8476. Seyferth-Gilbert Reagent

Nomenclature

CAS number: 27491-70-9
(Diazomethyl)phosphonic acid dimethyl ester; dimethyl diazomethylphosphonate.
C3H7N2O3P; mol wt 150.07.
C 24.01%, H 4.70%, N 18.67%, O 31.98%, P 20.64%.

Description and references

Divalent carbon transfer reagent. Prepn: D. Seyferth, R. S. Marmor, Tetrahedron Lett. 11, 2493 (1970); and applications in organophosphorus syntheses: D. Seyferth et al., J. Org. Chem. 36, 1379 (1971). Reactions with aldehydes and aryl ketones to form alkynes: J. C. Gilbert, U. Weerasooriya, ibid. 47, 1837 (1982). Improved prepn: D. G. Brown et al., ibid. 61, 2540 (1996).

Chemical structure

Properties

Distillable yellow liquid, bp0.42 59°. nD25 1.4585.

Use

Reagent for one-carbon homologation of aldehydes and ketones to alkynes.