Olefins, Michaelis-Arbuzov reaction

The reaction of trialkylphosphines, especially triphenylphosphine, with alkyl halides is particularly useful since the resultant phosphonium salts are easily converted to the phosphonium ylid on treatment with a suitable base (sec. 8.8r kk Ylids are, of course, the reactive species in the well-known Wittig olefination reaction, which will be discussed in section 8.8.A.i. A related Sn2 process involves reaction of a trialkylphosphite with an alkyl halide, the Arbuzov reaction (sometimes called the Michaelis-Arbuzov reaction). Triethylphos-phite (70) reacts with iodomethane to give the phosphonium salt, 71. Heating generates the monoalkyl phos-phonic ester (72). This type of phosphonic ester can be converted to an ylid and used in the well-known Horner-Wadsworth-Emmons oiefination (sec. 8.8.A.iii). 

Michael Reaction Michaelis-Arbuzov Reaction Miescher Degradation Mignonac Reaction Milas Hvdroxvlation of Olefins Miller (see Doebner-Miller Reaction)... 

Dittrich, R. and Hagele, G., Michaelis-Arbuzov perhalogentation reaction of olefins. III. The trifluorovinyl halide, CF2CFX, Phosph. Sulf, 10, 127, 1981. 

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