A novel approach to inherently chiral calix[4]arenes by direct introduction of a substituent at the meta position

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 selecti...

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Bibliographic Details
Published in:Tetrahedron 1995-01, Vol.51 (2), p.499-512
Main Authors: Verboom, Willem, Bodewes, Paul J., van Essen, Georget, Timmerman, Peter, van Hummel, Gerrit J., Harkema, Sybolt, Reinhoudt, David N.
Format: Article
Language:English
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Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(94)00911-D