Catenanes, Rotaxanes, and Knots

Organic Chemistry, Volume 22: Catenanes, Rotaxanes, and Knots provides information pertinent to the synthesis of catenanes and rotaxanes. This book discusses the manner of interaction between the molecular subunits in catenanes in the solid, liquid, and gaseous states.

Organized into 19 chapters, this volume begins with an overview of the idea of synthesizing molecules composed of separate entities that are mechanically connected to one another. This text then examines the stereochemistry and the other physical and chemical properties related to the mechanical connections in these compounds. Other chapters consider the determination of the absolute configuration of catenanes by extension of the Cahn-Ingold-Prelog rules. This book discusses as well the bond that mechanically connects the catenated rings. The final chapter deals with the model studies of the synthesis of knots, double wound rotaxanes, and higher linear catenanes.

This book is a valuable resource for chemists, students, and research workers.

Inhalt
Preface

1. History


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2. Chemical Topology


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3. Nomenclature of Catenanes and Rotaxanes


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4. Stereochemistry of Catenanes, Rotaxanes, and Knots


4.1. Catenanes


4.2. Rotaxanes


4.3. Knots


5. Absolute Configuration


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6. Naturally Occurring Catananes


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[2]-Catenanes


7. Methods for the Synthesis of Catenanes and Ring Size Requirements


7.1. Statistical Methods


7.2. Directed Syntheses


7.3. Möbious Strips


8. Invistigations of the Statistical Syntheses of Catenanes


8.1. Scheme 1


8.2. Scheme 2


8.3. Scheme 3


8.4. Scheme 4


8.5. Scheme 5


9. Investigations of the Directed Syntheses of [2]-Catenanes


9.1. Triansa Compounds from 2,5-Diaminohydroquinone Polymethylene Ethers


9.2. Stereochemistry of Di- and Triansa Compounds


9.3. Investigations of the Cleavage of Triansa Compounds from 2,5-Diaminohydroquinone Polymethylene Ethers


9.4. Cleavable Diansa Compounds as Model Compounds and as Starting Materials for Catenanes and Rotaxanes


9.5. Diansa Compounds from 5-Aminobenzodioxoles Having Long-Chain -Substituted Alkyl Substrates


9.6. Precatenanes from the Cyclization of 5-Aminobenzodioxole Diansa Compounds Having -Substituted Long-Chain Alkyl Substrates


9.7. Synthesis of Precatenanes by the Attachment of Two Additional Bridges to a 3,5-Polymethylene Catechol


9.8. Catenanes from 5-Aminobenzodioxole Triansa Compounds


9.9. Diansa Compounds from 4,7-Dialkyl-5-amino-6-methoxybenzodioxoles


10. The Mass Spectrum of Catenanes


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[3]-Catenanes


11. Methods for Synthesis of [3]-Catenanes


11.1. Procedure 1


11.2. Procedure 2


12. Investigations of the Synthesis of [3]-Catenanes According to Procedure 1


12.1. Preliminary Investigations


12.2. Synthesis


13. Investigations of the Synthesis of [3]-Catenanes According to Procedure 2


13.1. Preliminary Investigations


[2]-Rotaxanes


14. Methods for the Synthesis of Rotaxanes


14.1. Statistical Methods


14.2. Directed Synthesis


15. Investigations of the Statistical Synthesis of Rotaxanes


15.1. Scheme 1


15.2. Scheme 2


16. Directed Synthesis of Rotaxanes


16.1. Synthesis of Molecular Subunits of Rotaxanes


Knots, Double Wound Catenanes and Rotaxanes, and Higher Linear Catenanes


17. Concepts of Synthesis


17.1. Concept for the Synthesis of a Knot


17.2. Concept for the Synthesis of Double Wound Catenanes and Rotaxanes


17.3. Concept for the Synthesis of Higher Linear Catenanes


18. Investigations of the Synthesis of Knots, Double Wound Catenanes and Rotaxanes, and Higher Linear Catenanes


18.1. Model Investigations


19. Tables of Compounds


Bibliography


Author Index


Subject Index

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