Modern Nucleophilic Aromatic Substitution

AvFrancois Terrier

Inbunden, Engelska, 2013

2 085 kr

Beställningsvara. Skickas inom 5-8 vardagar. Fri frakt över 249 kr.

Fler format och utgåvor

E-bok

2 453 kr

E-bok

2 367 kr

Beskrivning

This book provides a comprehensive overview of nucleophilic aromatic substitutions, focusing on the mechanistic and synthetic features that govern these reactions. The first chapter presents a detailed mechanistic analysis of the factors determining the feasibility of SNAr substitutions, providing decisive information to predict regioselectivity of many reactions and to define the conditions for concerted SNAr processes. Reflecting the key role played by these species as intermediates in most SNAr reactions, chapter 2 then discusses the chemistry of anionic sigma-complexes. Chapter 3 describes the concept of superelectrophilicity in SNAr substitutions, as it has recently emerged from the reactivity of strongly electron-deficient aromatic and heteroaromatic structures. The numerous synthetic applications are considered in depth in the chapters 4 and 5 that follow on intermolecular and intramolecular nucleophilic aromatic substitutions. Then, chapter 6 focuses on substitutions proceeding formally through displacement of a hydride ion, a hot topic in the field. The final chapter brings together concise yet comprehensive discussions surrounding SNAr photosubstitutions, radical substitutions, and ANRORC substitutions.Authored by a highly respected chemist who has contributed greatly to the field over the past two decades, this is a valuable information source for all organic chemists working in academia or the pharmaceutical and agrochemical industries.

Produktinformation

Utgivningsdatum:2013-06-12
Mått:177 x 248 x 28 mm
Vikt:1 166 g
Format:Inbunden
Språk:Engelska
Antal sidor:488
Förlag:Wiley-VCH Verlag GmbH
ISBN:9783527318612

Utforska kategorier

Kemi inom Naturvetenskap och teknik

Mer om författaren

Francois Terrier obtained his PhD in 1968 from the University Pierre et Marie Curie in Paris. After postdoctoral research with Professor Bernasconi at the University of California, Santa Cruz, he was appointed Professor at the University of Rouen. In 1991 he moved to the new University of Versailles, where he holds a Professorship of organic chemistry. As the Head of the Department of Chemistry he developed a research lab focusing on various topics dealing with reactivity and physical organic chemistry, namely nucleophilic aromatic substitutions and sigma-complexation processes, alfa-effect nucleophiles and proton transfers at carbon. He has published over 200 papers, as well as a number of book chapters and review articles.

Innehållsförteckning

THE SNAr REACTIONS: MECHANISTIC ASPECTSIntroductionActivation of the Aromatic System: Driving Force for SNAr ReactionsLeaving Group, Nucleophile, Solvent, and Medium EffectsEffects of Specific Structural Variations in the Activated RingSpectral Evidence for the Intermediacy of sigma-Complexes in SNAr ReactionsBase Catalysis in SNAr ReactionsRegioselectivity in SNAr ReactionsAsymmetric SNAr SubstitutionsConcerted SNAr SubstitutionsConclusion STRUCTURE AND REACTIVITY OF ANIONIC SIGMA-COMPLEXESIntroductionStructural Features of sigma-ComplexesThermodynamics and Kinetics of sigma-Complex Formation THE SUPERELECTROPHILIC DIMENSION IN SNAr AND RELATED SIGMA-COMPLEXATION PROCESSESIntroductionThe Classical Domain of SNAr and Anionic sigma-Complexation ReactivityReaching the Superelectrophilic DimensionThe Synthetic Potential of sigma-Complexation and SNAr Reactivity in the Superelectrophilic DimensionOrigin of the Superelectrophilicity of Neutral 10pi Heteroaromatics SYNTHETIC ASPECTS OF INTERMOLECULAR SNAr REACTIONSIntroductionIntermolecular Displacements of a Nitro GroupIntermolecular Displacements of Halogen and Other Leaving GroupsConclusion INTRAMOLECULAR SNAr REACTIONSIntroductionSNAr CyclizationsSmiles RearrangementsConclusion NUCLEOPHILIC AROMATIC SUBSTITUTIONS OF HYDROGENIntroductionReactions Involving Oxidation of sigma-Complex-Type IntermediatesVicarious Nucleophilic Aromatic Substitutions of Hydrogen (VNS)Deoxygenative SNArH SubstitutionsCine and Tele SubstitutionsConclusion OTHER SNAr SUBSTITUTION PATHWAYSSN(ANRORC) SubstitutionsRadical Nucleophilic Aromatic SubstitutionsNucleophilic Aromatic Photosubstitutions