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Handbook of Synthetic Photochemistry

A. Albini (Editor), Maurizio Fagnoni (Editor)
ISBN: 978-3-527-32391-3
484 pages
February 2010
Handbook of Synthetic Photochemistry (3527323910) cover image
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.
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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 Paterṇ-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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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.
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"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)

 

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