Advances in Heterocyclic Chemistry (eBook)

Cover 1
Advances in Heterocyclic Chemistry, Volume 16 4
Copyright Page 5
Contents 6
Contributors 8
Preface 10
Chapter 1. Base-Catalyzed Hydrogen Exchange 12
I. Introduction 12
II. Experimental Methods 13
III. Five-Membered Rings 15
IV. Six-Membered Rings 29
V. Discussion 39
Chapter 2. 1,2,3-Triazoles 44
I. Introduction 44
II. Synthesis of the Triazole Ring 45
III. Structure and Physical Properties 74
IV. Reactions of 1,2,3-Triazoles 80
Chapter 3. Nitrogen-Bridged Six-Membered Ring Systems: 7-Azabicyclo[2.2.1]-hepta-2,5-dienes, Naphthalen-1,4-imines, and Anthracen-9,10-imines 98
I. Introduction 98
II. 7-Azabicyclo[2.2.1] heptanes and 7-Azabicyclo[2.2. heptadienes 100
III. Naphthalen-1,4-imines 113
IV. Anthracen-9,10-imines 128
Chapter 4. Advances in Homolytic Substitution of Heteroaromatic Compounds 134
I. Introduction 134
II. Alkylation 136
III. Acylation 161
IV. a-0xyalkylation 170
V. Amidation 177
VI. Arylation 182
VII. Other Reactions 189
VIII. Conclusions 190
Chapter 5. Recent Advances in the Chemistry of Dibenzothiophenes 192
I. Introduction 192
II. Naturally Occurring Dibenzothiophenes 194
III. Molecular Structure and Physical Properties of Dibenzothiophenes 198
IV. Synthesis of Dibenzothiophenes 232
V. Ring-Reduced Dibenzothiophenes 242
VI. Derivatives of Dibenzothiophene 250
VII. Polymers of Dibenzothiophenes 296
Chapter 6. Cationic Polar Cycloaddition 300
I. Introduction 300
II. Polar Cycloadditions in Which Cationic Aromatic Systems Act as Electrophiles 301
III. Polar Cycloadditions in Which the Electrophilic System Contains Two Atoms of an Aromatic Ring 316
V. The Mechanism of Polar Cycloaddition 327
Author Index 336
Cumulative Index of Titles 358