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Full-Text Articles in Physical Sciences and Mathematics
One-Pot Silyl Ketene Imine Formation-Nucleophilic Addition Reactions Of Acetonitrile With Acetals And Nitrones, C. Wade Downey, Grace Ann L. Robertson, Jhonmattew Santa, Kari R. Flicker, William M. Stith
One-Pot Silyl Ketene Imine Formation-Nucleophilic Addition Reactions Of Acetonitrile With Acetals And Nitrones, C. Wade Downey, Grace Ann L. Robertson, Jhonmattew Santa, Kari R. Flicker, William M. Stith
Chemistry Faculty Publications
Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and a trialkylamine base promote the conversion of acetonitrile to its silyl ketene imine in situ when acetonitrile is employed as solvent. Residual TMSOTf acts as a Lewis acid catalyst to activate acetals and nitrones in the reaction mixture, yielding β-methoxynitriles and β-(silyloxy)aminonitriles, respectively. Some reaction products undergo elimination under the reaction conditions to provide the α,β-unsaturated nitrile directly.