Calixhydroquinones: A novel access to conformationally restricted, meta-substituted calixarenes

Mark Mascal; Ralf Warmuth; Russell T. Naven; Ross A. Edwards; Michael B. Hursthouse; David E. Hibbs

doi:10.1039/a906442g

Calixhydroquinones: A novel access to conformationally restricted, meta-substituted calixarenes

Mark Mascal, Ralf Warmuth, Russell T. Naven, Ross A. Edwards, Michael B. Hursthouse, David E. Hibbs

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

31 Scopus citations

Abstract

An efficient and versatile synthetic route to calixhydroquinones is described. These macrocycles are activated towards meta substitution, and reaction with bromine gives the first examples of persubstituted, phenol-derived calixarenes. The effect of meta substitution on calixarene mobility is demonstrated by the fixation of an otherwise mobile calix[4] system in the partial cone conformer, and the slowing of the ring inversion rate in calix[8]arenes.

Original language	English (US)
Pages (from-to)	3435-3441
Number of pages	7
Journal	Journal of the Chemical Society - Perkin Transactions 1
Issue number	23
DOIs	https://doi.org/10.1039/a906442g
State	Published - Dec 7 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Chemistry

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10.1039/a906442g

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abstract = "An efficient and versatile synthetic route to calixhydroquinones is described. These macrocycles are activated towards meta substitution, and reaction with bromine gives the first examples of persubstituted, phenol-derived calixarenes. The effect of meta substitution on calixarene mobility is demonstrated by the fixation of an otherwise mobile calix[4] system in the partial cone conformer, and the slowing of the ring inversion rate in calix[8]arenes.",

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T2 - A novel access to conformationally restricted, meta-substituted calixarenes

AU - Mascal, Mark

AU - Warmuth, Ralf

AU - Naven, Russell T.

AU - Edwards, Ross A.

AU - Hursthouse, Michael B.

AU - Hibbs, David E.

PY - 1999/12/7

Y1 - 1999/12/7

N2 - An efficient and versatile synthetic route to calixhydroquinones is described. These macrocycles are activated towards meta substitution, and reaction with bromine gives the first examples of persubstituted, phenol-derived calixarenes. The effect of meta substitution on calixarene mobility is demonstrated by the fixation of an otherwise mobile calix[4] system in the partial cone conformer, and the slowing of the ring inversion rate in calix[8]arenes.

AB - An efficient and versatile synthetic route to calixhydroquinones is described. These macrocycles are activated towards meta substitution, and reaction with bromine gives the first examples of persubstituted, phenol-derived calixarenes. The effect of meta substitution on calixarene mobility is demonstrated by the fixation of an otherwise mobile calix[4] system in the partial cone conformer, and the slowing of the ring inversion rate in calix[8]arenes.

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JF - Journal of the Chemical Society - Perkin Transactions 1

IS - 23

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Calixhydroquinones: A novel access to conformationally restricted, meta-substituted calixarenes

Abstract

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