Oxidation of N-t-butylazetidine derivatives was performed at -30℃ in chloroform followed by its increase up to room temperature. It was found that azetidine N-oxides formed are not stable at room temperature and the decomposition of the compounds al...
Oxidation of N-t-butylazetidine derivatives was performed at -30℃ in chloroform followed by its increase up to room temperature. It was found that azetidine N-oxides formed are not stable at room temperature and the decomposition of the compounds always provides t-butyl nitroso compound which is easily characterized by its blue color regardless of alkyl substituents at the neighboring ring carbon of nitrogen.
The hydrogen-transfer reaction which is more favorable for alkyl substitution at ring carbon of aziriding N-oxides was failed probably due the lack of coplanar formation between N-oxide bond and the other bond formed between a neighboring ring carbon of nitrogen and alkyl substituted carbon of azetidines.
The rate of oxidation of the unsubstituted azetidine was absorbed to the faster than that substituted azetidine probably due to the fact that of nuclearphilic attack of unshared election pair of nitrogen is much hindered by the bulky alkyl group.