Takudrei

080
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.

Title080
Derivatization of Pyrogallarenes
AuthorA. Åhman, M. Luostarinen, C. A. Schalley, M. Nissinen, K. Rissanen
Date20050620
IdentifierDOI 10.1002/ejoc.200500039
Source(s)
CitationEur. J. Org. Chem. 2005, 2793-2801