Handbook of Synthetic Photochemistry

Abstract

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 Paterno-Buchi 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