A one-pot, two step synthesis of 2,2-disubstituted 1-nitroalkenes

The reactions of ketones , nitromethane , and a stoichiometric amount of piperidine or ethylenediamine in the presence of mercaptan in THF or CH3CN solution give high yields of β-nitrosulfides . The latter can be oxidized by (m-CPBA or m-CPBA/AcOH) at 0°C, (H2O2/AcOH), or (H2O2) at room temperature, thus generating β-nitroalkylsulfoxides , which then undergo elimination to produce medium to high yields of 2,2-disubstituted-1-nitroalkenes , when refluxed in a solution of ClCH2CH2Cl (1,2-dichloroethane). After preparation from , , , and , were oxidized with , or in a mixture of CH3CN and ClCH2CH2Cl to generate β-nitrosulfoxides , which then underwent elimination under refluxing under one-pot conditions. Compounds and were also prepared using , , , and , in a similar manner.