Abstract
Treatment of 3‐C‐cyano‐1,2:5,6‐di‐O‐isopropylidene‐3‐O‐(toluene‐p‐sulfonyl)‐α‐D‐allofurannose with AlLiH4 or RMgX yields spiro‐aziridines with two identical substituents on C(3′) (H, CH3, C2H5). Reactions of these products and their derivatives are briefly described. If the C(3′) substituents are protons, the aziridine ring is easily opened. In acidic media (HCl), an amino‐sugar containing the branched chain CH2Cl is produced; with hydrogenation, a CH3 branched chain results. If the C(3′) substituents are methyl groups, the aziridine ring cannot be opened neither with HCl nor with hydrogen. The acetylated derivative of this latter compound rearranges to the corresponding allylamide with HCl. For both types of spiro‐aziridine, the nitrous deamination leads to the corresponding alkene.
Published Version
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