Jones / Bean / Blomquist The Chemistry of Pyrroles

Organic Chemistry: A Series of Monographs, Vol. 34
1. Auflage 2013
ISBN: 978-1-4832-1847-2
Verlag: Elsevier Science & Techn.
Format: PDF
Kopierschutz: 1 - PDF Watermark

E-Book, Englisch, 538 Seiten, Web PDF

The Chemistry of Pyrroles, Volume 34 aims to provide a comprehensive survey of the synthesis of simple pyrroles and to present, wherever possible, a mechanistic and theoretical rationale for the multitude of reactions known for pyrroles. The book discusses the structure and reactivity of pyrrole; the synthesis of the pyrrole ring; and the electrophilic substitution of the pyrrole ring. The text also describes the oxidation and reduction of the pyrrole ring; the rearrangement and addition reactions; and the ketones, aldehydes, and carboxylic acid derivatives of pyrrole. Alkylpyrroles and related compounds; hydroxy- and aminopyrroles and related compounds; and azafulvenes are also considered. The book further tackles the physico-organic properties of pyrrole. Chemists and researchers of pyrrole chemistry will find the text invaluable.

Autoren/Hrsg.

Jones, R. Alan

Bean, Gerritt P.

Blomquist, Alfred T.

Wasserman, Harry H.

Inhaltsverzeichnis

1;Front Cover;1
2;The Chemistry of Pyrroles;4
3;Copyright Page;5
4;Table of Contents;8
5;Foreword;6
6;Abbreviations and Nomenclature;7
7;Chapter 1. INTRODUCTION;12
7.1;References;15
8;Chapter 2. THE STRUCTURE AND REACTIVITY OF PYRROLE;18
8.1;A. Molecular and Electronic Structure of Pyrrole;18
8.2;B. Aromaticity and Resonance Energy;22
8.3;C. Molecular Orbital Calculations on Pyrroles;28
8.4;D. Theoretical Treatment of the Reactivity of Pyrrole with Electrophiles;45
8.5;References;57
9;Chapter 3. THE SYNTHESIS OF THE PYRROLE RING;62
9.1;A. Introduction;62
9.2;B. 2+2 Carbon Units;62
9.3;C. 1+3 Carbon Units;85
9.4;D. From Four Carbon Units;88
9.5;E. Ring-contractions;104
9.6;F. Miscellaneous Reactions;112
9.7;References;114
10;Chapter 4. ELECTROPHILIC SUBSTITUTION OF THE PYRROLE RING;126
10.1;A. Introduction;126
10.2;B. Protonation of the Pyrrole Ring;128
10.3;C. Nitration and Nitrosation;133
10.4;D. Halogenation;140
10.5;E. C-Alkylation Reactions;154
10.6;F. C-Acylation Reactions;162
10.7;G. Reactions with Carbonyl Compounds;175
10.8;H. Reactions of the Pyrryl Anion;184
10.9;I. Miscellaneous Electrophilic Reactions;198
10.10;J. Summary of the Reactivity of Pyrrole and Orientation Effects of Substituents;203
10.11;References;206
11;Chapter 5. OXIDATION AND REDUCTION OF THE PYRROLE RING;220
11.1;A. The Reactions of Pyrroles with Molecular Oxygen;220
11.2;B. Oxidation by Chemical Reagents;230
11.3;C. Anodic Oxidation of Pyrroles;247
11.4;D. Reduction of the Pyrrole Ring;249
11.5;References;254
12;Chapter 6. REARRANGEMENT AND ADDITION REACTIONS;260
12.1;A. Thermal Rearrangements retaining the Pyrrole Ring;260
12.2;B. Photochemical Rearrangements retaining the Pyrrole Ring;263
12.3;C. Addition Reactions;267
12.4;D. Reactions with Radicals;287
12.5;References;288
13;Chapter 7. KETONES, ALDEHYDES AND CARBOXYLIC ACID DERIVATIVES OF PYRROLE;294
13.1;A. Resonance Interaction between the Pyrrole Ring and the Carbonyl Substituent;294
13.2;B. Chemical Reactivity;300
13.3;References;346
14;Chapter 8. ALKYLPYRROLES AND RELATED COMPOUNDS;356
14.1;A. Tautomerism;390
14.2;B. Chemical Reactivity;360
14.3;C. Silylpyrroles;375
14.4;D. Pyrrolophanes and other Bridged Pyrroles;377
14.5;References;384
15;Chapter 9. HYDROXY– AND AMINOPYRROLES AND RELATED COMPOUNDS;390
15.1;A. Tautomerism;390
15.2;B. Synthesis;395
15.3;C. Chemical Reactivity;407
15.4;D. Pyrrylthiols;427
15.5;References;430
16;Chapter 10. AZAFULVENES;436
16.1;A. Structure and Reactivity;436
16.2;B. Synthesis;440
16.3;C. Spectroscopic Properties;444
16.4;References;448
17;Chapter 11. PHYSICO-ORGANIC PROPERTIES OF PYRROLE;450
17.1;A. Molecular Association;450
17.2;B. Basicity and Acidity Measurements;457
17.3;C. Dipole Moments;462
17.4;D. Polarographic Properties;469
17.5;E. Electronic Spectra;471
17.6;F. IR and Raman Spectra;474
17.7;G. NMR Spectra;483
17.8;H. Mass Spectra;489
17.9;References;497
18;Index;514