Due to the large dimension of their annulus, calix[8]arenes are promising substrates for the synthesis of molecular receptors for medium-sized organic compounds. To this end, their selective functionalization and conformational preorganization are of central interest. Examples of selectively derivatized calix[8]arenes or examples with reduced conformational mobility are reviewed. Partial O-alkylation is usually obtained in the presence of a weak base, which drives the reaction through the ''alternate alkylation'' route. Inhibition of conformational interconversion is achieved by simple intramolecular bridging, while a complete preorganization requires a multiple anchoring and a concomitant reduction of the tendency to self-fill the cavity.

Selective functionalization and preorganization of calix[8]arenes

NERI, Placido;
1996-01-01

Abstract

Due to the large dimension of their annulus, calix[8]arenes are promising substrates for the synthesis of molecular receptors for medium-sized organic compounds. To this end, their selective functionalization and conformational preorganization are of central interest. Examples of selectively derivatized calix[8]arenes or examples with reduced conformational mobility are reviewed. Partial O-alkylation is usually obtained in the presence of a weak base, which drives the reaction through the ''alternate alkylation'' route. Inhibition of conformational interconversion is achieved by simple intramolecular bridging, while a complete preorganization requires a multiple anchoring and a concomitant reduction of the tendency to self-fill the cavity.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11386/3136523
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