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 / Della Sala, Paolo; Gaeta, Carmine; Navarra, Wanda; Talotta, Carmen; De Rosa, Margherita; Brancatelli, Giovanna; Geremia, Silvano; Capitelli, Francesco; Neri, Placido. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 81:13(2016), pp. 5726-5731. [10.1021/acs.joc.6b00803]
Improved Synthesis of Larger Resorcinarenes
BRANCATELLI, GIOVANNA;GEREMIA, SILVANO;
2016-01-01
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.| File | Dimensione | Formato | |
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