Dehydrobenzene and Cycloalkynes

IntroductionNomenclature and FormulaeGeneral ReferencesHistoryLiteratureChapter 1 Formation of Dehydrobenzene 1.1. Formation of Dehydrobenzene from Orthο-Anionized Benzene Derivatives 1.1.1. Halides as Leaving Groups 1.1.2. Other Anionic Leaving Groups in Ortho-Anionized Benzene Derivatives 1.1.3. Neutral Molecules as Leaving Groups from Ortho-Anionized Benzene Derivatives 1.2. Generation of Dehydrobenzene by Cleavage of Cyclic Systems 1.2.1. Cleavage of Heterocycles with Loss of Molecular Nitrogen 1.2.2. Further Attempts of Obtain Dehydrobenzene by Ring Cleavage 1.3. Generation of Dehydrobenzene by Photolytic Methods and by Free Radical Reactions LiteratureChapter 2 Polar Additions to Dehydrobenzene 2.1.1. Nucleophilic Additions of Anions and their Conjugate Acids to Dehydrobenzene 2.1.2. Order of Nucleophilicity Towards Dehydrobenzene 2.2. Addition of Nucleophiles to Unsymmetrically Substituted Dehydroaromatic Intermediates 2.2.1. The Isomer Ratio as a Function of the Substituent Present 2.2.2. The Isomer Ratio as a Function of the Attacking Nucleophile 2.3. Ring Closure Reactions Via Polar Addition to Dehydroaromatic Intermediates 2.4. Addition of Nucleophiles to Dehydrobenzene to Form Betaines and Ylides 2.4.1. Addition of Sulfides to Dehydrobenzene 2.4.2. Addition of Neutral Phosphorus Compounds to Dehydrobenzene 2.4.3. Addition of Tertiary Amines to Dehydrobenzene 2.4.4. The Reaction of Dehydrobenzene with Ethers and N-Oxides 2.4.5. Electrophilic Attack of Dehydrobenzene at Unsaturated Carbon Atoms 2.5. Addition of Electrophiles to Dehydrobenzene LiteratureChapter 3 Reactions of Dehydrobenzene with Nonpolar Partners 3.1. Reduction of Dehydrobenzene 3.2. Reaction of Dehydrobenzene with Carbon Hydrogen Bonds 3.2.1. "Insertion" Reactions 3.2.2. Ene Reactions 3.3. Cycloadditions Involving Dehydrobenzene 3.3.1. Cycloadditions Leading to Three-Membered Rings 3.3.2. Cycloadditions Leading to Four-Membered Rings 3.3.3. Cycloadditions Leading to Five-Membered Rings 3.3.4. Diels-Alder Additions 3.3.5. Further Cycloadditions LiteratureChapter 4 Radical Reactions of Dehydrobenzene LiteratureChapter 5 Structure and Reactivity of Dehydrobenzene 5.1. The Selectivity of Dehydrobenzene 5.2. The Structural Features of Dehydrobenzene 5.3. Existence of Dehydrobenzene in the Gas Phase 5.4. The Structure of Dehydrobenzene LiteratureChapter 6 Dehydroheterocyclic Intermediates 6.1. Generation of Dehydroheterocyclic Intermediates from Ortho-Anionized Halogeno Heterocycles 6.1.1. Reaction of Halogeno Heterocycles with Base 6.1.2. Other Routes to Ortho-Anionized Halogeno Heterocycles 6.1.3. Stability of the Ortho-Anionized Halogeno Heterocycles 6.2. Other Methods of Generating Dehydroheterocyclic Intermediates 6.3. Polar Additions to Dehydroheterocyclic Intermediates 6.3.1. Substituent Orientation after Polar Addition to Dehydroheterocyclic Intermediates 6.4. Cycloadditions to Dehydroheterocyclic Intermediates LiteratureChapter 7 Other Dehydroaromatic Intermediates 7.1. 1,3-Dehydroaromatic Intermediates 7.2. 1,4-Dehydroaromatic Intermediates 7.3. 1,2-Dehydroferrocene 7.4. 2,3-Dehydro-1,6-Methano-[10]annulene LiteratureChapter 8 Cycloalkynes 8.1. Generation of Cycloalkynes 8.1.1. Generation of Cycloalkynes from 1-Halogenocycloalkenes 8.1.2. Generation of Cycloalkynes from 1,2-Dihalogenocycloalkenes 8.1.3. Generation of Cycloalkynes by Rearrangement of Cycloalkylidenehalogenocarbanions 8.1.4. Generation of Cycloalkynes Via 1,2-Bis-Diazocycloalkanes 8.1.5. Further Methods of Generating Cycloalkynes 8.2. Polar Additions to Cycloalkynes 8.3. Cycloadditions to Cycloalkynes 8.3.1. Diels-Alder Additions to Cycloalkynes 8.3.2. 1,3-Dipolar Additions to Cycloalkynes 8.4. Isomerization and Oligomerization of Cycloalkynes 8.5. Reactivity of the Cycloalkynes LiteratureAuthor IndexSubject Index