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Conformational Aspects of the O-acetylation of C- tetra(phenyl)calixpyrogallol[4]arene

Conformational Aspects of the O-acetylation of C- tetra(phenyl)calixpyrogallol[4]arene

José Luis Casas-Hinestroza, Mauricio Maldonado

Molecules. 2018 May 20;23(5):1225.

PMID: 29783780

Abstract:

Reaction between pyrogallol and benzaldehyde results in a conformational mixture of C-tetra(phenyl)pyrogallol[4]arene (crown and chair). The conformer mixture was separated using crystallization procedures and the structures were determined using FTIR, ¹H-NMR, and 13C-NMR. O-acetylation of C-tetra(phenyl)pyrogallol[4]arene (chair) with acetic anhydride, in pyridine results in the formation of dodecaacetyl-tetra(phenyl)pyrogallol[4]arene. The structure was determined using ¹H-NMR and 13C-NMR finding that the product maintains the conformation of the starting conformer. On the other hand, the O-acetylation reaction of C-tetra(phenyl)pirogallol[4]arene (crown) under same conditions proceeded efficiently, and its structure was determined using ¹H-NMR and 13C-NMR. Dynamic ¹H-NMR of acetylated pyrogallolarene was studied by means of variable temperature in DMSO-d₆ solution, and it revealed that two conformers are formed in the solution. Boat conformations for acetylated pyrogallolarene showed a slow interconversion at room temperature.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP285977777	Acetic anhydride-13C4,d6		285977-77-7	Price

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