Michaelis-Arbuzov Reaction

Michaelis-Arbuzov Reaction

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  • Generality
  • Reagent Availability
  • Experimental User Friendliness
  • General Characteristics

The reaction between phosphorous acid esters (phosphites) and alkyl halides gives phosphonic acid esters.

When the phosphite and the alkyl halide have the same alkyl group, the amount of the alkyl halide can be substoichiometric.

This reaction is used commonly to synthesize the reagents for the Witting-Horner / Horner-Wadsworth-Emmons reactions.

In the case of α-haloketones, the products are enol phosphates (the Perkow reaction).

  • General References

・Michaelis, A.; Kaehne, R. Ber. 1898, 31, 1048.
・Arbuzov, A. E. J. Russ. Phys. Chem. Soc. 1906, 38, 687.
・Arbuzov, B. A. Pure Appl. Chem. 1964, 9, 307. doi:10.1351/pac196409020307
・Review: Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415. doi:10.1021/cr00044a004
・Kosolapoff, G. M. Org. React. 1951, 6, 276.
・Redmore, D. Chem. Rev. 1971, 71, 315. DOI: 10.1021/cr60271a003
・Bauer, G.; Haegele, G. Angew. Chem. Int. Ed. 1977, 16, 477. DOI: 10.1002/anie.197704771
・Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415. DOI: 10.1021/cr00044a004
・Faure, B. et al. Chem. Commun. 1989, 805.
・Yadav, V. K. Synth. Commun. 1990, 20, 239. DOI: 10.1080/00397919008052289              

  • Reaction Mechanism

p-p-1.2.gif

  •  Examples

Example 1.[1]

p-p-1.1.gif

  • Experimental Procedure

  • Experimental Tips

  • References

[1] Burton, D. J.; Flynn, R. M. Synthesis 1979, 615.

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