Phosphorohydrazidates reactions

Phosphoryl trihydrazide, OP(NHNH2)3, is made from POCI3 and N2H4 (7.52). Whereas reaction (7.211) is favoured by near-anhydrous conditions, under aqueous conditions a ring compound is formed (7.215). On the other hand, the action of heat on diphenyl phosphorohydrazide is to produce the condensed compound (7.216), which can also be made by reaction (7.217). The chloro analogue of (7.217) is hydrolytically unstable, but the phenyl phosphonium salt can be prepared by reaction (7.218). 

Phosphoric acid diesters. 1-Ethylpiperidinium phenyl phosphorohydrazidate allowed to react with the stoichiometric amount of ethanol in dry pyridine in the presence of iodine ethyl phenyl hydrogen phosphate. Y good. F. reactions s. D. M. Brown and N. K. Hamer, Proc. Chem. Soc. 1960, 212. 

Finally, to prove that phosphorus and its compounds fall squarely in the field of organic chemistry, Majoral et al. have reported novel reactions of the phosphorohydrazidic derivatives (438) with aldehydes to produce the macropolycycles (439) and (440). 

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