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Chemical Creativity: Ideas from the Work of Woodward, Hückel, Meerwein, and Others

ISBN: 978-3-527-29754-2
207 pages
May 1999
Chemical Creativity: Ideas from the Work of Woodward, Hückel, Meerwein, and Others (3527297545) cover image
Where are the origins of chemical ideas? How did the pioneers in chemistry recognize the fundamental intellectual issues of their time? What skills of reasoning and experiment did they use to solve these problemes? How did the circumstances of personality and competition influence their careers and scientific accomplishments? If we can answer these questions, we may be able to improve our own chances of success in research.


»This is a marvelous book of people and chemical ideas! The author, Jerry Berson, is known as a chemical stylist, a physical organic chemist possessed of the highest analytical powers. In a unique approach to the history of chemistry (indeed the history of science) he brings that style, as well as his insider's knowledge and a perceptive sensivity to the societal setting of chemists, to the analysis of some key chapters in modern organic chemistry.« Roald Hoffmann, Nobel Laureate
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INTRODUCTION
The Nature of Science and the History of Science
An Experiment
DISCOVERIES MISSED, DISCOVERIES MADE -
TWO CASE STUDIES OF CREATIVITY IN CHEMISTRY
Science and the Individual
Diels, Alder, Their Competitors, and the Discovery of the Diene Synthesis
Thiele
The Alternation Effect and the Discovery of Orbital Symmetry
ERICH HÜCKEL AND THE THEORY OF AROMATICITY -
REFLECTIONS ON THEORY AND EXPERIMENT
Debye-Hückel Theory of Electrolytic Solutions
Nature of the Double Bond
Hybridization in Double Bonds
Benzene Problem
MO Description of Conjugated Cyclic Compounds
Orbital Symmetry (Woodward-Hoffmann Rules)
Extension of Cyclic p-Electron MO Theory to Transition States of Pericyclic Reactions
Violation of Hund's Rule in Biradicals
Reflections on Hückel's Career
THE DIENONE-PHENOL MYSTERIES
Isolations of Estrogens
Approaches to the Estrogens by Aromatization of Ring A
Alicyclic Steroids
Woodward's Challenge
Misgivings about the Structures
Why did Woodward Undertake the Correction of the Phenolic Structures?
Woodward and the Total Synthesis of Steroids
Approaches and Achievements
Mechanistic Motivation
MEDITATIONS ON THE SPECIAL CONVICTIVE POWER OF SYMMETRIZATION EXPERIMENTS
Enolization as a Mechanism of Symmetrization
The Menthone Problem
Tricyclene and the Wagner-Meerwein Rearrangement
The Pinacol Controversy
The Favorskii Rearrangement
Symmetrization
Racemization Machines with no Achiral Parts
Direct Nucleophilic Displacement Reaction
The Walden Inversion
Biological and Evolutionary Attraction of Symmetry
Epilogue
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Jerome A. Berson received a B.S. in chemistry from the City College of New York in 1944. After a brief period in the industry with Hoffmann-La Roche in New Jersey, he served in the Army of the United Stated (1944-1946, China-Burma-India Theater). In 1946, he entered graduate study at Columbia University where he took M.A. and Ph.D. degrees with W. von E. Doering. He was a post-doctoral fellow at Harvard University (with R. B. Woodward) in 1949-1950. Subsequently, he taught chemistry at the University of Southern California (1950-1963), the University of Wisconsin (1963-1969), and Yale University (since 1969). He is presently Sterling Professor Emeritus of Chemistry at Yale.
His research group has concentrated its efforts on the elucidation of reaction mechanisms and the synthesis of molecules of theoretical interest. In the latter category, a principal activity has been the study of non-Kekulé compounds.
In recent years, he has written on the history of science, producing a number of articles and two books, both published by Wiley-VCH: Chemical Discovery and the Logicians' Program (2003) and the present book, Chemical Creativity.
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