Cyclohexanespiro-3 -oxaziridine

Nucleophiles react with /V-H and Al-acyl oxaziridines with transfer of NH and /V-acyl, respectively. Much of this chemistry (91S327) has been carried out with cyclohexanespiro-3 -oxaziridine (26) attack at the NH group gives intermediate (27) which gives cyclohexanone and animation of the nucleophile. Transfers of NH to N-, 0-, S-, and C-nucleophiles, enable the syntheses of hydrazines, /V-amino-peptides, hydroxyamines, sulfenamides, thiooximes, sulfonamides, aziridines, and a-amino acids. 

Amination of C-nucleophiles, where deprotonation was possible using weak bases such as aqueous alkali and DABCO, has been explored by Schmitz and co-workers with cyclohexanespiro-3 -oxaziridine (51) <91S327>. Some examples are given in Table 5. 

The aziridination of alkenes by cyclohexanespiro-3 -oxaziridine (51) at 100°C has been described (74KGS1629, 91S327). The reaction is stereospecific for example tran.j-/ -methylstyrene gives exclusively the trans-aziridine (Equation (10)). 

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