Intermediates for the Convenient Synthesis of Bicyclic Aziridinocarbamates

3,4,5,6-Tetrahydro-5-iodo-4,4-dimethyl-2H-1,3-oxazin-2-one, C₆H₁₀INO₂, (1), 4,5-dihydro-4-(1-iodoethyl)-4-methyl-3H-1,3-oxazol-2-one, C₆H₁₀INO₂, (2), and 3,4,5,6-tetrahydro-5-iodo-6-(n-pentyl)-2H-1,3-oxazin-2-one, C₉H₁₆INO₂, (3), are examples of a series of readily prepared inter­mediates in a convenient synthesis of bicyclic aziridinocarbamates. The structures obtained confirm the stereochemistries deduced from spectroscopic data. Compounds (1) and (2) exist in the solid state as centrosymmetric N-H...O hydrogen-bonded dimers: (1) O1...N' = 2.901 (8), (2) N...O2′ = 2.902 (4) Å. Compound (3) crystallizes with two independent molecules in the asymmetric unit which are hydrogen-bonded to form centrosymmetric tetramers: O2...N2′ = 2.970 (6), O4...N1′ = 2.819 (6) Å.

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