organic mechanisms - reactions, stereochemistry and synthesis

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[...]... electrons) and alkenes, including a, b-unsaturated esters (by cleavage of a pi bond) As might be expected, there are overall substitutions involving addition(s) and fragmentation(s) You will learn more about these options in the following sections Bruckner R (author), Harmata M (editor) In: Organic Mechanisms – Reactions, Stereochemistry and Synthesis Chapter DOI: 10.1007/97 8-3 -6 4 2-0 365 1-4 _1, © Springer-Verlag... 148 150 150 152 4 b-Eliminations 157 4.1 Concepts of Elimination Reactions 4.1.1 The Concepts of a,b- and 1,n-Elimination 4.1.2 The Terms syn- and anti-Elimination 4.1.3 When Are syn- and anti-Selective Eliminations Stereoselective? 4.1.4 Formation of Regioisomeric Alkenes by b-Elimination: Saytzeff and Hofmann Product(s)... 14.5.2 Ireland-Claisen Rearrangements 14.4 14.5 595 596 598 598 615 622 623 624 627 629 630 632 632 634 15 Thermal Cycloadditions 643 15.1 Driving Force and Feasibility of One-Step [4+2 ]- and [2+2]-Cycloadditions Transition State Structures of Selected One-Step [4+2 ]- and [2+2]-Cycloadditions... Prepared Enolates and Aza-enolates; Chain-Elongating Syntheses of Carbonyl Compounds and Carboxylic Acid Derivatives 13.2.1 Chain-Elongating Syntheses of Carbonyl Compounds 13.2.2 Chain-Elongating Syntheses of Carboxylic Acid Derivatives Hydroxyalkylation of Enolates with Carbonyl Compounds (“Aldol Addition”): Synthesis of b-Hydroxyketones and b-Hydroxyesters... Julia–Lythgoe- and (Sylvestre) Julia–Kocienski Olefination 12 The Chemistry of Enols and Enamines 487 12.1 12.3 12.4 Keto-Enol Tautomerism; Enol Content of Carbonyl and Carboxyl Compounds a-Functionalization of Carbonyl and Carboxyl Compounds via Tautomeric Enols a-Functionalization of Ketones via Their Enamines a-Functionalization... Helmchen, and Enders), diastereoselective aldol additions (Heathcock method, Zimmerman-Traxler model), ClaisenIreland rearrangements, transition metal-mediated C,C-coupling reactions, Swern and DessMartin oxidations, reductive lithiations, enantioselective carbonyl reductions (Noyori, Brown, and Corey-Itsuno methods), and asymmetric olefin hydrogenations The presentations of many reactions integrate discussions... Three-Membered Rings 3.3.2 Additions to C෇C Double Bonds That Are Related to Cycloadditions and Also Form Three-Membered Rings 3.3.3 cis-Hydration of Alkenes via the Hydroboration/Oxidation/ Hydrolysis Reaction Sequence 3.3.4 Heterogeneous Hydrogenation Enantioselective cis-Additions to C෇C Double Bonds 3.4.1 Vocabulary of Stereochemistry and. .. has become less relevant and, for this reason, the following reactions were omitted: Darzens glycidic ester synthesis, Cope elimination, SNi reaction, iodoform reaction, ReimerTiemann reaction, Stobbe condensation, Perkin synthesis, benzoin condensation, Favorskii rearrangement, benzil-benzilic acid rearrangement, Hofmann and Lossen degradation, Meerwein-Ponndorf reduction and Cannizarro reaction A... of Hᮍ vs ipso-Substitution 5.1.2 Thermodynamic Aspects of Ar-SE Reactions 5.1.3 Kinetic Aspects of Ar-SE Reactions: Reactivity and Regioselectivity in Reactions of Electrophiles with Substituted Benzenes Ar-SE Reactions via Sigma Complexes: Individual Reactions 5.2.1 Ar—Hal Bond Formation by Ar-SE Reaction 5.2.2 Ar—SO3H Bond Formation by Ar-SE Reaction... Ar—NO2 Bond Formation by Ar-SE Reaction 5.2.4 Ar—N෇N Bond Formation by Ar-SE Reaction 5.2.5 Ar—Alkyl Bond Formations by Ar-SE Reaction 5.2.6 Ar—C(OH) Bond Formation by Ar-SE Reactions and Associated Secondary Reactions 5.2.7 Ar—C(෇O) Bond Formation by Ar-SE Reaction 5.2.8 Ar—C(෇O)H Bond Formation through Ar-SE Reaction Electrophilic . Missouri-Columbia 601 S. College Avenue Columbia, Missouri 65211 harmatam@missouri.edu Translation: Karin Beifuss ISBN: 97 8-3 -6 4 2-0 365 0-7 e-ISBN: 97 8-3 -6 4 2-0 365 1-4 DOI: 10.1007/97 8-3 -6 4 2-0 365 1-4 Library. class="bi x0 y0 w0 h0" alt="" Organic Mechanisms Reactions, Stereochemistry and Synthesis Reinhard Bruckner Organic Mechanisms Reactions, Stereochemistry and Synthesis Edited by Michael Harmata With. and Enders), diastereoselective aldol additions (Heathcock method, Zimmerman-Traxler model), Claisen- Ireland rearrangements, transition metal-mediated C,C-coupling reactions, Swern and Dess- Martin

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Xem thêm: organic mechanisms - reactions, stereochemistry and synthesis, organic mechanisms - reactions, stereochemistry and synthesis, 1 Bonding and Preferred Geometries in Carbon Radicals, Carbenium Ions and Carbanions, 4 SN2 Reactions: Kinetic and Stereochemical Analysis—Substituent Effects on Reactivity, 5 SN1 Reactions: Kinetic and Stereochemical Analysis; Substituent Effects on Reactivity, 7 Getting by with Help from Friends, or a Least Neighbors: Neighboring Group Participation, 5 Additions that Take Place Diastereoselectively as trans-Additions (Additions via Onium Intermediates), 2 β-Eliminations of H/Het via Cyclic Transition States, 4 E2 Eliminations of H/Het and the E2/SN2 Competition, 5 E1 Elimination of H/Het from Rtert—X and the E1/SN1 Competition, 2 Mechanisms, Rate Laws, and Rate of Nucleophilic Substitution Reactions at the Carboxyl Carbon, 5 SN Reactions of Hydride Donors, Organometallics, and Heteroatom-Stabilized “Carbanions” on the Carboxyl Carbon, 1 Suitable Hydride Donors and Organometallic Compounds; the Structure of Organolithium Compounds and Grignard Reagents, Similarities and Differences in the Reactions of Organolithium vs. Grignard Reagents with Carbonyl Compounds, 6 1,4-Additions of Organometallic Compounds to α,β-Unsaturated Ketones; Structure of Copper- Containing Organometallic Compounds, 4 (Marc) Julia–Lythgoe– and (Sylvestre) Julia–Kocienski Olefination, 1 Keto-Enol Tautomerism; Enol Content of Carbonyl and Carboxyl Compounds, 2 α-Functionalization of Carbonyl and Carboxyl Compounds via Tautomeric Enols, 3 α-Functionalization of Ketones via Their Enamines, 4 α-Functionalization of Enol Ethers and Silyl Enol Ethers, 2 Alkylation of Quantitatively Prepared Enolates and Aza-enolates; Chain-Elongating Syntheses of Carbonyl Compounds and Carboxylic Acid Derivatives, 3 Hydroxyalkylation of Enolates with Carbonyl Compounds (“Aldol Addition”): Synthesis of β-Hydroxyketones and β -Hydroxyesters, 4 Condensation of Enolates with Carbonyl Compounds: Synthesis of Michael Acceptors, 3 [1,2]-Rearrangements in Species with a Valence Electron Sextet, 4 [1,2]-Rearrangements without the Occurrence of a Sextet Intermediate, 1 Oxidation Numbers in Organic Chemical Compounds, and Organic Chemical Redox Reactions

organic mechanisms - reactions, stereochemistry and synthesis

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Cover Page

Title Page

ISBN 3642036503

Biographies

Reinhard Bruckner

Michael Harmata

Dedication Page

Foreword

Preface to the English Edition

Preface to the 1st German Edition

Preface to the 2nd German Edition

Preface to the 3rd German Edition

Table of Contents

1 Radical Substitution Reactions at the Saturated C Atom

2 Nucleophilic Substitution Reactions at the Saturated C Atom

3 Electrophilic Additions to the C=C Double Bond

4 β-Eliminations

5 Substitution Reactions on Aromatic Compounds

6 Nucleophilic Substitution Reactions at the Carboxyl Carbon

7 Carboxylic Compounds, Nitriles, and Their Interconversion

8 Carbonic Acid Derivatives and Heterocumulenes and Their Interconversion

9 Additions of Heteroatom Nucleophiles to Carbonyl Compounds and Subsequent Reactions—Condensations of Heteroatom Nucleophiles with Carbonyl Compounds

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