4.7 Article

Synthesis and conformational studies on hexa-O-alkyl p-unsubstituted calix[6]arenes

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JOURNAL OF ORGANIC CHEMISTRY
卷 70, 期 25, 页码 10400-10407

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AMER CHEMICAL SOC
DOI: 10.1021/jo0516638

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In this article we describe the selective O-benzylation of para-unsubstituted calix[6]arene I in rings 1 and 4 (2a-c) and the subsequent alkylation of phenol groups with alpha-haloesters (methyl esters 3a, 3c, and 3e; tert-butyl esters 3b, 3d, and 3f) to determine the effect of these groups on their conformational behavior. 2D NMR studies at 188 K reveal that compounds 2a-c, 3b, 3d, and 3f are less flexible, showing a 1,2,3-alternate conformation. The same conformation has been observed in the solid state.

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