Reaction of Nucleophiles with 1,1-Dinitro-2,2-diphenylethylene

Article abstract of DOI:10.1021/jo00220a038

Products of the reaction of a variety of nucleophiles with Ph2C=C(NO2)2 are reported.Michael-type adducts have been isolated: (Ph2C(N)CH(NO2)2) for N^- = (RO)2PO^-, (RO)2PS^-, RCOCH2^-.With the nucleophiles MeO^- or Me2C=NO2^- in Me2SO the adducts are formed but are hydrolyzed upon workup with 5percent aqueous HCl at 25 deg C to yield benzophenone.Benzophenone is also the major product from reaction with the nucleophiles NO2^-, AcO^-, MeC(=S)O^-, EtO^-, and Me3CO^- in Me2SO.With N^- = Me3CS^-, ArS^-, PhO^-, or PhSe^- in Me2SO, vinylic substitution occurs to yield Ph2C=C(N)NO2.With ArSO2^- in DMF nucleophilic aromatic substitution occurs to yield p-ArSO2C6H4COPh.