Synthetic Organic Photochemistry PDF
Preview Synthetic Organic Photochemistry
Synthetic Organic Photochemistry Copyright © 2005 by Marcel Dekker MOLECULAR AND SUPRAMOLECULAR PHOTOCHEMISTRY Series Editors V.Ramamurthy Professor Department of Chemistry Tulane University New Orleans,Louisiana Kirk S.Schanze Professor Department of Chemistry University of Florida Gainesville,Florida 1. Organic Photochemistry, edited by V. Ramamurthy and Kirk S. Schanze 2. Organic and Inorganic Photochemistry, edited by V. Ramamurthy and Kirk S. Schanze 3. Organic Molecular Photochemistry, edited by V. Ramamurthy and Kirk S. Schanze 4. Multimetallic and Macromolecular Inorganic Photochemistry, edited by V. Ramamurthy and Kirk S. Schanze 5. Solid State and Surface Photochemistry, edited by V. Ramamurthy and Kirk S. Schanze 6. Organic, Physical, and Materials Photochemistry, editedby V. Ramamurthy and Kirk S. Schanze 7. Optical Sensors and Switches, edited by V. Ramamurthy and Kirk S. Schanze 8. Understanding and Manipulating Excited-State Processes, edited by V. Ramamurthy and Kirk S. Schanze 9. Photochemistry of Organic Molecules in Isotropic and Anisotropic Media,edited by V. Ramamurthy and Kirk S. Schanze 10. Semiconductor Photochemistry and Photophysics, edited by V. Ramamurthy and Kirk S. Schanze 11. Chiral Photochemistry, edited by Yoshihisa Inoue and V. Ramamurthy 12. Synthetic Organic Photochemistry, edited by Axel G. Griesbeck and Jochen Mattay Copyright © 2005 by Marcel Dekker Synthetic Organic Photochemistry edited by Axel G. Griesbeck Universität zu Köln, Köln, Germany Jochen Mattay Universität Bielefeld, Bielefeld, Germany MarcelDekker NewYork TM Copyright © 2005 by Marcel Dekker Although great care has been taken to provide accurate and current information, neither the author(s) nor the publisher, nor anyone else associated with this publication, shall be liable for any loss, damage, or liability directly or indirectly caused or alleged to be caused by this book. The material contained herein is not intended to provide specificadvice orrecommendations for anyspecific situation. Trademark notice: Product or corporate names may be trademarks or registered trademarks and are used only for identification and explanation without intent to infringe. Library of Congress Cataloging-in-Publication Data A catalog recordfor this bookisavailable from the Libraryof Congress. ISBN: 0-8247-5736-X This bookisprintedon acid-freepaper. Headquarters Marcel Dekker,270Madison Avenue, NewYork, NY 10016, U.S.A. tel: 212-696-9000;fax: 212-685-4540 Distribution andCustomer Service Marcel Dekker,Cimarron Road,Monticello, NewYork 12701,U.S.A. tel: 800-228-1160;fax: 845-796-1772 World WideWeb http://www.dekker.com The publisher offers discounts on this book when ordered in bulk quantities. For moreinformation,writetoSpecialSales/ProfessionalMarketingattheheadquarters address above. Copyright (cid:1)2005byMarcelDekker. All Rights Reserved. Neitherthisbooknoranypartmaybereproducedortransmittedinanyformorby any means, electronic or mechanical, including photocopying, microfilming, and recording,orbyanyinformationstorageandretrievalsystem,withoutpermissionin writing from the publisher. Current printing (last digit): 10 9 8 7 6 5 4 3 2 1 PRINTED INTHE UNITED STATES OFAMERICA Copyright © 2005 by Marcel Dekker Preface Photochemistry is a highly valuable tool for modern organic synthesis. It has had a very strong first period of prosperity in the early fifties and sixties of the last century, when numerous light-induced reactions were discovered, modified and applied to synthetic problems. A milestone of development is related to the famous Woodward-Hoffmann rules and the photochemical reactions which served as the experimental basis. Subse- quently, expectations from the ‘‘synthetic community’’ were high and the actualoutputinfactremarkable,aschemistsbecameawareofthereactivity potential of electronic excited states of a molecule. Indeed, photochemistry means in many cases a multiplication of reactivity options, i.e. in addition to the ground state, the electronically excited singlets and triplets show differentchemicalbehaviorandoftendiffersoremarkablythattheybehave as completely new molecules. If you don’t want to use them, however, they simply disappear again by radiative or non-radiative pathways (a key principlealsoofgreenchemistry).Thetechniquesoftime-resolvedspectros- copy approaching new fascinating time domains (‘‘femtochemistry’’) in the last decades, enable the photochemistry community to describe a photo- physical process in full detail and also to predict photochemical reactivity. In spite of these exceptional advantages, light-induced reactions were onlylittlebylittleacceptedbythesyntheticorganiccommunity.Upto1995, onlyabout1%oftheproceduresandreactionsinOrganicSynthesesandin Organic Reactions dealt with photochemistry! In our opinion this results from two major problems: First, photochemistry is always linked to photophysical aspects—the nature of the excited state, its lifetime, its radiative and non-radiative iii Copyright © 2005 by Marcel Dekker iv Preface deactivation paths have to be considered (and to be optimized) in order to design a productive light-induced process—which makes things less easy. Second, photochemical processes require appropriate (and some- times also expensive) equipment, a fact which often discouraged the interested user. In the meanwhile, interdisciplinary research became more and more essentialandphotochemistrybecameaperfectexampleasapowerfulbridge between chemistry, physics, and biology, between material science, life science, and synthesis. Until recently organic photochemistry has only partially focused on stereoselective synthesis, one of the major challenges and research areas in modern organic synthesis. This situation has dramatically changed in the last decade and highly chemo-, regio-, diastereo- as well as enantioselective reactionshavebeendeveloped.Chemistsallovertheworldbecameawareof the fascinating synthetic opportunities of electronically excited molecules and definitely this will lead to a new period of prosperity. Photochemical reactions can be performed at low temperatures, in the solid or liquid state or under gas-phase conditions, with spin-selective direct excitation or sensitization, and even multi-photon processes start to enter the synthetic scenery. Withcontributionsfrom24internationalsubjectauthorities,Synthetic Organic Photochemistry comprises a leading-edge presentation of the most recent and in-demand applications of photochemical methodologies. Outlining a wide assortment of reaction types, entailing cycloadditions, cyclizations, isomerizations, rearrangements, and other organic syntheses, this reference also ties in critical considerations that overlap in modern photochemistry and organic chemistry, such as stereoselectivity. Select experimental procedures demonstrate the industrial and academic value of reactions presented in the text. Containing a remarkable 2113 references, this volume (cid:1) reviews [2þ2], [4þ2], and ene photooxygenation reactions, (cid:1) illustrates photocycloadditions of alkenes to excited alkenes or carbonyls, (cid:1) clarifies abstractions of g- and (g(cid:2)n) hydrogens by excited carbonyls, (cid:1) describes di-p-methane and oxa-di-p-methane rearrangements, (cid:1) explores photoinduced electron transfer cyclizations using radical ions, (cid:1) studies photogenerated nitrene additions to p-bonds, (cid:1) surveys reactions with photoinduced aromatic nucleophilic substitutions, Copyright © 2005 by Marcel Dekker Preface v (cid:1) coversseveralotherphotochemicalmethodsforspecificsyntheses, (cid:1) inspects medium effects on photoinduced processes. Synthetic Organic Photochemistry is an ideal resource for photo- chemists, organic and physical chemists, and graduate students in these disciplines. Axel G. Griesbeck Jochen Mattay Copyright © 2005 by Marcel Dekker Contents Preface iii Contributors ix 1. Synthetic Organic Photochemistry 1 Axel G. Griesbeck and Jochen Mattay 2. Abstraction of g-Hydrogens by Excited Carbonyls 11 Peter J. Wagner 3. Abstraction of (g(cid:2)n)-Hydrogen by Excited Carbonyls 41 Pablo Wessig and Olaf Mu¨hling 4. Photocycloadditions of Alkenes to Excited Carbonyls 89 Axel G. Griesbeck 5. Photocycloaddition of Alkenes to Excited Alkenes 141 Steven A. Fleming 6. Di-p-Methane Rearrangement 161 Diego Armesto, Maria J. Ortiz, and Antonia R. Agarrabeitia 7. Oxa-Di-p-Methane Rearrangements 189 V. Jayathirtha Rao and Axel G. Griesbeck vii Copyright © 2005 by Marcel Dekker viii Contents 8. Photocycloaddition of Cycloalk-2-enones to Alkenes 211 Paul Margaretha 9. Photocycloaddition of Alkenes (Dienes) to Dienes ([4þ2]/[4þ4]) 239 Scott McN. Sieburth 10. Photoinduced Electron Transfer Cyclizations via Radical Ions 269 Michael Oelgemo¨ller, Jens Otto Bunte, and Jochen Mattay 11. Photo-oxygenation of the [4þ2] and [2þ2] Type 299 Maria Rosaria Iesce 12. Photo-oxygenation of the Ene-Type 365 Edward L. Clennan 13. Photogenerated Nitrene Addition to p-Bonds 391 Hans-Werner Abraham 14. C¼C Photoinduced Isomerization Reactions 417 Tadashi Mori and Yoshihisa Inoue 15. Photoinduced CX Cleavage of Benzylic Substrates 453 Angelo Albini and Maurizio Fagnoni 16. Photoinduced Aromatic Nucleophilic Substitution Reactions 495 Roberto A. Rossi 17. Ortho-, Meta-, and Para-Photocycloaddition of Arenes 529 Norbert Hoffmann 18. Medium Effects on Photochemical Processes: Organized 553 and Confined Media Lakshmi S. Kaanumalle, Arunkumar Natarajan, and V. Ramamurthy Copyright © 2005 by Marcel Dekker
Description:The list of books you might like
