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DOI: 10.1055/sos-SD-030-00003

Kibayashi, C.; Yamazaki, N.Science of Synthesis, (2007308.

In general, the oxidation of aldehyde-derived hydrazones with lead(IV) acetate in acetic acid solution usually gives N-acyl-N-acetylhydrazines, whereas the oxidation of ketone-derived hydrazones normally affords diazenyl acetates posessing an OCN function.[‌3‌] For example, the oxidation of hydrazone 12 with lead(IV) acetate leads to the corresponding gem-diazenyl acetate 13.[‌4‌] In this reaction, the diastereoselectivity is high and no detectable epimer is formed (Scheme 4). Similarly, the oxidation of cyclohex-2-enone methylhydrazone 14 with lead(IV) acetate affords the diazenyl acetate 15 in 70% yield.[‌5‌]

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