The synthesis of the larger resorcin[5 and 6]arene macrocycles [5]OMe and [6]OMe has been realized by a Lewis acid-catalyzed condensation of 1,3-dimethoxy-2-methylbenzene with paraformaldehyde in o-dichlorobenzene as the solvent. The methoxy-resorcin[5 and 6]arenes were quantitatively demethylated by treatment with BBr3 to obtain the corresponding macrocycles with free OH groups. X-ray studies showed that in the solid state both the conformation and the packing of [6]OMe and [5]OMe are driven by C–H···O, C–H···π, and π···π interactions.

Improved Synthesis of Larger Resorcinarenes

BRANCATELLI, GIOVANNA;GEREMIA, SILVANO;
2016

Abstract

The synthesis of the larger resorcin[5 and 6]arene macrocycles [5]OMe and [6]OMe has been realized by a Lewis acid-catalyzed condensation of 1,3-dimethoxy-2-methylbenzene with paraformaldehyde in o-dichlorobenzene as the solvent. The methoxy-resorcin[5 and 6]arenes were quantitatively demethylated by treatment with BBr3 to obtain the corresponding macrocycles with free OH groups. X-ray studies showed that in the solid state both the conformation and the packing of [6]OMe and [5]OMe are driven by C–H···O, C–H···π, and π···π interactions.
http://pubs.acs.org/doi/suppl/10.1021/acs.joc.6b00803
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11368/2889722
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