Brønsted acid TfOH-mediated reactions of 2-(arylmethylene)cyclopropylcarbinols with acetonitrile

We report herein Brønsted acid TfOH-mediated reactions of 2-(arylmethylene)cyclopropylcarbinols with acetonitrile to give the corresponding ring-enlarged N-(3-arylmethylidenecyclobutyl)acetamides in moderate to good yields under mild conditions. A plausible mechanism is proposed on the basis of previous investigations.

Brønsted acid TfOH-mediated reactions of 2-(arylmethylene)cyclopropylcarbinols 1, another kinds of MCPs bearing a hydroxymethyl group, with acetonitrile produced the corresponding ring-enlarged N-(3-arylmethylidenecyclobutyl)acetamides 2 in moderate to good yields at 60 °C.Figure optionsDownload as PowerPoint slide