Catenanes, Rotaxanes, and Knots

Catenanes, Rotaxanes, and Knots

1st Edition - January 1, 1971

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  • Author: Gottfried Schill
  • eBook ISBN: 9781483275666

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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

  • Preface

    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

Product details

  • No. of pages: 204
  • Language: English
  • Copyright: © Academic Press 1971
  • Published: January 1, 1971
  • Imprint: Academic Press
  • eBook ISBN: 9781483275666

About the Author

Gottfried Schill

About the Editor

Alfred T. Blomquist

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