organic mechanisms - reactions, stereochemistry and synthesis

[...]... 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