TETRA-O-BENZYLATED CALIX[8]ARENES WITH C(4) SYMMETRY

被引：25

作者：

NERI, P

GERACI, C

PIATTELLI, M

机构：

[1] Istituto per lo Studio delle Sostanze Naturali di Interesse Alimentare e Chimico-Farmaceutico, C.N.R., I-95028 Valverde, CT

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 20期

关键词：

CALIX[8]ARENES; TETRAALKYLATION; 1,3,5,7-TETRABENZYL ETHERS; C(4) SYMMETRY;

D O I：

10.1016/S0040-4039(00)73693-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first procedure for the selective partial O-alkylation of p-tert-butylcalix[8]arene 1 affording well defined products is described. Treatment of 1 with p-X-benzyl bromides (X = H, Me, tert-Bu, NO2, CN) and K2CO3 in THF/DMF gives the corresponding 1,3,5,7-tetrabenzyl ethers 2-6 having C4 symmetry. Their structures were firmly established by FAB(+) MS, H-1- and C-13-NMR. Variable temperature NMR studies evidenced conformational flexibility for 2-6. A possible rationale is proposed in order to explain the origin of the 1,3,5,7-substitution pattern.

引用

页码：3319 / 3322

页数：4

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