Catenanes, Rotaxanes, and Knots - 1st Edition - ISBN: 9780126254501, 9781483275666

Catenanes, Rotaxanes, and Knots

1st Edition

Authors: Gottfried Schill
Editors: Alfred T. Blomquist
eBook ISBN: 9781483275666
Imprint: Academic Press
Published Date: 1st January 1971
Page Count: 204
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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.

Table of Contents


1. History


2. Chemical Topology


3. Nomenclature of Catenanes and Rotaxanes


4. Stereochemistry of Catenanes, Rotaxanes, and Knots

4.1. Catenanes

4.2. Rotaxanes

4.3. Knots

5. Absolute Configuration


6. Naturally Occurring Catananes



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 ω-Substituted Alkyl Substrates

9.6. Precatenanes from the Cyclization of 5-Aminobenzodioxole Diansa Compounds Having ω-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



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


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


Author Index

Subject Index


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© Academic Press 1971
Academic Press
eBook ISBN:

About the Author

Gottfried Schill

About the Editor

Alfred T. Blomquist

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