles were reported by the one-pot condensation of 2,7-dimethoxynaphthalene and paraformaldehyde

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Summary

Introduction

Methoxy-prism[5]arene PrS[5]Me is demethylated by a supramolecularly assisted reaction. PrS[5]Me was reacted with BBr3 under the conditions reported in Scheme 1, at −78 °C for 1 h and 0 °C for 3 h, but analogously, a mixture of per-hydroxylated PrS[5]OH (55%) and PrS[6]OH (40%) derivatives was obtained.

Results
Conclusion
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