Azide Decomposition as a Pathway to Intramolecularly Upper-Rim-Bridged Calix[4]arenes

Martin Tlustý; Václav Eigner; Pavel Lhoták

doi:10.1055/a-1668-9694

Synthesis, Table of Contents

Synthesis 2022; 54(05): 1301-1308
DOI: 10.1055/a-1668-9694

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Azide Decomposition as a Pathway to Intramolecularly Upper-Rim-Bridged Calix[4]arenes

Martin Tlustý

^aDepartment of Organic Chemistry, University of Chemistry and Technology, Prague, Technická 5, 16628 Prague 6, Czech Republic

,

Václav Eigner

^bDepartment of Solid State Chemistry, University of Chemistry and Technology, Prague, Technická 5, 16628 Prague 6, Czech Republic

,

Pavel Lhoták ∗

^aDepartment of Organic Chemistry, University of Chemistry and Technology, Prague, Technická 5, 16628 Prague 6, Czech Republic

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Abstract

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Abstract

Proximally single-atom-bridged calix[4]arenes possess a rigidified cavity and, thus, unusual complexation properties. Here, we report on the synthesis of the first such heteroatom-bridged compound: amine-bridged calix[4]arene. This compound, prepared by thermal decomposition of 4-azidocalix[4]arene, was obtained alongside very interesting rearranged, inherently chiral 10H-azepino[1,2-a]indole derivatives. NMR titration confirmed the suitability of the amine cavity for the complexation of methylammonium cations; moreover, the –NH– bridge function enables its further derivatization.

Key words

calixarenes - azide decomposition - bridging - inherent chirality - complexation

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References

References

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