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Quinone Methides

S. E. Rokita

ISBN: 978-0-470-45287-5 February 2009 456 Pages



Multidisciplinary perspectives and approaches to quinone methides research

The Wiley Series on Reactive Intermediates in Chemistry and Biology investigates reactive intermediates from the broadest possible range of disciplines. The contributions in each volume offer readers fresh insights into the latest findings, emerging applications, and ongoing research in the field from a diverse perspective.

This inaugural volume in the series, Quinone Methides, represents the first book devoted to this fascinating and useful intermediate. The authors of this work reflect the many disciplines and approaches to quinone methides research. The volume therefore covers a broad range of topics, including theoretical treatments, generation and detection of intermediates, characterization and applications in chemistry and biochemistry, and biological reactivity. Among the chapters are:

  • Photochemical generation and characterization of quinone methides
  • Quinone methide stabilization by metal complexation

  • Self-immolative dendrimers based on quinone methides

  • Characterization of quinone methides by spectral global fitting and 13C labeling

  • Formation and reactions of xenobiotic quinone methides in biology

  • Quinone methides in lignification

With this collection of topics, readers already familiar with quinone methides have the opportunity to advance their own research by discovering new inspiration and opportunities in allied areas. Moreover, the range of topics and perspectives covered make this volume accessible to readers with a broad range of interests, including organic and physical chemistry, biochemistry, biotechnology, and pharmaceutics.

Chapter 1: Photochemical Generation and Characterization of Quinone-Methides (Matthew Lukeman).

Chapter 2: Modeling Properties and Reactivity of Quinone Methides by DFT calculations (Mauro Freccero and Filippo Doria).

Chapter 3: Quinone Methide Stabilization by Metal Complexation (David Milstein and Elena Poverenov).

Chapter 4: Intermolecular Applications of o-Quinone Methides (o-QMs) Anionically Generated at Low Temperatures; Kinetic Conditions (Thomas Pettus and Liping Pettus).

Chapter 5: Self-Immolative Dendrimers Based on Quinone Methides (Doron Shabat and Rotem Erez).

Chapter 6: Ortho-Quinone Methides in Tocopherol Chemistry (Thomas Rosenau and Stefan Böhmdorfer).

Chapter 7: Characterizing Quinone Methides by Spectral Global Fitting and 13C Labeling (Edward B. Skibo).

Chapter 8: Natural Diterpene and Triterpene Quinone Methides: Structures, Synthesis and Biological Potentials (Qibing Zhou).

Chapter 9: Reversible Alkylation of DNA by Quinone Methides (Steven E. Rokita).

Chapter 10: Formation and Reactions of Xenobiotic Quinone Methides in Biology (Judy L. Bolton and John A. Thompson).

Chapter 11: Quinone Methides and Aza-Quinone Methides as Latent Alkylating Species in the Design of Mechanism-Based Inhibitors of Serine Proteases and ß-Lactamases (Michèle Reboud-Ravaux and Michel Wakselman).

Chapter 12: Quinone Methides in Lignification (John Ralph, Paul F. Schatz, Fachuang Lu,Hoon Kim, Takuya Akiyama, and Stephen F. Nelsen).

"Well produced, concise and well illustrated by structures, reactions and spectra." (Phytochemistry, January 2010)

"I believe that many chemists, both in academia and in industry, will find this volume to be a useful addition to their libraries. I would also recommend this book for institutional library collections, where it will serve as a valuable reference source." (Journal of the American Chemical Society, October 2009)

"This volume, part of a series structured to illustrate the widest range of literature on specific reactive intermediaries, illustrates the literature on quinone methides, quinone analogues in which carbonyl oxygens are replaced by methylene groups." (Book News, September 2009)