Publication

Improved cis selectivities of carbonyl substituted, stable phosphorus ylides

Manfred Schlosser
1993
Journal Articles

Abstract

Tris(2-methoxymethoxyphenyl)phosphine was readily quaternized when treated with Me bromoacetate. The resulting phosphornium salt was deprotonated to give the corresponding ylide (2-MeOCH2OC6H4)3P+CH-CO2Me (I). I reacted with satd., unsatd., or a-alkoxy substituted aliph. aldehydes to produce a,b-unsatd. esters with moderate to excellent cis-selectivity when methanol was used as the solvent. Thus, I reacted with isobutyraldehyde in MeOH to give a 91:9 mixt. of cis- and trans-Me2CHCH:CHCO2Me. Similarly, aldehyde II gave a 95:5 mixt. of cis- and trans-ester III. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/bd2cacdc-c729-4587-ad38-38b632c38fd9

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Manfred Schlosser
1993
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/bd2cacdc-c729-4587-ad38-38b632c38fd9

About this result

Related concepts (11)

Wittig reagents

In organic chemistry, Wittig reagents are organophosphorus compounds of the formula R3P=CHR', where R is usually phenyl. They are used to convert ketones and aldehydes to alkenes: Because they typically hydrolyze and oxidize readily, Wittig reagents are prepared using air-free techniques. They are typically generated and used in situ. THF is a typical solvent. Some are sufficiently stable to be sold commercially. Wittig reagents are usually prepared from a phosphonium salt, which is in turn prepared by the quaternization of triphenylphosphine with an alkyl halide.

Organophosphorus chemistry

Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents. Phosphorus, like nitrogen, is in group 15 of the periodic table, and thus phosphorus compounds and nitrogen compounds have many similar properties.

Triphenylphosphine

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether. Triphenylphosphine can be prepared in the laboratory by treatment of phosphorus trichloride with phenylmagnesium bromide or phenyllithium.