Synthesis of p-tert-Butyl-5,5-bicalix[4]arene and Access to 5,5-Bicalix[4] arenes Functionalized at the Upper Rim

Title: Synthesis of p-tert-Butyl-5,5-bicalix[4]arene and Access to 5,5-Bicalix[4] arenes Functionalized at the Upper Rim

Volume: 2 Issue: 3

Author(s): Grazia M.L. Consoli, Francesca Cunsolo, Corrada Geraci and Placido Neri

Affiliation:

Keywords: calixarenes, bicalixarenes, macrocycles, alkylation, ipso -nitration

Abstract: Compound 1, a double p-tert-butylcalix[4]arene with direct para-para linkage, was obtained by FeCl3- mediated oxidative coupling of 5,11,17-tri-p-tert-butyl-26,27,28-tribenzoyloxycalix[4]arene-25-ol (4) followed by alkaline hydrolysis. With respect to the de-tert-butylated counterpart 1a, a different reactivity of 1 was observed in the NaH-promoted propylation, which gave octapropyl double-cone atropisomer 6 with higher stereoselectivity. Under competitive conditions 6 was selectively mononitrated at the biphenyl system, whereas ipso-nitration at t-Bubearing rings was obtained using a larger excess of HNO3.

Cite this article as:

Consoli M.L. Grazia, Cunsolo Francesca, Geraci Corrada and Neri Placido, Synthesis of p-tert-Butyl-5,5-bicalix[4]arene and Access to 5,5-Bicalix[4] arenes Functionalized at the Upper Rim, Letters in Organic Chemistry 2005; 2 (3) . https://dx.doi.org/10.2174/1570178053765357