title: Ipso-Nitration of calix[6]azacryptands: intriguing effect of the small rim capping pattern on the large rim substitution selectivity.
abstract: The ipso-nitration of calix[6]arene-based molecular receptors is a important synthetic pathway for the elaboration of more sophisticated systems. This reaction has been studied for a variety of capped calixarenes, and a general trend for the regioselective nitration of three aromatic units out of six in moderate to high yield has been observed. This selectivity is, in part, attributed to the electronic connection between the protonated cap at the small rim and the reactive sites at the large rim. In addition, this work highlights the fact that subtle conformational properties can drastically influence the outcome of this reaction.
authors.affiliation: Laboratoire de Chimie Organique, Université Libre de Bruxelles (U.L.B.), avenue F. D. Roosevelt, 50 CP160/06, B-1050 Bruxelles, Belgium.
authors.forename: Manuel
authors.initials: M
authors.lastname: Lejeune
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Picron
authors.forename: Alice
authors.initials: A
authors.lastname: Mattiuzzi
authors.forename: Angélique
authors.initials: A
authors.lastname: Lascaux
authors.forename: Stéphane
authors.initials: S
authors.lastname: De Cesco
authors.forename: Andrea
authors.initials: A
authors.lastname: Brugnara
authors.forename: Gregory
authors.initials: G
authors.lastname: Thiabaud
authors.forename: Ulrich
authors.initials: U
authors.lastname: Darbost
authors.forename: David
authors.initials: D
authors.lastname: Coquière
authors.forename: Benoit
authors.initials: B
authors.lastname: Colasson
authors.forename: Olivia
authors.initials: O
authors.lastname: Reinaud
authors.forename: Ivan
authors.initials: I
authors.lastname: Jabin