10334. O-(Diphenylphosphinyl)hydroxylamine

Nomenclature

CAS number: 72804-96-7
(Aminooxy)diphenylphosphine oxide; ODPH.
C12H12NO2P; mol wt 233.20.
C 61.80%, H 5.19%, N 6.01%, O 13.72%, P 13.28%.

Description and references

Activated hydroxylamine used in electrophilic aminations. Prepn from diphenylphosphinic chloride and hydroxylamine: N. Kreutzkamp, H. Schindler, Arch. Pharm. 293, 296 (1960) DOI PubMed. Corrected structural assignment and reactivity studies: M. J. P. Harger, J. Chem. Soc. Chem. Commun. 1979, 768 DOI; idem, J. Chem. Soc. Perkin Trans. 1 1981, 3284 DOI. Synthetic applications: G. Boche et al., Tetrahedron Lett. 23, 5399 (1982) DOI; G. Sosnovsky, K. Purgstaller, Z. Naturforsch. 44b, 582 (1989); R. Badorrey et al., Tetrahedron: Asymmetry 6, 2787 (1995) DOI; A. Armstrong et al., Org. Lett. 9, 351 (2007) DOI PubMed. Reviews: G. Boche in Encyclopedia of Reagents for Organic Synthesis, 4, L. A. Paquette, Ed. (John Wiley & Sons, New York, 1995) pp 2240-2242; E. Bodio, Synlett 2008, 1744-1745 DOI.

Chemical structure

Properties

Solid from methanol, mp 131° (dec) (Kreutzkamp, Schindler); mp 133-134° (Sosnovsky). Sparingly sol in aprotic solvents incl ether, chloroform, dichloromethane. Dec in solns of acetone, dimethylsulfoxide. Stable for up to one year when stored below 0°.

Use

Reagent in synthetic organic chemistry.