Facile Synthesis of Alpha-Deuterated Acrylics and Activated Vinyls

摘要

A simple, direct exchange reaction has been discovered for vinyl groups in which the exchangeable deuterium of alcohols (e.g. CH3OD) or water (D2O) replaces only the alpha-hydrogen of activated vinyls under catalysis by DABCO (1,4-diazabicylo-(2.2.2.) octane). Acrylate esters, acrylonitrile, acrylamides and methyl vinyl ketone were found to go rapid exchange at room temperature to give easily isolated, pure and readily polymerizable alpha-deuterated compounds. This procedure is the most general efficient and cost-effective one available for obtaining such isotopically labeled materials.