Part 1 Introduction to macrocycle chemistry: crown ether precursor work; Pedersen's discovery of crown ethers; Simmons' in-out bicyclic amines; Lehn's cryptands; cram and carbanions; classes of crown ethers and cryptands; naturally occurring relatives of crown ethers; nomenclature and its problems; toxicity of crown ether compounds. Part 2 Syntheses of crowns, cryptands and their relatives: Pedersen's first crowns; the ethylencoxy structural unit; the template effect; early syntheses of crowns; syntheses of crown ethers; incorporation of aromatic subunits; nitrogen-containing macrocycles; crown ethers containing sulfur; syntheses of cryptands; spherands, cavitands, and carcerands. Part 3 Complexation by crowns and cryptands: the extraction technique; homogeneous cation binding constants; binding dynamics; cation transport; complexation of organic cations; anions. Part 4 Structural aspects of crowns, cryptands, and their complexes: uncomplexed crown and cryptand ligands; simple crown ether complexes of metal cations; complexes of cryptands; crown ether complexes of other ions and molecules; podand complexes. Part 5 Applications of crowns and cryptands: solubilization phenomena; cation deactivation; anion activation - phase transfer catalysis; sensors and switching; polymeric crown systems; membranes and channels; chirality, complexation and enzyme models; receptor molecules; miscellaneous applications and developments; the future of crown ether chemistry. Part 6 Additional reading: books crown ethers cryptands, and polyethers; monographs on phase transfer catalysis; reviews and articles.
