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A tandem Brook rearrangement/silicon Polonovski reaction has been achieved by in situ generation of ammonium ylides via the oxidation of α-silyl-tertiary amines. Furthermore, we found that the oxidation of N-(1-cyano-1-silyl)methyl-tertiary amines with peracids induced the tandem Brook rearrangement/silicon Polonovski reaction/fragmentation to give formamide derivatives in moderate yields.

Tandem Brook Rearrangement/Silicon Polonovski Reaction <i>via</i> Oxidative Generation of Ammonium Ylides