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Synthesis and Characterization of Upper and Lower Rim Functionalized [6]Cavitands

โœ Scribed by Christoph Naumann; Brian O. Patrick; John Sherman

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
204 KB
Volume
8
Category
Article
ISSN
0947-6539

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โœฆ Synopsis

A [6]cavitand has been selectively derivatized on both the lower and upper rims. On the lower rim, two out of six potential sites were oxidized to produce a 1,4 substituted [6]cavitand bisketone, which was converted to a corresponding diol as well as a bisacetate [6]cavitand. The crystal structures of the bisketone and the diol were solved. On the upper rim, all six ArCH(3) groups were selectively brominated to ArCH(2)Br groups to produce the hexabromomethyl [6]cavitand, which was converted to the corresponding hexabenzylthiol and hexabenzylthioacetate [6]cavitands. The conformational properties of all compounds are discussed.

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