Silicon carbide → N-tert-Butyl-a-phenylnitrone

Participants

Reaction Conditions

Reaction Steps

To a nitrogen charged 250 ml, 3-necked, round bottom flask equipped with a magnetic stir bar, nitrogen gas flow, pot thermometer, and condenser was added 119.3 gm (0.674 moles) of the 2-t-butyl-3-phenyloxaziridine as prepared in Example 2 and several silicon carbide boiling chips. The system was continuously flushed with nitrogen while gradually heated to 120° C. Upon reaching 120°, the heat was removed as the exothermic rearrangement brought the reaction temperature to about 134° C. before slowly subsiding. The pale yellow 2-t-butyl-3-phenyloxaziridine gradually turned to a clear, dark brown color. The reaction was cooled after a total reaction time of about 1 hour and a GC analysis, as described in Example 1, of the crude product 25 indicated a complete conversion to the corresponding nitrone (a peak having a retention time of 6.45 minutes). Upon cooling, the liquid N-t-butylphenylnitrone crystallized to form a solid having a crude yield of 109.4 gm (91.7% of theoretical yield).

Provenance & Evidence