The oxidation of organic compounds is one of the most important methods for the introduction and manipulation of functional groups. Among the most modern of these transformations is the use of the fascinating family of oxidants known as dioxiranes. A dioxirane can, by transferring one of its oxygen atoms to organic substrates, effect a remarkable array of oxidative processes such as epoxidation, C–H insertion, and heteroatom (N, S, P, I) oxidation. In addition to their versatility, dioxiranes can be generated catalytically under mild conditions and produce no toxic waste stream as part of the oxidation process. Moreover, some of the most exciting recent developments involve the enantioselective introduction of oxygen atoms via chiral dioxiranes. This book represents the first single volume dedicated to the comprehensive coverage of the myriad of oxidations of organic compounds performed by dioxiranes. The contents of this book are extracted from comprehensive reviews of the topics contained in the Organic Reactions series and cover the oxidation of alkenes and the oxidation of all other organic substrates. In addition, updated lists of references for each of the chapters are provided, bringing the literature coverage up to June 2008.
The authors of these chapters are among the pioneers of dioxirane chemistry and draw on extensive firsthand knowledge of the subject. As with all Organic Reactions content, the presentation emphasizes the preparative aspects of the reactions and pays particular attention throughout to substrate scope, limitations, structural and electronic influences, and stereochemical aspects. For the student or experienced practitioner, both general guidelines for carrying out the reactions as well as detailed experimental procedures are provided. Most importantly, all known examples of dioxirane oxidations have been compiled in easy–to–scan tables covering over 500 pages.
Oxidation of Organic Compounds by Dioxiranes is an indispensable working resource for organic and medicinal chemists as well as anyone wishing to own the definitive treatise on this fascinating and useful class of oxidants.
PREFACE AND ACKNOWLEDGMENTS.
1. DIOXIRANE EPOXIDATION OF ALKENES (Waldemar Adam, Chantu R. Saha–Möller, and Cong–Gui Zhao).
2. DIOXIRANE OXIDATIONS OF COMPOUNDS OTHER THAN ALKENES (Waldemar Adam, Cong–Gui Zhao, and Kavitha Jakka).