LEADER 05377nam 2200673 a 450 001 9910811550103321 005 20200520144314.0 010 $a1-282-68959-2 010 $a9786612689598 010 $a0-470-45288-9 010 $a0-470-45287-0 035 $a(CKB)1000000000719610 035 $a(EBL)427827 035 $a(OCoLC)476270996 035 $a(SSID)ssj0000231779 035 $a(PQKBManifestationID)11207821 035 $a(PQKBTitleCode)TC0000231779 035 $a(PQKBWorkID)10207014 035 $a(PQKB)11359298 035 $a(MiAaPQ)EBC427827 035 $a(Au-PeEL)EBL427827 035 $a(CaPaEBR)ebr10297699 035 $a(CaONFJC)MIL268959 035 $a(PPN)160579104 035 $a(EXLCZ)991000000000719610 100 $a20090727d2009 uy 0 101 0 $aeng 135 $aur|n|---||||| 181 $ctxt 182 $cc 183 $acr 200 00$aQuinone methides /$fedited by Steven E. Rokita 205 $a1st ed. 210 $aHoboken, N.J. $cWiley$d2009 215 $a1 online resource (460 p.) 225 1 $aWiley series on reactive intermediates in chemistry and biology 300 $aDescription based upon print version of record. 311 $a0-470-19224-0 320 $aIncludes bibliographical references and index. 327 $aQUINONE METHIDES; CONTENTS; Preface to Series; Introduction; Contributors; 1 Photochemical Generation and Characterization of Quinone Methides; 1.1 Introduction; 1.2 Quinone Methides from Benzylic Photoelimination; 1.2.1 Photoelimination of Fluoride; 1.2.2 Photodehydration; 1.2.3 Photoelimination of Quaternary Ammonium Salts; 1.2.4 Photoelimination of Alcohols and Esters; 1.3 Quinone Methides from ESIPT to Unsaturated Systems; 1.3.1 Quinone Methides from ESIPT to Carbonyls; 1.3.2 Quinone Methides from ESIPT to Alkenes and Alkynes; 1.3.3 Quinone Methides from ESIPT to Aromatic Carbon 327 $a1.4 Other Photochemical Routes to Quinone Methides1.5 Conclusions and Outlook; References; 2 Modeling Properties and Reactivity of Quinone Methides by DFT Calculations; 2.1 Introduction; 2.2 QM Reactivity as Alkylating Agents; 2.2.1 Computational Models; 2.2.1.1 Basis Set Choice; 2.2.1.2 Energetics of the Benzylation by o-QM in the Gas Phase and in Aqueous Solution; 2.2.2 H-Bonding and Solvent Effects in the Benzylation of Purine and Pyrimidine Bases; 2.2.2.1 Cytosine Benzylation under Kinetic Control; 2.2.2.2 Stability/Reactivity of the QM-Cytosine Conjugates 327 $a2.2.2.3 Purine Bases Benzylation: Kinetic and Thermodynamic Aspects2.3 Reactivity as Heterodiene; 2.4 Tautomerizations Involving Quinones and Quinone Methides; 2.4.1 QM Versus Quinone Stability: Substituent Effects; 2.5 o-Quinone Methide Metal Complexes; 2.5.1 Geometries and Reactivity as Function of the Metal and the Structural Features; 2.6 Generation of o-QM; 2.6.1 Generation of o-QM Tethered to Naphthalene Diimides by Mild Activation; 2.6.2 Thermal Generation of o-QM in Oxidative Processes in the Gas Phase; 2.7 Thermal Decomposition of o-QM in the Gas Phase 327 $a2.8 QM Generation in Lignin Formation2.9 Conclusion and Perspective; References; 3 Quinone Methide Stabilization by Metal Complexation; 3.1 Introduction; 3.2 QM-Based Pincer Complexes; 3.2.1 Formation; 3.2.2 Reactivity and Modifications; 3.2.3 Os-Based, p-QM Complexes; 3.3 One-Site Coordinated QM Complexes; 3.3.1 ?(2)-ortho-QM Complexes; 3.3.1.1 Formation; 3.3.1.2 Release and Reactivity of ?(2)-o-QMs; 3.3.2 ?(2)-p-QM Complexes; 3.3.2.1 Formation; 3.3.2.2 Controlled Release and Modification of ?(2)-p-QMs; 3.4 ?(4)-Coordinated QM Complexes; 3.4.1 Formation of ?(4)-Coordinated QM Complexes 327 $a3.4.2 Reactivity of ?(4)-Coordinated QM Complexes3.4.3 ?(4)-Coordinated QM Complexes of Mn; 3.5 Characterization of QM Complexes; 3.5.1 IR; 3.5.2 (1)H and (13)C {(1)H} NMR; 3.5.3 X-Ray; 3.6 Conclusion and Future Applications; Acknowledgments; References; 4 Intermolecular Applications of o-Quinone Methides (o-QMs) Anionically Generated at Low Temperatures: Kinetic Conditions; 4.1 Introduction to o-QMs; 4.2 Thermal Generation Conditions; 4.3 Low-Temperature Kinetic Generation of o-QMs; 4.3.1 Formation of the o-QMs Triggered by Fluoride Ion; 4.3.2 Stepwise Formation of o-QMs 327 $a4.3.3 Kinetically Controlled Cycloadditions 330 $a Multidisciplinary perspectives and approaches to quinone methides research The Wiley Series on Reactive Intermediates in Chemistry and Biology investigates reactive intermediates from the broadest possible range of disciplines. The contributions in each volume offer readers fresh insights into the latest findings, emerging applications, and ongoing research in the field from a diverse perspective. This inaugural volume in the series, Quinone Methides, represents the first book devoted to this fascinating and useful intermediate. The authors of this work reflect the many disciplines 410 0$aWiley series on reactive intermediates in chemistry and biology. 606 $aIntermediates (Chemistry) 615 0$aIntermediates (Chemistry) 676 $a547.2 676 $a547/.2 701 $aRokita$b Steven Edward$01636134 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9910811550103321 996 $aQuinone methides$93977278 997 $aUNINA