E-Book Overview
Content: v. 1. Three-membered heterocycles, together with all fused systems containing a three-membered heterocyclic ring / volume editor, Albert Padwa -- v. 2. Four-membered heterocycles together with all fused systems containing a four-membered heterocyclic ring / volume editor, Christian Stevens -- v. 3. Five-membered rings with one heteroatom together with their benzo and other carbocyclic-fused derivatives / volume editors, Gurnos Jones, Christopher A. Ramsden -- v. 4. Five-membered rings with two heteroatoms, each with their fused carbocyclic derivatives / volume editor, John Joule -- v. 5. Five-membered rings: triazoles, oxadiazoles, thiadiazoles and their fused carbocyclic derivatives / volume editor, Viktor V. Zhdankin -- v. 6. Other five-membered rings with three or more heteroatoms, and their fused carbocyclic derivatives / volume editor, Viktor V. Zhdankin -- v. 7. Six-membered rings with one heteroatom, and their fused carbocyclic derivatives / volume editor, David StC. Black -- v. 8. Six-membered rings with two heteroatoms, and their fused carbocyclic derivatives / volume editor, R. Alan Aitken -- v. 9. Six-membered rings with three or more heteroatoms, and their fused carbocyclic derivatives / volume editor, Kenneth Turnbull -- v. 10. Ring systems with at least two fused heterocyclic five- or six-membered rings with no bridgehead heteroatom / volume editor, Ray C.F. Jones -- v. 11. Bicyclic 5-5 and 5-6 fused ring systems with at least one bridgehead (ring junction) N / volume editor, Janine Cossy -- v. 12. Five- and six-membered fused systems with bridgehead (ring junction) heteroatoms concluded: 6-6 bicyclic with one or two N or other heteroatoms; polycyclic; spirocyclic / volume editor, Keith Jones -- v. 13. Seven-membered heterocyclic rings and their fused derivatives / volume editor, George R. Newkome -- v. 14. Eight-membered and larger heterocyclic rings and their fused derivatives, other seven-membered rings / volume editor, George R. Newkome -- v. 15. Cumulative subject index
E-Book Content
4.01 Pyrazoles L. Yet Albany Molecular Research, Inc., Albany, NY, USA ª 2008 Elsevier Ltd. All rights reserved. 4.01.1 4.01.1.1 4.01.2
Introduction
3
Survey of Possible Structures
5
Theoretical Methods
5
4.01.2.1
Structure and Reactivity of Pyrazoles
5
4.01.2.2
Structure and Reactivity of Indazoles
7
4.01.3
Experimental Structural Methods
8
4.01.3.1
X-Ray Diffraction
8
4.01.3.2
Microwave and Photoelectron Spectroscopy
4.01.3.3
l
H and 13C NMR Spectroscopy
4.01.3.3.1 4.01.3.3.2
9 10
Aromatic systems Nonaromatic systems
10 12
4.01.3.4
I9
4.01.3.5
15
N NMR Spectroscopy
4.01.3.6
13
C and 15N CP/MAS NMR Spectroscopy
4.01.3.7
UV and IR Spectroscopy
15
Mass Spectrometry and Ion Cyclotron Resonance Studies
16
4.01.3.8 4.01.4 4.01.4.1
F NMR Spectroscopy
17
Stability and Stabilization
17
Thermochemistry
17
Tautomerism
4.01.4.2.1 4.01.4.2.2
4.01.5
14
Thermodynamic Aspects
4.01.4.1.1
4.01.4.2
13 13
17
Annular (ring) tautomerism Substituent (chain) tautomerism
17 19
Reactivity of Fully Conjugated Rings
21
4.01.5.1
Thermal and Photochemical Reactions
21
4.01.5.2
Electrophilic Attack at Nitrogen
22
4.01.5.2.1 4.01.5.2.2 4.01.5.2.3 4.01.5.2.4 4.01.5.2.5 4.01.5.2.6 4.01.5.2.7 4.01.5.2.8 4.01.5.2.9
4.01.5.3
Proton acids on neutral