Percycloalkylated cyclohexanes: attempted synthesis of a trispropellane

The acid catalyzed rearrangement of two cyclohexanols of spiroannelated four-membered rings has been studied. In accordance with molecular mechanics calculations, far-reaching reorganizations with formation of unsaturated hexacyclic systems, including a fully cycloalkylated cyclohexene with a bispropellane partial structure, were observed. Attempts to convert this bispropellane to a trispropellane failed.

The acid catalyzed rearrangement of two pentaspiranes of four-membered rings yields five hexacyclic systems, including a bispropellane. Several attempts to convert it to a trispropellane failed.Figure optionsDownload as PowerPoint slide