Alicyclic Compounds
Monocarbocyclic Compounds to and Including Five Ring Atoms, Six- and Higher-Membered Monocarbocyclic Compounds (Partial: Chapter 5 in This Volume)
- 2nd Edition - June 24, 2016
- Imprint: Elsevier
- Editor: Malcolm Sainsbury
- Language: English
- Paperback ISBN:9 7 8 - 1 - 4 8 3 1 - 1 2 1 8 - 3
- eBook ISBN:9 7 8 - 1 - 4 8 3 1 - 4 4 6 0 - 3
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… Read more
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Request a sales quoteRodd'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.
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 σ-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
- Edition: 2
- Published: June 24, 2016
- Imprint: Elsevier
- Language: English
- Paperback ISBN: 9781483112183
- eBook ISBN: 9781483144603