A NOVEL-APPROACH TO INHERENTLY CHIRAL CALIX[4]ARENES BY DIRECT INTRODUCTION OF A SUBSTITUENT AT THE META POSITION

Citation
W. Verboom et al., A NOVEL-APPROACH TO INHERENTLY CHIRAL CALIX[4]ARENES BY DIRECT INTRODUCTION OF A SUBSTITUENT AT THE META POSITION, Tetrahedron, 51(2), 1995, pp. 499-512
Citations number
28
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
0040-4020
Volume
51
Issue
2
Year of publication
1995
Pages
499 - 512
Database
ISI
SICI code
0040-4020(1995)51:2<499:ANTICC>2.0.ZU;2-J
Abstract
A novel method for the preparation of inherently chiral calix[4]arenes is described by direct introduction of a substituent in para-acetamid o substituted calix[4]arenes. Bromination and nitration of mono(acetam ido)calix[4]arenes 5, 6 afforded calix[4]arenes 7-10, in which the sub stituent was selectively introduced adjacent to the acetamido moiety, in 58-98% yield. Bromination of bis(acetamido)calix[4]arene 13 gave a mixture from which dibromo- (14) and tribromocalix[4]arene 15 were iso lated in 10% and 22% yield, respectively. The structure of 14 was conf irmed by single-crystal X-ray structure determination. Nitration of 13 gave 4,16-dinitro- (16) and 4,18-dinitrocalix[4]arene 17 in 53% and 1 8% yield, respectively.