Alicyclic Compounds - 1st Edition - ISBN: 9780444814838, 9781483100913

Alicyclic Compounds

1st Edition

A Modern Comprehensive Treatise

Editors: Malcolm Sainsbury
eBook ISBN: 9781483100913
Imprint: Elsevier
Published Date: 23rd February 1994
Page Count: 666
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Rodd's Chemistry of Carbon Compounds, Volume II: Alicyclic Compounds focuses on alicyclic chemistry. The book first ponders on acyclic and monocyclic monoterpenoids, including artemisyl, santolinyl, chrysanthemyl, and other irregular systems; naturally occurring halogenated monoterpenoids; cyclobutanes; and tetramethylcyclohexanes. The text discusses the carotenoid group of natural products. Trends in carotenoid chemical research; improved methodology; optical isomerism including aliene isomerism; and geometrical isomerism are described. The book discusses cycloheptanes and cyclooctanes, large alicyclic ring systems, and polycarbonic compounds with separate ring systems and spiro compounds. The text describes polycyclic compounds and polycarbocyclic bridged ring compounds, and then discusses bicarbocyclic natural products. The Wagner-Meerwein rearrangement; camphor and related compounds; fenchone and related compounds; and carane, thujane, and pinane groups are also considered. The text is a valuable reference for readers interested in the study of carbon compounds.

Table of Contents

Alicyclic Compounds; Six- and Higher-Membered Monocarbocyclic Compounds (Partial)

Poiycarbocyclic Compounds excluding Steroids


List of Contributors


List of Common Abbreviations and Symbols Used

Chapter 6. Acyclic and Monocyclic Monoterpenoids

1. Introduction

2. Artemisyl, Santolinyl, Chrysanthemyl and Other Irregular Systems

3. 2,6-Dimethyloctanes

4. Naturally-Occurring Halogenated Monoterpenoids

5. Cyclobutanes

6. Cyclopentanes

7. Tetramethylcyclohexanes

8. Menthanes

(a) o-Menthanes

(b) m-Menthanes

(c) p-Menthanes

Chapter 7. The Carotenoid Group of Natural Products

1. Scope of Presentation

2. Relevant Literature Overviews

3. Trends in Carotenoid Chemical Research

4. Improved Methodology

(a) Isolation and Chromatography

(b) NMR-Spectroscopy

(c) Circular Dichroism

(d) Other Spectroscopic Techniques

5. Partial and Total Synthesis

6. New Structures

(a) Higher Carotenoids (C45, C50)

(b) Nor-Carotenoids

(c) Apo-Carotenoids (C<40)

(d) C30-Carotenoids (diapo)

(e) Sulfates

(f) Glycosides and Glycosyl Esters

(g) Epoxides and Oxabicycloheptanes

(h) In-Chain-Methyl Oxidized Carotenoids

(i) Alienes

(j) Acetylenes

(k) 7,8-Dihydrocarotenoids

(l) Other Carotenes and Xanthophylls

(m) Carotenoproteins

7. Optical Isomerism including Aliene Isomerism

8. Geometrical Isomerism

9. Artifacts

10. Interdisciplinary Fields

(a) Biosynthesis

(b) Chemosystematics

(c) Metabolism

(d) Functions

(e) Photochemistry and Photoprotection

(f) Vision

(g) Aquaculture

(h) Medical Applications

Chapter 8a. The Cycloheptanes and Cyclooctanes

1. Introduction

2. Preparation of Cycloheptanes and Cyclooctanes

(a) Ring Expansion Methods

(b) Cyclisation Reactions

(c) Functional Group Modification

3. Properties and Reactions

(a) Conformation and Structure

(b) Reactions

4. Biochemistry

Chapter 8b. Large Alicyclic Ring Systems

1. Introduction

2. Preparation of Macrocyclic Hydrocarbons

(a) Ring Expansion Methods

(b) Ring Contraction Methods

(c) Cyclisation Reactions

(d) Functional Group Modification

3. Properties and Reactions

(a) Conformation and Structure

(b) Transannular Reactions

(c) Complex Formation

4. Biochemistry

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

1. Introduction

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

(a) Polycyclopropanes and Polycyclopropenes

(b) Cyclopropylcyclobutanes and Cyclopropylbutenes

(c) Polycyclobutanes

(d) Polycyclopentanes and Polycyclopentenes

(e) Cyclopropylcyclopentanes and Cyclopropylcyclopentenes

(f) Cyclopropylcyclohexanes

(g) Cyclobutylcyclohexanes

(h) Cyclopentylcyclohexanes

(i) Polycyclohexanes and Polycyclohexenes

(j) Cyclopentylcycloheptanes and Cyclopentylcycloheptenes

(k) Cyclohexylcycloheptadienes

(l) Polycycloheptenes

(m) Miscellaneous Bicyclic Compounds

3. Spiro Compounds; Spiranes

(a) The Spiro[2,2]Pentane Group

(b) The Spiro[2,3]Hexane Group

(c) The Spiro[2,4]Heptane Group

(d) The Spiro[2,5]Octane Group

(e) The Spiro[2,6]Nonane Group

(f) The Spiro[3,3]Heptane Group

(g) The Spiro[3,4]Octane Group

(h) The Spiro[3,5]Nonane Group

(i) The Spiro[4,4]Nonane Group

(j) The Spiro[4,5]Decane Group

(k) The Spiro[5,5]Undecane Group

(l) Miscellaneous Groups

(m) Polyspiranes

Chapter 10. Polycyclic Compounds. Fused or Condensed Cyclic Systems

1. Bicyclo[n.1.O]Alkanes

(a) General Physical and Spectroscopic Properties

(b) General Chemical Reactions

2. Bicyclo[n.1.0]alk-2-enes

(a) Synthesis

3. The Bicyclo[1.1.0]Butane Group

(a) Synthesis

(b) Reactions

4. Bicyclo[2.1.0]Pentane

(a) General Properties

(b) Reactions

5. Bicyclo[3.1.0]Hexanes

(a) Synthesis

(b) Structure and Spectra

(c) Chemical Reactions

6. Bicyclo[4.1.0]Heptanes

(a) Synthesis

(b) Structure

(c) Reactions

7. Bicyclo[5.1.0]Octanes and Bicyclo[6.1.0]Nonanes

(a) Structure and Physical Properties

(b) Synthesis

(c) Reactions

8. Bicyclo[7.1.0]Decene

9. Bicyclo[10.1.0]Tridecane

10. Bicyclo[m.n.0]Alkanes

(a) Spectrometry, Spectroscopy and General Chemistry

11. Bicyclo[2.2.0]Hexanes and Bicyclo[3.2.0]Heptanes

(a) Structure

(b) Reactions

12. Bicyclo[2.2.0]Hexenes and Bicyclo[3.2.0]Heptenes

13. Bicyclo[4.2.0]Octanes and Bicyclo[5.2.0]Nonanes

14. Bicyclo[3.3.0]Octane (Hexahydropentalene)

15. Bicyclo[4.30]Nonane (Octahydro-1H-Indene), Bicyclo[5.3.0]Decane (Decahydroazulene), and Bicyclo[6.3.0]Undecane

16. Bicyclo[4.4.0]Decanes (Decalins)

(a) Structure and Stereochemistry

(b) Reactions


(a) Bicyclo[3.3.0]Octane Group

(b) Bicyclo[4.3.0]Nonanes, Bicyclo[4.4.0]Decanes, Bicyclo[3.1.0]Hexanes, and Bicyclo[4.1.0]Heptanes

Chapter 11. Poiycarbocyclic Bridged Ring Compounds

1. Introduction

2. General Methods of Synthesis

(a) Prom Simple Monocyclic and Nonbridged Polycyclic Compounds

(b) Elaboration of Bridged Bicyclic and Tricyclic Compounds into Higher Polycyclics

3. Strained Poiycarbocyclic Alkenes

(a) Syntheses of Anti-Bredt Systems

(b) Syntheses of Pyramidalized Alkenes

4. Special Topics

(a) Propellanes

(b) The Tricyclo[,7]Decane (Adamantane) Group

5. Acknowledgment

Chapter 12. Bicarbocyclic Natural Products

1. Introduction

2. The Thujane Group

(a) Hydrocarbons

(b) Alcohols

(c) Ketones

3. The Carane Group

(a) Hydrocarbons

(b) Alcohols and Epoxides

(c) Ketones

(d) Carboxylic Acids

(e) Halogeno and Cyano Derivatives

(f) Norcaranes and Norcarenes

4. The Wagner-Meerwein Rearrangement

5. The Pinane Group

(a) Hydrocarbons

(b) Epoxides, Alcohols, Aldehydes, Ketones, and Acids

(c) Halogeno, Amino, and Other Derivatives

6. Tricyclene

7. The Norbomane Group: Camphor and Related Compounds

(a) Camphene and Related Compounds

(b) Camphor, Epicamphor and Related Compounds

(c) Alcohols

(d) Bases of Bornane Series

8. The Norbomane Group: Fenchone and Related Compounds

(a) Ketones and Alcohols

(b) Hydrocarbons

Chapter 13. The Sesquiterpenoids

1. Introduction

2. Acyclic Compounds

3. Monocyclic Compounds

4. Bicyclo[4.4,0]Decanes

5. Bicyclo[4.3.0]Nonanes

6. Cyclopentyl Cyclohexanes

7. Spiro Compounds

8. Bicyclo[5.3.0]Decanes

9. Macrocyclic Compounds

10. Triquinanes

11. Other Polycyclic Systems

Chapter 14. Diterpenoids and Sesterterpenoids

1. Introduction

2. Acyclic and Related Diterpenoids

3. Bicyclic Diterpenoids

(a) Labdanes

(b) Clerodanes

4. Tricyclic Diterpenoids

5. Tetracyclic Diterpenoids

(a) Kaurenes

(b) Gibberellins

(c) Atiserenes, Beyerenes and Trachylobanes

(d) Aphidicolin and Stemaranes

6. Cembranes

7. Miscellaneous Diterpenoids

8. Sesterterpenoids

Chapter 15, Steroids

1. Introduction

2. Technical Steroid Synthesis

(a) Corticosteroid Synthesis

(b) Synthesis of 19-Norsteroids

3. Steroid Total Synthesis

(a) Intramolecular Diels-Alder Cycloadditions

(b) Intermolecular Diels-Alder Cycloadditions

(c) Asymmetric Cyclizations

(d) Free-Radical Cyclizations

(e) Cationic Cyclizations

4. Remote Functionalization of Non-Activated Positions in Steroids

5. The Brassinosteroids

(a) Introduction

(b) Synthesis of Brassinosteroids

6. Synthesis of Vitamin D and Analogues

(a) Introduction

(b) Partial Syntheses Starting with Cholesterol or Ergosterol

(c) Microbiological Route to 1α-Hydroxy Derivatives

(d) Introduction of the 1α-Hydroxyl Group in the Secotriene Stage

(e) Convergent Syntheses of Vitamin D and Analogues

7. Biosynthesis of the Steroids

Chapter 16. Glycosides, Saponins and Sapogenins

1. Isolation

(a) Structure Elucidation

(b) Mass Spectroscopy

(c) NMR Spectroscopy

(d) X-Ray Crystallography

2. Biological Activity

(a) Action on Metabolism

(b) Antitumour and Antileukemic Activity

(c) Antimicrobial Activity

(d) Mollusciddal Activity

(e) Miscellaneous

3. Biogenesis

4. Steroid Saponins and Sapogenins

(a) Saponins

(b) Sapogenins

(c) References

(d) Nomenclature and Configuration

(e) Triterpenoid Saponins and Sapogenins

(f) Synthesis

(g) Production of Saponins by Cell Culture

Chapter 17. Triterpenoids

1. The Squalene Group

2. The Lanostane Group

3. The Dammarane Group

4. The Baccharane/Shionane Group

5. The Lupane Group

6. The Oleanane Group

7. The Ursane Group

8. The Hopane Group

9. The Stictane Group

10. Miscellaneous

Guide to the Index



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© Elsevier 1994
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About the Editor

Malcolm Sainsbury

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