Oxaziranes structure

The oxazirane structure (12) for kasugamycin was also eliminated by negative reactions characteristic of the oxazirane group (4) and by the observation of no proton corresponding to an oxazirane group in the NMR spectrum of kasugamycin. 

This resolution formed the comeietone of the assignment nf tho oxazirane structure to theo compounds. Complete resolution of these products has not as yet been achieved, hem ever. 

The UV and IR spectra eliminate structures with a CN double bond. The isomerism of nitrones and oxaziranes thus cannot be a result of CIS or traris arrangement of substituents about a double bond. The carbon atoms of an oxazirane are still at the oxidation level of the carbonyl compound used in its syntheses. By acid hydrolysis, for example, 2-terf-butyl-3-phenyloxazirane (9) can be split into benzaldehyde and tert-butylhydroxylamine fEq. (8)]. ... 

Thus the structure of the oxazirane must formally involve elimination of water from one molecule each of the carbonyl compound and of an alkyl hydroxylamine. (In the synthesis of oxazirane from N-methylhydroxylamine-O-sulfonic acid and benzaldehyde, this method... 

Further indications of the structure of the oxaziranes are obtained by reduction and isomerization. None of the reactions described in the following sections is incompatible with the three-membered ring structure. 

Oxaziranes. A class of organic compels containing the ring structure... 

As mentioned above, the oxazirane ring ha limited stability. The products of its thermal decomposition vary considerably with the structure of the oxaoirane and also with the pyrolysis conditions. The products of thermal decomposition of the 3-arytoxaziraoes are the isomeric nitrones. This is apparently a general reaction and may be conveniently accomplished by beating solutions of the oxasiraun in... 

The most useful preparation of oxaziranes is the very ready oxidation of imines with organic peraoids. This is a remarkably general reaction, and, since imines of widely varying structure can easily be... 

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