A tetrahydroxycalix[4]arene derivative with all bridges monosubstituted with methoxy groups

Norbert Itzhak, Silvio E. Biali

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Abstract Reduction of the carbonyl groups of tetrahydroxyketocalix[4]arene with NaBH4 in propan-2-ol, followed by heating the product to reflux in MeOH-H2SO4, yields a mixture of stereoisomers of the tetrahydroxycalix[4]arene derivative with all bridges monosubstituted by a methoxy group. To structurally characterize the compound, the mixture of isomers was derivatized by reaction with di-tert-butyl dicarbonate-DMAP. X-ray crystal structure analysis of the all-cis isomer of the product (obtained by fractional crystallization), corroborates the presence of Boc protecting groups at the lower rim (and thus underivatized OH groups in the starting material), and four methoxy groups at the bridges.

Original languageAmerican English
Article numberss-2014-z0758-op
Pages (from-to)1678-1682
Number of pages5
JournalSynthesis
Volume47
Issue number11
DOIs
StatePublished - 2 Jun 2015

Bibliographical note

Publisher Copyright:
© Georg Thieme Verlag.

Keywords

  • calixarenes
  • carbocation
  • phenols
  • protecting group
  • reduction

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