1,4-Cycloaddition Reaction: The Diels-Alder Reaction in Heterocyclic Syntheses
The Diels-Alder Reaction in Heterocyclic Syntheses
- 1st Edition - November 12, 2012
- Latest edition
- Editor: Jan Hamer
- Language: English
Organic Chemistry, Volume 8: 1,4-Cycloaddition Reactions: The Diels-Alder Reaction in Heterocyclic Syntheses describes 1,4-cycloaddition reactions leading to the formation of five-… Read more
Organic Chemistry, Volume 8: 1,4-Cycloaddition Reactions: The Diels-Alder Reaction in Heterocyclic Syntheses describes 1,4-cycloaddition reactions leading to the formation of five- or six-membered heterocyclic compounds. Divided into 13 chapters, this book starts with an overview of various 1,4-cycloaddition reaction equations in the presence of at least one atom other than carbon. The following chapters describe the reaction mechanisms of five- or six-membered ring formed upon reaction with a dienophile, which contains an atom other than carbon. Considerable chapters are devoted to compounds used as dienophiles, including trivalent phosphorus, cyanogens and cyanogens-like compounds, imino, azo, carbonyl, thiocarbonyl, and diene compounds, as well as oxygen. Other chapters highlight some 1,4-cycloaddition reactions taking place through free radical intermediates. This book is of value to organic and research chemists, as well as undergraduate and graduate organic chemistry students.
List of Contributors
Preface
Chapter 1 Systems Capable of 1,4-Cycloaddition Reactions
I. Introduction
II. Five-membered Heterocyclic Systems
III. Six-membered Heterocyclic Systems
References
Chapter 2 Formation of Five-membered Cyclic Sulfones
I. Introduction
II. Survey of the Conjugated Diene-Sulfur Dioxide Cycloaddition Reaction
III. Thermal Dissociation of 2,5-Dihydrothiophene-1,1-dioxides
IV. Related Cycloaddition Reactions
References
Chapter 3 Trivalent Phosphorus Compounds as Dienophiles
I. Introduction
II. Reaction of Phosphonous Dihalides with Dienes
III. Reaction of Phosphorus Trihalides with Dienes
IV. Reaction of Halophosphites with Dienes
V. Related Diene-Phosphonous Dichloride Reactions
VI. 1,4-Additions Involving Carbonyl Compounds
Addendum
References
Chapter 4 Cyanogen and Cyanogen-like Compounds as Dienophiles
I. Introduction
II. Reaction Energetics
III. Experimental Techniques and Results
IV. Mechanism of Reaction
V. Summarizing Tables
References
Chapter 5 Imino Compounds as Dienophiles
I. Introduction
II. Imines and Schiff Bases
III. Immonium Salts
IV. Imino Compounds of the —C(X)=NH Type
V. Tables and Experimental Conditions
References
Chapter 6 Azo Compounds as Dienophiles
I. Introduction
II. Reactions with Acyclic Dienes
III. Reactions with Cyclic Dienes
IV. Reactions with Aromatic Compounds
V. Reactions with Miscellaneous Compounds
Appendix. Tabular Survey of the Diels-Alder Reaction Involving Azo Dienophiles
References
Chapter 7 Dienes Containing Two Nitrogen Atoms in the Conjugated System
I. Introduction
II. N=N—C=C Conjugated Systems
III. N=C—N=C Conjugated Systems
IV. C=N—N=C Conjugated Systems
V. N=C—C=N Conjugated Systems
VI. Heterocyclic Compounds
VII. Experimental Procedures
References
Chapter 8 Carbonyl and Thiocarbonyl Compounds as Dienophiles
I. Scope and Introduction
II. Carbonyl Compounds as Dienophiles
III. Thiocarbonyl Compounds as Dienophiles
Appendix
References
Chapter 9 α,ß-Unsaturated Carbonyl Compounds as Dienes
I. Dimerization Reactions
II. α,ß-Unsaturated Carbonyl Compounds as Dienes
Conclusions
References
Chapter 10 Oxygen as a Dienophile
I. General Aspects
II. Photosensitized Cycloaddition of Oxygen to Conjugated Diene Systems
III. Photochemical Cycloaddition of Oxygen to Aromatic Compounds
IV. Photochemical Cycloaddition of Oxygen to Aryl-substituted Carbo- and Heterocyclic Pentadienes
Appendix. Tabular Survey of Adducts of Aromatic Hydrocarbons
References
Chapter 11 Cycloadditions to o-Quinones, 1,2-Diketones, and Some of Their Derivatives
I. General Survey
II. Formation of 2,3-Dihydro-l,4-dioxins ("1,4-Dioxenes")
III. Formation of 1,3,2-Dioxathioles
IV. Formation of 1,3,2-Dioxaphospholes
V. Formation of 1,3-Dioxoles
VI. Formation of Oxazoles
VII. Formation of 1,4,5-Oxadiazepines
References
Chapter 12 Nitroso Compounds as Dienophiles
I. Introduction
II. The Formation of Oxazine Derivatives
III. Structure Proof of the Cycloaddition Products
IV. The Direction of the Cycloaddition Reaction
V. The Kinetics of the Cycloaddition Reaction
VI. Properties and Synthetic Use of the Cycloadducts
VII. Experimental Procedures
References
Chapter 13 N-Sulfinyl Compounds as Dienophiles
I. Introduction and Scope
II. 1,4-Cycloaddition Reactions of N-Sulfinyl Compounds
III. Orientation in the 1,4-Cycloaddition Reaction
IV. Properties of the Cycloadducts
V. Reactions of the Cycloadducts
VI. Experimental Procedures
References
Addendum
Author Index
Subject Index
- Edition: 1
- Latest edition
- Published: November 12, 2012
- Language: English
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