American Chemical Society
ol5024536_si_001.pdf (2.42 MB)

Regioselective Halogenation of Thiacalix[4]arenes in the Cone and 1,3-Alternate Conformations

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journal contribution
posted on 2014-10-03, 00:00 authored by Jan Lukášek, Stanislav Böhm, Hana Dvořáková, Václav Eigner, Pavel Lhoták
Monohalogenation of thiacalix[4]­arene in the cone conformation gave either the meta- or para-substituted isomers depending on the halogen and reaction conditions used. Surprisingly, the same reaction with the 1,3-alternate conformer led only to the meta isomer. This is the first example of such a conformation-dependent regioselectivity in calixarene/thiacalixarene chemistry. As the halogen-substituted calixarenes are useful synthetic intermediates, this provided the unique opportunity to functionalize the basic skeleton at two different positions.