Michaelis–Arbuzov reaction

Overview

The Michaelis–Arbuzov reaction (also called the Arbuzov reaction) is the chemical reaction of a trivalent phosphorus ester with an alkyl halide to form a pentavalent phosphorus species and another alkyl halide. The picture below shows the most common types of substrates undergoing the Arbuzov reaction; phosphite esters (1) react to form phosphonates (2), phosphonites (3) react to form phosphinates (4) and phosphinites (5) react to form phosphine oxides (6).

Actions

• This entry doesn't have stoichiometric equivalents on file yet — the Reaction Scale Calculator needs at least one participant tagged with an equivalents value.
• Mechanism / source ↗
• View as JSON ↗

Search literature

• Google Scholar ↗
• PubMed ↗
• Wikipedia ↗

More Addition reactions

• 1,2-ADDITION OF A FUNCTIONALIZED ZINC-COPPER ORGANOMETALLIC [RCu(CN)ZnI] TO AN α,β-UNSATURATED ALDEHYDE: (E)-2-(4-HYDROXY-6-PHENYL-5-HEXENYL)-1H-ISOINDOLE-1,3(2H)-DIONE (1H-Isoindole-1,3(2H)-dione, 2-(4-hydroxy-6-phenyl-5-hexenyl)-) Addition
• 3'-NITRO-1-PHENYLETHANOL BY ADDITION OF METHYLTRIISOPROPOXYTITANIUM TO m-NITROBENZALDEHYDE (Benzenemethanol, α-methyl-3-nitro-) Addition
• 3-TRIMETHYLSILYL-3-BUTEN-2-ONE: A MICHAEL ACCEPTOR (3-Buten-2-one, 3-(trimethylsilyl)-) Addition
• 3-TRIMETHYLSILYL-3-BUTEN-2-ONE AS MICHAEL ACCEPTOR FOR CONJUGATE ADDITION-ANNELATION: cis-4,4a,5,6,7,8-HEXAHYDRO-4a,5-DIMETHYL-2(3H)-NAPHTHALENONE (2(3H)-Napthalenone, 4,4a,5,6,7,8-hexahydro-, 4a,5-dimethyl-, cis-, (±)-) Addition
• [4+2] CYCLOADDITION OF 1-DIMETHYLAMINO-3-tert-BUTYLDIMETHYLSILOXY-1,3-BUTADIENE WITH METHYL ACRYLATE: 4-HYDROXYMETHYL-2-CYCLOHEXEN-1-ONE (2-Cyclohexen-1-one, 4-(hydroxymethyl)-) Cycloaddition
• [4+3] CYCLOADDITION IN WATER. SYNTHESIS OF 2,4-endo,endo-DIMETHYL-8-OXABICYCLO[3.2.1]OCT-6-EN-3-ONE (8-Oxabicyclo[3.2.1]oct-6-en-3-one, 2,4-dimethyl-, (endo,endo)-) Cycloaddition