Unique formation of oxapentacycloundecanones by catalytic flash vacuum thermolysis of tricyclo[5.2.1.02,6]decenone epoxides using mineral solid acids

✍ Scribed by André J. Derksen; Adri C.L.M. van der Waals; Marieke H.A. van Ham; Mark van Dongen; Jan H. Borkent; René de Gelder; Antonius J.H. Klunder; Binne Zwanenburg

• Book ID: 104211214
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 71 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01665-8

✦ Synopsis

Tricyclodecenone exo-and endo-epoxides 1 and 9 underwent an unexpected isomerization to oxa-pentacycloundecanones 2 and 10, respectively, under flash vacuum thermolysis conditions using various solid acid catalysts. The structure of a derivative of 2 (R=CO 2 Et) has been elucidated by X-ray diffraction analysis. A tentative mechanism for the formation of 2 from 1 is proposed.