Alkynes in cycloadditions
- author, Irina A. Maretina ; translated from the Russian by Boris I. Ionin ; consulting editor, John C. Tebby.
- Chichester, West Sussex : John Wiley & Sons, Inc., 2014.
- Physical description
- 1 online resource.
- Preface xi Acknowledgment xiii Biography xv 1 Introduction 1 2 Regioselective Syntheses of Polysubstituted BenzenesCatalyzed by Transition Metal Complexes 5 2.1 Reactions of [2+2+2] Cycloaddition of Acetylene Units 5 2.2 Stereochemical Aspect of The Problem of IntermolecularReactions of Diynes with Monoalkynes 18 2.3 Heteroatom Bound to the Triple Bond 28 2.4 Heterohelicens. Asymmetric Syntheses 34 2.5 Aromatic Rings with Boron and Silicon Substituents 38 2.6 [2+2+2] Cycloaddition Reactions of 1-Alkynylphosphines andTheir Derivatives 40 2.7 Intramolecular [2+2+2] Cycloaddition of Diynes to Alkenes45 2.8 Polysubstituted Benzenes. Reactions of [4+2] Cycloadditionand Other Approaches 53 2.9 Combined Reactions 63 2.10 Construction of Polycyclic Systems 71 3 Radical Cycloaromatization of Systems Containing(Z)-3-hexene-1,5-diynes and (Z)-1,2,4-heptatrien-6-ynes and RelatedHeteroatomic Blocks 107 3.1 The Historical Aspect of the Chemistry of Enediynes, Enyne-Allenes and Enyne-Cumulenes 107 3.2 Routes to the Cycloaromatization of Enediyne andEnyne-Allene Systems. Bergman and Myers Saito Cyclization113 3.3 Cycloaromatization by C1 C5, C2 C7 andC2 C6 (Myers Saito and Schmittel) Routes toIndeno-Fused Structures 135 3.4 External Initiation of the Enediyne Cycloaromatization157 3.5 Features of Cycloaromatization of Heteroatomic Enediynes179 3.6 Cycloaromatization of Hetero-Systems 223 4 Selected Cycloaddition and Heterocyclization Reactions withUnusual Acetylenic and Allenic Starting Compounds 233 4.1 Cycloaddition and Heterocyclization Reactions of AcetylenicCompounds with Electron-Withdrawing Substituents 233 4.2 Diels Alder [4+2] Cycloaddition: Acetylenes asDienophiles 235 4.3 Formation of Cyclobutene Derivatives by [2+2]-Cycloaddition237 4.4 [2+2] Cyclization of Some 1,3-Butadienes Produced fromAcetylenic Alcohols of Propargyl Type 243 4.5 Heterocyclization of Electron-Deficient Acetylenes withNucleophilic Reagents 245 5 Concluding Remarks 249 Index.
- (source: Nielsen Book Data)
- Publisher's Summary
- Acetylene systems present a new route to cyclic compounds as analternative to more traditional methods employed in classicalorganic chemistry. The synthesis of cyclic structures based onacetylene systems has important applications in the formation ofnanostructures, naturally occurring compounds and chemosensorymaterials for the design of nonlinear optics, electronic andphotonic devices. Alkynes in Cycloadditions presents a modern review ofregioselective synthesis of aromatic and non-aromatic carbocyclicand heterocyclic ring systems based primarily on [2+2+2] and [4+2]cycloadditions, and other reactions of acetylenic units includingenediynes and enyne-allenes. Topics covered include: * New strategies for the formation of aromatic and polynuclearhydrocarbons based on (Z)-hex-3-en-1,5-diyne and(Z)-hepta-1,2,4-triene-6-yne blocks. * One-step synthesis of benzene derivatives, -substitutednaphthalenes and acenes by the cycloaromatization of enediynes andenyne-allenes by Bergman, Myers-Saito and Shmittel. * Mechanisms of cycloaromatization resulting in the formation offulvene and indene systems. * Heterocyclization involving enyne-carbodiimides. * New achievements in classical cycloaddition reactions such asthe Diels-Alder condensation with acetylenic dienophiles and [2+2]cycloadditions with acetylene components Alkynes in Cycloadditions presents a comprehensivesummary of the literature on methods for the synthesis of ringsystems from acetylenes for academic researchers working in thefields of organic synthesis, physical organic chemistry, organometallic chemistry, catalysis, materials science, nanomaterials and biochemistry.
(source: Nielsen Book Data)
- Publication date
- Includes index.
- Available in another form
- Print version: Maretina, Irina A. Alkynes in cycloadditions Chichester, West Sussex : John Wiley & Sons, Inc., 2014 9781118615324 (DLC) 2013019891
- 9781118709313 (electronic bk.)
- 1118709314 (electronic bk.)
- 9781118709337 (electronic bk.)
- 1118709330 (electronic bk.)
- 9781118615324 (cloth)