Handbook of Synthetic Photochemistry

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