Alicyclic compounds

Author(s)

• Bolton, R. (Roger)

Bibliographic Information

Alicyclic compounds

（Second supplements to the 2nd edition of Rodd's chemistry of carbon compounds : a modern comprehensive treatise / edited by Malcolm Sainsbury, v. 2）

Elsevier, 1992-1994

• pt. A and B
• pt. B,C,D and E

Note

pt. A and B, contributors, R. Bolton ... [et al.]

Includes bibliographical references and indexes

Contents of Works

• pt. A. Monocarbocyclic compounds to and including five ring atoms
• pt. B. Six- and higher-membered monocarbocyclic compounds
• pt. C. Polycarbocyclic compounds excluding steroids
• pt. D and E. Steroids

Description and Table of Contents

Volume

pt. B,C,D and E ISBN 9780444814838

Description

The theme of this volume is alicyclic chemistry, which is a very broad area embracing nature products such as terpenes, steroids and carotenoids and an array of synthetic compounds, including both medium size and large ring monocycles and polycycles. Much of this supplement deals with the chemistry of terpenoids, a subject which has received considerable interest following the discovery of many new structural types with wide-ranging biological activities.

Table of Contents

• Part 1 Acyclic and monocyclic monoterpenoids, D.H. Grayson: artemisyl, santolinyl, chrysanthemyl and other irregular systems
• 2,6-dimethyloctanes
• naturally-occurring halogenated monoterpenoids
• cyclobutanes
• cyclopentanes
• tetramethylcyclohexanes
• menthanes. Part 2 The carotenoid group of natural products, S. Liaaen-Jensen: relevant literature overviews
• trends in carotenoid chemical research
• improved methodology
• partial and total synthesis
• new structures
• optical isomerism including allene isomerism
• geometrical isomerism
• artifacts
• interdisciplinary fields. Part 3 The cycloheptanes and cyclooctanes, D.F. Ewing: preparation of cycloheptanes and cyclooctanes
• properties and reactions
• biochemistry. Part 4 Large alicyclic ring systems, D.F. Ewing: preparation of macrocyclic hydrocarbons
• properties and reactions biochemistry. Part 5 Polycarbocyclic compounds with separate ring systems, and spiro compounds, M. Wills: compounds with rings joined directly or through a carbon chain
• spiro compounds
• spiranes. Part 6 Polycyclic compounds, fused or condensed cyclic systems, M. Sainsbury: bicyclo[n.1.0]alkanes
• bicyclo[n.1.0]alk-2-enes
• the bicyclo[1.1.0]butane group
• bicyclo[2.1.0]pentane
• bicyclo[3.1.0]hexanes
• bicyclo[4.1.0]heptanes
• bicyclo[5.1.0]octanes and bicyclo[6.1.0]nonanes
• bicyclo[7.1.0]decene
• bicyclo[10.1.0]tridecane
• bicyclo[m.n.0]alkanes
• bicyclo[2.2.0]]hexanes and bicyclo[3.2.0]heptanes
• bicyclo[2.2.0]hexenes and bicyclo[3.2.0]heptenes
• bicyclo[4.2.0]octanes and bicyclo[5.2.0]nonanes
• bicyclo[3.3.0]octane (hexahydropentalene)
• bicyclo[4.3.0]nonane (octahydro-1H-indene), bicyclo[5.3.0]decane
• bicyclo[4.4.0]decanes (decalins). Part 7 Polycarbocyclic bridged ring compounds, A.P. Marchand: general methods of synthesis
• strained polycarbocyclic alkenes
• special topics. Part 8 Bicarbocyclic natural products, R. Livingstone: the thujane group
• the carane group
• the Wagner-Meerwein rearrangement
• the pinane group
• tricyclene
• the norbornane group - camphor and related compounds, fenchone and related compounds. Part 9 The sesquiterpenoids, A.T. Hewson: acyclic compounds
• monocyclic compounds
• bicyclo[4.4.0]decanes
• bicyclo[4.3.0]nonanes
• cyclopentyl cyclohexanes
• spiro compounds
• bicyclo[5.3.0]decanes
• macrocyclic compounds
• triquinanes
• other polycyclic systems. Part 10 Diterpenoids and sesterterpenoids, J.R. Hanson: acyclic and related diterpenoids
• bicyclic diterpenoids
• tricyclic diterpenoids
• tetracyclic diterpenoids
• cembranes
• miscellaneous diterpenoids
• sesterterpenoids. Part 11 Steroids, F.J. Zeelan: technical steroid synthesis
• steroid total synthesis
• remote functionalization of non-activated positions in steroids
• the brassinosteroids
• synthesis of vitamin D and analogues
• biosynthesis of the steroids. (Part Contents).

Volume

pt. A and B ISBN 9780444898449

Description

Rodd's Chemistry of Carbon Compounds, Volume II: Alicyclic Compounds surveys advances in the chemistry of three- to six-membered monocarbocycles from 1973 to 1991. This book begins with a detailed review of the conformations and stereochemical analyses of alicycles, including higher members of the series, and then proceeds to deal with the chemistry of individual ring systems. The next chapters cover the prostaglandins and their allies and natural products bearing a cyclohexane, cyclohexene, or cyclohexadiene ring system. A review of the chemistry of the cyclohexadienes and their metallic complexes is provided at the end. This text also includes a list of common abbreviations and symbols. This volume benefits chemical engineering students, particularly those studying the components of organic chemicals.

Table of Contents

• Preface List of Common Abbreviations and Symbols Used Chapter 1. Alicyclic Hydrocarbons, Conformation and Stereochemistry 1. Introduction 2. Three-Membered Rings (a) Cyclopropanes with Unsaturated Substituents (b) Cyclopropanes with Saturated Substituents 3. Four-Membered Rings (a) Cyclobutanes (b) Monosubstituted Cyclobutanes (c) Disubstituted Cyclobutanes (d) Unsaturated Four-Membered Ring Carbocycles (e) Cyclobutanones 4. Five-Membered Rings (a) Cyclopentane (b) Cyclopentene (c) Cyclopentanone 5. Six-Membered Rings (a) Cyclohexane (b) Monosubstituted Cyclohexanes (c) 1,1-Disubstituted Cyclohexanes (d) 1,2-Disubstituted Cyclohexanes (e) 1,1,2-Trisubstituted Cyclohexanes (f) 1,3- and 1,3,5-Substituted Cyclohexanes (g) 1,4-Disubstituted Cyclohexanes (h) Sterically Crowded Cyclohexanes (i) Cyclohexene (j) 1,3-Cyclohexadiene (k) 1,4-Cyclohexadienes (l) Exomethylenecyclohexane (m)Cyclohexanones, Cyclohexanediones and Cyclohexenones 6. Seven-Membered Rings (a) Cycloheptanes (b) Cycloheptanones (c) Cycloheptene and Cycloheptene Oxide (d) Cyeloheptadienes and Cycloheptatrienes 7. Eight-Membered Rings (a) Cyclooctanes (b) Cyclooctanones (c) Cyclooctene, Cyclooctyne and 1,2-Cyclooctadiene (d) 1,3-, 1,4- and 1,5-Cyclooctadienes (e) Cyclooctatrienes 8. Nine-Membered Rings (a) Cyclononane, Cyclononanone and Cyclononyne (b) 1,2-Cyclononadiene and 1,5-Cyclononadiene (c) Cyclononatrienes 9. Ten-Membered Rings 10. Ring Systems Larger than Ten-Membered Chapter 2. The Cyclopropanes 1. Introduction 2. Preparation of Cyclopropanes (a) Intramolecular Nucleophilic Substitution (b) Simmons-Smith Reaction (c) Reaction of Alkenes with Diazo Compounds (d) Reaction of Alkenes with Dihalocarbenes and Other Carbenoids (e) Ring Contraction of Cyclobutanes (F) Reactions of Electron Deficient Carbon-Carbon Double Bonds with Phosphoranes, Sulfuranes and Arsenic Ylides (G) Photochemical Reaction (H) Radical Mediated Reaction (I) Organometallic Reaction (J) Miscellaneous Reaction 3. Use of Cyclopropanes in Organic Synthesis (a) Thermal Ring Fission (b) Reductive and Oxidative Ring Fission (c) Electrophilic and Nucleophilic Ring Fission (d) Radical Mediated Ring Fission (e) Metal Salt Mediated Ring Fission Chapter 3. The Cyclobutanes 1. Introduction, Structure, Properties, and Theoretical Considerations 2. Synthesis of the Cyclobutane Ring System (a) [2+2] Cycloaddition Reactions (b) Intramolecular Cyclisations (c) Ring Expansion Reactions (d) Ring Contractions 3. Reactions of Cyclobutanes (a) Solvolyses and Rearrangements of Cyclobutanes and Cyclobutenes (b) Electrocyclic Ring Opening-Ring Closing Reactions (c) Miscellaneous Reactions of Cyclobutanes and Cyclobutenes (d) Reactions of Cyclobutanols, Cyclobutanones and Cyclobutenones (e) Reactions of Cyclobutenenitriles (F) Reactions of Squaric and Semisquaric Acids Chapter 4a. The Cyclopentanes 1. Reviews, Theoretical and Structural Aspects, General Properties 2. Synthesis (a) Cyclisation Reactions Leading to Cyclopentanes, Cyclopentenes
• General Cyclopentane Ring Synthesis (b) Cyclopentanes and Cyclopentenes by Cycloaddition Reactions (c) Cyclopentanes and Cyclopentenes by Ring Expansion and Ring Contraction Processes (d) Cyclopentanones and Cyclopentenones by Cyclisation Processes (e) Cyclopentanones and Cyclopentenones by Cycloaddition Reactions (F) Cyclopentanones and Cyclopentenones by Ring Expansion and Ring Contraction Reactions (G) Cyclopentanones and Cyclopentenones by Rearrangements and by Miscellaneous Reactions 3. Reactions (a) Cyclopentanes, Cyclopentenes, and Simple Derivatives (b) Cyclopentanones, Cyclopentenones, and Derivatives Chapter 4b. Natural Products Containing the Cyclopentane Sub-Unit: Prostaglandins 1. Introduction 2. Structure and Nomenclature 3. Prostaglandin Biosynthesis (a) Mammalian Biosynthesis (b) Non-Mammalian Biosynthesis 4. Prostaglandin Total Synthesis (a) Corey's Bicyclic Lactone Approach (b) Approaches via Polycyclic Intermediates (c) Conjugate Addition and Three Component Coupling Approaches (d) Recent Synthetic Approaches to PGs (e) PG Metabolism and Analogue Synthesis (F) Synthesis of Non-mammalian Prostanoids 5. Bibliography (a) General and Biological (b) Synthetic Chapter 4c. Cyclopentadiene 1. Introduction 2. Preparation of s-Bonded Cyclopentadiene Derivatives (a) Deuteriated Cyclopentadiene (b) Alkyl Substituents (c) Cyano, Carbonyl, Carboxyl and Trifluoromethyl Substituents (d) Phosphine Substituents (e) Other Substituents 3. Ionic Metal Derivatives 4. Fluxionality of Cyclopentadienyl Derivatives 5. Metal Complexes - Structure and Reactions (a) The Cyclopentadienyl Ligand (b) Monoligating Cyclopentadienyl Complexes (c) Bridged Biscyclopentadiene Complexes (d) Bifunctional Cyclopentadienyl Ligands 6. Metal Complexes - Applications 7. Reactions of Cyclopentadiene Chapter 5a. Cyclohexane and Its Derivatives Introduction 1. Cyclohexane (a) Synthesis 2. Halogenocyclohexanes (a) Fluorocyclohexane and Derivatives (b) Chlorocyclohexane (c) Bromocyclohexane (d) Halogenocyclohexanes through Addition to Benzene Rings 3. Cyclohexadienyl Intermediates (a) Cyclohexadienyl Radical (b) Muonium Attack (c) Cyclohexadienylium Ion 4. Cyclohexanol and Cyclohexanone (a) Synthesis 5. Cyclohexadienones and Derivatives (a) Identification and Preparation 6. Cyclohexanamine (Cyclohexylamine) Chapter 5b. Natural Products Containing a Cyclohexane, Cyclohexene, or Cyclohexadiene Subunit 1. Simple Examples (a) Nonfunctionalized (b) Functionalized 2. Nonfunctionalized or Unusual Terpenoids (a) Mono Terpenoids (b) Nonfunctionalized Sesquiterpenes (c) Norsesquiterpenes (d) Furanoterpenes (e) Oxygenated Norterpenoids (F) Rearranged or Unusual Terpenoids 3. C13 Norterpenoids 4. Flavonoid, Chalcone, and Coumarin Types 5. Shikimic Acid Pathway (a) Mechanistic Aspects (b) Synthesis (c) Natural Occurrence 6. Cyclitols (a) Natural Occurrence (b) Synthesis (c) Cyclitol Epoxides 7. Inositols (a) Natural Occurrence (b) Synthesis 8. Pseudosugars (a) Natural Occurrence (b) Synthesis 9. Aminocyclitols (a) Natural Occurrence (b) Synthesis 10. Benzoquinones 11. Quinols 12. Halogenated Tyrosine Metabolites 13. Concluding Remarks Chapter 5c. Cyclohexadienes 1. Introduction 2. Preparation of Cyclohexadienes (a) Metal-Ammonia (Birch) Reduction of Aromatic Compounds (b) Microbial Oxidation of Aromatic Compounds (c) Cyclohexadienes from Cyclohexenones 3. Reactions of Cyclohexadienes (a) Conjugation of 1,4-Cyclohexadienes (b) Cycloaddition Reactions (c) Palladium-Catalyzed 1,4-Difunctionalization 4. Metal Complexes of Cyclohexadienes (a) Cyclohexadiene-Fe(CO)2L Complexes (b) Cyclohexadiene-CoCp Complexes and the Derived Cyclohexadienyl-CoCp Cations (c) Cyclohexadiene-Mo(CO)2Cp and Related Complexes Guide to the Index Index

by "Nielsen BookData"

Details

• NCID: BA19288189
• ISBN:
  • 0444898441
  • 0444814833
• LCCN: 91016129
• Country Code: ne
• Title Language Code: eng
• Text Language Code: eng
• Place of Publication: Amsterdam ; Tokyo
• Pages/Volumes: 2 v.
• Size: 24 cm
• Parent Bibliography ID:
  • BA12826216