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

被引：63

作者：

VERBOOM, W

BODEWES, PJ

VANESSEN, G

TIMMERMAN, P

VANHUMMEL, GJ

HARKEMA, S

REINHOUDT, DN

机构：

[1] UNIV TWENTE,ORGAN CHEM LAB,7500 AE ENSCHEDE,NETHERLANDS

[2] UNIV TWENTE,CHEM PHYS LAB,7500 AE ENSCHEDE,NETHERLANDS

来源：

TETRAHEDRON | 1995年 / 51卷 / 02期

关键词：

D O I：

10.1016/0040-4020(94)00911-D

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method for the preparation of inherently chiral calix[4]arenes is described by direct introduction of a substituent in para-acetamido substituted calix[4]arenes. Bromination and nitration of mono(acetamido)calix[4]arenes 5, 6 afforded calix[4]arenes 7-10, in which the substituent 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 isolated in 10% and 22% yield, respectively. The structure of 14 was confirmed 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 18% yield, respectively.

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页码：499 / 512

页数：14

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