Nitroalkanes as ketone synthetic equivalent in C-N and C-S bond formation reaction

The umpolung strategy has been explored with 2-nitropropane derivatives featuring stabilized carbanion to latent ketone equivalents. The consequence of changing intrinsic polarity at -carbon of nitroalkanes induces simultaneous installation of the C-N bond at geminal and C-S bond at vicinal positions of the nitro functionality. Although the vicinal position of nitroalkanes bears poor electronic bias, the latent ketone formation facilitates C-S bond formation in the dithiole-3-thione core structure. The application of this methodology is also demonstrated with the synthesis of amino derivatives of isothia-zole-3-thione.