Homoaldol condensation of aromatic ketones in fluoroalkyl end-capped 2-acrylamido-2-methylpropanesulfonic acid oligomeric gel network cores

Aromatic ketones such as 4′-methoxyacetophenone (MAP), acetophenone (AP), 4-acetylbiphenyl (ABP), and 2-acetyl-6-methoxynapthalene (AMN) interacted with fluoroalkyl end-capped 2-acrylamido-2-methylpropanesulfonic acid oligomer [RF-(AMPS)n-RF] at 80°C for 3 h to give the corresponding fluorinated oligomer/aromatic ketones composites. In these composites, the RF-(AMPS)n-RF/MAP and /AP composites were found to give the homoaldol condensation products of MAP and AP, respectively. In contrast, the corresponding non-fluorinated AMPS oligomer/MAP and sulfuric acid/MAP composites could not give the homoaldol product at all under similar conditions. This suggests that the RF-(AMPS)n-RF oligomer could provide the suitable fluorinated oligomeric gel newtwok cores to interact with MAP or AP as a guest molecule, and the homoaldol condensation of encapsulated MAP and AP should proceed smoothly in the fluorinated oligomeric gel network cores. The RF-(AMPS)n-RF/ABP and /AMN composites could not give the homoaldol products at all under similar conditions, indicating that the more bulky aromotic ketones than MAP or AP are not likely to be encapasulated as guest molecules into the fluorinated AMPS oligomeric gel netwok cores. Copyright © 2013 John Wiley & Sons, Ltd.