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Synthesis 1972; 1972(5): 235-253
DOI: 10.1055/s-1972-21859
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Synthesewege zu Cycloalkalinen mittlerer Ringgröße

Herbert MEIER*
  • *Chemisches Institut der Universität, D-74 Tübingen, Wilhelmstraße 33
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Publication Date:
27 September 2002 (online)

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Synthetic routes to stable cycloalkynes of medium ring size are discussed. Included are systems having additional unsaturated functions or aromatic rings and cycloalkynes containing heteroatoms in the ring. A bibliography of previous reviews providing information on cycloalkynes is given1-4. 1. Stability and Isomerization Tendency of Cycloalkynes 2. Syntheses of Cycloalkynes 2.1. Dehalogenation Reactions 2.2. Dehydrohalogenation Reactions 2.3. Oxidative Elimination of Nitrogen from Bis-hydrazones and 1,2,3-Triazoles 2.4. Photolytic Elimination of Nitrogen from Bis-tosylhydrazones 2.5. Thermolysis of Bicyclic Compounds 2.6. Fragmentation of α,β-Epoxy-ketone Derivatives 2.7. Photochemical Valence Isomerization of 1,4;2,3-Bis-[polymethylene]-cyclobutenes 2.8. Ring Closure of Open-Chain Alkynes by Coupling Reactions 3. Comparison of the Methods for the Preparation of Cycloalkynes