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The Chemistry of Heterocyclic Compounds, Volume 59: Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry

Toward Heterocycles and Natural Products. Edited by Albert Padwa and William H. Pearson.

ISBN: 0-471-38726-6

SYNTHETIC APPLICATIONS OF 1,3-DIPOLAR CYCLOADDITION

CHEMISTRY TOWARD HETEROCYCLES

AND NATURAL PRODUCTS

This is the ﬁfty-ninth volume in the series

THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS

A SERIES OF MONOGRAPHS

EDWARD C. TAYLOR AND PETER WIPF, Editors

ARNOLD WEISSBERGER, Founding Editor

SYNTHETIC APPLICATIONS

OF 1,3-DIPOLAR

CYCLOADDITION

CHEMISTRY TOWARD

HETEROCYCLES AND

NATURAL PRODUCTS

Edited by

Albert Padwa

Department of Chemistry

Emory University

William H. Pearson

Department of Chemistry

University of Michigan

AN INTERSCIENCE 1 PUBLICATION

JOHN WILEY & SONS, INC.

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ISBN 0-471-22190-2

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The Chemistry of Heterocyclic Compounds

Introduction to the Series

The chemistry of heterocyclic compounds is one of the most complex and

intriguing branches of organic chemistry, of equal interest for its theoretical

implications, for the diversity of its synthetic procedures, and for the physiological

and industrial signiﬁcance of heterocycles.

The Chemistry of Heterocyclic Compounds has been published since 1950 under

the initial editorship of Arnold Weissberger, and later, until his death in 1984,

under the joint editorship of Arnold Weissberger and Edward C. Taylor. In 1997,

Peter Wipf joined Prof. Taylor as editor. This series attempts to make the

extraordinarily complex and diverse ﬁeld of heterocyclic chemistry as organized

and readily accessible as possible. Each volume has traditionally dealt with

syntheses, reactions, properties, structure, physical chemistry, and utility of com-

pounds belonging to a speciﬁc ring system or class (e.g., pyridines, thiophenes,

pyrimidines, three-membered ring systems). This series has become the basic

reference collection for information on heterocyclic compounds.

Many broader aspects of heterocyclic chemistry are recognized as disciplines of

general signiﬁcance that impinge on almost all aspects of modern organic

chemistry, medicinal chemistry, and biochemistry, and for this reason we initiated

several years ago a parallel series entitled General Heterocyclic Chemistry, which

treated such topics as nuclear magnetic resonance, mass spectra, and photoche-

mistry of heterocyclic compounds, the utility of heterocycles in organic synthesis,

and the synthesis of heterocycles by means of 1,3-dipolar cycloaddition reactions.

These volumes were intended to be of interest to all organic, medicinal, and

biochemically oriented chemists, as well as to those whose particular concern is

heterocyclic chemistry. It has, however, become increasingly clear that the above

distinction between the two series was unnecessary and somewhat confusing, and

we have therefore elected to discontinue General Heterocyclic Chemistry and to

publish all forthcoming volumes in this general area in The Chemistry of Hetero-

cyclic Compounds series.

It is a major challenge to keep our coverage of this immense ﬁeld up to date. One

strategy is to publish Supplements or new Parts when merited by the amount of new

material, as has been done, inter alia, with pyridines, purines, pyrimidines,

quinazolines, isoxazoles, pyridazines and pyrazines. The chemistry and applica-

tions to synthesis of 1,3-dipolar cycloaddition reactions in the broad context of

organic chemistry were ﬁrst covered in a widely cited two-volume treatise edited by

Prof. Albert Padwa that appeared in 1984. Since so much has been published on this

fascinating and broadly useful subject in the intervening years, we felt that a

Supplement would be welcomed by the international chemistry community, and we

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