Oxaziranes 2.3.3- trialkyl

The composition of the products is reminiscent of the decomposition of the trialkyl-oxaziranes by ferrous salts. Here also the nitrogen atom is dealkylated and the carbon atom of the oxazirane ring is found as a ketone group. 

The mechanism proposed by Emmons thus corresponds in part to the decomposition of the trialkyl-oxaziranes by ferrous salts. By radical attack on the 7V-alkyl group of the oxazirane, the radical 32 is formed which rearranges with ring opening to 33. Radical 33 propagates the chain by attack on a further molecule of oxazirane. It takes up an H-atom and is decomposed to ketone and ammonia. The aldehyde produced from the M-alkyl group is converted to tar. 

The conversion of mines into oxazirane is a reasonably selective oxidation and may be carried out in the presence of functional groups, e.g. ethylenic unaaturation, winch normally react with per dds. AIwq, 1,9,6-trialkyl perhydro -triazitxea obtained from condensation of formaldehyde and primary amines can bo oxidized to oxazivaoee. 

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