杂环化学THOMAS L.GILCHRIST（第3版）

Preface to the third edition.
Preface to the second edition
Preface to the first edition
A cknowledgemen ts
1 Introduction: uses of heterocyclic compounds
2 Aromatic heterocycles
　2.1 The common structural types
　　2.1.1 Six-atom， six-π-electron heterocycles
　　2.1.2 Five-atom， six-π-electron heterocycles
　　2.1.3 Benzo-fused ring systems
　　2.1.4 Other fused heterocycles
　2.2 Some criteria of aromaticity in heterocycles
　　2.2.1 Bond lengths
　　2.2.2 Ring current effects and chemical shifts in 1H NMR spectra
　　2.2.3 Molecular orbitals and delocalization energy
　　2.2.4 Resonance energies
　　2.2.5 Dewar resonance energies and other calculated resonance energies
　　2.2.6 General conclusions
　2.3 Aromatic character and other types of unsaturated heterocycles
　　2.3.1 Monocyclic systems that conform to the Huckel rule
　　2.3.2 Other unsaturated heterocycles
2.4 Reactivity of heteroaromatic compounds
2.5 Tautomerism of heteroaromatic compounds
Summary
Problems
3 Nonaromatic heleroeydes
3.1 Introduction
3.2 Bond angle strain
3.2.1 Angle strain and bonding in small-ring heterocycles
3.2.2 Some consequences of bond angle strain in sr~lall rings
3.2.3 Angle strain in larger rings
3.3 Torsional energy barriers
3.3.1 Single bonds
3.3.2 Double bonds and partial double bonds
3.4 Influence of bond lengths and van der Waals radii: conformadonal preferences of flexible heterocycles
3.4.1 Saturated six-membered heterocycles
3.4.2 Four- and flve-membered heterocycles
3.5 Other types of interaction in saturated heterocycles
3.5.1 'Through-bond' orbitaI interacflons: the anomeric effect
3.5.2 Attractive 'through-space' interactions
Summary
Problems
4 Ring synthesis
4.1 Introduction
4.2 Cycllzation reactions
4.2.1 Reaction types
4.2.2 Displacement at saturated carbon
4.2.3 Intramolecular nucleophilic addition to carbonyl groups
4.2.4 Intramolecular addition of nucleophiles to other double bends
4.2.5 Cyclization on to triple bonds
4.2.6 Radical cyclization
4.2.7 Carbene and nitrene cyclizatiml
4.2.8 Electrocycllc reactions
4.3 Cycloaddition reactions
4.3.1 Reaction types
4.3.2 1,3-Dipolar cycloaddition
4.3.3 Hetero-Diels Alder reactions
4.3.4 [2 + 2] Cyeloaddition
4.3.5 Cheletropic reactions
4.3.6 Ene reactions
Summary
Problems
5 Six-membered ring compounds with one heteroatom
6 Five-memeberd ring compounds with one heteroatom
7 Six-membered ring compounds with two or mor heteroatoms
8 Five-membered ring compoumnds with two or more heteroatoms
9 Three-and four-membered ring compounds
10 Seven-membered ring compoumds
11 Nomenclature
Answers and references to selected problems
Index