Nitroalkanes as Ketone Synthetic Equivalents in C-N and C-S Bond Formation Reactions
Shubham Tiwari1, Guddeangadi N Gururaja1
1School of Chemical Sciences, Central University of Gujarat, Gandhinagar, Gujarat 382030, India.
Abstract:
The umpolung strategy has been explored with 2-nitropropane derivatives featuring stabilized carbanion to latent ketone equivalents. The consequence of changing intrinsic polarity at the α-carbon of nitroalkanes induces simultaneous installation of the C-N bond at the geminal and C-S bond at the 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 isothiazole-3-thione.
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