Hydrazines diimide synthesis from

The route to 4-2 outlined here is unlikely to be profitable, because oxidation of Itydrazine leads to diimide, HNNH, rather than the dihydroxy hydrazine 4-4 [49], Precursor 4-3 is appeahng because it might be possible to photochemically extrade the very stable molecule benzene from it, providing 4. However, the bicyclic precursor to 4-5 suffers from the same kind of synthetic problem as 4-4. Indeed, organic compounds with N-O bonds are uncommon, and the synthesis of 4-2 or 4-3 may require some audacity. One unorthodox approach would be the reaction of a hydrazine metal salt ( rather inaccessible species [50]) with an acyl hypohalite [51], e.g. (surprisingly, 4-6 seems to be unknown) ... 

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