ChemInform Abstract: Synthesis of 1-Substituted Derivatives of Pentacyclo(6.3.0.02,6.03,10.05,9)undecane (Symmetric Tris-Homocubane).

ChemInform Abstract

Adamantanone (I) and the pentacycloundecanone (III) react with BBr₃, according to method A), to yield the geminal dibromo derivatives (II) or (IV). Protoadamantanone (V), on treatment according to method A), undergoes a skeletal rearrangement to give 1,2-dibromoadamantane (VI). The pentacycloundecanedione (VII), on treatment with BBr₃ according to method A), also undergoes skeletal rearrangement to afford the tribromoundecanol (VIII) with a pentacyclo(6.3.0.02,6.03,10.05,9)undecane skeleton. Starting from (VIII), the derivatives (X)-(XII), (XIV), (XV), (XVII), (XVIII) and (XX) are prepared; these have the same carbon skeleton as (VIII).