New partially alkylated calix[6]arenes have been synthesized. Depending on the conditions, mono-, 1,2-di-, 1,3-di, 1,2,3-tri-, 1,3,5-tri-, 1,2,4,5-tetra-, and 1,2,3,4,5-pentamethylated derivatives of p-tert-butylcalix[6]arene could be obtained in moderate to good yields. Methylation or benzylation of the parent calix[6]arene showed a regioselectivity towards 1,2-di-, and 1,2,3-trisubstitution. The solid state structure of 1,2,4,5-tetrasubstituted p-tert-butylcalix[6]arene [R=O(CH2CH2O)2CH3] has been elucidated by X-ray analysis.
Procedures for the Selective Alkylation of Calix[6]arenes at the Lower Rim / R. G., Jansen; W., Verboom; D. N., Reinhoudt; Casnati, Alessandro; M., Freriks; Pochini, Andrea; Ugozzoli, Franco; Ungaro, Rocco; P. M., Nieto; M., Carramolino; F., Cuevas; P., Prados; J., DE MENDOZA. - In: SYNTHESIS. - ISSN 0039-7881. - (1993), pp. 380-386. [10.1055/s-1993-25868]
Procedures for the Selective Alkylation of Calix[6]arenes at the Lower Rim
CASNATI, Alessandro;POCHINI, Andrea;UGOZZOLI, Franco;UNGARO, Rocco;
1993-01-01
Abstract
New partially alkylated calix[6]arenes have been synthesized. Depending on the conditions, mono-, 1,2-di-, 1,3-di, 1,2,3-tri-, 1,3,5-tri-, 1,2,4,5-tetra-, and 1,2,3,4,5-pentamethylated derivatives of p-tert-butylcalix[6]arene could be obtained in moderate to good yields. Methylation or benzylation of the parent calix[6]arene showed a regioselectivity towards 1,2-di-, and 1,2,3-trisubstitution. The solid state structure of 1,2,4,5-tetrasubstituted p-tert-butylcalix[6]arene [R=O(CH2CH2O)2CH3] has been elucidated by X-ray analysis.| File | Dimensione | Formato | |
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