Regioselective Friedel-Crafts acylation of calix[4]arenes

0451274 - FZÚ 2016 RIV GB eng J - Journal Article
Skácel, J. - Budka, J. - Eigner, Václav - Lhoták, P.
Regioselective Friedel-Crafts acylation of calix[4]arenes.
Tetrahedron. Roč. 71, č. 13 (2015), s. 1959-1965. ISSN 0040-4020. E-ISSN 1464-5416
R&D Projects: GA ČR(CZ) GA14-03276S
Institutional support: RVO:68378271
Keywords : calixarene acylation * regioselectivity * complexation * neutral guests
Subject RIV: CC - Organic Chemistry
Impact factor: 2.645, year: 2015

FriedeleCrafts acylation of 25,27-dialkoxycalix[4]arenes has been studied. Direct acylation of de-tertbutylated calixarene using acyl chlorides and AlCl3 in 1,2-dichloroethane provided the corresponding diacyl derivatives regioselectively in high yields. Furthermore, ipso-substitution in the tert-butylated series under the same reaction conditions is possible, albeit in lower yields. As indicated by the unsuccessful application of this chemistry to O-acyl derivatives, the ipso-acylation reaction of calix[4]arenes proceeds by direct attack at the upper rim and not by a Fries rearrangement mechanis m.
Permanent Link: http://hdl.handle.net/11104/0252445