Behavior of arylvinylketones in zeolites: A systematic study

The zeolite-promoted cyclization of arylvinylketones to indanones has been investigated, regarding zeolite nature and substitution pattern in the starting materials. 2-Substituted arylvinylketones reacted more readily in H-ZSM5, giving high yield (>90%) of the corresponding indanones, while the 3-substituted are more efficiently converted to the corresponding indanones by H-USY. Rearranged product and solvent addition products were also isolated in a few cases, giving insight into cyclization mechanisms.

Arylvinylketones were efficiently converted to indanones through zeolite-promoted cyclization. The zeolite nature and the substitution pattern in the starting materials proved critical, the 2-substituted arylvinylketones reacting more readily in H-ZSM5, while the 3-substituted required H-USY. The characterization of rearranged product and solvent addition formed as side-products in a few cases offer insight into the mechanism, suggesting dicationic intermediates.Figure optionsDownload as PowerPoint slide