Stereochemistry of radical reactions : concepts, guidelines, and synthetic applications / / Dennis P. Curran, Ned A. Porter, Bernd Giese ; with a foreword by Ernest L. Eliel

• Autore: Curran Dennis P.
• Pubblicazione: Weinheim, Germany : , : VCH, , 1996; ©1996
• Descrizione fisica: 1 online resource (294 p.)
• Disciplina: 541.223; 547.139
• Soggetto topico: Free radical reactions; Radicals (Chemistry); Stereochemistry
• Persona (resp. second.): PorterNed A.; GieseBernd <1940->; ElielErnest L.
• Note generali: Description based upon print version of record.
• Nota di bibliografia: Includes bibliographical references at the end of each chapters and index.
• Nota di contenuto: Stereochemistry of Radical Reactions; Table of Contents; Chapter 1 Radical Reactions in Organic Synthesis; 1.1 Introduction; 1.2 Principles of Radical Reactions; 1.2.1 General Considerations; 1.2.2 Medium and Temperature Effects; 1.2.3 Stereochemical Features of Carbon-Centered Radicals; 1.2.4 Reactions of Radicals; 1.3 Methods to Conduct Radical Reactions; 1.3.1 Chain Methods; 1.3.1.1 Tributyltin and Tris(trimethylsilyl)silicon Hydride; 1.3.1.2 Allyltributylstannane; 1.3.1.3 Atom and Group Transfer Reactions; 1.3.1.4 Thiohydroxamates; 1.3.2 Non-Chain Methods ; 1.4 Comparisons of Stereoselective Radical Reactions with Ionic and Pericyclic AnalogsReferences; Chapter 2 Substrate Control: Radical Cyclizations; 2.1 Introduction; 2.2 Face-Selective Radical Cyclizations to Multiple Bonds; 2.2.1 Butenyl and Related Radical Cyclizations; 2.2.2 Pentenyl and Related Radical Cyclizations; 2.2.3 Hexenyl and Related Radical Cyclizations; 2.2.3.1 5-Exo Cyclizations, the Beckwith-Houk Transition State Model; 2.2.3.2 Stereoselectivities of Acyclic Hexenyl Radicals; 2.2.3.3 Stereoselectivities in Cyclic Systems; 2.2.3.4 6-Endo Cyclizations ; 2.2.4 Heptenyl and Related Radical Cyclizations2.2.5 Higher Cyclizations; 2.2.6 Radicals Bearing Stereocenters Outside the Cyclizing Unit; 2.3 Stereocontrol in Cyclization/Fragmentation Sequences; 2.4 Group-Selective Cyclizations; 2.4.1 Two Acceptors/One Precursor; 2.4.2 Two Precursors/One Acceptor; 2.5 Cyclizations under Thermodynamic Control; 2.6 Cyclization by Intramolecular Homolytic Substitution; References; Chapter 3 Substrate Control: Cyclic Systems; 3.1 Cyclic Radicals; 3.1.1 Three- and Four-Membered Cyclic Radicals; 3.1.2 Five-Membered Cyclic Radicals; 3.1.2.1 Endocyclic Substituents ; 3.1.2.2 Exocyclic Substituents3.1.2.3 Additive and Medium Effects; 3.1.2.4 Multiple Substitution; 3.1.3 Six-Membered Cyclic Radicals; 3.1.3.1 Steric Effect of Substituents; 3.1.3.2 Stereoelectronic Effects; 3.1.3.3 Exocyclic Substituents; 3.1.3.4 Medium Effects; 3.1.3.5 Multiple Substitution; 3.2 Cyclic Radical Traps; References; Chapter 4 Substrate Control: Acyclic Systems; 4.1 Acyclic Radicals; 4.1.1 Allylic Strain Effects: Ester-Substituted Radicals; 4.1.1.1 Effect of Polar Substituents; 4.1.1.2 Hydrogen Bond and Complexation Effects ; 4.1.1.3 Effect of Substituents at the Prostereogenic Center4.1.2 Allylic Strain-Inducing Substituents; 4.1.3 The Felkin-Anh Rule for Radicals; 4.1.3.1 Complexation Effects; 4.1.4 Sulfoxides and Phosphine Oxides; 4.2 Acyclic Radical Traps; References; Chapter 5 Chiral Auxiliary Control; 5.1 General Considerations; 5.1.1 Radical Addition; 5.1.2 Atom and Group Transfer Reactions; 5.2 Auxiliary Group Attached to the Radical Center; 5.2.1 Radical Stabilization by Delocalization; 5.2.2 Structure and Dynamics of Radicals a to Amides; 5.2.3 Amide Chiral Auxiliaries for Acyclic Free Radical Reactions ; 5.2.3.1 C2 Symmetry
• Sommario/riassunto: As little as a decade ago, radicals were regarded as interesting reactive intermediates with little synthetic use. However, recent results show that radicals have an enormous potential for applications in stereoselective reactions - it's all a matter of knowing what method to use and how to apply it.Three world experts in the field have combined their expertise and present the concepts to understand and even to predict the course of stereoselective radical reactions. In addition, guidelines are established which will enable the readers to plan and carry out their own stereoselective sy
• Titolo autorizzato: Stereochemistry of radical reactions
• ISBN: 1-281-84273-7; 9786611842734; 3-527-61523-7; 3-527-61522-9
• Formato: Materiale a stampa
• Livello bibliografico: Monografia
• Lingua di pubblicazione: Tedesco
• Record Nr.: 9910830960003321
• Lo trovi qui: Univ. Federico II