Reactions of methylenecyclobutanes with silver acetate and iodine

Methylenecyclobutanes undergo an interesting rearrangement reaction in the presence of silver acetate and iodine at room temperature (20 °C) in dichloromethane to give the corresponding aryl-(1-arylcyclobutyl)methanones in good to high yields within short reaction time. A plausible reaction mechanism has been discussed on the basis of control and O18-labeling experiments.

Graphical abstract The rearrangement reaction of methylenecyclobutanes 1 in the presence of silver acetate and iodine proceeded smoothly to give the corresponding aryl-(1-arylcyclobutyl)methanones 2 in moderate to good yields within short reaction time under mild conditions.Figure optionsDownload full-size imageDownload as PowerPoint slide