FACILE SYNTHESIS OF ALPHA-DEUTERIATED ACRYLATES AND ACTIVATED VINYLS

The authors propose a DABCO-catalyzed equilibration in which deuterium incorporation can be driven to high levels by use of a large excess of the deuterium donor. Levels of incorporation greater than 80% were obtained in minutes with a single exchange process. This procedure is straightforward in contrast to previously reported multistep methods of alpha -deuteriation of acrylates. It is shown that while either CH//3OD or D//2O served in the exchange for acrylonitrile, hydrolysis of the intermediate species formed from acrylate esters occurred in D//2O. In addition, higher alkyl esters underwent minor transesterification to methyl acrylate if the exchange reaction was extended.