Ipso-Nitration of calix[6]azacryptands: intriguing effect of the small rim capping pattern on the large rim substitution selectivity.

Lejeune, Manuel; Picron, Jean-François; Mattiuzzi, Alice; Lascaux, Angélique; De Cesco, Stéphane; Brugnara, Andrea; Thiabaud, Gregory; Darbost, Ulrich; Coquière, David; Colasson, Benoit; Reinaud, Olivia; Jabin, Ivan

Lejeune, Manuel; Picron, Jean-François; Mattiuzzi, Alice; Lascaux, Angélique; De Cesco, Stéphane; Brugnara, Andrea; Thiabaud, Gregory; Darbost, Ulrich; Coquière, David; Colasson, Benoit; Reinaud, Olivia; Jabin, Ivan.

Afiliación

Lejeune M; Laboratoire de Chimie Organique, Université Libre de Bruxelles (U.L.B.), avenue F. D. Roosevelt, 50 CP160/06, B-1050 Bruxelles, Belgium.

J Org Chem ; 77(8): 3838-45, 2012 Apr 20.

Article en En | MEDLINE | ID: mdl-22428688

RESUMEN

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.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2012 Tipo del documento: Article País de afiliación: Bélgica Pais de publicación: Estados Unidos

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