Intramolecularly Bridged Calix[4]arenes with Pronounced Complexation Ability toward Neutral Compounds

Petr Slavík; Václav Eigner; Pavel Lhoták

doi:10.1021/acs.orglett.5b01200

Intramolecularly Bridged Calix[4]arenes with Pronounced Complexation Ability toward Neutral Compounds

Petr Slavík, Václav Eigner, Pavel Lhoták

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Regioselective derivatization via an organomercury intermediate allowed for the introduction of carboxylic acid functionality into the meta position of the calix[4]arene skeleton. Intramolecular Friedel-Crafts cyclization led to a novel type of calixarene containing a ketone bridging moiety. Subsequent attack of the ketone by organometallic compounds occurred selectively from outside providing tertiary alcohols with the OH group oriented inside the cavity. These compounds can complex neutral molecules both in the solid state (X-ray) and in solution (NMR) using the cooperative effect of hydrogen bonding (OH) and CH-π interactions from within the cavity.

Original language	English
Pages (from-to)	2788-91
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.5b01200
Publication status	Published - 14 May 2015

Keywords

Journal Article

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10.1021/acs.orglett.5b01200

Cite this

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abstract = "Regioselective derivatization via an organomercury intermediate allowed for the introduction of carboxylic acid functionality into the meta position of the calix[4]arene skeleton. Intramolecular Friedel-Crafts cyclization led to a novel type of calixarene containing a ketone bridging moiety. Subsequent attack of the ketone by organometallic compounds occurred selectively from outside providing tertiary alcohols with the OH group oriented inside the cavity. These compounds can complex neutral molecules both in the solid state (X-ray) and in solution (NMR) using the cooperative effect of hydrogen bonding (OH) and CH-π interactions from within the cavity. ",

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AU - Lhoták, Pavel

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AB - Regioselective derivatization via an organomercury intermediate allowed for the introduction of carboxylic acid functionality into the meta position of the calix[4]arene skeleton. Intramolecular Friedel-Crafts cyclization led to a novel type of calixarene containing a ketone bridging moiety. Subsequent attack of the ketone by organometallic compounds occurred selectively from outside providing tertiary alcohols with the OH group oriented inside the cavity. These compounds can complex neutral molecules both in the solid state (X-ray) and in solution (NMR) using the cooperative effect of hydrogen bonding (OH) and CH-π interactions from within the cavity.

KW - Journal Article

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