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Derivatisation of Pyrogallarenes
Author(s) -
Åhman Antti,
Luostarinen Minna,
Schalley Christoph A.,
Nissinen Maija,
Rissanen Kari
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500039
Subject(s) - chemistry , intramolecular force , regioselectivity , hydrogen bond , molecule , stereochemistry , crystal structure , organic chemistry , catalysis
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. © Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)