?-Nitroalkyl selenides: Synthesis and reaction with nucleophilic and electrophilic reagents

Abstract

1. The reaction of nitrocarbanions with selenium halide proceeds by C-selenylation with the formation of α-nitroalkyl selenides. 2. α-Polynitroalkyl selenides are split under mild conditions at the\(C_{NO_2 } - Se\) bond by the action of both nucleophilic reagents such as water, alcohols, and bases and electrophilic reagents such as halogens, SO2Cl2, ClSO3F, HCl, and N-chloropiperidine with the formation of the corresponding polynitroalkanes and selenic acids. The nucleophile binds to the selenium atom and the electrophile binds to the α-carbon atom bearing the nitro groups.