Synthetic organic photochemistry

edited by William M. Horspool

[目次]

  • 1. Photoaddition and Photocyclization Processes of Aromatic Compounds.- 1. Introduction.- 2. Intermolecular Reactions.- 2.1. Arenes and Ethenes.- 2.2. Arenes and Acetylenes.- 2.3. Arenes and 1,3-Dienes.- 2.4. Acyclic Additions to Arenes and Reduction Processes.- 2.5. Arene Photodimerizations.- 3. Intramolecular Cyclization Processes.- 3.1. Arene-Ethene and Arene-Ethyne Systems.- 3.1.1. Hydrocarbon Systems.- 3.1.2. Aryl Enones.- 3.1.3. Aryl Ethenyl Ethers, Thioethers, and N- Aryl Enamines.- 3.1.4. Cyclizations of N-Arylanilides and N-Benzoylenamines.- 3.2. Aryl Butadiene and Butenyne Systems.- 3.3. Intramolecular Photocoupling of Arenes.- 3.3.1. Stilbene-Phenanthrene-Type Cyclizations.- 3.3.2. Photocoupling of Arenes with Intervening Units Other Than Ethylene.- 3.3.3. Coupling of Arenes as a Result of Halogen Acid Photoelimination.- 3.4. Photocyclizations of o-Substituted Arenes.- References.- 2. Enone Photochemical Cycloaddition in Organic Synthesis.- 1. Introduction.- 2. The Reaction Mechanism.- 3. Regiochemistry of Enone Cycloaddition.- 4. Stereochemistry of Enone Cycloaddition.- 5. Intramolecular Enone Cycloadditions.- 6. The de Mayo Reaction.- 6.1. Cyclic Diketones.- 6.2. Acyclic 1,3-Diketones.- 6.3. Intramolecular Additions of Enolized Diketones.- 7. Intermolecular Enone Cycloaddition.- 8. Photochemical Cycloaddition between Enones and Allenes.- References.- 3. Synthetic Aspects of Photochemical Electron Transfer Reactions.- 1. Introduction.- 1.1. Synthetic Applications of Photochemical Reactions.- 1.2. Electron Transfer in Excited-State Chemistry.- 1.2.1. Exciplex Formation and Decay.- 1.2.2. Electron Transfer Efficiencies and Rates.- 1.3. Chemical Consequence of Electron Transfer.- 1.3.1. General Survey and Predictions.- 1.3.2. Overview of Coverage.- 2. Reaction Pathways Followed in Electron Transfer Photochemistry.- 2.1. Alkenes and Strained Ring Hydrocarbons.- 2.1.1. Alkenes as Electron Acceptors and Donors.- 2.1.2. Cyclopropene Electron Transfer Photochemistry.- 2.1.3. Cyclopropanes and Other Strained Ring Systems as Electron Donors.- 2.2. Amines.- 2.2.1. General Considerations.- 2.2.2. Amine-Olefin Electron Transfer Photochemistry.- 2.2.3. Amine-Ketone Electron Transfer Photochemistry.- 2.3. Ketones.- 2.3.1. General Considerations.- 2.3.2. Ketone Electron Transfer Photochemistry.- 2.3.3. Quinone Electron Transfer Photochemistry.- 2.4. Electron Transfer Photooxygenations.- 2.4.1. General Considerations.- 2.4.2. Class 1 Photooxygenations.- 2.4.3. Class 2 Photooxygenations.- 2.4.4. Class 3 Photooxygenations.- 2.5. Aromatic Systems.- 2.5.1. Aromatic Photosubstitution Reactions.- 2.5.2. Photobenzylations by Electron Transfer Mechanisms.- 2.5.3. Birch and Related Photoreductions of Aromatic Compounds.- 2.6. Electron Transfer Photochemistry of Nitrogen Heteroaromatic Salts and Related Systems.- 2.6.1. General Considerations.- 2.6.2. Electron Transfer Photochemistry of Pyridinium and Related Salts.- 2.6.3. Iminium Salt Photochemistry.- 2.7. Other Electron Transfer Initiated Photoreactions.- 2.7.1. Olefin Cycloadditions and Retro Processes.- 2.7.2. Phthalimide Photochemistry.- 2.7.3. Photodecarboxylations.- 2.7.4. Metal Catalyzed Photoreactions.- References.- 4. Phthalimide and Its Derivatives.- 1. Introduction.- 2. Hydrogen Abstraction.- 2.1. Photoreduction and Photoaddition.- 2.2. Intramolecular Photocyclization.- 3. Reaction with Alkenes.- 3.1. Ring Expansion.- 3.2. Solvent Incorporation.- 3.3. Intramolecular Reaction.- 4. Cleavage Reactions.- 4.1. ?-Cleavage.- 4.2. ?-Cleavage.- 5. Spectra and Excited States.- 6. Summary.- References.- 5. Photochemical Addition Reactions in the Benzo(b)Thiophene, Benzo(b)Furan, and Indole Series.- 1. Introduction.- 1.1. Absorption and Emission Characteristics.- 2. Photochemistry.- 2.1. Oxetan Formation.- 2.2. Dimerization.- 2.3. Photochemical Reactions with Acetylene Esters.- 3. Benzo(b)thiophene.- 4. Indoles.- 5. Benzo(b)thiophenes.- 6. Benzo(b)furans.- 7. Thermal Reactions of the 2-Hetero-bicyclo(3.2.0)heptadienes.- 8. 1,3-Dimethylindole.- 9. Photocycloadditions of Benzo(b)thiophene to Alkenes.- References.- 6. Azirine Photolysis and Cycloaddition Reactions.- 1. Introduction.- 1.1. UV Spectra of Arylazirines.- 1.1.1. Evidence for Nitrile Ylide Formation.- 2. Cycloaddition Reactions.- 2.1. Addition with Electron-Deficient Olefins.- 2.1.1. Mechanism of Cycloaddition to Olefines.- 2.2. Addition to Aldehydes and Ketones.- 2.3. Addition to Esters.- 2.4. Additions to Acid Chloride and Anhydrides.- 2.5. Additions to Carbon Dioxide and Carbon Disulfide.- 2.6. Additions to Ketenes, Carbodiimides, Isocyanates, and Isothiocyanates.- 3. Photodimerization of Azirines.- 4. Intramolecular Cycloaddition Reactions.- 4.1. Rearrangement of 2-Vinylazirines.- 4.2. Rearrangements of Isoxazoles and Oxazoles.- 5. Mechanisms for Cycloaddition Reactions of Nitrile Ylides.- 5.1. The 1,1-Cycloaddition Process.- 5.2. Summary of 1,1-Cycloaddition Mode.- 5.3. Other Examples of 1,1-Cycloaddition.- 5.4. 1,1- and 1,3-Cycloaddition in Competition.- 6. Fragmentation Reactions.- 6.1. Competitive Involvement of Ylide Formation.- 7. Group Migration Reactions.- References.- 7. Photoremovable Protecting Groups.- 1. Introduction.- 2. Alcohols.- 2.1. Sulfonic Acid Esters.- 2.2. o-Nitrobenzyl Ethers.- 2.3. Nitrates, Nitrites, Dimelhylthiocarbamates, and Aryl Azides.- 3. Diols.- 4. Phenols.- 5. Aldehydes and Ketones.- 6. Carboxylic Acids and Amides.- 6.1. o-Nitrobenzyl Esters.- 6.2. o-Nitrophenylamino Derivatives.- 6.3. Phenacyl Esters.- 6.4. 2,4-Dinitrophenylthio Esters, Benzoin Esters, and Aryl Azides.- 7. Amines.- 7.1. Benzyloxycarbonyl Compounds.- 7.2. Sulfonamides.- 7.3. Formamides, N-Oxides, and 4,5-Diaryl-4-oxazoline-2-ones.- 8. Phosphates.- 9. Conclusion.- References.- 8. Photochemical Synthesis of Oxetans.- 1. Introduction.- 2. Reaction Mechanism.- 2.1. Carbonyl Excited States.- 2.2. Triplet Energies.- 2.3. Competing Reactions.- 2.4. Hydrogen Abstraction.- 3. Alkene Addends.- 3.1. Simply Substituted Alkenes.- 3.2. Dienes and Trienes.- 3.3. Allenes and Ketenimines.- 3.4. Electron-Deficient Alkenes.- 3.5. Vinyl Ethers.- 3.6. Heteroaromatics.- 4. Carbonyl Addends.- 4.1. ?-Dicarbonyls.- 4.2. Quinones.- 4.3. Miscellaneous Carbonyls.- 4.4. Enones and Ynones.- 5. Intramolecular Cycloadditions.- 6. Chemical Reactions of Oxetans.- References.- 9. Equipment and Techniques.- 1. Mercury Vapor Lamps.- 2. Lamps in Conjunction with Filters.- 3. Photochemical Apparatus.- 4. Actinometry.- 4.1. Solution Phase Systems.- 4.2. Electronic Actinometers.- 5. Purity of Solvents and Gases.- References.

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この本の情報

書名 Synthetic organic photochemistry
著作者等 Horspool, William M.
Horspool W.M.
出版元 Plenum Press
刊行年月 c1984
ページ数 xvii, 534 p.
大きさ 23 cm
ISBN 030641449X
NCID BA0002246X
※クリックでCiNii Booksを表示
言語 英語
出版国 アメリカ合衆国

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