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Attempted synthesis of a meta-metalated calix[4]arene.

ABSTRACT: An evidence for the formation of a rare meta-metalated inherently chiral calix[4]arene is described. Our strategy involved using a mesoionic carbene to direct C-H activation, but proved to form an unexpectedly unstable intermediate that was identified through high-resolution mass spectrometry. On route to our target, a new optimized method to mononitrocalix[4]arenes was developed, including optimized and high yielding transformations to azide and 1,2,3-triazole derivatives which may have application in other areas of research.

SUBMITTER: Jurisch CD

PROVIDER: S-EPMC6719732 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Attempted synthesis of a <i>meta</i>-metalated calix[4]arene.

Jurisch Christopher D CD Arnott Gareth E GE

Beilstein journal of organic chemistry 20190822

An evidence for the formation of a rare <i>meta</i>-metalated inherently chiral calix[4]arene is described. Our strategy involved using a mesoionic carbene to direct C-H activation, but proved to form an unexpectedly unstable intermediate that was identified through high-resolution mass spectrometry. On route to our target, a new optimized method to mononitrocalix[4]arenes was developed, including optimized and high yielding transformations to azide and 1,2,3-triazole derivatives which may have ...[more]

PMID: 31501666

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