Description
Wiley Handbook of Synthetic Photochemistry 2010 Edition by Angelo Albini, Maurizio Fagnoni
Unique in its focus on preparative impact rather than mechanistic details, this handbook provides an overview of photochemical reactions classed according to the structural feature that is built in the photochemical step, so as to facilitate use by synthetic chemists unfamiliar with this topic. An introductory section covers practical questions on how to run a photochemical reaction, while all classes of the most important photocatalytic reactions are also included. Perfect for organic synthetic chemists in academia and industry. Table of contents : - 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