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

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.

The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community. The series consists of topic related volumes edited by renowned editors with contributions of experts in the field.

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.

An accessible and step-by-step exploration of organic reaction mechanisms In Reaction Mechanisms in Organic Chemistry, eminent researcher Dr. Metin Balci delivers an excellent textbook for understanding organic reaction mechanisms. The book offers a way for undergraduate and graduate students to understand???rather than memorize???the principles of reaction mechanisms. It includes the most important reaction types, including substitution, elimination, addition, pericyclic, and C-C coupling reactions. Each chapter contains problems and accompanying solutions that cover central concepts in organic chemistry. Students will learn to understand the foundational nature of ideas like Lewis acids and bases, electron density, the mesomeric effect, and the inductive effect via the use of detailed examples and an expansive discussion of the concept of hybridization. Along with sections covering aromaticity and the chemistry of intermediates, the book includes: A thorough introduction to basic concepts in organic reactions, including covalent bonding, hybridization, electrophiles and nucleophiles, and inductive and mesomeric effects Comprehensive explorations of nucleophilic substitution reactions, including optical activity and stereochemistry of SN2 reactions Practical discussions of elimination reactions, including halogene elimination and Hofmann elimination In-depth examinations of addition reactions, including the addition of water to alkenes and the epoxidation of alkenes Perfect for students of chemistry, biochemistry, and pharmacy, Reaction Mechanisms in Organic Chemistry will also earn a place in the libraries of researchers and lecturers in these fields seeking a one-stop resource on organic reaction mechanisms.