Direct Synthesis of Deuterium-Labeled O -, S -, N -Vinyl Derivatives from Calcium Carbide

A novel methodology for the preparation of trideuterovinyl derivatives of high purity directly from alcohols, thiols, and NH-compounds was developed. Commercially available calcium carbide and D2O acted as a D-2-acetylene source, and DMSO-d(6)was used to complete the formation of the D2C=C(D)-X fragment (X = O, S, N). Polymerization of a selected trideuterovinylated compound showed a very promising potential of these substances in the synthesis of labeled polymeric materials. Biological activity of the synthesized trideuterovinyl derivatives was evaluated and the results indicated a significant increase of cytotoxicity upon deuteration.