雜環(huán)化學(xué)

內(nèi)容概要

The material of the second edition has been revised with two principal aims in mind. The first is to bring the contents up to date. To this end, Chapter 1 and several parts of other chapters have been rewritten, the references have been updated (with more emphasis given to recent review articles) and several new reaction schemes have been introduced. These new schemes are intended to illustrate aspects of heterocyclic chemistry that are becoming more important. Organopalladium and other organometaUic species are increasingly used in ring synthesis and in substitution reactions; some of the new schemes provide examples. New applications of heterocyclic compounds as pharmaceuticals, as intermediates in organic synthesis and as ligands are also illustrated.

書籍目錄

Preface to the third edition.Preface to the second editionPreface to the first editionA cknowledgemen ts1 Introduction: uses of heterocyclic compounds2 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  Problems3 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  Problems4 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  Problems5 Six-membered ring compounds with one heteroatom6 Five-memeberd ring compounds with one heteroatom7 Six-membered ring compounds with two or mor heteroatoms8 Five-membered ring compoumnds with two or more heteroatoms9 Three-and four-membered ring compounds10 Seven-membered ring compoumds11 NomenclatureAnswers and references to selected problemsIndex

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