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

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Verboom, Willem and Bodewes, Paul J. and Essen, Georget van and Timmerman, Peter and Hummel, Gerrit J. van and Harkema, Sybolt and Reinhoudt, David N. (1995) A novel approach to inherently chiral calix[4]arenes by direct introduction of a substituent at the meta position. Tetrahedron, 51 (2). pp. 499-512. ISSN 0040-4020

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Abstract: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.
Item Type:Article
Copyright:© 1995 Elsevier Science
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Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/12432
Official URL:http://dx.doi.org/10.1016/0040-4020(94)00911-D
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