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Handbook of heterocyclic chemistry.
Heterocyclic compounds play a vital role in the metabolism of living cells. Their practical applications range from extensive clinical use to fields as diverse as agriculture, photography, biocide formulation and polymer science. Written by leading scholars and industry experts, the Handbook of Hete...
| Clasificación: | Libro Electrónico |
|---|---|
| Otros Autores: | |
| Formato: | Electrónico eBook |
| Idioma: | Inglés |
| Publicado: |
Oxford :
Elsevier,
©2010.
|
| Edición: | 3rd ed. / |
| Temas: | |
| Acceso en línea: | Texto completo |
MARC
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| 245 | 0 | 0 | |a Handbook of heterocyclic chemistry. |
| 250 | |a 3rd ed. / |b Alan Katritzky [and others]. | ||
| 260 | |a Oxford : |b Elsevier, |c ©2010. | ||
| 300 | |a 1 online resource (1004 pages) : |b illustrations | ||
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| 520 | |a Heterocyclic compounds play a vital role in the metabolism of living cells. Their practical applications range from extensive clinical use to fields as diverse as agriculture, photography, biocide formulation and polymer science. Written by leading scholars and industry experts, the Handbook of Heterocyclic Chemistry contains more than 1500 clearly drawn structures and reactions. The highly systematic coverage given to the subject makes this one of the most authoritative single-volume accounts of modern heterocyclic chemistry available. | ||
| 505 | 0 | 0 | |g Contents note continued: |g 3.5.2. |t Thermal and Photochemical Reactions, Not Formally Involving Other Species -- |g 3.5.2.1. |t Fragmentation Reactions -- |g 3.5.2.2. |t Rearrangements -- |g 3.5.3. |t Electrophilic Attack on Ring Heteroatoms -- |g 3.5.3.1. |t Protonation -- |g 3.5.3.2. |t Complex Formation -- |g 3.5.3.3. |t Alkylation, Arylation, and Acylation -- |g 3.5.4. |t Nucleophilic Attack on Ring Heteroatoms -- |g 3.5.5. |t Nucleophilic Attack on Ring Carbon Atoms -- |g 3.5.5.1. |t Reactions of Three-Membered Rings -- |g 3.5.5.2. |t Reactions of Four-Membered Rings -- |g 3.5.5.3. |t Reactions of Carbonyl Derivatives of Four-Membered Rings -- |g 3.5.5.4. |t Large Rings -- |g 3.5.6. |t Base Attack on Protons Attached to Ring Atoms -- |g 3.5.7. |t Attack by Radicals or Electron-Deficient Species. Oxidation and Reduction -- |g 3.5.7.1. |t Reactions with Radicals and Carbenes -- |g 3.5.7.2. |t Oxidation -- |g 3.5.7.3. |t Reduction -- |g 3.5.8. |t Reactions with Cyclic Transition States -- |g 3.5.8.1. |t [2+4] Cycloadditions -- |g 3.5.8.1.1. |t Heterocycles as dienophiles -- |g 3.5.8.1.2. |t Heterocycles as dienes -- |g 3.5.8.2. |t 1,3-Dipolar Cycloadditions -- |g 3.5.9. |t Reactivity of Transition Metal Complexes -- |g 3.5.10. |t Reactivity of Substituents Attached to Heteroatom or Ring Carbon Atoms -- |g 3.5.10.1. |t C-Linked Substituents -- |g 3.5.10.2. |t N- and S-Linked Substituents -- |g 4. |t Synthesis of Heterocycles -- |g 4.1. |t Overview -- |g 4.1.1. |t Aims and Organization -- |g 4.1.2. |t Ring Formation from Two Components -- |g 4.1.2.1. |t By Reaction between Electrophilic and Nucleophilic Centers -- |g 4.1.2.2. |t Ring Formation via Cycloaddition -- |g 4.1.2.2.1. |t [2+2] Cycloadditions -- |g 4.1.2.2.2. |t 1,3-Dipolar cycloadditions -- |g 4.1.3. |t Ring Closure of a Single Component -- |g 4.1.3.1. |t By Reaction between Electrophilic and Nucleophilic Centers -- |g 4.1.3.2. |t Electrocyclic Reactions -- |g 4.1.3.3. |t By Radical, Carbene, or Nitrene Intermediates -- |g 4.1.3.4. |t By Intramolecular Cyclodditions -- |g 4.1.4. |t Modification of an Exiting Ring -- |g 4.1.4.1. |t Ring Atom Interchange -- |g 4.1.4.2. |t Incorporation of New Ring Atoms: No Change in Ring Size -- |g 4.1.4.3. |t Ring Expansions -- |g 4.1.4.4. |t Ring Contractions -- |g 4.1.4.5. |t Ring Closure with Simultaneous Ring Opening -- |g 4.2. |t Synthesis of Monocyclic Rings with One Heteroatom -- |g 4.2.1. |t Ring Containing No Endocyclic Double Bonds -- |g 4.2.1.1. |t From Acyclic Compounds by Concerted Formation of Two Bonds -- |g 4.2.1.1.1. |t Three-membered rings -- |g 4.2.1.1.2. |t Four-membered rings -- |g 4.2.1.1.3. |t Five-membered rings -- |g 4.2.1.2. |t From Acyclic Compounds by Formation of One or Two C-Z Bonds -- |g 4.2.1.2.1. |t Three-membered rings -- |g 4.2.1.2.2. |t Four-membered rings -- |g 4.2.1.2.3. |t Five-membered rings -- |g 4.2.1.2.4. |t Six-membered rings -- |g 4.2.1.2.5. |t Larger rings -- |g 4.2.1.3. |t From Acyclic Compounds by Formation of One C-C Bond -- |g 4.2.1.4. |t From Carbocyclic Compounds -- |g 4.2.1.5. |t From Other Heterocyclic Compounds -- |g 4.2.1.5.1. |t Reactions involving ring expansion -- |g 4.2.1.5.2. |t Reactions without change in ring size -- |g 4.2.1.5.3. |t Ring contraction -- |g 4.2.2. |t Rings Containing One Endocyclic Double Bond -- |g 4.2.2.1. |t From Acyclic Compounds by Concerted Formation of Two Bonds -- |g 4.2.2.2. |t From Acyclic Compounds by Formation of One or Consecutive Formation of Two C-Z Bond (s) -- |g 4.2.2.2.1. |t Z Atom component acting as nucleophile -- |g 4.2.2.2.2. |t Z Atom component acting as electrophile -- |g 4.2.2.3. |t From Acyclic Compounds by Ring-Closing Metathesis -- |g 4.2.2.4. |t From Carbocycles -- |g 4.2.2.5. |t From Heterocycles -- |g 4.2.3. |t Rings Containing Two Endocyclic Double Bonds -- |g 4.2.3.1. |t Overview -- |g 4.2.3.2. |t Synthesis of Pyrroles, Furans, and Thiophenes by Substituent Introduction or Modification -- |g 4.2.3.3. |t Synthesis of Pyrroles, Furans, and Thiophenes from Acyclic Precursors -- |g 4.2.3.3.1. |t From C4Z or C4 units -- |g 4.2.3.3.2. |t From C3ZC or C3 and CZ units -- |g 4.2.3.3.3. |t From C2 and ZCC units -- |g 4.2.3.3.4. |t From C2 and CZC units -- |g 4.2.3.3.5. |t From two C2 and Z units -- |g 4.2.3.4. |t Synthesis of Pyrans, Dihydropyridines, and their Thio and Oxo Derivatives from Acyclic Precusors -- |g 4.2.3.4.1. |t From C5 units -- |g 4.2.3.4.2. |t With C-C bond formation -- |g 4.2.3.5. |t Synthesis of Four-, Five-, and Six-Membered Rings from Carbocyclic or Heterocyclic Precursors -- |g 4.2.3.5.1. |t With ring expansion -- |g 4.2.3.5.2. |t No change in ring size -- |g 4.2.3.5.3. |t With ring contraction -- |g 4.2.3.6. |t Synthesis of Seven-and Eight-Membered Rings -- |g 4.2.4. |t Rings Containing Three Endocyclic Double Bonds -- |g 4.2.4.1. |t Synthetic Methods for Substituted Pyridines -- |g 4.2.4.2. |t Synthesis of Six-Membered Rings from Acyclic Compounds -- |g 4.2.4.2.1. |t From or via pentane-1,5-diones -- |g 4.2.4.2.2. |t From pent-2-ene-1,5-diones -- |g 4.2.4.2.3. |t Other Methods -- |g 4.2.4.3. |t Synthesis of Six-Membered Rings from Other Heterocycles -- |g 4.2.4.3.1. |t From five-membered rings -- |g 4.2.4.3.2. |t From other six-membered rings -- |g 4.2.4.4. |t Synthesis of Seven-Membered and Larger Rings -- |g 4.3. |t Synthesis of Monocyclic Rings with Two or More Heteroatoms -- |g 4.3.1. |t Substituent Introduction and Modification -- |g 4.3.1.1. |t Overview -- |g 4.3.1.2. |t Substituents Introduction and Modification in Azoles -- |g 4.3.1.3. |t Substituents Introduction and Modification in Azines -- |g 4.3.2. |t Two Heteroatoms in the 1,2-Positions -- |g 4.3.2.1. |t Three-membered Rings -- |g 4.3.2.2. |t Four-membered Rings -- |g 4.3.2.2.1. |t 1,2-Diazetidines -- |g 4.3.2.2.2. |t 1,2-Oxazetidines -- |g 4.3.2.2.3. |t 1,2-Thiazetidines -- |g 4.3.2.2.4. |t 1,2-Dioxetanes -- |g 4.3.2.2.5. |t 1,2-Oxathietanes -- |g 4.3.2.2.6. |t 1,2-Dithietanes -- |g 4.3.2.3. |t Five-membered Rings: Pyrazoles, Isoxazoles, Isothiazoles, etc. -- |g 4.3.2.3.1. |t Synthesis from hydrazine, hydroxylamine, and hydrogen disulfide derivatives -- |g 4.3.2.3.2. |t Synthesis by Z-Z bond formation -- |g 4.3.2.3.3. |t Other methods from acyclic precursors -- |g 4.3.2.3.4. |t From other heterocycles -- |g 4.3.2.4. |t Six-membered Rings: Pyridazines, 1,2-Oxazines, etc. -- |g 4.3.2.4.1. |t Synthesis from hydrazine or hydroxylamine derivatives -- |g 4.3.2.4.2. |t By cycloaddition reactions -- |g 4.3.5.2.2. |t Other methods -- |g 4.3.5.3. |t Six-membered Rings -- |g 4.3.6. |t Three Heteroatoms in the 1,2,4-Positions -- |g 4.3.6.1. |t Five-membered Rings -- |g 4.3.6.1.1. |t From acyclic intermediates containing the preformed Z-Z' bond -- |g 4.3.6.1.2. |t From acyclic intermediates by formation of the Z-Z' bond -- |g 4.3.6.1.3. |t From heterocyclic precursors -- |g 4.3.6.1.4. |t By the 'monocyclic rearrangement' -- |g 4.3.6.2. |t Six-membered Rings -- |g 4.3.6.2.1. |t 1,2,4-Triazines -- |g 4.3.6.2.2. |t Rings containing O or S atoms -- |g 4.3.6.3. |t Seven-membered Rings -- |g 4.3.6.3.1. |t Heteroatoms in the 1,2,4-positions -- |g 4.3.6.3.2. |t Seven-membered rings with heteroatoms in the 1,2,5-positions -- |g 4.3.7. |t Three Heteroatoms in the 1,3,5-Positions -- |g 4.3.7.1. |t s-Triazines -- |g 4.3.7.2. |t Compounds Containing O or S Atoms -- |g 4.3.7.3. |t Synthesis from Heterocyclic Precursors -- |g 4.3.7.4. |t Seven-membered Rings -- |g 4.3.8. |t Four or More Heteroatoms -- |g 4.3.8.1. |t Five-membered Rings -- |g 4.3.8.2. |t Six-membered Rings -- |g 4.4. |t Synthesis of Bicyclic Ring Systems Without Ring Junction Heteroatoms -- |g 4.4.1. |t Synthesis by Substituent Introduction and Modification -- |g 4.4.1.1. |t In the Heterocyclic Ring -- |g 4.4.1.2. |t In the Benzene Ring -- |g 4.4.2. |t One Heteroatom Adjacent to a Ring Junction -- |g 4.4.2.1. |t Three-and Four Membered Rings -- |g 4.4.2.1.1. |t Three -membered rings -- |g 4.4.2.1.2. |t Four-membered rings -- |g 4.4.2.2. |t Five-Membered Rings -- |g 4.4.2.2.1. |t Survey of Syntheses for indoles, benzofurans, and benzothiophenes -- |g 4.4.2.2.2. |t Ring closure by formation of Z-C(2) bond -- |g 4.4.2.2.3. |t Ring closure by formation of ring -C bond -- |g 4.4.2.2.4. |t Ring closure by formation of C(2)-C(3) bond -- |g 4.4.2.2.5. |t Ring closure by formation of ring-Z bond -- |g 4.4.2.2.6. |t From other heterocycles -- |g 4.4.2.3. |t Six-Membered Rings -- |g 4.4.2.3.1. |t Survey of synthetic methods for quinolines, benzo[b]pyrans, and their derivatives -- |g 4.4.2.3.2. |t Ring closure of o-substituted anilines or phenols -- |g 4.4.2.3.3. |t Formation of a C-C bond by reaction of a multiple bond with a benzene ring -- |g 4.4.2.3.4. |t Synthesis via cycloaddition reactions -- |g 4.4.2.3.5. |t Synthesis from other heterocycles -- |g 4.4.2.4. |t Seven-Membered and Larger Rings -- |g 4.4.3. |t One Heteroatom Not Adjacent to a Ring Junction -- |g 4.4.3.1. |t Five-Membered Rings: Isoindoles and Related Compounds -- |g 4.4.3.2. |t Six-Membered Rings -- |g 4.4.3.2.1. |t Overview of ring synthes, of isoquinolines, benzo[c]pyrans, and their derivatives |
| 505 | 0 | 0 | |g -- |g 4.4.3.2.2. |t Ring closure of an o-disubstituted benzene -- |g 4.4.3.2.3. |t From a [beta]-phenethylamine -- |g 4.4.3.2.4. |t From a benzylimine -- |g 4.4.3.3. |t Seven-Membered and Larger Rings -- |g 4.4.4. |t Two Heteroatoms 1,2 to a Ring Junction -- |g 4.4.4.1. |t Four-Membered Rings -- |g 4.4.4.2. |t Five-Membered Rings -- |g 4.4.4.2.1. |t Indazoles -- |g 4.4.4.2.2. |t Anthranils, benzisothiazoles, and saccharins -- |g 4.4.4.3. |t Six-Membered Rings -- |g 4.4.4.3.1. |t Cinnolines -- |g 4.4.4.3.2. |t Rings containing O or S atoms -- |g 4.4.4.4. |t Seven-Membered Rings -- |g 4.4.5. |t Two Heteroatoms 1,3 to a Ring Junction -- |g 4.4.5.1. |t Five-Membered Rings -- |g 4.4.5.1.1. |t Ring closure of an o-disubstituted benzene or hetarene -- |g 4.4.5.1.2. |t Other methods -- |g 4.4.5.2. |t Six -Membered Rings -- |g 4.4.5.2.1. |t Quinazolines and azinopyrimidines by cyclization procedures -- |g 4.4.5.2.2. |t Rings containing O or S atoms -- |g 4.4.5.2.3. |t From other heterocycles -- |g 4.4.5.3. |t Seven-Membered Rings -- |g 4.4.5.3.1. |t Seven-membered rings with heteroatoms 1,3 to a ring junction -- |g 4.4.5.3.2. |t Seven-membered rings with heteroatoms 2,4 to a ring junction -- |g 4.4.6. |t Two Heteroatoms 1,4 to a Ring Junction -- |g 4.4.6.1. |t Quinoxalines and Azinopyrazines -- |g 4.4.6.2. |t 1,4-Benzoxazines and 1,4-Benzothiazines -- |g 4.4.6.3. |t Rings Containing Oxygen and/or Sulfur Atoms. |
| 505 | 0 | |a Structure of Heterocycles -- Reactivity of Heterocycles -- Synthesis of Heterocycles. | |
| 504 | |a Includes bibliographical references and index. | ||
| 588 | 0 | |a Print version record. | |
| 590 | |a Knovel |b ACADEMIC - Chemistry & Chemical Engineering | ||
| 650 | 0 | |a Heterocyclic chemistry. | |
| 650 | 4 | |a Heterocyclic chemistry | |
| 650 | 4 | |a Science | |
| 650 | 4 | |a Chemistry | |
| 650 | 4 | |a Organic Chemistry | |
| 650 | 4 | |a Physical Sciences & Mathematics | |
| 650 | 6 | |a Chimie des composés hétérocycliques. | |
| 650 | 7 | |a SCIENCE |x Chemistry |x Organic. |2 bisacsh | |
| 650 | 7 | |a Heterocyclic chemistry |2 fast | |
| 650 | 7 | |a Heterocykliska föreningar. |2 sao | |
| 655 | 7 | |a Handbooks and manuals |2 fast | |
| 700 | 1 | |a Katritzky, Alan R. | |
| 776 | 0 | 8 | |i Print version: |t Handbook of heterocyclic chemistry. |b 3rd ed. |d Oxford : Elsevier, ©2010 |z 9780080958439 |w (OCoLC)620294093 |
| 856 | 4 | 0 | |u https://appknovel.uam.elogim.com/kn/resources/kpHHCE0002/toc |z Texto completo |
| 880 | 0 | 0 | |6 505-00/(S |g Contents note continued: |g 3.2.1.2.2. |t Rearrangement to or elimination via Dewar heterobenzenes -- |g 3.2.1.2.3. |t Rearrangement to or via heteroprismanes and heterobenzvalenes -- |g 3.2.1.2.4. |t Rearrangement to or via 1,3-bridged heterocycles -- |g 3.2.1.2.5. |t Ring opening -- |g 3.2.1.3. |t Electrophilic Attack at Nitrogen -- |g 3.2.1.3.1. |t Introduction -- |g 3.2.1.3.2. |t Effect of substituents -- |g 3.2.1.3.3. |t Orientation of reaction of azines -- |g 3.2.1.3.4. |t Proton acids -- |g 3.2.1.3.5. |t Metal ions -- |g 3.2.1.3.6. |t Alkyl and aryl halides and related compounds -- |g 3.2.1.3.7. |t Acyl halides and related compounds and Michael-type reactions -- |g 3.2.1.3.8. |t Halogens -- |g 3.2.1.3.9. |t Peracids -- |g 3.2.1.3.10. |t Aminating agents -- |g 3.2.1.3.11. |t Other Lewis acids -- |g 3.2.1.4. |t Electrophilic Attack at Carbon -- |g 3.2.1.4.1. |t Species undergoing reaction and the reaction mechanism -- |g 3.2.1.4.2. |t Reactivity and effect of substituents -- |g 3.2.1.4.3. |t Orientation -- |g 3.2.1.4.4. |t Nitration -- |g 3.2.1.4.5. |t Sulfonation -- |g 3.2.1.4.6. |t Acid-catalyzed hydrogen exchange -- |g 3.2.1.4.7. |t Halogenation -- |g 3.2.1.4.8. |t Acylation and alkylation -- |g 3.2.1.4.9. |t Mercuration -- |g 3.2.1.4.10. |t Nitrosation, diazo coupling, Mannich reaction, Kolbe reaction, and reaction with aldehydes -- |g 3.2.1.4.11. |t Oxidation -- |g 3.2.1.5. |t Attack at Ring Sulfur Atoms -- |g 3.2.1.5.1. |t Reactions with electrophiles -- |g 3.2.1.5.2. |t Reactions with nucleophiles -- |g 3.2.1.6. |t Nucleophllic Attack at Carbon -- |g 3.2.1.6.1. |t Ease of reaction -- |g 3.2.1.6.2. |t Effect of substituents -- |g 3.2.1.6.3. |t Hydroxide ion -- |g 3.2.1.6.4. |t Amines and amide ions -- |g 3.2.1.6.5. |t Sulfur nucleophiles -- |g 3.2.1.6.6. |t Phosphorus nucleophiles -- |g 3.2.1.6.7. |t Halide ions -- |g 3.2.1.6.8. |t Carbon nucleophiles -- |g 3.2.1.6.9. |t Chemical reduction -- |g 3.2.1.7. |t Nucleophilic Attack at Ring Nitrogen -- |g 3.2.1.8. |t Attack by Bases at Hydrogen Attached to Ring Carbon or Ring Nitrogen -- |g 3.2.1.8.1. |t Metallation at a ring carbon atom -- |g 3.2.1.8.2. |t Hydrogen exchange at ring carbon in neutral azines, N-oxides, and azinones -- |g 3.2.1.8.3. |t Hydrogen exchange at ring carbon in azinium cations -- |g 3.2.1.8.4. |t Proton loss from a ring nitrogen atom -- |g 3.2.1.9. |t Reactions with Radicals and Electron-Deficient Species; Reactions at Surfaces -- |g 3.2.1.9.1. |t Carbenes and nitrenes -- |g 3.2.1.9.2. |t Radical attack at ring carbon atoms -- |g 3.2.1.9.3. |t Electrochemical reactions and reactions with free electrons -- |g 3.2.1.9.4. |t Other reactions at surfaces -- |g 3.2.1.10. |t Reactions with Cyclic Transition States -- |g 3.2.1.10.1. |t Introduction -- |g 3.2.1.10.2. |t Heterocycles as inner dienes in [2+4] cycloadditions -- |g 3.2.1.10.3. |t Heterocycles as inner dienes in [1+4] cycloadditions -- |g 3.2.1.10.4. |t Heterocycles as 1,3-dipoles -- |g 3.2.1.10.5. |t Heterocycles as dienophiles -- |g 3.2.1.10.6. |t [2+2] Cycloadditions -- |g 3.2.1.10.7. |t Heterocycles as 4π-components in [4+4] cycloaddition -- |g 3.2.2. |t Reactions of Nonaromatic Compounds -- |g 3.2.2.1. |t 8π-Electron Systems: 1,2- and 1,4-Dioxins, -Oxathiins, and -Dithiins -- |g 3.2.2.1.1. |t Intramolecular thermolysis and photolysis reactions -- |g 3.2.2.1.2. |t Reactions with electrophiles -- |g 3.2.2.1.3. |t Reactions with nucleophiles -- |g 3.2.2.2. |t Thiabenzenes and Related Compounds -- |g 3.2.2.3. |t Dihydro Compounds -- |g 3.2.2.3.1. |t Introduction -- |g 3.2.2.3.2. |t Annular tautomerism -- |g 3.2.2.3.3. |t Aromatization -- |g 3.2.2.3.4. |t Electron loss to form radicals -- |g 3.2.2.3.5. |t Electrocyclic ring opening (valence tautomerism) -- |g 3.2.2.3.6. |t Proton loss to an 8π-electron-conjugated system -- |g 3.2.2.3.7. |t Electrophilic substitution -- |g 3.2.2.3.8. |t Cycloaddition reactions -- |g 3.2.2.3.9. |t Other reactions -- |g 3.2.2.4. |t Tetra- and Hexahydro Compounds -- |g 3.2.2.4.1. |t Tautomeric equilibria -- |g 3.2.2.4.2. |t Aromatization -- |g 3.2.2.4.3. |t Ring fission -- |g 3.2.2.4.4. |t Other reactions -- |g 3.2.2.4.5. |t Stereochemistry -- |g 3.2.3. |t Reactions of Substituents -- |g 3.2.3.1. |t General Survey of Reactivity of Substituents on Ring Carbon Atoms -- |g 3.2.3.1.1. |t carbonyl analogy -- |g 3.2.3.1.2. |t Effect of number, type, and orientation of heteroatoms -- |g 3.2.3.1.3. |t effect of one substituent on the reactivity of another -- |g 3.2.3.1.4. |t Reactions of substituents not directly attached to the heterocyclic ring -- |g 3.2.3.2. |t Benzenoid Rings -- |g 3.2.3.2.1. |t Fused benzene rings: Unsubstituted -- |g 3.2.3.2.2. |t Fused benzene rings: Substituted -- |g 3.2.3.3. |t Alkyl Groups -- |g 3.2.3.3.1. |t Reactions similar to those of toluene -- |g 3.2.3.3.2. |t Alkyl groups: Reactions via proton loss -- |g 3.2.3.3.3. |t Alkylazines: Reactions involving essentially complete anion formation -- |g 3.2.3.3.4. |t Alkylazines: Reactions involving traces of reactive anions or traces of methylene enamines -- |g 3.2.3.3.5. |t Alkyl-azonium and -pyrylium compounds -- |g 3.2.3.3.6. |t Tautomerism of alkyl derivatives -- |g 3.2.3.4. |t Further carbon Functional Groups -- |g 3.2.3.4.1. |t Aryl groups -- |g 3.2.3.4.2. |t Carboxylic acids and derivatives -- |g 3.2.3.4.3. |t Aldehydes and ketones -- |g 3.2.3.4.4. |t Other substituted alkyl groups -- |g 3.2.3.4.5. |t Vinyl groups -- |g 3.2.3.5. |t Amino and Imino Groups -- |g 3.2.3.5.1. |t Orientation of reactions of aminopyridines and -azines with electrophiles -- |g 3.2.3.5.2. |t Reaction of aminoazines with electrophiles at the amino group -- |g 3.2.3.5.3. |t Diazotization of amino compounds -- |g 3.2.3.5.4. |t Reactions of amino compounds with nucleophiles and bases -- |g 3.2.3.5.5. |t Intramolecular reactions of amino group producing rings -- |g 3.2.3.5.6. |t Amino-Imino tautomerism -- |g 3.2.3.6. |t Other N-Linked Substituents -- |g 3.2.3.6.1. |t Nitro groups -- |g 3.2.3.6.2. |t Nitramino compounds -- |g 3.2.3.6.3. |t Hydrazino groups -- |g 3.2.3.6.4. |t Azides -- |g 3.2.3.6.5. |t Nitroso groups -- |g 3.2.3.7. |t Hydroxy and Oxo Groups -- |g 3.2.3.7.1. |t Hydroxy groups and hydroxy-oxo tautomeric equilibria -- |g 3.2.3.7.2. |t Pyridones, pyrones, thiinones, azinones, etc: General pattern of reactivity -- |g 3.2.3.7.3. |t Pyridones, pyrones, and azinones: Electrophilic attack at carbonyl oxygen -- |g 3.2.3.7.4. |t Pyridones, pyrones, and azinones; Nucleophilic displacement of carbonyl oxygen -- |g 3.2.3.7.5. |t Heterocyclic quinones -- |g 3.2.3.8. |t Other O-Linked Substituents -- |g 3.2.3.8.1. |t Alkoxy and aryloxy groups -- |g 3.2.3.8.2. |t Acyloxy groups -- |g 3.2.3.9. |t S-Linked Substituents -- |g 3.2.3.9.1. |t Mercapto-thione tautomerism -- |g 3.2.3.9.2. |t Thiones -- |g 3.2.3.9.3. |t Alkylthio, alkylsulfinyl, and alkylsulfonyl groups -- |g 3.2.3.9.4. |t Sulfonic acid groups -- |g 3.2.3.10. |t Halogen Atoms -- |g 3.2.3.10.1. |t Pattern of reactivity -- |g 3.2.3.10.2. |t Replacement of halogen by hydrogen or a metal (including transmetallation) or by coupling -- |g 3.2.3.10.3. |t Reactions via hetarynes -- |g 3.2.3.10.4. |t SRN mechanistic pathway -- |g 3.2.3.10.5. |t ANRORC reactions -- |g 3.2.3.10.6. |t Nucleophilic displacement by classical SAE mechanism -- |g 3.2.3.11. |t Metals and Metalloids -- |g 3.2.3.11.1. |t Organometallic nucleophiles -- |g 3.2.3.11.2. |t Transition metal-catalyzed processes -- |g 3.2.3.12. |t Substituents Attached to Ring Nitrogen Atoms -- |g 3.2.3.12.1. |t Introduction -- |g 3.2.3.12.2. |t Alkyl groups -- |g 3.2.3.12.3. |t Other C-linked substituents -- |g 3.2.3.12.4. |t N-Linked substituents -- |g 3.2.3.12.5. |t O-Linked substituents -- |g 3.2.3.12.6. |t Other substitents attached to nitrogen -- |g 3.2.3.13. |t Substituents Attached to Ring Sulfur Atoms -- |g 3.3. |t Reactivity of Five-Membered Rings with One Heteroatom -- |g 3.3.1. |t Reactions at Heteroaromatic Rings -- |g 3.3.1.1. |t General Survey of Reactivity -- |g 3.3.1.1.1. |t Comparison with aliphatic series -- |g 3.3.1.1.2. |t Effect of aromaticity -- |g 3.3.1.2. |t Thermal and Photochemical Reactions Involving No Other Species -- |g 3.3.1.3. |t Electrophilic Attack on Ring Heteroatoms -- |g 3.3.1.3.1. |t Pyrrole anions -- |g 3.3.1.3.2. |t Thiophenes, selenophenes, and tellurophenes -- |g 3.3.1.4. |t Electrophilic Attack on Carbon: General Considerations -- |g 3.3.1.4.1. |t Relative reactivities of heterocycles -- |g 3.3.1.4.2. |t Directing effects of the ring heteroatom -- |g 3.3.1.4.3. |t Directing effects of substituents in monocyclic compounds -- |g 3.3.1.4.4. |t Directing effects of fused benzene rings -- |g 3.3.1.4.5. |t Range of substitution reactions -- |g 3.3.1.5. |t Electrophilic Attack on Carbon: Specific Reactions -- |g 3.3.1.5.1. |t Proton acids -- |g 3.3.1.5.2. |t Nitration -- |g 3.3.1.5.3. |t Sulfonation -- |g 3.3.1.5.4. |t Halogenation -- |g 3.3.1.5.5. |t Acylation -- |g 3.3.1.5.6. |t Alkylation -- |g 3.3.1.5.7. |t Reactions with aldehydes and ketones -- |g 3.3.1.5.8. |t Mercuration -- |g 3.3.1.5.9. |t Diazo coupling |
| 880 | 0 | 0 | |g -- |g 3.3.1.5.10. |t Nitrosation -- |g 3.3.1.5.11. |t Electrophilic oxidation -- |g 3.3.1.6. |t Reactions with Nucleophiles and Bases -- |g 3.3.1.6.1. |t Deprotonation at nitrogen -- |g 3.3.1.6.2. |t Deprotonation at carbon -- |g 3.3.1.6.3. |t Reactions of cationic species with nucleophiles -- |g 3.3.1.6.4. |t Vicarious nucleophilic substitution and related reactions -- |g 3.3.1.6.5. |t Nucleophilic attack on sulfur -- |g 3.3.1.7. |t Reactions with Radicals and Electron-Deficient Species; Reactions at Surfaces -- |g 3.3.1.7.1. |t Carbenes and nitrenes -- |g 3.3.1.7.2. |t Radical attack -- |g 3.3.1.7.3. |t Electrochemical reactions -- |g 3.3.1.7.4. |t Reactions with free electrons -- |g 3.3.1.7.5. |t Catalytic hydrogenation -- |g 3.3.1.7.6. |t Reduction by dissolving metals -- |g 3.3.1.7.7. |t Desulfurization -- |g 3.3.1.8. |t Reactions with Cyclic Transition States -- |g 3.3.1.8.1. |t Heterocycles as inner ring dienes -- |g 3.3.1.8.2. |t Five-membered heterocycles as dienophiles -- |g 3.3.1.8.3. |t [2+2] Cycloaddition reactions -- |g 3.3.1.8.4. |t Other cycloaddition reactions -- |g 3.3.2. |t Reactivity of Nonaromatic Compounds -- |g 3.3.2.1. |t 2H-Pyrroles (Pyrrolenines) and 3H-Indoles (Indolenines) -- |g 3.3.2.2. |t Thiophene Sulfones and Sulfoxides -- |g 3.3.2.3. |t Dihydro Derivatives -- |g 3.3.2.3.1. |t Aromatization of dihydro compounds -- |g 3.3.2.3.2. |t Behavior analogous to aliphatic analogues. |
| 880 | 0 | 0 | |6 505-00/(S |g Machine generated contents note: |g 1. |t Preliminaries -- |g 2. |t Structure of Heterocycles -- |g 2.1. |t Overview -- |g 2.1.1. |t Relationship of Heterocyclic and Carbocyclic Aromatic Compounds -- |g 2.1.2. |t Arrangement of Structure Chapters -- |g 2.1.3. |t Nomenclature -- |g 2.1.4. |t Computer-Aided Studies of Heterocyles -- |g 2.1.4.1. |t Huckel Calculations and Related π-Electron Methods -- |g 2.1.4.2. |t Semiempirical Methods -- |g 2.1.4.3. |t Ab Initio and DFT Calculations -- |g 2.1.4.4. |t Molecular Mechanics -- |g 2.1.5. |t Glossary of General Terms Used in Chapter 2.2-2.5 -- |g 2.2. |t Structure of Six-membered Rings -- |g 2.2.1. |t Survey of Possible Structures and Nomenclature -- |g 2.2.1.1. |t Nitrogen Rings Without Exocylic Conjugation -- |g 2.2.1.1.1. |t Fully-conjugated aromatic rings -- |g 2.2.1.1.2. |t Fully-conjugated nonaromatic rings -- |g 2.2.1.1.3. |t Rings without cyclic conjugation -- |g 2.2.1.2. |t Nitrogen Rings with Exocyclic Conjugation -- |g 2.2.1.2.1. |t Pyridones and related systems -- |g 2.2.1.2.2. |t Mesomeric betaines (1,3-dipoles and 1,4-dipoles) -- |g 2.2.1.2.3. |t N-Oxides and related systems -- |g 2.2.1.3. |t Oxygen and Sulfur Rings without Exocyclic Conjugation -- |g 2.2.1.3.1. |t Fully-conjugated aromatic rings -- |g 2.2.1.3.2. |t Fully-conjugated nonaromatic rings -- |g 2.2.1.3.3. |t Rings without cyclic conjugation -- |g 2.2.1.4. |t Oxygen and Sulfur Rings with Exocylic Conjugation -- |g 2.2.1.5. |t Rings Containing Nitrogen with Oxygen and/or Sulfur -- |g 2.2.2. |t Theoretical Methods -- |g 2.2.2.1. |t General Trends -- |g 2.2.2.2. |t Calculation of Molecular Properties -- |g 2.2.2.2.1. |t Geometries -- |g 2.2.2.2.2. |t Magnetic properties -- |g 2.2.2.2.3. |t Tautomerism -- |g 2.2.3. |t Structural Methods -- |g 2.2.3.1. |t X-Ray Diffraction -- |g 2.2.3.2. |t Microwave Spectroscopy -- |g 2.2.3.3. |t 1H NMR Spectra -- |g 2.2.3.3.1. |t Chemical shifts -- |g 2.2.3.3.2. |t Coupling constants -- |g 2.2.3.4. |t 13C NMR Spectra -- |g 2.2.3.4.1. |t Aromatic systems: Chemical shifts -- |g 2.2.3.4.2. |t Aromatic systems: Coupling constants -- |g 2.2.3.4.3. |t Saturated systems -- |g 2.2.3.5. |t Nitrogen and Oxygen NMR Spectra -- |g 2.2.3.6. |t Ultraviolet and Related Spectra -- |g 2.2.3.7. |t IR and Raman Spectra -- |g 2.2.3.8. |t Mass Spectrometry -- |g 2.2.3.9. |t Photoelectron Spectroscopy -- |g 2.2.4. |t Thermodynamic Aspects -- |g 2.2.4.1. |t Intermolecular Forces -- |g 2.2.4.1.1. |t Melting and boiling points -- |g 2.2.4.1.2. |t Solubility -- |g 2.2.4.1.3. |t Gas-liquid chromatography -- |g 2.2.4.2. |t Aromaticity of Fully-Conjugated Rings -- |g 2.2.4.2.1. |t Background -- |g 2.2.4.2.2. |t Energetic criteria -- |g 2.2.4.2.3. |t Structural criteria -- |g 2.2.4.2.4. |t Magnetic criteria -- |g 2.2.4.3. |t Conformations of Partially- and Fully-Reduced Rings -- |g 2.2.5. |t Tautomerism -- |g 2.2.5.1. |t Prototropic Tautomerism -- |g 2.2.5.1.1. |t Prototropic tautomerism of fully-conjugated rings -- |g 2.2.5.1.2. |t Prototropic tautomerism of rings without cyclic conjugation -- |g 2.2.5.2. |t Ring-Chain Tautomerism -- |g 2.2.5.3. |t Valence Tautomerism -- |g 2.2.6. |t Supramolecular Structures -- |g 2.3. |t Structure of Five-Membered Rings with One Heteroatom -- |g 2.3.1. |t Survey of Possible Structures and Nomenclature -- |g 2.3.1.1. |t Rings Without Exocyclic Conjugation -- |g 2.3.1.1.1. |t Fully-conjugated rings -- |g 2.3.1.1.2. |t Rings without cyclic conjugation -- |g 2.3.1.2. |t Rings with Exocyclic Conjugation -- |g 2.3.1.2.1. |t Fully-conjugated rings -- |g 2.3.1.2.2. |t Rings without cyclic conjugation -- |g 2.3.2. |t Theoretical Methods -- |g 2.3.2.1. |t General Trends -- |g 2.3.2.2. |t Calculation of Molecular Properties -- |g 2.3.2.2.1. |t Structure and energy -- |g 2.3.2.2.2. |t Reactions and equilibria -- |g 2.3.3. |t Structural Methods -- |g 2.3.3.1. |t X-Ray Diffraction -- |g 2.3.3.2. |t Microwave Spectroscopy -- |g 2.3.3.3. |t 1H NMR Spectroscopy -- |g 2.3.3.3.1. |t Parent aromatic compounds -- |g 2.3.3.3.2. |t Substituted aromatic compounds -- |g 2.3.3.3.3. |t Saturated and partially-saturated compounds -- |g 2.3.3.4. |t 13C NMR Spectroscopy -- |g 2.3.3.5. |t Heteroatom NMR Spectroscopy -- |g 2.3.3.6. |t UV Spectroscopy -- |g 2.3.3.7. |t IR Spectroscopy -- |g 2.3.3.7.1. |t Ring vibrations -- |g 2.3.3.7.2. |t Substituent vibrations -- |g 2.3.3.8. |t Mass Spectrometry -- |g 2.3.3.8.1. |t Parent monocycles -- |g 2.3.3.8.2. |t Substituted monocycles -- |g 2.3.3.8.3. |t Benzo derivatives -- |g 2.3.3.8.4. |t Saturated compounds -- |g 2.3.3.9. |t Photoelectron Spectroscopy -- |g 2.3.3.9.1. |t Parent monocycles -- |g 2.3.3.9.2. |t Substituted monocycles -- |g 2.3.3.9.3. |t Benzo derivatives -- |g 2.3.3.9.4. |t Reduced compounds -- |g 2.3.3.9.5. |t Core-ionization energies -- |g 2.3.4. |t Thermodynamic Aspects -- |g 2.3.4.1. |t Intermolecular Forces -- |g 2.3.4.1.1. |t Melting and boiling points -- |g 2.3.4.1.2. |t Solubility -- |g 2.3.4.1.3. |t Gas chromatography -- |g 2.3.4.2. |t Aromaticity of Fully-Conjugated Rings -- |g 2.3.4.2.1. |t Background -- |g 2.3.4.2.2. |t Energetic criteria -- |g 2.3.4.2.3. |t Structural criteria -- |g 2.3.4.2.4. |t Magnetic criteria -- |g 2.3.4.3. |t Conformations of Heteroaryl Derivatives: Rotamers and Atropisomers -- |g 2.3.4.3.1. |t Rotamers -- |g 2.3.4.3.2. |t Atropisomers -- |g 2.3.4.4. |t Conformations of Partially-and Fully-Reduced Rings -- |g 2.3.5. |t Tautomerism -- |g 2.3.5.1. |t Prototropic Tautomerism of Fully-Conjugated Rings -- |g 2.3.5.1.1. |t Annular tautomerism -- |g 2.3.5.1.2. |t Oxo-hydroxy tautomerism -- |g 2.3.5.1.3. |t Thiono-mercapto and amino-imino tautomerism -- |g 2.4. |t Structure of Five-membered Rings with Two or More Heteroatoms -- |g 2.4.1. |t Survey of Possible Structures and Nomenclature -- |g 2.4.1.1. |t Nitrogen Rings without Exocyclic Conjugation -- |g 2.4.1.1.1. |t Fully-conjugated aromatic rings -- |g 2.4.1.1.2. |t Rings without cyclic conjugation -- |g 2.4.1.2. |t Nitrogen Rings with Exocyclic Conjugation -- |g 2.4.1.3. |t Oxygen and Sulfur Rings without Exocyclic Conjugation -- |g 2.4.1.3.1. |t Fully-conjugated aromatic rings -- |g 2.4.1.3.2. |t Rings without cyclic conjugation -- |g 2.4.1.4. |t Oxygen and Sulfur Rings with Exocyclic Conjugation -- |g 2.4.1.5. |t Rings Containing Nitrogen with Oxygen and/or Sulfur -- |g 2.4.2. |t Theoretical Methods -- |g 2.4.2.1. |t General Trends -- |g 2.4.2.2. |t Calculation of Molecular Properties -- |g 2.4.2.2.1. |t Structure and energy -- |g 2.4.2.2.2. |t Magnetic properties -- |g 2.4.2.2.3. |t Reactions and equilibria -- |g 2.4.3. |t Structural Methods -- |g 2.4.3.1. |t X-Ray Diffraction -- |g 2.4.3.2. |t Microwave Spectroscopy -- |g 2.4.3.2.1. |t Aromatic rings -- |g 2.4.3.2.2. |t Partially- and fully-saturated ring systems -- |g 2.4.3.3. |t 1H NMR Spectroscopy -- |g 2.4.3.3.1. |t Fully-conjugated aromatic rings -- |g 2.4.3.3.2. |t Other ring systems -- |g 2.4.3.4. |t 13C NMR Spectroscopy -- |g 2.4.3.5. |t Nitrogen and Oxygen NMR Spectroscopy -- |g 2.4.3.6. |t UV Spectroscopy -- |g 2.4.3.6.1. |t Parent compounds -- |g 2.4.3.6.2. |t Benzo derivatives -- |g 2.4.3.6.3. |t Effect of substituents -- |g 2.4.3.7. |t IR Spectroscopy -- |g 2.4.3.7.1. |t Aromatic rings without carbonyl groups -- |g 2.4.3.7.2. |t Azole rings containing carbonyl groups -- |g 2.4.3.7.3. |t Substituent vibrations -- |g 2.4.3.8. |t Mass Spectrometry -- |g 2.4.3.9. |t Photoelectron Spectroscopy -- |g 2.4.4. |t Thermodynamic Aspects -- |g 2.4.4.1. |t Intermolecular Forces -- |g 2.4.4.1.1. |t Melting and boiling points -- |g 2.4.4.1.2. |t Solubility of heterocyclic compounds -- |g 2.4.4.1.3. |t Gas-liquid chrometography -- |g 2.4.4.2. |t Aromaticity of Fully-Conjugated Rings -- |g 2.4.4.2.1. |t Background -- |g 2.4.4.2.2. |t Energetic criteria -- |g 2.4.4.2.3. |t Structural criteria -- |g 2.4.4.2.4. |t Magnetic criteria -- |g 2.4.4.2.5. |t N-Heterocyclic carbenes (NHCs) -- |g 2.4.4.3. |t Conformations of Heteroaryl Derivatives -- |g 2.4.4.4. |t Conformations of Partially-and Fully-Reduced Rings -- |g 2.4.5. |t Tautomerism -- |g 2.4.5.1. |t Prototropic Tautomerism of Rings -- |g 2.4.5.1.1. |t Annular tautomerism -- |g 2.4.5.1.2. |t Annular elementotropy -- |g 2.4.5.2. |t Prototropic Tautomerism of OH, NH2, and SH Substituents -- |g 2.4.5.2.1. |t Pyrazoles, isoxazoles, and isothiazoles -- |g 2.4.5.2.2. |t Imidazoles, oxazoles, and thiazoles -- |g 2.4.5.3. |t Ring-Chain Tautomerism -- |g 2.4.5.4. |t Valence Tautomerism -- |g 2.5. |t Structure of Small and Large Rings -- |g 2.5.1. |t Survey of Possible Structures and Nomenclature -- |g 2.5.1.1. |t Three-and Four-Membered Rings -- |g 2.5.1.1.1. |t Without exocyclic conjugation -- |g 2.5.1.1.2. |t With exocyclic conjugation -- |g 2.5.1.2. |t Seven-Membered Rings -- |g 2.5.1.3. |t Larger Rings -- |g 2.5.2. |t Theoretical Methods -- |g 2.5.2.1. |t Three- and Four-Membered Rings -- |g 2.5.2.2. |t Seven- and Eight-Membered Rings -- |g 2.5.2.3. |t Larger Rings -- |g 2.5.3. |t Structural Methods -- |g 2.5.3.1. |t X-Ray Diffraction -- |g 2.5.3.2. |t Microwave Spectroscopy -- |g 2.5.3.3. |t 1H NMR Spectroscopy -- |g 2.5.3.3.1. |t Three- and four-membered rings -- |g 2.5.3.3.2. |t Seven or more ring atoms -- |g 2.5.3.4. |t 13C and |
| 880 | 0 | 0 | |t Heteronuclear NMR Spectroscopy -- |g 2.5.3.5. |t UV Spectroscopy -- |g 2.5.3.5.1. |t Electronic spectra of small-ring heterocyclic compounds -- |g 2.5.3.5.2. |t Electronic spectra of large-ring heterocyclic compounds -- |g 2.5.3.6. |t IR Spectroscopy -- |g 2.5.3.7. |t Mass Spectrometry -- |g 2.5.3.8. |t Photoelectron spectroscopy (PES) -- |g 2.5.4. |t Thermodynamic Aspects -- |g 2.5.4.1. |t Stability and Stabilization -- |g 2.5.4.1.1. |t Ring strain -- |g 2.5.4.1.2. |t Aromaticity and antiaromaticity -- |g 2.5.4.2. |t Conformation -- |g 2.5.4.2.1. |t Small rings -- |g 2.5.4.2.2. |t Large rings -- |g 2.5.5. |t Tautomerism -- |g 2.5.5.1. |t Annular Tautomerism -- |g 2.5.5.2. |t Valence Tautomerism -- |g 3. |t Reactivity of Heterocycles -- |g 3.1. |t Overview -- |g 3.1.1. |t Reaction Types -- |g 3.1.2. |t Heteroaromatic Reactivity -- |g 3.1.3. |t Arrangement of the Reactivity Sections -- |g 3.2. |t Reactivity of Six-membered Rings -- |g 3.2.1. |t Reactivity of Aromatic Rings -- |g 3.2.1.1. |t General Survey of Reactivity -- |g 3.2.1.1.1. |t Pyridines -- |g 3.2.1.1.2. |t Azines -- |g 3.2.1.1.3. |t Cationic rings -- |g 3.2.1.1.4. |t Pyridones, N-oxides, and mesomeric betaines -- |g 3.2.1.1.5. |t Anionic rings -- |g 3.2.1.1.6. |t Aromaticity and reversion to type -- |g 3.2.1.2. |t Intramolecular Thermal and Photochemical Reactions -- |g 3.2.1.2.1. |t Fragmentation. |
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