Synthese und Reaktionen von Bicyclo[6.4.0]dodecan-3-carbonsäure-Derivaten

✍ Scribed by Gerhard Buchbauer; Johanna Gabmeier; Ernst Haslinger; Wolfgang Robien; Harald Steindl

• Book ID: 102254140
• Publisher: John Wiley and Sons
• Year: 1985
• Tongue: German
• Weight: 315 KB
• Volume: 68
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19850680129

✦ Synopsis

Synthesis and Reactions of the Bicyclo[6.4.0]dodecane‐3‐carboxylic Acid Derivatives

The synthesis and some consecutive reactions of the compounds 5‐8, derivatives of bicyclo[6.4.0]dodecane‐3‐carboxylic acid (1), are described. The esters 7 and 8 can be obtained by Baeyer‐Villiger oxidation of 2‐hydroxy‐8‐methyltricyclo[7.3.1.0^2,7^]tridecan‐13‐one (4) and subsequent hydrolysis of the lactone 5. The structure and configuration of these compounds has been evaluated by spectroscopic techniques (mainly 2D‐NMR methods). The formation of 7 via 1,2‐H shift and subsequent isomerization to 8 has been studied. The esters 11 and 13 are formed stereospecifically from 7 and 8.