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Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

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

Volume 2, Issue 3, 2005

Page: [252 - 257] Pages: 6

DOI: 10.2174/1570178053765357

Price: $65


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.

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

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