PREFACE
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OUR
U N D E R S T A N D I N G O F T H E R E A C T I O N S of popular reagents dates
back to the early 1920s, when Lewis, L o w r y , and Br0nsted began developing their acid-base theories. Shortly thereafter, Lapworth, who had pioneered the study of carbonyl addition reaction mechanisms in the early 1900s, proposed the classification of polar reagents into the classes we know today as electrophiles and nucleophiles. In the early 1930s, Ingold proposed that nucleophilic displacement reactions be divided into S 1 and S 2 types. Could he have known how broadly these classifications might apply? Consider the novel gas-phase displacement by a hydride ion of benzene from a chromium center: H + C H Cr(CO) — • HCr(CO) + C H Squires and Lane recently found that this reaction may be similar to a simple S 2 reaction. The present book is the outgrowth of a symposium on nucleophilicity held in Chicago in September 1985. The chapters were contributed b y symposium participants. Although it is impossible to cover the topic completely in this format, we attempted to arrange the symposium and solicit chapters so as to cover the major areas of endeavor. We apologize to those whose interests or works may have been slighted. This book and the symposium upon which it is based were made possible b y the financial support of the A C S Division of Organic Chemistry, the U.S. Army Research Office, and the Petroleum Research Fund, administered b y the American Chemical Society. We gratefully acknowledge this support. Also, we thank the contributors to this book for their timely submission of manuscripts. N
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J. MILTON HARRIS S A M U E L P. M C M A N U S
Department of Chemistry University of Alabama in Huntsville Huntsville, A L 35899 September 1985
xiii Harris and McManus; Nucleophilicity Advances in Chemistry; American Chemical Society: Washington, DC, 1987.
