Regioselective Halogenation of Thiacalix[4]arenes in the Cone and 1,3-Alternate Conformations
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- 作者：Jan Luk谩拧ek ; Stanislav B枚hm ; Hana Dvo艡谩kov谩 ; V谩clav Eigner ; Pavel Lhot谩k
- 刊名：Organic Letters
- 出版年：2014
- 出版时间：October 3, 2014
- 年：2014
- 卷：16
- 期：19
- 页码：5100-5103
- 全文大小：304K
- ISSN：1523-7052
文摘
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.