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In addition to the amines shown in Table 1, NaN3 (in refluxing MeOH/H2O) and NaCN (in refluxing CH3CN) also reacted with 6 to give the corresponding ring-opened adducts 9j and 9k in 85 and 87% yields, respectively. Interestingly, reaction of NaN3 with non-activated aziridine 5 in refluxing 2-ethoxyethanol afforded amino azide 16 in 70% yield see Exp. Sect, Chemical Equation Presented
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3 with non-activated aziridine 5 in refluxing 2-ethoxyethanol afforded amino azide 16 in 70% yield (see Exp. Sect.). (Chemical Equation Presented)
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1H NMR spectroscopic data of the crude reaction mixture.
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2 afforded 12e, although contaminated with side-products probably as a result of the reaction of the aniline moiety with the putative benzyl cation intermediate formed in the course of the deprotection reaction.
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