Synlett 1994; 1994(10): 765-776
DOI: 10.1055/s-1994-23003
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The Chemistry of [1 n ]Orthocyclophanes; New Classes of Ionophores, Starands and Ketonands

Woo Young Lee*
  • *Department of Chemistry, Seoul National University, Seoul 151-742, South Korea
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Publication Date:
22 March 2002 (online)

This review reports on the chemistry of [1 n ]orthocyclophanes ([1 n ]OCPs) as a new field of the cyclophanes chemistry. The potential pathways leading to every size of the [1 n ]OCP cycles are described. The modification of the cycles to novel ionophores is also demonstrated. Oxidation of odd-numbered [1 n ]OCPs resulted in ketonic crowns, which are referred to as "ketonands". Oxidation of even-numbered [1 n ]OCPs gave rise to star-shaped crown ethers, which are referred to as "starands". Complexation behavior of the starands and ketonands has been studied. The functionalization of the [ 1 n ]OCPs at the aromatic rings was also carried out to give polyphenolic derivatives, which might be precursors to various supramolecules. 1. Introduction 2. Regioselectivity Rule in the Acid-Catalyzed Cycloalkylation of o-Benzylbenzylic Alcohols 3. Retrosynthetic Analysis of [1 n ]Orthocyclophanes 4. Terminal Aromatic Dibromides as Synthetic Building Blocks 5. Terminal Aromatic Dialdehydes as Synthetic Building Blocks 6. Starands 7. Ketonands 8. Complexation Behavior of Starands and Ketonands 9. Functionalization of [1 n ]OCPs at the Aromatic Rings 10. Conclusion and Perspective