Synthesis of Highly Polarized Carbon-Carbon Double Bonds from Cyanoacetophenone, Isothiocyanates, and Imidoyl Chlorides

The formation of carbon-heteroatom bond is of interest due to its wide application in organic synthesis and pharmaceutical chemistry. The concept of polarized (or push-pull) olefinic systems has played an important role in organic chemistry for four decades. Substitution of one C-atom of the C=C bond with electron-donating groups and of the other with electron-withdrawing groups diminishes the C=C bond order by charge separation.1 The polarized structure of the C=C bond is discernible by 13C NMR spectroscopy due to the extreme deshielded position of the alkene C-atom on the donor side and the contrastingly shielded position of the C-atom on the acceptor side of the push-pull alkene. Various aspects of these systems will be presented and discussed.