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Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides

Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides

Michael P. Doyle, M. Anthony McKervey, Tao Ye

ISBN: 978-0-471-13556-2 January 1998 652 Pages


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This much-needed resource brings together a wealth of procedures for the synthesis and practical use of diazocarbonyl compounds. It features methods for the preparation of important catalysts and for applications of diazocarbonyl compounds within each of the main transformation categories-including in-depth coverage of cyclopropanation, C-H and X-H insertion, Wolff rearrangement, ylide formation, aromatic cycloaddition and substitution, and many other useful reactions.

Written by leading experts in the field, this book contains cutting-edge material on highly enantioselective transformations, and presents new ways of thinking about diazocarbonyl compounds and their applications, from donor-acceptor cyclopropanes in organic synthesis to macrocyclic cyclopropanation.

Complete with illustrative examples of procedures in each chapter, clear diagrams, and a detailed bibliography, this practical reference gives readers the tools they need to put diazocarbonyl compounds to work for their own projects-an invaluable source of guidance for synthetic organic chemists, chemical scientists, and advanced students.
Synthesis of Alpha-Diazocarbonyl Compounds.

Catalysts for Metal Carbene Transformations.

Insertion Reactions.

Intermolecular Cyclopropanation and Related Addition Reactions.

Intramolecular Cyclopropanation and Related Addition Reactions.

Cycloaddition and Substitution Reactions with Aromatic and Heteroaromatic Compounds.

Generation and Reactions of Ylides from Diazocarbonyl Compounds.

X-H Insertion Reactions of Diazocarbonyl Compounds (X = N,O,S,Se,P, Halogen).

The Wolff Rearrangement and Related Reactions.

Reactions of Alpha-Diazocarbonyl Compounds with Aldehydes and Ketones.

Acid-Promoted Cyclization of Unsaturated and Aromatic Diazo Ketones.

Miscellaneous Diazocarbonyl Reactions.