Bestmann-Ohira Reagent

Title: Bestmann-Ohira Reagent
CAS Registry Number: 90965-06-3
CAS Name: (1-Diazo-2-oxopropyl)phosphonic acid dimethyl ester
Additional Names: dimethyl (1-diazo-2-oxopropyl)phosphonate
Molecular Formula: C5H9N2O4P
Molecular Weight: 192.11
Percent Composition: C 31.26%, H 4.72%, N 14.58%, O 33.31%, P 16.12%
Literature References: Diazoalkylphosphonate reagent; converted in situ to the Seyferth-Gilbert reagent, q.v. Prepn: P. Callant et al., Synth. Commun. 14, 155 (1984). Synthetic applications: S. Ohira, ibid. 19, 561 (1989); S. Müller et al., Synlett 1996, 521; G. J. Roth et al., Synthesis 2004, 59; E. Quesada, R. J. K. Taylor, Tetrahedron Lett. 46, 6473 (2005).
Use: Reagent for transformation of aldehydes to terminal alkynes and ketones to methyl enol ethers.
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