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Organic Chemistry 4th by Janice Smith PDF Ebook

Organic Chemistry 4th by Janice Smith PDF Ebook

ORGANIC CHEMISTRY 4TH EDITION BY JANICE SMITH books

A guidebook to Mechanism in organic chemistry 6 edition by Peter Sypes

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A guidebook to Mechanism in organic chemistry 6 edition by Peter Sypes

A guidebook to Mechanism in organic chemistry 6 edition by Peter Sypes

Famous chemistry book: Organic Chemistry (6E 2005) L. G. Wade

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<span style="font-size: x-large;">Free chemistry book, Famous chemistry book: Organic Chemistry (6E 2005) L. G. Wade</span></h2>
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Famous chemistry book: Organic Chemistry (6E 2005) L. G. Wade

Free chemistry book, Famous chemistry book: Organic Chemistry (6E 2005) L. G. Wade

Aromatic Chemistry - John D Hepworth, Mike J Waring, David R

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Aromatic Chemistry - John D Hepworth, Mike J Waring, David R

Famous chemistry books : Aromatic Chemistry - John D Hepworth, Mike J Waring, David R

Inorganic Structural Chemistry, 2nd Edition Ulrich Muller

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Inorganic Structural Chemistry, 2nd Edition Ulrich Muller

Famous chemistry books :Inorganic Structural Chemistry, 2nd Edition Ulrich Muller

MARCH’S ADVANCED ORGANIC CHEMISTRY

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<span style="font-size: x-large;">Free chemistry book download :March's Advanced Organic Chemistry 6th Edition</span></h2>
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MARCH’S ADVANCED ORGANIC CHEMISTRY

Free chemistry book download :March's Advanced Organic Chemistry 6th Edition

Advanced Organic Chemistry-Part A: Structure and Mechanisms

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Advanced Organic Chemistry-Part A: Structure and Mechanisms

Chemistry and creativity : Advanced Organic Chemistry-Part A: Structure and Mechanisms

Advanced Organic Chemistry PartB - Reaction and Synthesis

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<span style="font-size: x-large;">Advanced Organic Chemistry PartB - Reaction and Synthesis by Francis A. Carey and Richard J. Sundberg</span></h2>
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<h3>
<span style="font-size: small;">Advanced Organic Chemistry PartB - Reaction and Synthesis</span></h3>
<div>
<div>
EDITION</div>
<div>
Part B: <b>Reactions and Synthesis</b></div>
<div>
<div>
<b>Advanced Organic Chemistry</b></div>
<div>
PART A: <b>Structure and Mechanisms</b></div>
<div>
PART B: <b>Reactions and Synthesis</b></div>
</div>
<div>
</div>
</div>
<div>
<br /></div>
<div>
<div>
The focus of Part B is on the closely interrelated topics of <b>reactions and synthesis</b>. In</div>
<div>
each of the first twelve chapters, we consider a group of related reactions that have</div>
<div>
been chosen for discussion primarily on the basis of their usefulness in synthesis. For</div>
<div>
each reaction we present an outline of the mechanism, its regio- and <b>stereochemical</b></div>
<div>
characteristics, and information on typical reaction conditions. For the more commonly</div>
<div>
used <b>reactions</b>, the schemes contain several examples, which may include examples of</div>
<div>
the <b>reaction </b>in relatively simple molecules and in more complex structures. The goal of</div>
<div>
these chapters is to develop a fundamental base of knowledge about organic reactions</div>
<div>
in the context of <b>synthesis</b>. We want to be able to answer questions such as: What</div>
<div>
transformation does a reaction achieve? What is the mechanism of the reaction? What</div>
<div>
reagents and reaction conditions are typically used? What substances can catalyze</div>
<div>
the reaction? How sensitive is the reaction to other functional groups and the steric</div>
<div>
environment? What factors control the stereoselectivity of the <b>reaction</b>? Under what</div>
<div>
conditions is the reaction enantioselective?</div>
<div>
<b>Synthesis </b>is the application of one or more reactions to the preparation of a</div>
<div>
particular target compound, and can pertain to a single-step transformation or to a</div>
<div>
number of sequential steps. The selection of a reaction or series of reactions for a</div>
<div>
synthesis involves making a judgment about the most effective possibility among</div>
<div>
the available options. There may be a number of possibilities for the synthesis of a</div>
<div>
particular compound. For example, in the course of learning about the reactions in</div>
<div>
Chapter 1 to 12, we will encounter a number of ways of making ketones, as outlined</div>
<div>
in the scheme that follows.</div>
</div>
<div>
<br /></div>
<div>
<div>
Chapter 1. Alkylation of Enolates and Other Carbon Nucleophiles . . . . . . 1</div>
<div>
Introduction........................................................................................................... 1</div>
<div>
1.1. Generation and Properties of Enolates and Other Stabilized Carbanions... 2</div>
<div>
1.1.1. Generation of Enolates by Deprotonation ........................................ 2</div>
<div>
1.1.2. Regioselectivity and Stereoselectivity in Enolate Formation</div>
<div>
from Ketones and Esters ................................................................... 5</div>
<div>
1.1.3. Other Means of Generating Enolates................................................ 14</div>
<div>
1.1.4. Solvent Effects on Enolate Structure and Reactivity ....................... 17</div>
<div>
1.2. Alkylation of Enolates.................................................................................. 21</div>
<div>
1.2.1. Alkylation of Highly Stabilized Enolates ......................................... 21</div>
<div>
1.2.2. Alkylation of Ketone Enolates.......................................................... 24</div>
<div>
1.2.3. Alkylation of Aldehydes, Esters, Carboxylic Acids, Amides,</div>
<div>
and Nitriles ........................................................................................ 31</div>
<div>
1.2.4. Generation and Alkylation of Dianions............................................ 36</div>
<div>
1.2.5. Intramolecular Alkylation of Enolates.............................................. 36</div>
<div>
1.2.6. Control of Enantioselectivity in Alkylation Reactions..................... 41</div>
<div>
1.3. The Nitrogen Analogs of Enols and Enolates: Enamines</div>
<div>
and Imine Anions ......................................................................................... 46</div>
<div>
General References............................................................................................... 55</div>
<div>
Problems ............................................................................................................... 56</div>
</div>
<div>
<div>
Chapter 2. Reactions of Carbon Nucleophiles</div>
<div>
with Carbonyl Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 63</div>
<div>
Introduction........................................................................................................... 63</div>
<div>
2.1. Aldol Addition and Condensation Reactions............................................... 64</div>
<div>
2.1.1. The General Mechanism ................................................................... 64</div>
<div>
2.1.2. Control of Regio- and Stereoselectivity of Aldol Reactions</div>
<div>
of Aldehydes and Ketones ................................................................ 65</div>
<div>
2.1.3. Aldol Addition Reactions of Enolates of Esters</div>
<div>
and Other Carbonyl Derivatives ....................................................... 78</div>
<div>
2.1.4. The Mukaiyama Aldol Reaction....................................................... 82</div>
<div>
2.1.5. Control of Facial Selectivity in Aldol and Mukaiyama Aldol</div>
<div>
Reactions............................................................................................ 86</div>
<div>
2.1.6. Intramolecular Aldol Reactions and the Robinson Annulation ....... 134</div>
<div>
2.2. Addition Reactions of Imines and Iminium Ions ........................................ 139</div>
<div>
2.2.1. The Mannich Reaction ...................................................................... 140</div>
<div>
2.2.2. Additions to N-Acyl Iminium Ions ................................................... 145</div>
<div>
2.2.3. Amine-Catalyzed Condensation Reactions....................................... 147</div>
<div>
2.3. Acylation of Carbon Nucleophiles............................................................... 148</div>
<div>
2.3.1. Claisen and Dieckmann Condensation Reactions ............................ 149</div>
<div>
2.3.2. Acylation of Enolates and Other Carbon Nucleophiles ................... 150</div>
<div>
2.4. Olefination Reactions of Stabilized Carbon Nucleophiles .......................... 157</div>
<div>
2.4.1. The Wittig and Related Reactions of Phosphorus-Stabilized</div>
<div>
Carbon Nucleophiles ......................................................................... 157</div>
<div>
2.4.2. Reactions of  -Trimethylsilylcarbanions with Carbonyl</div>
<div>
Compounds........................................................................................ 171</div>
<div>
2.4.3. The Julia Olefination Reaction ......................................................... 174</div>
<div>
2.5. Reactions Proceeding by Addition-Cyclization ........................................... 177</div>
<div>
2.5.1. Sulfur Ylides and Related Nucleophiles........................................... 177</div>
<div>
2.5.2. Nucleophilic Addition-Cyclization of  -Haloesters......................... 182</div>
<div>
2.6. Conjugate Addition by Carbon Nucleophiles .............................................. 183</div>
<div>
2.6.1. Conjugate Addition of Enolates........................................................ 183</div>
<div>
2.6.2. Conjugate Addition with Tandem Alkylation .................................. 189</div>
<div>
2.6.3. Conjugate Addition by Enolate Equivalents..................................... 190</div>
<div>
2.6.4. Control of Facial Selectivity in Conjugate</div>
<div>
Addition Reactions ............................................................................ 193</div>
<div>
2.6.5. Conjugate Addition of Organometallic Reagents............................. 197</div>
<div>
2.6.6. Conjugate Addition of Cyanide Ion.................................................. 198</div>
<div>
General References............................................................................................... 200</div>
<div>
Problems ............................................................................................................... 200</div>
<div>
Chapter 3. Functional Group Interconversion</div>
<div>
by Substitution, Including Protection and Deprotection . . . . . . 215</div>
<div>
Introduction........................................................................................................... 215</div>
<div>
3.1. Conversion of Alcohols to Alkylating Agents............................................. 216</div>
<div>
3.1.1. Sulfonate Esters ................................................................................. 216</div>
<div>
3.1.2. Halides ............................................................................................... 217</div>
</div>
<div>
<div>
3.2. Introduction of Functional Groups by Nucleophilic Substitution</div>
<div>
at Saturated Carbon ...................................................................................... 223</div>
<div>
3.2.1. General Solvent Effects..................................................................... 224</div>
<div>
3.2.2. Nitriles ............................................................................................... 225</div>
<div>
3.2.3. Oxygen Nucleophiles ........................................................................ 226</div>
<div>
3.2.4. Nitrogen Nucleophiles....................................................................... 229</div>
<div>
3.2.5. Sulfur Nucleophiles ........................................................................... 233</div>
<div>
3.2.6. Phosphorus Nucleophiles .................................................................. 233</div>
<div>
3.2.7. Summary of Nucleophilic Substitution at Saturated Carbon ........... 234</div>
<div>
3.3. Cleavage of Carbon-Oxygen Bonds in Ethers and Esters........................... 238</div>
<div>
3.4. Interconversion of Carboxylic Acid Derivatives ......................................... 242</div>
<div>
3.4.1. Acylation of Alcohols ....................................................................... 243</div>
<div>
3.4.2. Fischer Esterification......................................................................... 252</div>
<div>
3.4.3. Preparation of Amides....................................................................... 252</div>
<div>
3.5. Installation and Removal of Protective Groups........................................... 258</div>
<div>
3.5.1. Hydroxy-Protecting Groups .............................................................. 258</div>
<div>
3.5.2. Amino-Protecting Groups ................................................................. 267</div>
<div>
3.5.3. Carbonyl-Protecting Groups.............................................................. 272</div>
<div>
3.5.4. Carboxylic Acid–Protecting Groups ................................................. 275</div>
<div>
Problems ............................................................................................................... 277</div>
<div>
Chapter 4. Electrophilic Additions to Carbon-Carbon Multiple Bonds . . . 289</div>
<div>
Introduction........................................................................................................... 289</div>
<div>
4.1. Electrophilic Addition to Alkenes................................................................ 290</div>
<div>
4.1.1. Addition of Hydrogen Halides.......................................................... 290</div>
<div>
4.1.2. Hydration and Other Acid-Catalyzed Additions of Oxygen</div>
<div>
Nucleophiles ...................................................................................... 293</div>
<div>
4.1.3. Oxymercuration-Reduction ............................................................... 294</div>
<div>
4.1.4. Addition of Halogens to Alkenes ..................................................... 298</div>
<div>
4.1.5. Addition of Other Electrophilic Reagents ........................................ 305</div>
<div>
4.1.6. Addition Reactions with Electrophilic Sulfur and Selenium</div>
<div>
Reagents............................................................................................. 307</div>
<div>
4.2. Electrophilic Cyclization .............................................................................. 310</div>
<div>
4.2.1. Halocyclization .................................................................................. 311</div>
<div>
4.2.2. Sulfenylcyclization and Selenenylcyclization................................... 320</div>
<div>
4.2.3. Cyclization by Mercuric Ion ............................................................. 324</div>
<div>
4.3. Electrophilic Substitution <span class="Apple-tab-span" style="white-space: pre;"> </span> to Carbonyl Groups........................................ 328</div>
<div>
4.3.1. Halogenation <span class="Apple-tab-span" style="white-space: pre;"> </span> to Carbonyl Groups ................................................ 328</div>
<div>
4.3.2. Sulfenylation and Selenenylation <span class="Apple-tab-span" style="white-space: pre;"> </span> to Carbonyl Groups ................ 331</div>
<div>
4.4. Additions to Allenes and Alkynes ............................................................... 333</div>
<div>
4.5. Addition at Double Bonds via Organoborane Intermediates ...................... 337</div>
<div>
4.5.1. Hydroboration.................................................................................... 337</div>
<div>
4.5.2. Reactions of Organoboranes ............................................................. 344</div>
<div>
4.5.3. Enantioselective Hydroboration ........................................................ 347</div>
<div>
4.5.4. Hydroboration of Alkynes................................................................. 352</div>
<div>
4.6. Hydroalumination, Carboalumination, Hydrozirconation,</div>
<div>
and Related Reactions .................................................................................. 353</div>
</div>
<div>
<div>
Chapter 5. Reduction of Carbon-Carbon Multiple Bonds, Carbonyl</div>
<div>
Groups, and Other Functional Groups . . . . . . . . . . . . . . . . . . . . . . 367</div>
<div>
Introduction........................................................................................................... 367</div>
<div>
5.1. Addition of Hydrogen at Carbon-Carbon Multiple Bonds.......................... 368</div>
<div>
5.1.1. Hydrogenation Using Heterogeneous Catalysts ............................... 368</div>
<div>
5.1.2. Hydrogenation Using Homogeneous Catalysts ................................ 374</div>
<div>
5.1.3. Enantioselective Hydrogenation........................................................ 376</div>
<div>
5.1.4. Partial Reduction of Alkynes ............................................................ 387</div>
<div>
5.1.5. Hydrogen Transfer from Diimide ..................................................... 388</div>
<div>
5.2. Catalytic Hydrogenation of Carbonyl and Other Functional Groups ......... 390</div>
<div>
5.3. Group III Hydride-Donor Reagents ............................................................. 396</div>
<div>
5.3.1. Comparative Reactivity of Common Hydride</div>
<div>
Donor Reagents ................................................................................. 396</div>
<div>
5.3.2. Stereoselectivity of Hydride Reduction ............................................ 407</div>
<div>
5.3.3. Enantioselective Reduction of Carbonyl Compounds...................... 415</div>
<div>
5.3.4. Reduction of Other Functional Groups by Hydride Donors............ 422</div>
<div>
5.4. Group IV Hydride Donors ........................................................................... 425</div>
<div>
5.4.1. Reactions Involving Silicon Hydrides .............................................. 425</div>
<div>
5.4.2. Hydride Transfer from Carbon ......................................................... 429</div>
<div>
5.5. Reduction Reactions Involving Hydrogen Atom Donors............................ 431</div>
<div>
5.6. Dissolving-Metal Reductions ....................................................................... 434</div>
<div>
5.6.1. Addition of Hydrogen ....................................................................... 435</div>
<div>
5.6.2. Reductive Removal of Functional Groups ....................................... 439</div>
<div>
5.6.3. Reductive Coupling of Carbonyl Compounds.................................. 444</div>
<div>
5.7. Reductive Deoxygenation of Carbonyl Groups........................................... 452</div>
<div>
5.7.1. Reductive Deoxygenation of Carbonyl Groups to Methylene ......... 452</div>
<div>
5.7.2. Reduction of Carbonyl Compounds to Alkenes............................... 454</div>
<div>
5.8. Reductive Elimination and Fragmentation................................................... 457</div>
<div>
Problems ............................................................................................................... 462</div>
<div>
Chapter 6. Concerted Cycloadditions, Unimolecular Rearrangements,</div>
<div>
and Thermal Eliminations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 473</div>
<div>
Introduction........................................................................................................... 473</div>
<div>
6.1. Diels-Alder Reactions................................................................................... 474</div>
<div>
6.1.1. The Diels-Alder Reaction: General Features.................................... 474</div>
<div>
6.1.2. Substituent Effects on the Diels-Alder Reaction.............................. 475</div>
<div>
6.1.3. Lewis Acid Catalysis of the Diels-Alder Reaction .......................... 481</div>
<div>
6.1.4. The Scope and Synthetic Applications</div>
<div>
of the Diels-Alder Reaction .............................................................. 487</div>
<div>
6.1.5. Diastereoselective Diels-Alder Reactions</div>
<div>
Using Chiral Auxiliaries ................................................................... 499</div>
<div>
6.1.6. Enantioselective Catalysts for Diels-Alder Reactions...................... 505</div>
<div>
6.1.7. Intramolecular Diels-Alder Reactions............................................... 518</div>
</div>
<div>
<div>
6.2. 1,3-Dipolar Cycloaddition Reactions ........................................................... 526</div>
<div>
6.2.1. Regioselectivity and Stereochemistry ............................................... 528</div>
<div>
6.2.2. Synthetic Applications of Dipolar Cycloadditions ........................... 531</div>
<div>
6.2.3. Catalysis of 1,3-Dipolar Cycloaddition Reactions ........................... 535</div>
<div>
6.3. [2 + 2] Cycloadditions and Related Reactions Leading</div>
<div>
to Cyclobutanes ............................................................................................ 538</div>
<div>
6.3.1. Cycloaddition Reactions of Ketenes and Alkenes............................ 539</div>
<div>
6.3.2. Photochemical Cycloaddition Reactions........................................... 544</div>
<div>
6.4. [3,3]-Sigmatropic Rearrangements............................................................... 552</div>
<div>
6.4.1. Cope Rearrangements........................................................................ 552</div>
<div>
6.4.2. Claisen and Modified Claisen Rearrangements................................ 560</div>
<div>
6.5. [2,3]-Sigmatropic Rearrangements............................................................... 581</div>
<div>
6.5.1. Rearrangement of Allylic Sulfoxides, Selenoxides,</div>
<div>
and Amine Oxides............................................................................. 581</div>
<div>
6.5.2. Rearrangement of Allylic Sulfonium and Ammonium Ylides......... 583</div>
<div>
6.5.3. Anionic Wittig and Aza-Wittig Rearrangements ............................. 587</div>
<div>
6.6. Unimolecular Thermal Elimination Reactions............................................. 590</div>
<div>
6.6.1. Cheletropic Elimination..................................................................... 591</div>
<div>
6.6.2. Decomposition of Cyclic Azo Compounds ...................................... 593</div>
<div>
6.6.3.  -Eliminations Involving Cyclic Transition Structures.................... 596</div>
<div>
Problems ............................................................................................................... 604</div>
<div>
Chapter 7. Organometallic Compounds of Group I and II Metals . . . . . . . 619</div>
<div>
Introduction........................................................................................................... 619</div>
<div>
7.1. Preparation and Properties of Organomagnesium</div>
<div>
and Organolithium Reagents ........................................................................ 620</div>
<div>
7.1.1. Preparation and Properties of Organomagnesium Reagents ............ 620</div>
<div>
7.1.2. Preparation and Properties of Organolithium Compounds .............. 624</div>
<div>
7.2. Reactions of Organomagnesium and Organolithium Compounds .............. 634</div>
<div>
7.2.1. Reactions with Alkylating Agents .................................................... 634</div>
<div>
7.2.2. Reactions with Carbonyl Compounds .............................................. 637</div>
<div>
7.3. Organometallic Compounds of Group IIB and IIIB Metals ....................... 650</div>
<div>
7.3.1. Organozinc Compounds .................................................................... 650</div>
<div>
7.3.2. Organocadmium Compounds............................................................ 661</div>
<div>
7.3.3. Organomercury Compounds ............................................................. 662</div>
<div>
7.3.4. Organoindium Reagents .................................................................... 663</div>
<div>
7.4. Organolanthanide Reagents.......................................................................... 664</div>
<div>
General References............................................................................................... 666</div>
<div>
Problems ............................................................................................................... 667</div>
<div>
Chapter 8. Reactions Involving Transition Metals. . . . . . . . . . . . . . . . . . . . . . . 675</div>
<div>
Introduction........................................................................................................... 675</div>
<div>
8.1. Organocopper Intermediates......................................................................... 675</div>
<div>
8.1.1. Preparation and Structure of Organocopper Reagents ..................... 675</div>
<div>
8.1.2. Reactions Involving Organocopper Reagents</div>
<div>
and Intermediates............................................................................... 680</div>
</div>
<div>
<div>
8.2. Reactions Involving Organopalladium Intermediates.................................. 706</div>
<div>
8.2.1. Palladium-Catalyzed Nucleophilic Addition</div>
<div>
and Substitution ................................................................................. 709</div>
<div>
8.2.2. The Heck Reaction............................................................................ 715</div>
<div>
8.2.3. Palladium-Catalyzed Cross Coupling ............................................... 723</div>
<div>
8.2.4. Carbonylation Reactions ................................................................... 748</div>
<div>
8.3. Reactions Involving Other Transition Metals.............................................. 754</div>
<div>
8.3.1. Organonickel Compounds................................................................. 754</div>
<div>
8.3.2. Reactions Involving Rhodium and Cobalt........................................ 759</div>
<div>
8.4. The Olefin Metathesis Reaction................................................................... 761</div>
<div>
8.5. Organometallic Compounds with </div>
<div>
-Bonding.............................................. 767</div>
<div>
General References............................................................................................... 771</div>
<div>
Problems ............................................................................................................... 771</div>
<div>
Chapter 9. Carbon-Carbon Bond-Forming Reactions</div>
<div>
of Compounds of Boron, Silicon, and Tin. . . . . . . . . . . . . . . . . . . . 783</div>
<div>
Introduction........................................................................................................... 783</div>
<div>
9.1. Organoboron Compounds............................................................................. 784</div>
<div>
9.1.1. <b>Synthesis </b>of Organoboranes.............................................................. 784</div>
<div>
9.1.2. Carbonylation and Other One-Carbon</div>
<div>
Homologation Reactions ................................................................... 786</div>
<div>
9.1.3. Homologation via <span class="Apple-tab-span" style="white-space: pre;"> </span>-Halo Enolates .................................................. 792</div>
<div>
9.1.4. Stereoselective Alkene Synthesis...................................................... 793</div>
<div>
9.1.5. Nucleophilic Addition of Allylic Groups from</div>
<div>
Boron Compounds............................................................................. 797</div>
<div>
9.2. Organosilicon Compounds ........................................................................... 809</div>
<div>
9.2.1. Synthesis of Organosilanes ............................................................... 809</div>
<div>
9.2.2. General Features of Carbon-Carbon Bond-Forming Reactions</div>
<div>
of Organosilicon Compounds ........................................................... 814</div>
<div>
9.2.3. Additions <b>Reactions </b>with Aldehydes and Ketones .......................... 815</div>
<div>
9.2.4. Reaction with Iminium Ions.............................................................. 825</div>
<div>
9.2.5. Acylation Reactions........................................................................... 826</div>
<div>
9.2.6. Conjugate Addition Reactions .......................................................... 830</div>
<div>
9.3. Organotin Compounds.................................................................................. 833</div>
<div>
9.3.1. Synthesis of Organostannanes........................................................... 833</div>
<div>
9.3.2. Carbon-Carbon Bond-Forming Reactions ........................................ 836</div>
<div>
9.4. Summary of Stereoselectivity Patterns ........................................................ 851</div>
<div>
General References............................................................................................... 852</div>
<div>
Problems ............................................................................................................... 853</div>
<div>
Chapter 10. <b>Reactions </b>Involving Carbocations, Carbenes,</div>
<div>
and Radicals as Reactive Intermediates . . . . . . . . . . . . . . . . . . . . . 861</div>
<div>
Introduction............................................................................................................. 861</div>
<div>
10.1. Reactions and Rearrangement Involving Carbocation Intermediates ......... 862</div>
<div>
10.1.1. Carbon-Carbon Bond Formation Involving Carbocations ............. 862</div>
<div>
10.1.2. Rearrangement of Carbocations ...................................................... 883</div>
<div>
10.1.3. Related Rearrangements.................................................................. 892</div>
<div>
10.1.4. Fragmentation Reactions ................................................................. 897</div>
</div>
<div>
<div>
10.2. Reactions Involving Carbenes and Related Intermediates .......................... 903</div>
<div>
10.2.1. Reactivity of Carbenes .................................................................... 905</div>
<div>
10.2.2. Generation of Carbenes................................................................... 909</div>
<div>
10.2.3. Addition <b>Reactions </b>.......................................................................... 916</div>
<div>
10.2.4. Insertion <b>Reactions </b>.......................................................................... 934</div>
<div>
10.2.5. Generation and Reactions of Ylides</div>
<div>
by Carbenoid Decomposition.......................................................... 938</div>
<div>
10.2.6. Rearrangement Reactions................................................................ 940</div>
<div>
10.2.7. Related <b>Reactions </b>............................................................................ 941</div>
<div>
10.2.8. Nitrenes and Related Intermediates ................................................ 944</div>
<div>
10.2.9. Rearrangements to Electron-Deficient Nitrogen ............................ 947</div>
<div>
10.3. Reactions Involving Free Radical Intermediates ......................................... 956</div>
<div>
10.3.1. Sources of Radical Intermediates.................................................... 957</div>
<div>
10.3.2. Addition Reactions of Radicals with Substituted Alkenes............. 959</div>
<div>
10.3.3. Cyclization of Free Radical Intermediates ..................................... 967</div>
<div>
10.3.4. Additions to C=N Double Bonds................................................... 973</div>
<div>
10.3.5. Tandem Radical Cyclizations and Alkylations............................... 979</div>
<div>
10.3.6. Fragmentation and Rearrangement Reactions ................................ 984</div>
<div>
10.3.7. Intramolecular Functionalization by Radical Reactions................. 989</div>
<div>
Problems ................................................................................................................. 992</div>
<div>
Chapter 11. Aromatic Substitution Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1003</div>
<div>
Introduction............................................................................................................. 1003</div>
<div>
11.1. Electrophilic Aromatic Substitution ............................................................. 1004</div>
<div>
11.1.1. Nitration........................................................................................... 1004</div>
<div>
11.1.2. Halogenation.................................................................................... 1008</div>
<div>
11.1.3. Friedel-Crafts Alkylation................................................................. 1014</div>
<div>
11.1.4. Friedel-Crafts Acylation.................................................................. 1017</div>
<div>
11.1.5. Related Alkylation and Acylation Reactions.................................. 1023</div>
<div>
11.1.6. Electrophilic Metallation ................................................................. 1026</div>
<div>
11.2. Nucleophilic Aromatic Substitution ............................................................. 1027</div>
<div>
11.2.1. Aryl Diazonium Ions as Synthetic Intermediates........................... 1027</div>
<div>
11.2.2. Substitution by the Addition-Elimination Mechanism................... 1035</div>
<div>
11.2.3. Substitution by the Elimination-Addition Mechanism................... 1039</div>
<div>
11.3. Transition Metal–Catalyzed Aromatic Substitution Reactions.................... 1042</div>
<div>
11.3.1. Copper-Catalyzed Reactions ........................................................... 1042</div>
<div>
11.3.2. Palladium-Catalyzed Reactions....................................................... 1045</div>
<div>
11.4. Aromatic Substitution Reactions Involving Radical Intermediates............. 1052</div>
<div>
11.4.1. Aromatic Radical Substitution ........................................................ 1052</div>
<div>
11.4.2. Substitution by the SRN 1 Mechanism ............................................. 1053</div>
<div>
Problems ................................................................................................................. 1056</div>
<div>
Chapter 12. Oxidations. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1063</div>
<div>
Introduction............................................................................................................. 1063</div>
<div>
12.1. Oxidation of Alcohols to Aldehydes, Ketones, or Carboxylic Acids ......... 1063</div>
<div>
12.1.1. Transition Metal Oxidants............................................................... 1063</div>
<div>
12.1.2. Other Oxidants................................................................................. 1070</div>
<div>
<br /></div>
<div>
Contents</div>
<div>
12.2. Addition of Oxygen at Carbon-Carbon Double Bonds ............................... 1074</div>
<div>
12.2.1. Transition Metal Oxidants............................................................... 1074</div>
<div>
12.2.2. Epoxides from Alkenes and Peroxidic Reagents............................ 1091</div>
<div>
12.2.3. Subsequent Transformations of Epoxides ...................................... 1104</div>
<div>
12.3. Allylic Oxidation .......................................................................................... 1116</div>
<div>
12.3.1. Transition Metal Oxidants............................................................... 1116</div>
<div>
12.3.2. Reaction of Alkenes with Singlet Oxygen ..................................... 1117</div>
<div>
12.3.3. Other Oxidants................................................................................. 1124</div>
<div>
12.4. Oxidative Cleavage of Carbon-Carbon Double Bonds ............................... 1126</div>
<div>
12.4.1. Transition Metal Oxidants............................................................... 1126</div>
<div>
12.4.2. Ozonolysis ....................................................................................... 1129</div>
<div>
12.5. Oxidation of Ketones and Aldehydes .......................................................... 1131</div>
<div>
12.5.1. Transition Metal Oxidants............................................................... 1131</div>
<div>
12.5.2. Oxidation of Ketones and Aldehydes by Oxygen</div>
<div>
and Peroxidic Compounds .............................................................. 1134</div>
<div>
12.5.3. Oxidation with Other Reagents....................................................... 1143</div>
<div>
12.6. Selective Oxidative Cleavages at Functional Groups.................................. 1144</div>
<div>
12.6.1. Cleavage of Glycols ........................................................................ 1144</div>
<div>
12.6.2. Oxidative Decarboxylation.............................................................. 1145</div>
<div>
12.7. Oxidations at Unfunctionalized Carbon....................................................... 1148</div>
<div>
Problems ................................................................................................................. 1151</div>
<div>
Chapter 13. Multistep Syntheses . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1163</div>
<div>
Introduction............................................................................................................. 1163</div>
<div>
13.1. <b>Synthetic Analysis</b> and Planning.................................................................. 1164</div>
<div>
13.1.1. Retrosynthetic Analysis................................................................... 1164</div>
<div>
13.1.2. Synthetic Equivalent Groups........................................................... 1166</div>
<div>
13.1.3. Control of <b>Stereochemistry </b>............................................................. 1171</div>
<div>
13.2. Illustrative <b>Syntheses</b>.................................................................................... 1173</div>
<div>
13.2.1. Juvabione ......................................................................................... 1174</div>
<div>
13.2.2. Longifolene...................................................................................... 1186</div>
<div>
13.2.3. Prelog-Djerassi Lactone .................................................................. 1196</div>
<div>
13.2.4. Baccatin III and Taxol .................................................................... 1210</div>
<div>
13.2.5. Epothilone A.................................................................................... 1220</div>
<div>
13.2.6. Discodermolide................................................................................ 1231</div>
<div>
13.3. Solid Phase <b>Synthesis</b>................................................................................... 1245</div>
<div>
13.3.1. Solid Phase Polypeptide <b>Synthesis </b>................................................. 1245</div>
<div>
13.3.2. Solid Phase <b>Synthesis </b>of Oligonucleotides..................................... 1250</div>
<div>
13.4. Combinatorial <b>Synthesis</b>............................................................................... 1252</div>
<div>
General References................................................................................................. 1259</div>
<div>
Problems ................................................................................................................. 1260</div>
</div>
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