Demethylenation of Tröger's Bases with Concomitant Hydrazine Formation


  • Dedicated to Professor Paul A. Wender


Trögers bases (TBs) react with dimethyldioxirane to produce the corresponding N-oxides in excellent yields. Upon treatment with acetic anhydride, these N-oxides undergo a Polonovski-type reaction that involves fragmentation and ultimate nitrogen–nitrogen bond formation to form hydrazines. Steric effects are evident in both the oxidation step and in the step involving the activation of the N-oxide, such that certain TBs are not amenable to the process.