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Author: Francois Terrier Publisher: John Wiley & Sons ISBN: 3527656162 Category : Science Languages : en Pages : 488
Book Description
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.
Author: Francois Terrier Publisher: John Wiley & Sons ISBN: 3527656162 Category : Science Languages : en Pages : 488
Book Description
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.
Author: Oleg N. Chupakhin Publisher: Academic Press ISBN: 0323140599 Category : Science Languages : en Pages : 378
Book Description
Nucleophilic aromatic substitution in carbo- and heteroaromatic systems is a subject of considerable interest to chemists. This book uniquely addresses the systematic analysis of a vast range of nucleophilic substitutions of aromatic hydrogen. - Nucleophilic displacement of hydrogen (the S N/H reactions) in pi-deficient aromatics, such as nitroarenes, arene-metal complexes, and the like - Nucleophilic displacement of hydrogen in heterocyclic substrates such as pyridines, their aza and benzo analogs, pyrylium and thiapyrylium cations, and other heterocycles - Mechanisms for the S N/H reactions (S N/H(AE), vicarious nucleophilic substitutions, and radical S N/H substitutions
Author: Mandeep Dalal Publisher: Dalal Institute ISBN: 8195242731 Category : Science Languages : en Pages : 448
Book Description
An advanced-level textbook of organic chemistry for the graduate (B.Sc) and postgraduate (M.Sc) students of Indian and foreign universities. This book is a part of the four-volume series, entitled “A Textbook of Organic Chemistry – Volume I, II, III, IV”. CONTENTS: CHAPTER 1. Nature of Bonding in Organic molecules: Delocalized Chemical Bonding; Conjugation; Cross Conjugation; Resonance; Hyperconjugation; Tautomerism; Aromaticity in Benzenoid and Nonbenzenoid Compounds; Alternant and Non-Alternant Hydrocarbons; Huckel’s Rule: Energy Level of p-Molecular Orbitals; Annulenes; Antiaromaticity; Homo-Aromaticity; PMO Approach; Bonds Weaker than Covalent; Addition Compounds: Crown Ether Complexes and Cryptands, Inclusion Compounds, Cyclodextrins; Catenanes and Rotaxanes CHAPTER 2. Stereochemistry: Chirality; Elements of symmetry; Molecules with more than one chiral centre: diastereomerism; Determination of relative and absolute configuration (octant rule excluded) with special reference to lactic acid, alanine & mandelic acid; Methods of resolution; Optical purity; Prochirality; Enantiotopic and diastereotopic atoms, groups and faces; Asymmetric synthesis: cram’s rule and its modifications, prelog’s rule; Conformational analysis of cycloalkanes (upto six membered rings); Decalins; Conformations of sugars; Optical activity in absence of chiral carbon (biphenyls, allenes and spiranes); Chirality due to helical shape; Geometrical isomerism in alkenes and oximes; Methods of determining the configuration CHAPTER 3. Reaction Mechanism: Structure and Reactivity: Types of mechanisms; Types of reactions; Thermodynamic and kinetic requirements; Kinetic and thermodynamic control; Hammond’s postulate; Curtin-Hammett principle; Potential energy diagrams: Transition states and intermediates; Methods of determining mechanisms; Isotope effects; Hard and soft acids and bases; Generation, structure, stability and reactivity of carbocations, carbanions, free radicals, carbenes and nitrenes; Effect of structure on reactivity; The Hammett equation and linear free energy relationship; Substituent and reaction constants; Taft equation CHAPTER 4. Carbohydrates: Types of naturally occurring sugars; Deoxy sugars; Amino sugars; Branch chain sugars; General methods of determination of structure and ring size of sugars with particular reference to maltose, lactose, sucrose, starch and cellulose. CHAPTER 5. Natural and Synthetic Dyes: Various classes of synthetic dyes including heterocyclic dyes; Interaction between dyes and fibers; Structure elucidation of indigo and Alizarin CHAPTER 6. Aliphatic Nucleophilic Substtitution: The SN2, SN1, mixed SN1 and SN2, SNi , SN1’, SN2’, SNi’ and SET mechanisms; The neighbouring group mechanisms; neighbouring group participation by p and s bonds; anchimeric assistance; Classical and nonclassical carbocations; Phenonium ions; Common carbocation rearrangements; Applications of NMR spectroscopy in the detection of carbocations; Reactivity- effects of substrate structure, attacking nucleophile, leaving group and reaction medium; Ambident nucleophiles and regioselectivity; Phase transfer catalysis. CHAPTER 7. Aliphatic Electrophilic Substitution: Bimolecular mechanisms – SE2 and SEi; The SE1 mechanism; Electrophilic substitution accompained by double bond shifts; Effect of substrates, leaving group and the solvent polarity on the reactivity CHAPTER 8. Aromatic Electrophilic Substitution: The arenium ion: mechanism, orientation and reactivity, energy profile diagrams; The ortho/para ratio, ipso attack, orientation in other ring systems; Quantitative treatment of reactivity in substrates and electrophiles; Diazonium coupling; Vilsmeir reaction; Gattermann-Koch reaction CHAPTER 9. Aromatic Nucleophilic Substitution: The ArSN1, ArSN2, Benzyne and SRN1 mechanisms; Reactivity – effect of substrate structure, leaving group and attacking nucleophile; The von Richter, Sommelet-Hauser, and Smiles rearrangements CHAPTER 10. Elimination Reactions: The E2, E1 and E1cB mechanisms; Orientation of the double bond; Reactivity –effects of substrate structures, attacking base, the leaving group and the medium; Mechanism and orientation in pyrolytic elimination CHAPTER 11. Addition to Carbon-Carbon Multiple Bonds: Mechanistic and stereochemical aspects of addition reactions involving electrophiles, nucleophiles and free radicals; Regio–and chemoselectivity: orientation and reactivity; Addition to cyclopropane ring; Hydrogenation of double and triple bonds; Hydrogenation of aromatic rings; Hydroboration; Michael reaction; Sharpless asymmetric epoxidation. CHAPTER 12. Addition to Carbon-Hetero Multiple Bonds: Mechanism of metal hydride reduction of saturated and unsaturated carbonyl compounds, acids, esters and nitriles; Addition of Grignard reagents, organozinc and organolithium; Reagents to carbonyl and unsaturated carbonyl compounds; Wittig reaction; Mechanism of condensation reactions involving enolates – Aldol, Knoevenagel, Claisen, Mannich, Benzoin, Perkin and Stobbe reactions; Hydrolysis of esters and amides; Ammonolysis of esters.
Author: Stéphane Caron Publisher: John Wiley & Sons ISBN: 1119448859 Category : Science Languages : de Pages : 850
Book Description
This book is a hands-on guide for the organic chemist. Focusing on the most reliable and useful reactions, the chapter authors provide the information necessary for a chemist to strategically plan a synthesis, as well as repeat the procedures in the laboratory. Consolidates all the key advances/concepts in one book, covering the most important reactions in organic chemistry, including substitutions, additions, eliminations, rearrangements, oxidations, reductions Highlights the most important reactions, addressing basic principles, advantages/disadvantages of the methodology, mechanism, and techniques for achieving laboratory success Features new content on recent advances in CH activation, photoredox and electrochemistry, continuous chemistry, and application of biocatalysis in synthesis Revamps chapters to include new and additional examples of chemistry that have been demonstrated at a practical scale
Author: Roman Valiulin Publisher: Walter de Gruyter GmbH & Co KG ISBN: 3110608375 Category : Science Languages : en Pages : 249
Book Description
This book summarizes 100 essential mechanisms in organic chemistry ranging from classical such as the Reformatsky Reaction from 1887 to recently elucidated mechanism such as the copper(I)-catalyzed alkyne-azide cycloaddition. The reactions are easy to grasp, well-illustrated and underpinned with explanations and additional information.
Author: John D. Roberts Publisher: ISBN: 9780805383218 Category : Chemistry, Organic Languages : en Pages : 1596
Book Description
Introduction what is organic chemistry all about?; Structural organic chemistry the shapes of molecules functional groups; Organic nomenclature; Alkanes; Stereoisomerism of organic molecules; Bonding in organic molecules atomic-orbital models; More on nomenclature compounds other than hydrocarbons; Nucleophilic substitution and elimination reactions; Separation and purification identification of organic compounds by spectroscopic techniques; Alkenes and alkynes. Ionic and radical addition reactions; Alkenes and alkynes; Oxidation and reduction reactions; Acidity or alkynes.
Author: G. H. Williams Publisher: Elsevier ISBN: 1483151131 Category : Science Languages : en Pages : 142
Book Description
Homolytic Aromatic Substitution deals with the theoretical aspects of homolytic aromatic substitution reactions. The effect of various kinds of free radicals on the substitution of atoms or groups (usually hydrogen) attached to aromatic nuclei is examined, and the preparative use of homolytic substitution reactions is also considered. This book is comprised of seven chapters and begins with an introduction to the general characteristics of homolysis, along with homolytic and heterolytic aromatic substitution. The discussion then turns to the various theoretical approaches used to rationalize aromatic substitution, particularly those that are germane to a consideration of the problems of orientation and reactivity in homolytic substitution. The following chapters explore homolytic arylation reactions, including those between aryl radicals and aromatic substrates; relative rates of arylation and partial rate factors for phenylation; the reaction mechanism underlying intramolecular arylation; and homolytic alkylation reactions. The final chapter deals with hydroxylation and some other substitution reactions such as benzoyloxylation, acetyloxylation, halogenation, amination and amidation, and mercuration. This monograph will be of interest to organic chemists.
Author: Peter E. Kündig Publisher: Springer ISBN: 3540369678 Category : Science Languages : en Pages : 236
Book Description
Metal-arene pi-complexes show a rich and varied chemistry. The metal adds a third dimension to the planar aromatic compounds and coordination of a metal to an arene thus not only altering the reactivity of ring-carbons and substituents but also makes possible reactions that lead to chiral non-racemic products. This book, organized in nine chapters and written by leading scientists in the field provides the reader with an up-to-date treatise on the subject organized according to reaction type and use. It covers the wide spectrum of arene activation: from the electrophilic activation of h6-bound arene by pi-Lewis acid metal complex fragments, to reactions of nucleophilic h2-coordinated arene complexes. The preparation of complexes is detailed, as are the scope, limitations and challenges of reactions in contemporary pi-arene metal chemistry with special attention given to asymmetric transformations. The emphasis of the book is on transformations of interest to organic synthesis and on the use of the complexes as catalysts or as chiral ligands. The book is written for academic and industrial researchers in organic, organometallic, and inorganic chemistry as well as for advanced chemistry students.
Author: Francois Terrier
Author: Francois Terrier
Author: Oleg N. Chupakhin
Author: Joseph Miller
Author: Mandeep Dalal
Author: Stéphane Caron
Author: Roman Valiulin
Author: John D. Roberts
Author: G. H. Williams
Author: Peter E. Kündig
Author: J. Miller (chemist.)