Publication

Enhanced cis-selectivities in olefination reactions employing ylides with modified stationary groups

Manfred Schlosser
1986
Journal Articles

Abstract

Whereas triphenylphosphonioethanide manifests unsatisfactory cis-selectivities (84.0-95.5%), tris(o,o'-difluorophenyl)- and tri-o-tolylphosphonioethanide react with aliph. or arom. aldehydes and, resp., 2-alkenals or 2-alkynals to afford the olefins with cis/trans-ratios of 99:1 and 96:4 (or better). Triphenylphosphoniobutanide like other higher-homolog std. ylides shows excellent stereoselectivity (99% cis) when condensed with aliph. aldehydes but fails to produce cis-olefins derived from arom. aldehydes with >96% or 97% isomeric purity. In such cases tris(o,o'-difluorophenyl)phosphoniobutanide gave a 99% level of selectivity. [on SciFinder (R)]

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https://infoscience.epfl.ch/entities/publication/f3f9aa11-2f14-48b6-862f-9e8d8afa62a8

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Manfred Schlosser
1986
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/f3f9aa11-2f14-48b6-862f-9e8d8afa62a8

About this result

Related concepts (12)

Olefin metathesis

Olefin metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins) by the scission and regeneration of carbon-carbon double bonds. Because of the relative simplicity of olefin metathesis, it often creates fewer undesired by-products and hazardous wastes than alternative organic reactions. For their elucidation of the reaction mechanism and their discovery of a variety of highly active catalysts, Yves Chauvin, Robert H. Grubbs, and Richard R.

Alkene

In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins. The International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc.

Alpha-olefin

In organic chemistry, alpha-olefins (or α-olefins) are a family of organic compounds which are alkenes (also known as olefins) with a chemical formula , distinguished by having a double bond at the primary or alpha (α) position. This location of a double bond enhances the reactivity of the compound and makes it useful for a number of applications. There are two types of alpha-olefins, branched and linear (or normal).

Related publications (1)

Enhanced cis-selectivities in olefination reactions employing ylides with modified stationary groups

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Metal-Hydride Catalysis for the Functionalization of Lignin-Derived Monomers and Asymmetric Hydroalkylation of Alkenes