By means of tertiary phosphites

Not only the Michaelis-Becker but also the Michaelis-Arbuzov reaction (cf. page 725) can be effected with alkylating agents other than alkyl halides. 

Diethyl ethylphosphonate 335 A mixture of triethyl phosphite (83 g, 0.5 mole) and ethyl /7-toluenesulfonate (10 g, 0.05 mole) is heated slowly under nitrogen until an exothermic reaction begins. After cooling, the product is fractionated through a Vigreux column, giving the phosphonate (76.1 g, 91.6%), b.p. 90-92°/18 mm, wD20 1.4156-1.4160. 

Dimethyl methylphosphonate is obtained analogously in 98-100% yield from trimethyl phosphite and methyl /7-toluene- or benzene-sulfonate. 

Catalytic amounts of dialkyl sulfates can also be used for preparation of phosphonates.252 The Arbuzov reaction with sultones affords phosphonylated sulfonic esters 337 

Lactones react analogously [although with dialkyl phosphites they give co-(hydroxyacyl)phosphonates if catalysed by base], but telomers are always formed as well as the monomers.3325 Unlike triethyl phosphite, triphenyl phosphite reacts with ethylene carbonate (l,3-dioxolan-2-one) in the presence of small amounts of copper powder to yield tetraphenyl ethylenebisphos-phonate.312 

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