Derivatization of Pyrogallarenes

A. Åhman, M. Luostarinen, C. A. Schalley, M. Nissinen, K. Rissanen— 2005

Derivatisation of upper-rim hydroxy groups of pyrogallarenes produced completely acylated and tosylated pyrogallarene derivatives. Mesitylation of pyrogallarene, however, resulted in a regioselective derivatisation of hydroxy groups, i.e. eight OH groups out of 12 were mesitylated. Crystal structures of the synthesised pyrogallarene derivatives indicate that completely substituted pyrogallarenes exist in a distorted crown conformation despite of the lack of stabilising intramolecular hydrogen bonds. In contrast, the partially substituted pyrogallarene adopts a boat conformation and has an open cavity for the inclusion of small guest molecules.

Derivatization of Pyrogallarenes
AuthorA. Åhman, M. Luostarinen, C. A. Schalley, M. Nissinen, K. Rissanen
IdentifierDOI 10.1002/ejoc.200500039
CitationEur. J. Org. Chem. 2005, 2793-2801