Alicyclic Compounds

Alicyclic Compounds

A Modern Comprehensive Treatise

2nd Edition - January 1, 1974

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  • Editor: M. F. Ansell
  • eBook ISBN: 9781483221304

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Supplements to the Second Edition of Rodd’s Chemistry of Carbon Compounds, Volume II: Alicyclic Compounds: Part C: Polycarbocyclic Compounds, Excluding Steroids covers the classification, natural products, and biogenesis of polycarbocyclic compounds. This book is divided into 11 chapters. Considerable chapters are devoted to the classification and nomenclature of polycarbocyclic compounds, including bicyclic monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpenoids, and triterpenoids. Other chapters deal with the classification and nomenclature of selective steroids, such as steroids, bile acids, sex hormones, saponins, and sapogenins. The concluding chapter highlights the biogenesis of terpenes and sterols. This book is an ideal source for organic chemists and researchers.

Table of Contents

  • Preface

    Official Publications; Scientific Journals and Periodicals

    List of Common Abbreviations and Symbols Used

    Chapter 9. Polycarbocyclic Compounds with Separate Ring-Systems, and Spiro Compounds

    1. Introduction

    2. Compounds with Rings Joined Directly or through a Carbon Chain

    3. Spiro Compounds; Spirans

    a. Preparative Methods

    b. Properties

    Chapter 10. Polycyclic Compounds. Fused or Condensed Cyclic Systems

    1. The Bicyclo[1.1.0]Butane Group

    2. The Bicyclo[2.1.0]Pentane Group

    3. The Bicyclo[3.1.0]Hexane Group

    4. The Bicyclo[4.1.0]Heptane Group

    5. The Bicyclo[5.1.0]Octane Group

    6. The Bicyclo[6.1.0]Nonane Group

    7. The Bicyclo[2.2.0]Hexane Group

    8. The Bicyclo[3.2.0]Heptane Group

    9. The Bicyclo[4.2.0]Octane Group

    10. The Bicyclo[6.2.0]Decane Group

    11. The Bicyclo[3.3.0]Octane Group

    12. The Bicyclo[4.3.0]Nonane Group

    13. The Bicyclo[4.4.0]Decane Group

    14. Highly Condensed Systems

    Chapter 11. Polycarbocyclic Bridged Ring Compounds

    1. Introduction

    a. General Methods of Synthesis

    b. Bredt's Rule

    c. Bridged Carbonium Ions

    d. Molecular Orbital Theory

    e. Nuclear Magnetic Resonance Spectroscopy (n.m.r.)

    f. Fluxional Molecules

    2. The Bicyclo[1.1.1]Pentane Group

    3. The Bicyclo[2.1.1]Hexane Group


    4. The Bicycloheptane Group

    a. The Bicyclo[3.1.1]Heptane Group

    b. The Bicyclo[2.2.1]Heptane Group

    5. Polycyclic Compounds Derived from Cyclopentadiene

    a. Oligomerisation Products of Cyclopentadiene

    6. The Bi- and Tri-Cyclooctane Group

    Mechanism and Structure

    a. The Bicyclo[2.2.2]Octane Group

    b. The Bicyclo[3.2.1]Octane Group

    c. The Tricyclo[,8]Octane Group

    7. The Polycyclo[3.3.1]Nonane Group

    a. The Bicyclo[3.3.1]Nonane Group

    b. The Tricyclo[,8]Nonane Group

    c. The Tricyclo[,7]Nonane Group

    d. The Tetracyclo[,8.04,6]Nonane, Triasterane, Group

    8. The Bicyclo[3.2.2]Nonane Group


    9. The Bicyclo[4.2.1]Nonane Group


    10. The Bicyclo[4.2.2]Decane Group

    Mechanism and Structure


    11. The Tricyclodecane Group

    a. The Tricyclo[,8]Decane Group

    b. The Tricyclo[,7]Decane, Adamantane, Group

    12. The Bicyclo[3.3.3]Undecane Group

    Chapter 12. Bicyclic Monoterpenoids

    1. Introduction

    2. The Thujane Group

    3. The Carane Group

    4. The Pinane Group

    5. The Norbornane Group

    a. Camphene and Related Compounds

    b. Bornane (Camphane) Derivatives

    c. Fenchane Derivatives

    Chapter 13. The Sesquiterpenoids

    1. Introduction

    2. Acyclic Types

    (i) Hydrocarbons

    (ii) Oxygenated Derivatives

    3. Monocyclic Types

    4. Cyclopentylcyclohexanes

    (i) Hydrocarbons

    (ii) Oxygenated Derivatives

    5. Bicyclo[4.1.0]Heptanes

    (i) Hydrocarbons

    (ii) Oxygenated Derivatives

    6. Bicyclo[4.4.0]Decanes

    (i) Hydrocarbons

    (ii) Oxygenated Derivatives

    7. Bicyclo[4.3.0]Nonanes

    8. Bicyclo[5.3.0]Decanes

    (i) Hydrocarbons

    (ii) Oxygenated Derivatives

    9. Spiro Compounds

    (i) Hydrocarbons

    (ii) Oxygenated Derivatives

    10. Polycyclic Systems

    (i) Hydrocarbons

    (ii) Oxygenated Derivatives

    11. Macrocyclic Sesquiterpenes

    (i) Hydrocarbons

    (ii) Oxygenated Derivatives

    Chapter 14. Diterpenoids, Sesterterpenoids and Triterpenoids

    1. Introduction

    2. Diterpenoids

    a. Bicyclic Diterpenoids

    b. Tricyclic Diterpenoids

    c. Tetracyclic Diterpenoids

    d. The Cembrane Group

    e. Eremolactone

    3. Sesterterpenoids

    4. Triterpenoids

    (a) The Fusidanes

    (b) Group A

    (c) Group B

    5. Laboratory Synthesis

    a. Diterpenoids

    b. Triterpenoids

    Chapter 15. Steroids: Sterols and Bile Acids

    1. Introduction

    2. Geometry of the Steroid Nucleus

    3. Structure in Relation to Physical Properties

    4. Principal Chemical Reactions

    (i) Color Reactions

    (ii) The 3,5-Cyclosteroid Rearrangement and Related Reactions

    (iii) Backbone Rearrangements and Related Reactions

    (iv) Side-Chain Oxidation

    (v) Epoxidation of Δ5-Stenols and Related Compounds

    (vi) Reactions of 7-Dehydrosterols

    (vii) Stanols

    (viii) Stanones

    (ix) Remote Oxidation

    5. individual Sterols and Related Compounds

    a. The Cholesterol Series

    b. Ergosterol and Related Compounds

    c. Other Sterols

    d. Miscellaneous Structural Type

    6. Bile Acids


    Chapter 16. Steroids: Sex Hormones; Adrenocortical Hormones

    1. Sex Hormones and Related Compounds

    a. Oestrogens

    b. The Gestogens

    c. The Androgens

    d. Homosteroids

    e. Synthesis of Adrenocortical Steroids

    2. Adrenocortical Hormones

    d. Aldosterone

    3. Cyclosteroids

    4. Dimeric Steroid Hormones

    5. Halogenated Steroids

    a. Oestrogens

    b. Androgens

    c. Gestogens

    6. Other Substituted Steroids

    b. Pregnane Series

    Chapter 17. Steroids: Cardiotonic Glycosides and Aglycons; Toad Poisons

    Digoxin Derivatives

    Digitoxigenin and Derivatives

    Canarigenin (Δ4-Analogue of Digitoxigenin)

    Uzarigenin and Related Compounds

    Digitalis Glycosides and Aglycons


    Toad Poisons, etc

    Chapter 18. Steroid Saponins and Sapogenins

    1. The Saponins

    2. The Sapogenins

    Sources and Isolation


    Physical Properties

    New Sapogenins


    Reactions of the Sapogenin Side-Chain

    Chapter 19. Biogenesis of Terpenes and Sterols

    1. Introduction

    2. Biosynthesis of Mevalonate (MVA)

    3. Hemiterpenes

    4. Monoterpenes

    5. Sesquiterpenes

    6. Diterpenes

    8. Triterpenes

    (i) General

    (ii) Demethylation Reactions

    (iii) Alkylation at C(24)

    (iv) Insertion of Double Bonds

    (v) Spirostanols

    (vi) Cardenolides

    (vii) Bufatenolides

    (viii) Ecdysones

    9. The Tetraterpenoids: the Carotenoids

    (i) Prephytoene

    (ii) Desaturation of Phytoene

    (iii) Cyclisation of Lycopene

    (iv) Xanthophyll Formation

    (v) C45 and C50 Carotenoids

    (vi) Biosynthesis in Photosynthetic Bacteria

    10. Terpenoid Quinones


Product details

  • No. of pages: 336
  • Language: English
  • Copyright: © Elsevier 1974
  • Published: January 1, 1974
  • Imprint: Elsevier
  • eBook ISBN: 9781483221304

About the Editor

M. F. Ansell

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