Michaelis-Arbuzov rearrangement

What is Michaelis-Arbuzov rearrangement?

The Michaelis-Arbuzov rearrangement is a chemical reaction used to produce monoalkylphosphonic esters from alkyl halides and trialkyl phosphites through the use of an intermediate phosphonium salt.

Michaelis-Arbuzov reaction
Michaelis-Arbuzov rearrangement


  • Michaelis, A. and Kaehne, R. (1898), Ueber das Verhalten der Jodalkyle gegen die sogen. Phosphorigsäureester oder O-Phosphine. [On the behavior of iodoalkyls against the so-called. Phosphorous acid esters or O-phosphines.] Ber. Dtsch. Chem. Ges., 31: 1048-1055. https://doi.org/10.1002/cber.189803101190
  • A.E. Arbuzov, J. Russ. Phys. Chem. Soc. 38, 687 (1906)
  • A.E. Arbuzov, Chem. Zentr. II, 1639 (1906)