Carbocation chemistry: applications in organic synthesis PDF
Preview Carbocation chemistry: applications in organic synthesis
Carbocation Chemistry Applications in Organic Synthesis NEW DIRECTIONS in ORGANIC and BIOLOGICAL CHEMISTRY Series Editor: Philip Page PUBLISHED TITLES Activated Metals in Organic Synthesis Carbocation Pedro Cintas The Anomeric Effect Chemistry Eusebio Juaristi and Gabriel Cuevas C-Glycoside Synthesis Maarten Postema Applications in Capillary Electrophoresis: Theory and Practice Patrick Camilleri Organic Synthesis Carbocation Chemistry: Applications in Organic Synthesis Jie Jack Li Chemical Approaches to the Synthesis of Peptides and Proteins Paul Lloyd-Williams, Fernando Albericio, and Ernest Giralt Chiral Sulfur Reagents M. Mikolajczyk, J. Drabowicz, and P. Kielbasins´ki Chirality and the Biological Activity of Drugs edited by Roger J. Crossley Jie Jack Li Concerted Organic and Bio-organic Mechanisms University of San Francisco Andrew Williams California, USA Cyclization Reactions C. Thebtaranonth and Y. Thebtaranonth Dianion Chemistry in Organic Synthesis Charles M. Thompson Mannich Bases: Chemistry and Uses Maurilio Tramontini and Luigi Angiolini Modern NMR Techniques for Synthetic Chemistry Julie Fisher Organozinc Reagents in Organic Synthesis Ender Erdik Boca Raton London New York CRC Press is an imprint of the Taylor & Francis Group, an informa business Carbocation Chemistry Applications in Organic Synthesis edited by Jie Jack Li University of San Francisco California, USA Boca Raton London New York CRC Press is an imprint of the Taylor & Francis Group, an informa business CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2017 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S. Government works Printed on acid-free paper Version Date: 20160815 International Standard Book Number-13: 978-1-4987-2908-6 (Hardback) This book contains information obtained from authentic and highly regarded sources. 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Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com Contents Series Preface ...........................................................................................................vii Preface.......................................................................................................................ix Editor ........................................................................................................................xi Contributors ...........................................................................................................xiii Chapter 1 Introduction ..........................................................................................1 Jie Jack Li Chapter 2 Nucleophilic Aliphatic Substitution: S 1 ...........................................33 N Yu Feng, Safiyyah Forbes, and Jie Jack Li Chapter 3 Nucleophilic Aliphatic Substitution: S 2 ...........................................71 N John W. Lippert III Chapter 4 Electrophilic Addition to Alkenes ......................................................87 Adam M. Azman Chapter 5 Electrophilic Aromatic Substitution .................................................117 Jie Jack Li Chapter 6 Rearrangement and Fragmentation Reactions .................................151 Hannah Payne, Sharon Molnar, and Micheal Fultz Index ......................................................................................................................195 v Series Preface NEW DIRECTIONS IN ORGANIC AND BIOLOGICAL CHEMISTRY Organic and biological chemistry forms a major division of chemistry research and continues to develop rapidly, with new avenues of research opening up in parallel with exciting progress in existing activities. This book series encompasses cutting- edge research across the entire field, including important developments in both new and fundamental aspects of the discipline. It covers all aspects of organic and bio- logical chemistry. The series is designed to be very wide in scope and provides a vehicle for the publication of edited review volumes, monographs, and “How to” manuals of experimental practice. Examples of topic areas would include Synthetic chemistry Natural products chemistry Materials chemistry Supramolecular chemistry Electrochemistry Organometallic chemistry Green chemistry, including catalysis and biocatalysis Polymer chemistry Protein–protein, protein–DNA, protein–lipid, and protein–carbohydrate interactions Enzyme/protein mechanism, including cofactor–protein interactions and mechanisms of action Pathways in cofactor (including metal) homeostasis Synthetic biology—the engineering of natural systems toward novel functions Development of physical methods and tools, for example, new spectroscopic methods, imaging techniques, and tools The volumes highlight the strengths and weaknesses of each topic and emphasize the latest developments emerging from current and recent research. The series is of primary interest to academic and industrial chemists involved broadly in organic, materials, biological, and medicinal chemistry. It is also intended to provide research students with clear and accessible books covering different aspects of the field. Philip C. Bulman Page, DSc, FRSC, CChem Series Editor School of Chemistry, University of East Anglia, Norwich, UK vii Preface Carbocation chemistry is one of the most important fields of organic chemistry. Yet, counter intuitively, the field is not represented by the number of books published. Indeed, the last book on carbocation chemistry was published a decade ago and the materials were mostly geared toward specialists in the field. This book, in contrast, is written by and for synthetic chemists, who are more interested in how to apply carbocation chemistry in synthesis. To that end, Chapter 1 summarizes the advancement of our understanding of the mechanisms of carbocation chemistry during the last decade. Chapters 2 and 3 cover the S 1 and S 2 reactions, respectively. The implication of carbocation intermedi- N N ates for the S 1 reactions is universal, the connection between carbocation interme- N diates and S 2 reactions is somewhat less rigorous. Chapter 4 covers electrophilic N addition to alkenes, and Chapter 5 covers electrophilic aromatic substitution, both of which are critical to our learning of the fundamentals of organic chemistry. Last but not least, Chapter 6 entails fragmentation and rearrangement reactions, which have historically shed much light on the mechanisms of carbocation chemistry and are now important to synthesis as well. I want to thank all the authors who painstakingly contributed to this manuscript. I am also indebted to John Hendrix for proofreading my chapters. As a consequence, this book is not just for chemists whose expertise is carboca- tion chemistry. The experts could learn a thing or two from the advancement of carbocation chemistry in the last decade. More than that, any practitioner in organic synthesis will find this manuscript helpful in gauging the literature of the last decade. Therefore, this book is useful to senior undergraduate students, graduate students, professors teaching organic chemistry, and researchers in pharmaceutical and chem- ical companies. Jie Jack Li San Francisco ix
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