Phenyl-N-f-butylnitrone

This procedure is an adaptation of that described by Emmons for the preparation of oxaziranes from imines using peracetic acid. Other procedures which may be more useful for oxazirane preparation in specific instances are the oxidation of imines with iw-chloroperbenzoic acid and the reaction of aldehydes or ketones with hydroxylamine 0-sulfonic acid in alkaline solution. 2-<-Butyl-3-phenyloxazirane has also been prepared by photolysis of a-phenyl-N-f-butylnitrone (a general reaction of considerable theoretical interest since it represents direct conversion of electromagnetic energy to chemical energy) and in low yields by ozonoly-sis of N-f-butylbenzaldimine. ... 

Atamna, H., PalerMartinez, A., and Ames, B. N. (2000). N-t-Butylhydroxylamine, a hydrolysis product of a-phenyl-N-f-butylnitrone, is more potent in delaying senescence in human lung fibroblasts. ]. Biol. Chem. 275, 6741-6748. 

Several studies have been done to establish the chain-carrying species in the oxidation of alcohol (29). The absence of peroxide in the photooxidation of 2-propanol suggests either that the chain carrier is a hydroperoxy radical and not the 2-hydroxy-2-propylperoxy radical or that 2-hydroperoxy-2-propanol is too unstable to accumulate, if formed under these conditions. Only the hydroperoxy radical could be trapped by the spin-trapping reagent phenyl-N-f-butylnitrone in the oxidation of 2-propanol at 25°C (28). The reported high rate constant (30) for the decomposition of the 2-hydroxy-2-propylperoxy radical to acetone and hydroperoxy radical also implies that the hydroperoxy radical is the predominant chain carrier. On the other hand, Schenck and his co-workers (31) isolated 2-hydroperoxy-2-propanol in the photooxidation of 2-propanol with 313-nm light. 

Propose a detailed mechanism for the reaction of a radical with a-phenyl-N-f-butylnitrone (99), and explain how such a reaction could be useful in studying the structures and properties of free radicals. 

Li, X.Y., Sun, S.Z. Bradamante, S., Piccinini, F. and Bolli, R (1993). Effects of the spin trap alpha-phenyl-N-tert-butylnitrone on myocardial function and flow a dose response study in the open chest dog and in the isolated rat heart. Free Rad. Biol. Med. 14 (3), 277-285. 

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