Strained Organic Molecules

Preface

Chapter 1 Energy and Entropy

l.A Reference States and Reference Books

l.B Origin of Molecular Strain

l.C Thermodynamics and Symmetry

l.D Potential Energy Curves and Zero-Point Energy

Chapter 2 Cyclopropane and Cyclobutane

2.A Conceptual Models for the Bonding in Cyclopropane

2.B Selected Reactions of Cyclopropanes

2.C Cyclobutane

Chapter 3 Unique Strained Groupings or Building Blocks

3.A Cycloalkanes

3.B Bicyclic, Spirocyclic, and Bridged Hydrocarbons

3.C Tetrahedrane

3.D Strained Alkenes: Molecules Lacking Torsional Strain

3.E Torsionally Distorted ð Bonds

3.F "Bredt Compounds" and Cyclic Alienes

3.G Cycloalkynes, Benzyne, and Cyclocumulenes

3.H Distorted Aromatic Rings

Chapter 4 Polycycles: Aesthetics, Rearrangements, and Topology

4.A Adamantanes and Higher Homologues

4.B Iceane

4.C Miscellaneous Acid-Catalyzed Rearrangements

4.D Strained Molecules of Formula (CH)n

4.E Additional Polycyclic Molecules

4.F Molecular Topology

Chapter 5 Kinetic and Thermodynamic Stability

5.A Introduction

5.B Orbital Symmetry and Stabilities of Benzene Valence Isomers

5.C Transition Metals and Strained Carbocyclic Molecules

5.D Strained Heterocyclic Molecules

5.E Substituted Derivatives of Strained Molecules

Chapter 6 A Potpourri of Pathologies

6. A When is Tetracoordinate Carbon Tetrahedral?

6.B Inverted Tetrahedra, Propellanes, Buttaflanes, and Paddlanes

6.C Planar Methane and Its Derivatives

6.D Five- and Six-Coordinate Carbon

Addendum

Index