The field of reactive intermediates has been blossoming at a rapid rate in recent years and its impact on chemistry, both "pure" and "applied," as well as on biology, astronomy, and other areas of science, is enormous. Several books have been published which cover the area; one, edited by McManus, surveys the subject in general at the senior undergraduate or beginning graduate level. In addition, a number of monographs have appeared which deal with individual topics such as carbenes, nitrenes, free radicals, carbanions, carbenium ions, and so on, in great depth. Our objective is somewhat…mehr
The field of reactive intermediates has been blossoming at a rapid rate in recent years and its impact on chemistry, both "pure" and "applied," as well as on biology, astronomy, and other areas of science, is enormous. Several books have been published which cover the area; one, edited by McManus, surveys the subject in general at the senior undergraduate or beginning graduate level. In addition, a number of monographs have appeared which deal with individual topics such as carbenes, nitrenes, free radicals, carbanions, carbenium ions, and so on, in great depth. Our objective is somewhat different. We hope that these Advances in . . . type of volumes will appear at irregular intervals of a year to 18 months each. We intend to publish up-to-date reviews in relatively new areas of the chemistry of reactive intermediates. These will be written by world authorities in the field, each one of whom will give the reader a current in-depth review of all aspects of the chemistry of each of these species. It is our plan that the subjects to be reviewed will cover not only organic chemistry but also inorganic, physical, bio-, industrial, and atmospheric chemistry. The volumes themselves, we hope, will end up being reasonably interdisciplinary, though this need not and probably will not be the case for the individual reviews.Hinweis: Dieser Artikel kann nur an eine deutsche Lieferadresse ausgeliefert werden.
1. Current Aspects of the Solution Chemistry of Arylnitrenes.- I. Introduction.- 1. Definition and Historical.- 2. Nomenclature.- 3. Methods of Generation and Evidence for Arylnitrenes.- A. Thermolysis of Aryl Azides.- B. Photolysis of Aryl Azides.- C. Reduction of Nitro and Nitrosoarenes.- D. Fragmentation of Heterocycles.- E. Oxidation of Amines.- F. Newer Methods of Generation.- 4. Spectral, Structural, and Theoretical Considerations.- II. Intermodular Reactions.- 1. Singlet Reactions.- A. Aromatic Substitution.- B. Addition to Alkenes.- C. Reactions with Nitriles.- D. Trapping by Carbon Monoxide.- E. Electrophilic Substitution at Nitrogen.- 2. Triplet Reactions.- A. Aniline Formation.- B. Dimerization .- C. Insertion into Aliphatic C-H Bonds.- D. Reaction with Nitrosoarenes.- E. Reaction with Oxygen.- F. Substitution of a Carbon-Fluorine Bond.- 3. Benzazirine Reactions.- A. With Nucleophiles.- B. With Electrophiles.- III. Intramolecular Reactions.- 1. Nitrene-Induced Cyclizations.- A. To form Five-Membered Rings.- B. Closure to Six-Membered Rings.- 2. Heterocyclic Rearrangements.- IV. Decomposition in the Presence of Protonic and Lewis Acids.- V. Current and Future Application.- References.- 2. Nitrile Ylides and Nitrenes From 2H-Azirines.- I. Generation of Nitrile Ylides.- II. Features of the Photocycloaddition Reaction of 2H-Azirines.- III. Photochemical Dimerizations of 2H-Azirines.- IV. Intramolecular 1,5-Electrocyclization Reactions of Vinyl Substituted 2H-Azirines.- V. Properties of Nitrile Ylides.- VI. Intramolecular Photocycloaddition Reactions of 2H -Azirines.- VII. Further Reactions of 2H-Azirines.- VIII. Thermal Reactions of2H-Azirines.- References.- 3. Radical Cyclizations by Intramolecular Additions.- I. Introduction.- II. General Presentation: The Early Results.- 1. The Unstabilized 5-Hexenyl Radicals.- 2. The Stabilized 5-Hexenyl Radicals.- III. Attempts to Rationalize the Selectivities Observed in the Cyclization of 5-Hexenyl Radicals.- 1. The Irreversible Pathway: Why Is the (Cy 5) Radical Favored?.- A. The Steric Hypothesis.- B. The Stereoelectronic Hypothesis.- C. The Entropic Hypothesis.- D. Conclusion.- 2. The Reversible Pathway Favoring the (Cy 6) Radical.- IV. Alkyl Substituted 5-Hexenyl Radicals.- V. Alkenyl Radicals Other than 5-Hexenyl.- 1. The Higher Homologs.- 2. The Lower Homologs.- A. The 4-Pentenyl Radicals.- B. The 3-Butenyl Radicals.- C. The Allyl Radical.- 3. Conclusion.- VI. Carbon-Centered Alkenyl Radicals Containing Heteroatoms.- 1. Introduction.- 2. Unsaturated Radicals Bearing a Heteroatom in the Chain.- 3. Diallylic Substrates.- 4. Unsaturated Radicals Bearing Fluorine Atoms on the Chain.- VII. Alkenyl Radicals Bearing Stabilizing Groups on the Carbon Radical Center.- 1. Introduction.- 2. The 5-Hexenyl-and 5-Hexenylalkyl-Substituted Radicals.- 3. Other Alkenyl Radicals.- 4. The Stabilizing Groups.- 5. Conclusion.- VIII. Heteroatom-Centered Radicals.- 1. Introduction.- 2. Oxygen-Centered Radicals.- A. Alkoxyl Radicals.- B. Aryloxyl Radicals.- C. Acyloxyl Radicals.- D. Peroxyl Radicals.- 3. Nitrogen-Centered Radicals.- A. Aminyl Radicals.- B. Arylaminyl Radicals.- C. Amidyl Radicals.- D. Nitroxide Radicals.- 4. Sulfur-Centered Radicals.- A. Unsaturated Thiyl Radicals Generated from Unsaturated Mercaptans.- B. Unsaturated Thiyl Radicals Generated from Unsaturated Sulfides or Disulfides.- C. Enethiyl-Unsaturated Radicals, Arylthiyl-Unsaturated Radicals and the Thio-Claisen Rearrangement.- 5. Other Heteroatom-Centered Radicals.- A. Phosphorus-Centered Radicals.- B. Silicon-Centered Radicals.- C. Germanium-Centered Radicals.- D. Tin-Centered Radicals.- E. Selenium-Centered Radicals.- 6. Conclusion.- IX. Intramolecular Addition to Other Carbon-Carbon Bonds.- 1. Introduction.- 2. Intramolecular Addition to Acetylenic Bonds of Carbon-Centered Radicals.- 3. Intramolecular Addition of Heteroatomic Radicals to Acetylenic Bonds.- 4. Intramolecular Addition to Allenes and Cyclopropanes.- X. Intra
1. Current Aspects of the Solution Chemistry of Arylnitrenes.- I. Introduction.- 1. Definition and Historical.- 2. Nomenclature.- 3. Methods of Generation and Evidence for Arylnitrenes.- A. Thermolysis of Aryl Azides.- B. Photolysis of Aryl Azides.- C. Reduction of Nitro and Nitrosoarenes.- D. Fragmentation of Heterocycles.- E. Oxidation of Amines.- F. Newer Methods of Generation.- 4. Spectral, Structural, and Theoretical Considerations.- II. Intermodular Reactions.- 1. Singlet Reactions.- A. Aromatic Substitution.- B. Addition to Alkenes.- C. Reactions with Nitriles.- D. Trapping by Carbon Monoxide.- E. Electrophilic Substitution at Nitrogen.- 2. Triplet Reactions.- A. Aniline Formation.- B. Dimerization .- C. Insertion into Aliphatic C-H Bonds.- D. Reaction with Nitrosoarenes.- E. Reaction with Oxygen.- F. Substitution of a Carbon-Fluorine Bond.- 3. Benzazirine Reactions.- A. With Nucleophiles.- B. With Electrophiles.- III. Intramolecular Reactions.- 1. Nitrene-Induced Cyclizations.- A. To form Five-Membered Rings.- B. Closure to Six-Membered Rings.- 2. Heterocyclic Rearrangements.- IV. Decomposition in the Presence of Protonic and Lewis Acids.- V. Current and Future Application.- References.- 2. Nitrile Ylides and Nitrenes From 2H-Azirines.- I. Generation of Nitrile Ylides.- II. Features of the Photocycloaddition Reaction of 2H-Azirines.- III. Photochemical Dimerizations of 2H-Azirines.- IV. Intramolecular 1,5-Electrocyclization Reactions of Vinyl Substituted 2H-Azirines.- V. Properties of Nitrile Ylides.- VI. Intramolecular Photocycloaddition Reactions of 2H -Azirines.- VII. Further Reactions of 2H-Azirines.- VIII. Thermal Reactions of2H-Azirines.- References.- 3. Radical Cyclizations by Intramolecular Additions.- I. Introduction.- II. General Presentation: The Early Results.- 1. The Unstabilized 5-Hexenyl Radicals.- 2. The Stabilized 5-Hexenyl Radicals.- III. Attempts to Rationalize the Selectivities Observed in the Cyclization of 5-Hexenyl Radicals.- 1. The Irreversible Pathway: Why Is the (Cy 5) Radical Favored?.- A. The Steric Hypothesis.- B. The Stereoelectronic Hypothesis.- C. The Entropic Hypothesis.- D. Conclusion.- 2. The Reversible Pathway Favoring the (Cy 6) Radical.- IV. Alkyl Substituted 5-Hexenyl Radicals.- V. Alkenyl Radicals Other than 5-Hexenyl.- 1. The Higher Homologs.- 2. The Lower Homologs.- A. The 4-Pentenyl Radicals.- B. The 3-Butenyl Radicals.- C. The Allyl Radical.- 3. Conclusion.- VI. Carbon-Centered Alkenyl Radicals Containing Heteroatoms.- 1. Introduction.- 2. Unsaturated Radicals Bearing a Heteroatom in the Chain.- 3. Diallylic Substrates.- 4. Unsaturated Radicals Bearing Fluorine Atoms on the Chain.- VII. Alkenyl Radicals Bearing Stabilizing Groups on the Carbon Radical Center.- 1. Introduction.- 2. The 5-Hexenyl-and 5-Hexenylalkyl-Substituted Radicals.- 3. Other Alkenyl Radicals.- 4. The Stabilizing Groups.- 5. Conclusion.- VIII. Heteroatom-Centered Radicals.- 1. Introduction.- 2. Oxygen-Centered Radicals.- A. Alkoxyl Radicals.- B. Aryloxyl Radicals.- C. Acyloxyl Radicals.- D. Peroxyl Radicals.- 3. Nitrogen-Centered Radicals.- A. Aminyl Radicals.- B. Arylaminyl Radicals.- C. Amidyl Radicals.- D. Nitroxide Radicals.- 4. Sulfur-Centered Radicals.- A. Unsaturated Thiyl Radicals Generated from Unsaturated Mercaptans.- B. Unsaturated Thiyl Radicals Generated from Unsaturated Sulfides or Disulfides.- C. Enethiyl-Unsaturated Radicals, Arylthiyl-Unsaturated Radicals and the Thio-Claisen Rearrangement.- 5. Other Heteroatom-Centered Radicals.- A. Phosphorus-Centered Radicals.- B. Silicon-Centered Radicals.- C. Germanium-Centered Radicals.- D. Tin-Centered Radicals.- E. Selenium-Centered Radicals.- 6. Conclusion.- IX. Intramolecular Addition to Other Carbon-Carbon Bonds.- 1. Introduction.- 2. Intramolecular Addition to Acetylenic Bonds of Carbon-Centered Radicals.- 3. Intramolecular Addition of Heteroatomic Radicals to Acetylenic Bonds.- 4. Intramolecular Addition to Allenes and Cyclopropanes.- X. Intra
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