p-(benzyloxy)calix[8]arene: One-pot synthesis and functionalization

被引:27
作者
Casnati, A [1 ]
Ferdani, R [1 ]
Pochini, A [1 ]
Ungaro, R [1 ]
机构
[1] UNIV PARMA,DIPARTIMENTO CHIM ORGAN & IND,I-43100 PARMA,ITALY
关键词
D O I
10.1021/jo970620r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The condensation of hydroquinone monobenzyl ether in the presence of several bases gives a mixture of cyclic oligomers. Using p-benzyloxyphenol, paraformaldehyde, and NaOH in 45:82:1 molar ratio in refluxing xylene, p-(benzyloxy)calix[8]arene (2) was selectively produced in 48% isolated yield. Compound 2 was also functionalized at the lower rim with acetoxy, methyl, pentyl, [(ethyloxy)carbonyl]methyl, and [(N,N-diethylamino)carbonyl]methyl groups. Replacement of the benzyl groups on these compounds allowed for the first time the high-yield syntheses of calix[8]hydroquinone and its derivatives.
引用
收藏
页码:6236 / 6239
页数:4
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