Michaelis–Arbuzov reaction

<p>The Michaelis–Arbuzov reaction (also called the Arbuzov reaction) is the <a href="/facts/Chemical_reaction/GpqWlKrz">chemical reaction</a> of a <a href="/facts/Trivalent/ck7cHByj">trivalent</a> phosphorus ester with an <a href="/facts/Alkyl_halide/Enb7LQqt">alkyl halide</a> to form a <a href="/facts/Pentavalent/ck7cHByj">pentavalent</a> phosphorus species and another alkyl halide. The picture below shows the most common types of substrates undergoing the Arbuzov reaction; <a href="/facts/Phosphite_ester/Uq54qjld">phosphite esters</a> (1) react to form <a href="/facts/Phosphonate/8mg6nNRP">phosphonates</a> (2),  <a href="/facts/Phosphonite/DjcnMaBP">phosphonites</a> (3) react to form <a href="/facts/Phosphinate/Je5Gckyh">phosphinates</a> (4) and <a href="/facts/Phosphinite/lFvHHEak">phosphinites</a> (5) react to form <a href="/facts/Phosphine_oxide/Tq9TMtn4">phosphine oxides</a> (6).
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<p>The reaction was discovered by <a href="/facts/August_Michaelis/xc78JSGt">August Michaelis</a> in 1898, and greatly explored by <a href="/facts/Aleksandr_Arbuzov/cMVqK6Vc">Aleksandr Arbuzov</a> soon thereafter.  This reaction is widely used for the synthesis of various phosphonates, <a href="/facts/Phosphinate/Je5Gckyh">phosphinates</a>, and <a href="/facts/Phosphine_oxide/Tq9TMtn4">phosphine oxides</a>.  Several reviews have been published.  The reaction also occurs for coordinated phosphite ligands, as illustrated by the demethylation of {(C5H5)Co[(CH3O)3P]3}2+ to give {(C5H5)Co[(CH3O)2PO]3}−, which is called the <a href="/facts/Klaui_ligand/C4JH1Dh8">Klaui ligand</a>.
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Michaelis–Arbuzov reaction open-in-new

Michaelis–Arbuzov reaction