Modern Nucleophilic Aromatic Substitution

ISBN: 9783527318612 出版年：2013 页码：488 Francois Terrier Wiley

THE SNAr REACTIONS: MECHANISTIC ASPECTS Introduction Activation of the Aromatic System: Driving Force for SNAr Reactions Leaving Group, Nucleophile, Solvent, and Medium Effects Effects of Specific Structural Variations in the Activated Ring Spectral Evidence for the Intermediacy of sigma-Complexes in SNAr Reactions Base Catalysis in SNAr Reactions Regioselectivity in SNAr Reactions Asymmetric SNAr Substitutions Concerted SNAr Substitutions Conclusion STRUCTURE AND REACTIVITY OF ANIONIC SIGMA-COMPLEXES Introduction Structural Features of sigma-Complexes Thermodynamics and Kinetics of sigma-Complex Formation THE SUPERELECTROPHILIC DIMENSION IN SNAr AND RELATED SIGMA-COMPLEXATION PROCESSES Introduction The Classical Domain of SNAr and Anionic sigma-Complexation Reactivity Reaching the Superelectrophilic Dimension The Synthetic Potential of sigma-Complexation and SNAr Reactivity in the Superelectrophilic Dimension Origin of the Superelectrophilicity of Neutral 10pi Heteroaromatics SYNTHETIC ASPECTS OF INTERMOLECULAR SNAr REACTIONS Introduction Intermolecular Displacements of a Nitro Group Intermolecular Displacements of Halogen and Other Leaving Groups Conclusion INTRAMOLECULAR SNAr REACTIONS Introduction SNAr Cyclizations Smiles Rearrangements Conclusion NUCLEOPHILIC AROMATIC SUBSTITUTIONS OF HYDROGEN Introduction Reactions Involving Oxidation of sigma-Complex-Type Intermediates Vicarious Nucleophilic Aromatic Substitutions of Hydrogen (VNS) Deoxygenative SNArH Substitutions Cine and Tele Substitutions Conclusion OTHER SNAr SUBSTITUTION PATHWAYS SN(ANRORC) Substitutions Radical Nucleophilic Aromatic Substitutions Nucleophilic Aromatic Photosubstitutions