O-Diphenylphosphinylhydroxylamine

Chemical properties

Light yellow or white powder solid

The Uses of O-Diphenylphosphinylhydroxylamine

Efficient reagent for direct conversion of aldehydes to nitriles in the presence of alcohol, ketone, ester, or amine functionality.

The Uses of O-Diphenylphosphinylhydroxylamine

O-Diphenylphosphinylhydroxylamine is a versatile reactant used in the synthetic preparation of various products such as trans-acylaziridines and aldohydrazones.

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 3835, 1982 DOI: 10.1016/S0040-4039(00)87720-5

Description

O-Diphenylphosphinylhydroxylamine (DPPH) is a versatile electrophilic amination reagent that has been used widely for the amination of stable carbanions, Grignard reagents, and π-electron-rich nitrogen heterocycles. Researchers have used DPPH for the aziridination of enones. Compared to other hydroxylamine derivatives typically stored as hydrochloride salts, this activated phosphinyl reagent exhibits good stability and can be stored indefinitely at 0 ℃. This compound in a single step from hydroxylamine hydrochloride and diphenylphosphinic chloride[1].

General Description

O-(Diphenylphosphinyl)hydroxylamine is a general reagent for electrophilic C-amination, which aminates a variety of stable carbanions and Grignard reagents.

References

[1] J. P. Anselm, J. L. Ferrari. “A New Journal for Organic Synthesis: Organic Preparations and Procedures International.” Journal of Chemical Education 48 5 (1971): 349.