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Synthesis 1979; 1979(5): 321-336
DOI: 10.1055/s-1979-28668
review
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Synthesis of Bicyclo[3.3.1]nonanes

J. A. Peters*
  • *Laboratory of Organic Chemistry, Delft University of Technology, Julianalaan 136, Delft, The Netherlands
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Publikationsdatum:
14. Mai 2002 (online)

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Methods for the synthesis of the synthetically and theoretically interesting bicyclo[3.3.1]nonane system are reviewed. The synthetic methods are classified in five general types: annulation of cyclohexanes, annulation of cyclooctanes, ring cleavage of adamantanes, skeletal isomerizations, and syntheses from other bicyclo[3.3.1 ]nonanes. Emphasis is placed on the 3- and 3,7-substituted bicyclo[3.3.1]nonanes in view of their importance as precursors for admantane derivatives. The literature published since the last review (1969) on this topic has been emphasized. 1. Introduction 2. Annulation of Cyclohexane Derivatives 3. Annulation of Cyclooctane Derivatives 4. Ring Cleavage of Adamantane Derivatives 5. Skeletal Isomerization Reactions 6. Synthesis from other Bicyclo[3.3.1]nonanes.