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Dieses besondere Handbuch der Photochemie konzentriert sich nicht auf mechanistische Details, sondern -- ganz praxisnah -- auf die präparative Chemie. Durch seine übersichtliche Ordnung nach chemischen Strukturen ist es alltagstauglich auch für organische Synthesechemiker, die sich sonst nicht mit Photochemie befassen.
Dieses besondere Handbuch der Photochemie konzentriert sich nicht auf mechanistische Details, sondern -- ganz praxisnah -- auf die präparative Chemie. Durch seine übersichtliche Ordnung nach chemischen Strukturen ist es alltagstauglich auch für organische Synthesechemiker, die sich sonst nicht mit Photochemie befassen.
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Autorenporträt
Angelo Albini is full professor of Organic Chemistry at the University of Pavia, Italy. He did postdoctoral work at the Max-Plack-Institut for Radiation Chemistry (Mülheim, Germany) and has been a visiting professor at the Universities of Western Ontario (Canada) and of Odense (Denmark) and a professor at the University of Torino. His scientific activity has always centered on organic photochemistry in different aspects, mechanistic studies, synthetic applications, mild generation of highly active intermediates, 'green chemistry', photoinduced degradation of pollutants, phototoxicity of drugs). Besides research papers, he is coauthor of two books and since 2009 senior reporter of the RSC Specialistic Report on Photochemisty. He has been the recipient of the Federchimica prize for creativity in chemistry in 1990.
Maurizio Fagnoni graduated at the University of Pavia (Italy) with a thesis on the use of photoinduced electron transfer reactions in organic synthesis under the guidance of Prof. Angelo Albini. He spent part of his PhD period at the University of Muenster (Germany) working on the photochemistry of cyclopropylketones (Prof. J. Mattay as the supervisor). In 1996 he obtained a fellowship from the "Istituto Superiore della Sanità" for the study of the photostability of drugs. He then moved to the Istituto Ronzoni (Milan) where he worked on the synthesis of peptidomimetics and functionalized chitosans. In 1998 he returned to the University of Pavia where in 2008 was appointed associate professor. His interests lie in the application of photochemistry to organic (green) synthesis encompassing photocatalysis and phenyl cation chemistry.
Inhaltsangabe
PHOTOCHEMICAL METHODS Photochemistry and Organic Synthesis Irradiation Apparatus Further Experimental Parameters Photochemical Steps in Synthesis CARBON-CARBON BOND FORMATION BY PHOTOELIMINATION OF SMALL MOLECULES IN SOLUTION AND IN CRYSTALS Introduction Photochemical C-C Bond Formation in Solution Reactions in the Solid State Conclusions INTERMOLECULAR ADDITION REACTIONS ONTO C-C MULTIPLE BONDS Introduction Addition to C-C Double Bonds Addition to C-C Triple Bonds Conclusions FORMATION OF A 3-MEMBERED RING Introduction Di-Pi-Methane Rearrangement Oxa-Di-Pi-Methane Rearrangement and Related Rearrangements [2+1] Cycloaddition of Alkenes with Carbenes Formation of a Cyclopropane Via Intramolecular Hydrogen Abstraction [3+2] Cycloaddition of Arenes with Alkenes Photochemical Synthesis of Three-Membered Heterocycles FORMATION OF A 4-MEMBERED RING I Introduction [2+2]-Photocycloaddition of Non Conjugated Alkenes [2+2]-Photocycloaddition of Aromatic Compounds Photochemical Electrocyclic Reactions Intramolecular Gamma-Hydrogen Abstraction (Yang Reaction) Metal Catalyzed Reactions Various Methods Conclusions FORMATION OF A 4-MEMBERED RING II Introduction [2+2]-Photocycloaddition of Enones (Substrate Type A1) [2+2]-Photocycloaddition of Vinylogous Amides and Esters (Substrate Clases A2 and A3) [2+2]-Photocycloaddition of Alpha, Beta-Unsaturated Carboxylic Acid Derivatives (Substrate Classes A4, A5 and A6) Conclusions and Perspectives FORMATION OF A 4-MEMBERED RING III (OXETANES) Introduction Generally Accepted Mechanisms of the Paternò-Büchi Reaction Regio- and Siteselective Synthesis of Oxetanes Stereoselective Syntheses of Oxetanes Conclusive Remarks FORMATION OF A 5-MEMBERED RING Formation of Five-Membered Ring: Intramolecular Delta-H Abstraction Formation of Five-Membered Rings Via [3+2]-Cycloadditions Photochemical Electrocyclization Reactions: Synthesis of Fused Five-Membered Ring Compounds Photoinduced Electron Transfer Radical Cation Mediated Cyclizations: Synthesis of Five-Membered Carbocyclic as well as Heterocyclic Ring Systems FORMATION OF 6-MEMBERED RING (AND LARGER RINGS) Introduction Photoelectron Transfer Initiated Cyclizations Photoinduced 6Pi-Electrocyclization Photocycloaddition Reactions Remote Intramolecular Hydrogen Abstraction Ring Contraction and Ring Enlargement Other Reactions Summary AROMATIC AND HETEROAROMATIC SUBSTITUTION BY SRN1 AND SN1 REACTIONS Introduction General Mechanistic Features Carbon-Carbon Bond Formation Carbon-Heteroatom Bond Formation Synthesis of Bi, Tri, and Poliaryls Synthesis of Carbocycles and Heterocycles SINGLET OXYGEN AS A REAGENT IN ORGANIC SYNTHESIS Introduction Dioxetanes Endoperoxides Allylic Hydroperoxides Tandem Singlet Oxygen Reactions Conclusion SYNTHESIS OF HETEROAROMATICS VIA REARRANGEMENT REACTIONS Introduction Synthesis of Five-Membered Rings with One Heteroatom Synthesis of Five-Membered Rings with Two Heteroatoms Synthesis of Five-Membered Rings with Three Heteroatoms Synthesis of Six-Membered Rings Synthesis of Seven-Membered Rings Concluding Remarks PHOTOLABILE PROTECTING GROUPS IN ORGANIC SYNTHESIS Introduction Photolabile Protecting Groups Chromatic Orthogonality Two-Photons Absorption Perspectives and Conclusion
PHOTOCHEMICAL METHODS Photochemistry and Organic Synthesis Irradiation Apparatus Further Experimental Parameters Photochemical Steps in Synthesis CARBON-CARBON BOND FORMATION BY PHOTOELIMINATION OF SMALL MOLECULES IN SOLUTION AND IN CRYSTALS Introduction Photochemical C-C Bond Formation in Solution Reactions in the Solid State Conclusions INTERMOLECULAR ADDITION REACTIONS ONTO C-C MULTIPLE BONDS Introduction Addition to C-C Double Bonds Addition to C-C Triple Bonds Conclusions FORMATION OF A 3-MEMBERED RING Introduction Di-Pi-Methane Rearrangement Oxa-Di-Pi-Methane Rearrangement and Related Rearrangements [2+1] Cycloaddition of Alkenes with Carbenes Formation of a Cyclopropane Via Intramolecular Hydrogen Abstraction [3+2] Cycloaddition of Arenes with Alkenes Photochemical Synthesis of Three-Membered Heterocycles FORMATION OF A 4-MEMBERED RING I Introduction [2+2]-Photocycloaddition of Non Conjugated Alkenes [2+2]-Photocycloaddition of Aromatic Compounds Photochemical Electrocyclic Reactions Intramolecular Gamma-Hydrogen Abstraction (Yang Reaction) Metal Catalyzed Reactions Various Methods Conclusions FORMATION OF A 4-MEMBERED RING II Introduction [2+2]-Photocycloaddition of Enones (Substrate Type A1) [2+2]-Photocycloaddition of Vinylogous Amides and Esters (Substrate Clases A2 and A3) [2+2]-Photocycloaddition of Alpha, Beta-Unsaturated Carboxylic Acid Derivatives (Substrate Classes A4, A5 and A6) Conclusions and Perspectives FORMATION OF A 4-MEMBERED RING III (OXETANES) Introduction Generally Accepted Mechanisms of the Paternò-Büchi Reaction Regio- and Siteselective Synthesis of Oxetanes Stereoselective Syntheses of Oxetanes Conclusive Remarks FORMATION OF A 5-MEMBERED RING Formation of Five-Membered Ring: Intramolecular Delta-H Abstraction Formation of Five-Membered Rings Via [3+2]-Cycloadditions Photochemical Electrocyclization Reactions: Synthesis of Fused Five-Membered Ring Compounds Photoinduced Electron Transfer Radical Cation Mediated Cyclizations: Synthesis of Five-Membered Carbocyclic as well as Heterocyclic Ring Systems FORMATION OF 6-MEMBERED RING (AND LARGER RINGS) Introduction Photoelectron Transfer Initiated Cyclizations Photoinduced 6Pi-Electrocyclization Photocycloaddition Reactions Remote Intramolecular Hydrogen Abstraction Ring Contraction and Ring Enlargement Other Reactions Summary AROMATIC AND HETEROAROMATIC SUBSTITUTION BY SRN1 AND SN1 REACTIONS Introduction General Mechanistic Features Carbon-Carbon Bond Formation Carbon-Heteroatom Bond Formation Synthesis of Bi, Tri, and Poliaryls Synthesis of Carbocycles and Heterocycles SINGLET OXYGEN AS A REAGENT IN ORGANIC SYNTHESIS Introduction Dioxetanes Endoperoxides Allylic Hydroperoxides Tandem Singlet Oxygen Reactions Conclusion SYNTHESIS OF HETEROAROMATICS VIA REARRANGEMENT REACTIONS Introduction Synthesis of Five-Membered Rings with One Heteroatom Synthesis of Five-Membered Rings with Two Heteroatoms Synthesis of Five-Membered Rings with Three Heteroatoms Synthesis of Six-Membered Rings Synthesis of Seven-Membered Rings Concluding Remarks PHOTOLABILE PROTECTING GROUPS IN ORGANIC SYNTHESIS Introduction Photolabile Protecting Groups Chromatic Orthogonality Two-Photons Absorption Perspectives and Conclusion
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