Reactions of Arenediazonium Tetrafluoroborates with 1,4-Bis(acryloyloxy)butane in the Presence of Thiocyanate Ion

The first thiocyanatoarylation reaction with an unsaturated compound containing two isolated multiple bonds, 1,4-bis(acryloyloxy)butane, was effected. The reactions of 1,4-bis(acryloyloxy)butane with arenediazonium tetrafluoroborates occur in aqueous acetone (1:2) in the presence of copper tetrafluoroborate and thiocyanate ion and involve only one multiple bond to give 1-acryloyloxy-4-(2-thiocyanato-3-arylpropionyloxy)butanes. Irrespective of reactant ratio, the second multiple bond undergoes no thiocyanatoarylation.