Tricyclo[6.3.0.01,6]Undecan-2-one and its isomerization to tricyclo[3.3.3.0]undecan-2-one

✍ Scribed by R.L. Cargill; J.R. Dalton; S. O'Connor; D.G. Michels

• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 108 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)95253-0

✦ Synopsis

We report the formation of the tricyclo[6.3.0.01*6]undecanones x and 2, and the unusual acid-catalyzed isomerization of $, to &$. Irradiation of 1" in hexane gave z3s4 as the sole product isolated in 92% yield. Similar irradiation of ,$" gave only 2 (83%). Wolff-Kishner reduction of the new ketones gave the same hydrocarbon, & In order to ascertain the orientation of the cycloaddition (whether the cycloadducts are 5 and 0 or x and 4") we irradiated 5 in hexane containing 3% methanol at -78' and obtained ester, 2, identical with the ester obtained from the irradiation of 2,' confirming the assigned structures.