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Issue 9, 2005
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Design and sterospecific synthesis of modular ligands based upon cis-1,3-trans-5-substituted cyclohexanes

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Abstract

A range of eight novel ligands, based on the cis-1,3-trans-5-substituted cyclohexane framework, have been synthesized by a stereospecific route starting from cis-1,3,5-cyclohexanetriol. This route depends on the use of efficient mono-silylation and mono-tosylation procedures, is well optimised, and due to isolation of the diazido alcohol precursor cis-3,5-diazido-trans-hydroxycyclohexane readily allows the synthesis of a sizeable family of related ligands via O-derivatisation. Such derivatisations allow systematic changes between various coordinating, hydrogen bonding and lipophilic groups, allowing potential for this ligand system to be utilised in supramolecular coordination chemistry.

Graphical abstract: Design and sterospecific synthesis of modular ligands based upon cis-1,3-trans-5-substituted cyclohexanes

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Article information


Submitted
10 Mar 2005
Accepted
13 Jun 2005
First published
08 Jul 2005

New J. Chem., 2005,29, 1152-1158
Article type
Paper

Design and sterospecific synthesis of modular ligands based upon cis-1,3-trans-5-substituted cyclohexanes

J. Fielden, J. Sprott and L. Cronin, New J. Chem., 2005, 29, 1152
DOI: 10.1039/B503606B

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