The Claisen rearrangement was observed in the reaction of (diethylamino) propiolonitrile with allyl alcohol in the presence of boron trifluoride etherate at room temperature. No amino-Claisen rearrangement occurred in the reactions of propiolonitrile, chloropropiolonitrile, or (diethylamino) propiolonitrile with allylamine or diallylamine.
The thio-Claisen rearrangement occurred in the reactions of chloropropiolonitrile and (diethylamino)propiolonitrile with prop-2-enethiol at room temperature. Some mechanisms are discussed.