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

Verboom, Willem and Bodewes, Paul J. and Essen van, Georget and Timmerman, Peter and Hummel van, Gerrit J. 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
Faculty:	Science and Technology (TNW)
Research Group:	Molecular Nanofabrication (MNF)
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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