Handbook of Synthetic Photochemistry

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 (Mulheim, 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 Sanita" 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.

"Given its organization and practical emphasis, I believe that this book would make an outstanding addition to the library of any synthetic organic chemist. It should certainly be on the acquisition lists of all institutional libraries." (Journal of the American Chemical Society, November 2010)

• PHOTOCHEMICAL METHODSPhotochemistry and Organic SynthesisIrradiation ApparatusFurther Experimental ParametersPhotochemical Steps in SynthesisCARBON-CARBON BOND FORMATION BY PHOTOELIMINATION OF SMALL MOLECULES IN SOLUTION AND IN CRYSTALSIntroductionPhotochemical C-C Bond Formation in SolutionReactions in the Solid StateConclusionsINTERMOLECULAR ADDITION REACTIONS ONTO C-C MULTIPLE BONDSIntroductionAddition to C-C Double BondsAddition to C-C Triple BondsConclusionsFORMATION OF A 3-MEMBERED RINGIntroductionDi-Pi-Methane RearrangementOxa-Di-Pi-Methane Rearrangement and Related Rearrangements[2+1] Cycloaddition of Alkenes with CarbenesFormation of a Cyclopropane Via Intramolecular Hydrogen Abstraction[3+2] Cycloaddition of Arenes with AlkenesPhotochemical Synthesis of Three-Membered HeterocyclesFORMATION OF A 4-MEMBERED RING IIntroduction[2+2]-Photocycloaddition of Non Conjugated Alkenes[2+2]-Photocycloaddition of Aromatic CompoundsPhotochemical Electrocyclic ReactionsIntramolecular Gamma-Hydrogen Abstraction (Yang Reaction)Metal Catalyzed ReactionsVarious MethodsConclusionsFORMATION OF A 4-MEMBERED RING IIIntroduction[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 PerspectivesFORMATION OF A 4-MEMBERED RING III (OXETANES)IntroductionGenerally Accepted Mechanisms of the Paterno-Buchi ReactionRegio- and Siteselective Synthesis of OxetanesStereoselective Syntheses of OxetanesConclusive RemarksFORMATION OF A 5-MEMBERED RINGFormation of Five-Membered Ring: Intramolecular Delta-H AbstractionFormation of Five-Membered Rings Via [3+2]-CycloadditionsPhotochemical Electrocyclization Reactions: Synthesis of Fused Five-Membered Ring CompoundsPhotoinduced Electron Transfer Radical Cation Mediated Cyclizations: Synthesis of Five-Membered Carbocyclic as well as Heterocyclic Ring SystemsFORMATION OF 6-MEMBERED RING (AND LARGER RINGS)IntroductionPhotoelectron Transfer Initiated CyclizationsPhotoinduced 6Pi-ElectrocyclizationPhotocycloaddition ReactionsRemote Intramolecular Hydrogen AbstractionRing Contraction and Ring EnlargementOther ReactionsSummaryAROMATIC AND HETEROAROMATIC SUBSTITUTION BY SRN1 AND SN1 REACTIONSIntroductionGeneral Mechanistic FeaturesCarbon-Carbon Bond FormationCarbon-Heteroatom Bond FormationSynthesis of Bi, Tri, and PoliarylsSynthesis of Carbocycles and HeterocyclesSINGLET OXYGEN AS A REAGENT IN ORGANIC SYNTHESISIntroductionDioxetanesEndoperoxidesAllylic HydroperoxidesTandem Singlet Oxygen ReactionsConclusionSYNTHESIS OF HETEROAROMATICS VIA REARRANGEMENT REACTIONSIntroductionSynthesis of Five-Membered Rings with One HeteroatomSynthesis of Five-Membered Rings with Two HeteroatomsSynthesis of Five-Membered Rings with Three HeteroatomsSynthesis of Six-Membered RingsSynthesis of Seven-Membered RingsConcluding RemarksPHOTOLABILE PROTECTING GROUPS IN ORGANIC SYNTHESISIntroductionPhotolabile Protecting GroupsChromatic OrthogonalityTwo-Photons AbsorptionPerspectives and Conclusion