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, beta-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 componentsAlkynes 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.

Preface xiAcknowledgment xiiiBiography xv1 Introduction 12 Regioselective Syntheses of Polysubstituted BenzenesCatalyzed by Transition Metal Complexes 52.1 Reactions of [2+2+2] Cycloaddition of Acetylene Units 52.2 Stereochemical Aspect of The Problem of IntermolecularReactions of Diynes with Monoalkynes 182.3 Heteroatom Bound to the Triple Bond 282.4 Heterohelicens. Asymmetric Syntheses 342.5 Aromatic Rings with Boron and Silicon Substituents 382.6 [2+2+2] Cycloaddition Reactions of 1-Alkynylphosphines andTheir Derivatives 402.7 Intramolecular [2+2+2] Cycloaddition of Diynes to Alkenes452.8 Polysubstituted Benzenes. Reactions of [4+2] Cycloadditionand Other Approaches 532.9 Combined Reactions 632.10 Construction of Polycyclic Systems 713 Radical Cycloaromatization of Systems Containing(Z)-3-hexene-1,5-diynes and (Z)-1,2,4-heptatrien-6-ynes and RelatedHeteroatomic Blocks 1073.1 The Historical Aspect of the Chemistry of Enediynes,Enyne-Allenes and Enyne-Cumulenes 1073.2 Routes to the Cycloaromatization of Enediyne andEnyne-Allene Systems. Bergman and Myers-Saito Cyclization1133.3 Cycloaromatization by C1-C5, C2-C7 andC2-C6 (Myers-Saito and Schmittel) Routes toIndeno-Fused Structures 1353.4 External Initiation of the Enediyne Cycloaromatization1573.5 Features of Cycloaromatization of Heteroatomic Enediynes1793.6 Cycloaromatization of Hetero-Systems 2234 Selected Cycloaddition and Heterocyclization Reactions withUnusual Acetylenic and Allenic Starting Compounds 2334.1 Cycloaddition and Heterocyclization Reactions of AcetylenicCompounds with Electron-Withdrawing Substituents 2334.2 Diels-Alder [4+2] Cycloaddition: Acetylenes asDienophiles 2354.3 Formation of Cyclobutene Derivatives by [2+2]-Cycloaddition2374.4 [2+2] Cyclization of Some 1,3-Butadienes Produced fromAcetylenic Alcohols of Propargyl Type 2434.5 Heterocyclization of Electron-Deficient Acetylenes withNucleophilic Reagents 2455 Concluding Remarks 249Index