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Direct introduction of CN- or NO2- into nucleophilic olefins has been the subject of considerable interest in the area of organic synthesis because of their unique synthetic potential.Reviewed herein are intriguing as well as useful examples of such reactions realized only by judicious choice of suitable organoselenium compounds. Direct cyanation of enamines, ketene silyl acetals, silyl enol ethers, and alkenes has been achieved by the use of phenyl selenocyanate, quantitatively prepared by the novel silicon-selenium exchange reaction. The products derived from alkenes were converted stereospecifically into conjugated cyanoalkenes. Direct nitration of alkenes and alkenylsilanes (vinylsilanes) via nitroselenenylation provided nitroselenides again stereospecifically, which were converted into conjugated nitroalkenes and nitroalkenylsilanes, respectively. These reactions have advantages over cyanosulfenylation (B. M. Trost, 1982) and nitromercuration (E. J. Corey, 1978) of alkenes in many respects.

Cyanoselenenylation and nitroselenenylation of nucleophilic olefins.